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The Perfect 3 Days in Chicago Itinerary (2024 Edition)

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  • Last Updated: February 4, 2024

If you’re planning a long weekend trip to the Windy City and aren’t quite sure what to do, keep reading for our epic 3 days in Chicago itinerary!

While Chicago is the 3rd-largest city in the US, it’s often overlooked by travellers who jet for one of the coasts.

In my opinion, Chicago is the best city in the country. New York and LA are great and all, but I’ll gladly take the friendly Midwestern vibe of Chicago instead.

Situated on Lake Michigan, the Chicago skyline is one of the most beautiful in the world. After all, it was here that the first skyscraper was built in 1885!

There’s so much going on here that you could spend a lifetime there and never run out of things to do.

With a solid Chicago itinerary, you can definitely check out the best of the city in 3 days. Let’s get to it!

Table of Contents

When to Visit Chicago

Chicago citypass, getting around chicago, loop walking tour, chicago hot dog, millennium park, art institute of chicago, willis tower, dinner and drinks, museum campus, riverwalk or river cruise, magnificent mile, chicago deep dish pizza, choose your own adventure, museum of your choice, 360 chicago, lincoln park, best hostel in chicago – hi chicago, best mid-range hotel – congress plaza, best luxury hotel – peninsula, brunch/lunch, how to spend a perfect 3 days in chicago itinerary.

Our 3 days in Chicago itinerary includes:

  • Shedd Aquarium
  • Skydeck Chicago
  • Field Museum
  • Adler Planetarium
  • 360 CHICAGO Observation Deck
  • Navy PierMuseum of Science and Industry
  • Ferris Wheel
  • Crown Fountain

Looking for more awesome things to add to your Chicago itinerary? Be sure to read our guide to the best things to do in Chicago !

3 Days In Chicago Itinerary

Travel Tips for Visiting Chicago

The first step in figuring out what to do during your 3 day Chicago itinerary is planning when you’ll visit.

Winter in Chicago can be painfully cold, which can definitely put a damper on your trip. Unless you enjoy frigid temperatures and cold, biting wind, I recommend skipping out on December-March.

Your best bet is to visit Chicago between May and October. It gets hot and crowded in the summer, but there’s so much going on that it’s worth dealing with those minor inconveniences.

Read Next: Don’t miss out on the best Chicago day trips !

Another huge tip I have before you visit Chicago is to purchase a Chicago CityPASS .

Essentially this is just a multi-use ticket that actually saves you a bunch of money (50% to be precise!) on many great Chicago attractions.

You buy the pass for USD$109, and it includes access to the following:

  • Skydeck Chicago and
  • Adler Planetarium or the Art Institute of Chicago
  • 360 CHICAGO Observation Deck or the Museum of Science and Industry

Best of all, those entrances are mostly express or premium tickets included with the CityPASS , meaning it not only saves you money but saves you time as well.

We highly recommend you pick one up when using our Chicago itinerary to make the most of your time in the city.

Lake Michigan Chicago

Thankfully, getting around Chicago is a breeze thanks to the CTA network of train and bus lines. Chicagoans refer to the train as the “L” because it’s mostly on “el-evated tracks.”

If you’re spending 3 days in Chicago, your best bet is to just pick up an unlimited CTA pass. These cost $20 and are added to a Ventra card.

You can pick up a Ventra card at vending machines for $5 and it’s credited back to your account after you register the card. Read all about getting around Chicago on the CTA website .

You can count on the CTA getting you as far south as the Museum of Science and Industry all the way north to Lincoln Park.

Or consider jumping on and off the open-top bus that will take you all over the city!

In the city center, lots of Chicago attractions are all within walking distance as well.

Now that some of the logistics are taken care of, let’s get this show on the road for your 3 day Chicago itinerary!

Day 1 – Morning

For day 1 of your Chicago itinerary , you’ll need to hit the ground running if you want to maximize your time.

Get a nice early start, crush a substantial breakfast and some coffee, and get ready to rock.

The best way to kick-off your Chicago itinerary is by taking a walking tour of the Loop. This area of downtown is where you’ll find a majority of the sights in Chitown.

You have several options for exploring the Loop. If you enjoy meeting people and getting the insight of a local guide, you can sign up for one of the many options with Free Tours by Foot .

If it’s your first time in Chicago I suggest joining their 10 AM tour of the Loop and Millennium Park. Or if you’re really into architecture, check out their 10:30 Birth of the Skyscraper tour. Both are excellent options!

3 Days In Chicago

Those who prefer a DIY approach can check out the many self-guided tours of Chicago from MetroWalkz. This Architecture/Loop tour makes for a fantastic introduction to the city and is pretty easy to follow.

Whichever option you choose, you’ll get to see some of the most iconic places in the city in just a few short hours. A few of the highlights include the historic start of Route 66, the great Chicago Theatre.

READ NEXT: While you’re exploring the Midwest, be sure to check out the best things to do in Minneapolis, Minnesota !

Day 1 – Afternoon

At this point, the order in which you do things depends on which type of tour you chose. You can be flexible, as it’s a short walk between the next couple of destinations.

Before we move along with the 3 day Chicago itinerary, it’s time for lunch! If you’re down in the Loop and you want to try a local favourite, the choice is easy…

There are countless restaurants to choose from in the Loop, but you don’t want to travel all the way to Chicago to get stuck eating at some overrated chain or overpriced tourist trap.

Al’s is a classic local joint serving up the famous Chicago style hot dogs and their specialty Italian beef sandwiches.

Chicago Hot Dog

One thing to know, a Chicago dog is an all-beef dog on a sesame seed bun. It comes topped with tomato, chopped onions, pickled peppers, relish, a pickle spear, and yellow mustard. Quite simply put, it’s heaven on a bun.

I would be remiss if I didn’t also mention Portillo’s. They also make one of the best Chicago style hot dogs out there.

While they’re a bit out of the way for today’s itinerary, keep them in mind if you’re craving another hot dog during your 3 days in Chicago (and trust me, you will).

Read More: Spending time exploring the Midwest? Be sure to check out our post on all of the best things to do in Kansas City !

Even if you visited on your walking tour, it’s worth it to double back to Millennium Park for further exploration.

Millenium Park Chicago

There’s a lot of cool stuff to see here, including the Crown Fountain and the Cloud Gate.

The latter is commonly referred to as “The Bean” and is one of Chicago’s most popular places to take photos in the city. Don’t forget to snap that quintessential Chicago shot for the ‘gram and keep on moving.

The Bean Chicago

Other Chicago attractions you must see in Millennium Park include the Jay Pritzker Pavilion, the BP Pedestrian Bridge, the Chicago Cultural Center, and the Lurie Garden.

You can easily spend a couple of hours in Millennium Park, especially on a nice day.

Buckingham Fountain and Grant Park are within this same area as well if you want to keep exploring on foot.

While there’s plenty of amazing public art in the Loop, you can’t top the collection at the Art Institute of Chicago. Art lovers will definitely want to include this on their 3 day Chicago itinerary.

Tucked away on Michigan Avenue on the south end of Millennium Park, the Art Institute of Chicago has a seriously impressive collection here and there are always new exhibits featuring modern and contemporary art.

Make the most of your Chicago CityPASS to gain fast entry into the Art Institute of Chicago.

Chicago Art Institute

The museum is open daily from 10:30 AM to 5 PM and stays open until 8 on Thursdays.

Day 1 – Evening

Before the day turns into night, it’s time to hustle over to your next destination of your 3 day Chicago itinerary. Try to time it just right so you make it there about an hour before sunset. Trust me, it’s worth it!

Whether or not you hit the museum, your next stop should be the Willis Tower. This is one of Chicago’s most iconic skyscraper in the city that invented them!

Chicago Skyline

Formerly known as the Sears Tower, this was the tallest building in the world for 25 years. It stands at 442 meters (1,450 feet) tall and is currently the 2nd-tallest building in the US.

If you plan to visit Chicago in 3 days, you definitely need to check the Willis Tower off your to-do list.

Head to the 103rd floor to access the Skydeck Chicago and step out onto “The Ledge” – a glass balcony that lets you look straight down. You’ll want to see views of the city from this spectacular perspective!

Willis Tower

Don’t forget, the best time to go to the Willis Tower is just before sunset. It stays open until 10 PM from March through September and tickets cost $25 for adults and $17 for children.

Once again though, no need to pay extra for a ticket, because the entrance to the Skydeck Chicago is included with your CityPASS .

To celebrate making it through a massive day 1 of the Chicago itinerary, it’s time for dinner and drinks! When it comes to wining and dining, the world really is your oyster in the Loop.

After such a big day, you may want to call it a (somewhat) early night. We’ve still got a lot of ground to cover with this 3 days in Chicago itinerary! Of course, if you want to go out and rage, go for it!

Day 2 – Morning

If you don’t have breakfast included at your hotel, I highly advise you to start day two off at Yolk’s South Loop location.

This is the perfect spot to load up with a big breakfast and coffee before another big day in the city. Go ahead and carb up – there’s going to be a lot of walking today!

After breakfast, walk across the street to check out Agora – a sculpture composed of 106 headless figures.

Keep walking east towards Lake Michigan to reach the Museum Campus. Here you’ll find the Field Museum, Shedd Aquarium, and the Adler Planetarium.

With just 3 days in Chicago, you’ll probably want to just visit one. Having been to all three, I’ll cast my vote for the Field Museum.

Chicago Field Museum

There are so many cool exhibits at the Field Museum and they’re always changing.

At the moment, they have: Inside Ancient Egypt, Bird’s of America, and Brewing Up Chicago, among others. Check their website to see what’s going on before you visit.

Tickets for the Field Museum cost $26 for adults and $19 for children for basic admission.

If you got the CityPASS, your admission is included in all three, unless you hit the Art Institute on day one. If you’ve got the pass, you might as well hit the aquarium as well.

Shedd Aquarium

To be honest, the aquarium is pretty sweet. Even if you don’t have the CityPASS, you should probably try to squeeze it in.

Tickets are $40 for adults and $30 for kids and you’ll definitely get your money’s worth.

Day 2 – Afternoon

There are a few cafes and food stands around the museum campus, so go ahead and grab a snack and a drink before powering on.

This is one of those days where it’s best to have a big breakfast and dinner and just graze during the day. When you’re trying to cross off so many things to do in Chicago in 3 days, you gotta keep moving!

The museum campus is the southern part of Grant Park. Known as “Chicago’s Front Yard,” this massive green space is to Chicago what Central Park is to NYC.

Take a stroll through the park to see such landmarks as the Buckingham Fountain, the Rose Garden, and the Seated Lincoln Statue. There are plenty of benches if you need to sit down and chill for a bit.

Grant Park Chicago

Grant Park also hosts some of the biggest events in the city, such as the Taste of Chicago and Lollapalooza.

Some are free and others cost hundreds of dollars, so be sure to check the calendar of events to see what’s happening before you book your trip.

Hug the coast and keep walking north along the Lake Michigan until you reach the Riverwalk. This scenic pedestrian path along the Chicago River is the perfect place for a leisurely stroll.

If your feet are feeling a bit tired from all the walking, you can enjoy the spectacular Chicago architecture on this fantastic river cruise instead .

Taking in the sights along the Chicago River is definitely one of the top things to do in a 3 day Chicago itinerary.

Chicago River

Wendella Boats has an architecture river cruise that comes highly recommended. Make sure you have your camera for this one, as you’ll get some epic views of the city.

Day 2 – Evening

I’m sure you’re ready to eat your hand by now, but you’ve just got to soldier on for a bit longer. Trust me, it’s going to be worth the wait!

On the other side of the Chicago River, you’ll find the Magnificent Mile, a short stretch of Michigan Avenue in downtown Chicago. This is the city’s premier commercial district, full of high-end shops, nice restaurants, and boutique hotels.

Along the Magnificent Mile, you’ll also see several historic skyscrapers, such as the Wrigley Building, Tribune Tower, and the Old Watertower.

The latter is home to the City Gallery, which has Chicago-focused photography exhibits. It’s totally free to visit, so you may as well check out while you’re in the area.

Even if you’re not doing any shopping, it’s worth a quick stroll along the famous Michigan Avenue. That’s because it’s leading you to…

You had the hot dog on day one, so it’s time to dig into some Chicago-style deep dish pizza.

Since it’s cooked in such a deep pan, a Chicago-style deep dish pizza can be stuffed with mountains of cheese. Of course, you can add whatever other toppings you like as well.

Now you see why I’ve been torturing you by making you walk around all day waiting for dinner! This deep dish pizza is seriously delicious and filling, so I wanted to make sure you could at least have a few slices.

Chicago Pizza

There are plenty of places cooking up Chicago-style deep dish pizza, but I brought you here because two of the best are easily accessible.

Get to the corner of Michigan and Superior and you have an important choice to make. Take a left and you’ll go to Giordano’s. Hook a right and you’ll be at Gino’s East.

Just go ahead and flip a coin because you win either way. Both places are legendary for their deep dish pizzas, so you really can’t go wrong.

Not far from the Magnificent Mile, you’ll find Navy Pier. If you’re spending 3 days in Chicago on a long weekend, this is the perfect place to be on a Saturday night.

First up, you can take a ride on the Centennial Ferris Wheel. Tickets cost $18 for adults and $16 for children, but you can save a few bucks if you book online .

Navy Pier Chicago

From the end of May until the end of August, Navy Pier also hosts bi-weekly fireworks shows. These happen on Wednesdays at 9:30 PM and Saturdays at 10:15.

To take in the spectacle, you can find a spot to stand on the Navy Pier or sign up for an evening cruise. Enjoying the fireworks as you cruise around is a great addition to your Chicago itinerary.

If you have any gas left in the tank after all of the activities at the Navy Pier, congratulations! I just ran you ragged all over Chicago on day two. That’s why it’s time to choose your own adventure!

For many, that will probably involve grabbing a casual drink from the hotel bar and getting some sleep. That’s totally fine. I’m getting to the age where that sounds like a perfect Saturday night!

For the young whipper-snappers among us, you’re probably itching to enjoy a big night out on the town. Go for it, you crazy kids!

Your options are endless. There’s live music of all varieties, comedy clubs, and just about every type of bar under the sun.

Whether you’re looking for a speakeasy that whips up creative cocktails, a classy wine & jazz joint, or just a good ole’ fashioned dive, you can find it in Chicago.

Tiki Bar Chicago

In this part of the city, one of my personal favourites is Three Dots & a Dash. This awesome tiki bar has an impressive selection of cocktails that will transport you to the Caribbean in no time.

If you’re going to go hard one night, this is the one to do it! Bars in Chicago typically close at 2 AM, but there are several that stay open as late as 4 on the weekend. You’ve been warned…

Day 3 – Morning

How early the last day of your 3 day Chicago itinerary starts depends entirely on how late your night went!

Those who already regret ordering that last round may need to sleep in a bit and smash a greasy brunch, while the go-getter set who actually slept will be up and at them. Life is all about choices, people!

Whatever you did the night before, get some food and caffeine in your system and get out there to wind down this 3 day Chicago itinerary.

Our third and final day in Chicago starts off with a leisurely museum visit. Within a few blocks of each other, you can take your pick between three excellent museums.

Art enthusiasts will gravitate towards the Museum of Contemporary Art, which highlights post-WWII art.

Those more interested in architecture and antiques may want to hit the Richard H. Driehaus Museum. It’s in a restored 19th-century mansion and brings you right back to the Gilded Age.

Chicago is very much a sports city, as people here are very passionate about their teams. Check out the Chicago Sports Museum, which is full of memorabilia and plenty of fun exhibits.

I know I already sent you to the Willis Tower on day one, but it’s still worth a trip to John Hancock’s 360 Chicago on Michigan Avenue.

This observation deck on the 94th floor of the John Hancock Building provides a whole different perspective on the city that you will definitely want to see.

Chicago Parks

Plus, if you bought a CityPASS your admission to the John Hancock building is already included! If you didn’t grab the pass, a ticket is $25 for adults or $15 for children.

Those who are feeling adventurous (and not hungover) may want to take a ride on Tilt – Chicago’s highest thrill ride.

If you need some hair of the dog instead, you can grab a ticket that includes your choice of adult beverage. Sunday Funday!

If you don’t purchase the Chicago CityPASS consider purchasing this ticket to enjoy the views from the 94th floor of the John Hancock building’s 360 Chicago.

Day 3 – Afternoon

Once you come down from 360 Chicago in John Hancock building, you have plenty of options for lunch. Within a few blocks, you can find Cuban, Vietnamese, Mediterranean, and the Chicago staple of deep dish pizza.

If you want a lunch with a view, consider eating at The Kennison. This upscale bar and restaurant offers sweeping views of Lincoln Park. The menu is modern American and they have lots of amazing cocktails and drinks.

Hop on the bus, order an Uber, or walk 30 minutes to our next destination – Lincoln Park.

There’s a lot to do in this huge park on the shores of Lake Michigan. North Avenue Beach is at the south end.

Chicago Beach

On a beautiful day in Chicago, it’s hard to beat lounging on the beach and swimming in the lake. You can also play some beach volleyball and rent a SUP or bike if you want some more activity.

In the middle is the Lincoln Park Zoo, which is totally free to visit. Sightseeing gets expensive, so this awesome free attraction is definitely one of the top things for any Chicago itinerary.

Lincoln Park Zoo

After such an action-packed 3 days in Chicago, you should definitely just take it easy and enjoy all that Lincoln Park has to offer. You’ve covered some serious ground in a short time, so congrats on that!

Day 3 – Evening

At this point in the journey, you have absolutely crushed 3 perfect days in Chicago. Order a celebratory drink or two and enjoy your last evening in the city!

What you choose to do with your final night all depends on when you’re visiting and what your interests are. That’s why it’s time once again to…

In a perfect world, the Cubs would be playing a night game while you are visiting Chicago. You could head north to Wrigley Field and enjoy America’s pastime at the 2nd-oldest ballpark in the country.

The Cubs play about 80 home games between April and September, so there’s a good chance they’ll be in town when you are. Even if you’re not a baseball fan, I recommend hitting a game if at all possible.

Wrigley Field

Chicago actually has two MLB teams. But the White Sox ballpark is way south of where you’ll be on day three and not worth the trip if you ask me.

If you’re making a trip to Chicago between October and April, you may be able to catch the Bulls (NBA), Blackhawks (NHL), or the Bears play a home game. Check their schedules to see what’s going on when you’re in town.

Those who prefer a good laugh can head back to the south end of Lincoln Park. Just a block away, you’ll find three of the city’s best comedy clubs – Second City, UP, and Zanies.

I pretty much always travel to Chicago for live music, so you know I’m going to toss that in here!

The city has an epic music scene and there’s always something playing here. Whether you’re into rock, hip-hop, jazz, electronic, blues, pop, or whatever it is you wacky Millenials listen to these days, there’s a show for you.

I usually check Jambase to see what shows are playing.

Congratulations, my friend. You made it through an insane 3 days in Chicago itinerary and experienced the best that the Windy City has to offer.

I’d say that calls for a toast! If you want to finish up with a true Chicago experience, order a shot of malort. This infamous Chicago liquor is pretty hard to describe, so I’ll let its label do the work:

“ Malort has the aroma and full-bodied flavor of an unusual botanical. Its bitter taste is savored by two-fisted drinkers .”

I’m not going to sugar coat it – this stuff is awful. It’s a rite of passage here in Chicago, though. Eat the hot dog. Drink the malort. Praise be to Ditka. You’re now a little bit Chicagoan.

After you finish that putrid shot of malort, switch to a delicious Chicago craft beer. There are plenty of choices here, including Lagunitas, Revolution, and Goose Island.

Chicago Bars

I hope you enjoyed this massive tour of Chicago!

From Navy Pier, to Millennium Park, the Chicago riverwalk, the famous Chicago hot dogs and more, visiting Chicago is never dull.

Hopefully this 3 day Chicago itinerary has been inspiring and gives you an idea of what to do in the Windy City.

Chicago Itinerary Travel Guide

Now that you know what to do with a long weekend in Chicago, I’ve gone ahead and put together a mini-guide to this awesome city to help you decide where to stay, where to eat, and of course where to drink!

Where to Stay in Chicago

You’re probably wondering where to stay, especially if it is your first time in Chicago.

Most first-time visitors choose to base themselves in downtown Chicago, and for good reason. Here are countless options for accommodation, sightseeing, dining, and nightlife.

As you might expect, staying downtown comes with a price tag. Other popular places to stay that are a bit cheaper include River North, Lincoln Park, Bucktown, and Wicker Park.

When it comes to places to lay your head, Chicago has it all. The city has 5-star luxury hotels, quaint B&Bs, dingy motels, fun hostels, and plenty of options on sites like Airbnb.

Here are a few options to suit all budgets:

Hostelling International is a trusted name in backpacker accommodation, and their downtown Chicago location is definitely the best hostel for visiting Chicago.

They have several different options for both private and dorm rooms. You can get a bunk for under $40 a night here – a steal for this fantastic location.This includes a free breakfast, and they also have free walking tours during the day and free activities at night.

That’s not all, though. They’ve also got a huge lounge with a ping pong table and a TV room with plenty of movies. Best of all, this hostel is environmentally-friendly. They have reusable products in the kitchen and recycling points all around the building.

This historic downtown Chicago hotel dates all the way back to 1893. Don’t worry – it’s had several updates over the years!

You really can’t beat the location of this place. I usually stay with friends in more residential neighbourhoods, but this is my go-to spot when I want to be in the middle of all the action.

From here, you’re just across the street from Grant Park. Many of the rooms here even boast a nice view of Lake Michigan. With rooms starting as low as $115 a night, it’s a pretty awesome deal staying here.

The 5-star Peninsula Chicago was recently named the 2nd best hotel in the country by US News & World Report. This place is fancy, people!

It’s located right on the Magnificent Mile, so it’s surrounded by high-end shops. This is definitely where the fabulous people stay.

In addition to the super swanky rooms, you can enjoy the hotel’s three different restaurants and its impressive fitness centre.

Taking up the top two floors of the building, it features a 25-meter pool and an award-winning spa. Rooms start at around $600 a night here.

Where to Eat and Drink in Chicago

I’m very fortunate to have a good friend who is heavily involved in the hospitality scene in Chicago.

I reached out to him to get a list to add to this guide. He’s never done me wrong with food & drink recommendations, so you can take these to the bank the next time you visit Chicago!

  • Dove’s Luncheonette
  • Joe’s Stone Crab: It’s a steakhouse and it’s hard to get into at night, but if you go for boozy brunch it’s great.
  • Parson’s Chicken & Fish: Not really brunch but just a great people-watching patio.
  • Big Star: Chicago classic taco joint with highly sought after patio
  • 3 Arts Club

Best Chicago Restaurants

  • Bavette’s Bar & Boeuf
  • The Roister
  • Green Street Smoked Meats: A great BBQ joint and High Five Ramen is below.
  • Maple & Ash
  • Nico Osteri
  • Billy Sunday
  • Aviary (try to get down to the office)
  • Violet Hour
  • Start at Scofflaw and work your way over to Best Intentions
  • Longman & Eagle 
  • The California Clipper: Been around since before prohibition!

DISCLAIMER: Some of the links in this article are affiliate links, which means if you book accommodation, tours or buy a product, we will receive a small commission at no extra cost to you. These commissions help us keep creating more free travel content to help people plan their holidays and adventures. We only recommend the best accommodations, tours and products that ourselves or our fantastic editorial team have personally experienced, and regularly review these. Thanks for your support, kind friend!

Picture of Sasha and Rachel

Sasha and Rachel

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I would love to visit Chicago in 2024! This itinerary looks perfect!

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She Wanders Abroad

  • 3 Days in Chicago: The Perfect Itinerary for First-Timers

Chicago Riverside

Are you planning to spend 3 days in Chicago but don ’t know where to start? Well, this guide is here to help you out!

Chicago is one of the most populated cities in the United States and sits on the shores of Lake Michigan. Known as ‘the Windy City’, Chicago attracts millions of visitors each year and it’s no surprise why.

With its iconic attractions, towering skyscrapers, and scenic views, this city has made it onto many people’s bucket lists. 

But how should you spend your 3 days in Chicago? This guide will go through the must-visit sites, how to get around the city, and the best places to stay. 

Without further ado, here is the ultimate 3-day Chicago itinerary!

* Disclosure: This post contains a few affiliate links, which means I may receive a small commission, at no cost to you, if you make a purchase through my link. *

Table of Contents

Overview of Your 3 Day Chicago Itinerary

Breakdown of your 3 days in chicago.

  • Day 1: Breakfast at ​​Goddess and the Baker, Millennium Park (Cloud Gate, Crown Fountain, Lurie Garden), The Art Institute of Chicago, Navy Pier, Dinner at Giordano’s, Sunset at Milton Lee Olive Park
  • Day 2: Breakfast either at Beatrix or Wildberry Pancakes & Cafe, Starbucks Reserve Roastery, Magnificent Mile, Chicago Riverwalk, Chicago Theatre, Chicago River Architecture Cruise, Nature Boardwalk at Lincoln Park Zoo, Sunset at North Avenue Beach, Dinner at Portillo’s Hot Dogs
  • Day 3: SkyDeck Chicago, Breakfast at Mojo Coffee, Grant Park & Buckingham Fountain, Museum Campus (Shedd Aquarium, Field Museum, Adler Planetarium, Soldier Field), Dinner at Lou Malnati’s Pizzeria

Map for your 3 day Chicago itinerary

Below you can find a customized map that includes all the locations you’re going to visit on this Chicago itinerary.

I marked your 3 days in Chicago with different colors – I used blue for the first, yellow for the second, and green for the third day, so you can easily see which places you’re going to visit each day.

How to use this map: This map is fully interactive, so you can move around, zoom in/zoom out, and click on the icons. If you want to see a larger map, click on the bracket in the upper right corner. To see more details and the different layers, click on the tab in the upper left corner. If you want to save it for later, click on the star icon next to the name of the map. Then simply open Google Maps either on your desktop or phone, go to ‘Saved’/’Maps’, and open the map whenever you need it.

Day 1 of Your 3 Days in Chicago

Breakfast at ​​goddess and the baker .

Grabbing a bite to eat at the Goddess and the Baker is the perfect way to fuel your day of exploring. It’s famous for its great food, amazing coffee, and fun treats!

They have a wide selection of breakfast options including yogurt parfait, omelets, bagels, and waffles so you won’t have a problem finding something to your taste here.

There are multiple locations of Goddess and the Baker, but this one is right across from Millenium Park (the next stop on your 3 day Chicago itinerary). You can either have breakfast first thing in the morning or after you’ve visited the park – it’s completely up to you! 

Breakfast at Goddess and The Baker Chicago

Millennium Park and The Bean

After (or before) breakfast, make your way to Millennium Park which is one of the most famous landmarks in Chicago. 

Spanning over 24.5 acres, this park is home to many popular attractions including the Cloud Gate (aka ‘The Bean’).

The Cloud Gate is a public sculpture that was designed by British artist Anish Kapoor. It’s made up of 168 stainless steel plates and weighs in at a whopping 110 tons!

You can walk around the sculpture, take photos, and even go underneath it. Thanks to its reflective surface, it has quickly become one of the most Instagrammable places in Chicago . So be prepared for the crowds as this is one of the most popular things to do in Chicago!

After you’ve had your fill of The Bean, continue exploring Millennium Park. There’s plenty to see and do here including visiting the Lurie Garden, which is a 2.5-acre public garden, or checking out the Crown Fountain which is a work of art in itself!

Cloud Gate, aka the Chicago Bean in Downtown Chicago

The Art Institute of Chicago

The Art Institute of Chicago is another popular attraction as it’s one of the world’s largest (and oldest) art museums. 

Aside from its ever-changing exhibitions, the museum has a permanent collection of around 300,000 art pieces which is pretty impressive. 

These ongoing exhibitions include the ‘Of Gods and Glamor’ exhibit, ‘a New View of African Art’, and the ‘Landscape in Light’ exhibit. 

The museum attracts around 1.5 million people annually and is a must-visit on your 3 day trip to Chicago. 

It’s important to note that the Art Institute of Chicago is closed on Tuesdays and Wednesdays, so you’ll have to time your visit right if you want to visit this spot.

Otherwise, it ’s open between 11 am – 5 pm from Thursday to Monday and general admission costs $25 per person.

TOP TIP: In case you want to visit multiple attractions, take a look at the Chicago CityPASS which can help you save 48% or more on the top attractions. It includes access to The Art Institute of Chicago, Shedd Aquarium and SkyDeck Chicago among many other popular sites.

visit chicago 3 days

Next up on your 3 days in Chicago itinerary is a visit to Navy Pier, a 3,300-foot-long pier that sits on the shores of Lake Michigan.

It’s one of the most popular tourist destinations in the city and it’s easy to see why with its many attractions, shops, and restaurants.

You’ll find plenty to do here including fairground rides, live music performances, theater productions, and special events. Not to mention the incredible views to be had from the pier itself!

One of the unmissable things to do in Navy Pier is going on a ride on the Centennial Wheel, which is a 200-foot tall Ferris wheel. From the top, you’ll be able to see amazing views of the cityscape and beyond! Since it’s a fairly popular attraction, it’s best to purchase your tickets in advance .

If you’re looking to do some shopping, Navy Pier is also home to a variety of stores selling everything from souvenirs to clothing.

Dinner at Giordano’s 

And when you’re ready to refuel, there are plenty of restaurants and cafes in Navy Pier to choose from including the food court which has options to suit all tastes.

My personal recommendation for today ’s dinner is Giordano ’s . They have multiple locations throughout the city but this one is actually at Navy Pier so you won’t have to wander far. 

Giordano ’s is home to the best deep-dish pizzas in all of Chicago, and you’ll find plenty of tasty topping options here.

Some of the most popular choices include ‘meat and more meat’, the ‘Chicago classic’, and the ‘super veggie’. You can even make your own if you fancy!

In case you’re not in the mood for pizza, they also have a delicious range of pasta dishes and sandwiches. If you’re looking to see (and taste) the best of Chicago in 3 days, this is the restaurant you need to visit!

Interior of Giordano's in Chicago

Sunset at Milton Lee Olive Park

Watching the sunset at Milton Lee Olive Park is the perfect way to end the first day of your 3 days in Chicago. 

The park is named after Milton Lee Olive who was given a medal of honor for his actions in the Vietnam War. 

It’s located on a man-made peninsula that juts out onto Lake Michigan, so naturally, it boasts spectacular views – especially at sunset. You’ll also find plenty of walks here that offer superb views of the Chicago skyline.

However, the highlight of Milton Lee Olive Park has to be the fountains! There are five circular fountains in total and each one is connected by walking trails. 

visit chicago 3 days

Day 2 of Your 3 Days in Chicago

Breakfast either at beatrix or wildberry pancakes & cafe .

Breakfast is the most important meal of the day, and these two places are incredible! 

Both Beatrix and the Wildberry Pancakes & Cafe have multiple locations throughout the city and you’ll find one relatively close to the Magnificent Mile (the next attraction on your 3 day Chicago itinerary).

Wildberry Pancakes & Cafe is one of the best choices when it comes to breakfast places in Chicago. As the name suggests, pancakes are their specialty and you’ll be spoiled for choice with all of the different flavors on offer.

There are also plenty of other breakfast options available including eggs, bacon, sausage, bagels, and more. Their French toasts are also incredible!

Breakfast at Wildberry Pancakes & Cafe Chicago

If pancakes aren’t your thing, another great option for breakfast is Beatrix . This restaurant has a focus on healthy and flavorful food with plenty of vegan and vegetarian options available.

You’ll find everything from avocado toast to quinoa bowls on the menu, as well as a selection of fresh juices and smoothies.

Breakfast at Beatrix Chicago

Starbucks Reserve Roastery

After breakfast, make your way to the Starbucks Reserve Roastery . This is a must-visit for any coffee lover!

Starbucks Reserve Roastery is home to a selection of the rarest and most extraordinary coffees on earth. Not only that, but it’s the largest Starbucks in the world with five floors covering over 35,000 sq ft. 

Usually, you’d head to a Starbucks for a quick coffee but not here! The Starbucks Reserve Roastery offers interactive tours, a rooftop deck to admire the city views, and delicious pastries. 

Trust me, if you’re into coffee then you don’t want to miss out on this place during your 3 day trip to Chicago.

Starbucks Reserve Roastery Chicago

Magnificent Mile

The Magnificent Mile is without a doubt one of the most popular places to visit in Chicago. It’s one of the most famous shopping destinations in the world and is home to huge shopping centers, boutique stores, and plenty of designer shops. 

However, there is so much more to do here than just shop! Some of the most popular attractions include the John Hancock Center, the Wrigley Building, and the Tribune Tower. You can also head to the free gallery within the Water Tower.

If you’re looking to do some shopping, you’ll find everything from high-end stores to budget-friendly options. And when you need a break from shopping, there are plenty of restaurants and cafes to choose from.

Chicago Riverwalk

After exploring the Magnificent Mile, make your way to the Chicago Riverwalk. This is a great spot to relax and take in the views of the city.

The Chicago Riverwalk is a 1.25 mile (2 km) path that is made up of four districts; the Arcade, the Civic, the Confluence, and the Esplanade. 

The path starts from Lake Street and runs along the Chicago River until it reaches Lake Michigan. 

Along the way, you’ll get to see a variety of public art including banners, murals, and sculptures so make sure you take your time walking this path. 

However, the highlights of the Chicago Riverwalk have to be the iconic Wrigley Building and the DuSable Bridge. With so much to offer, this riverwalk needs to be on your 3 days in Chicago itinerary! 

River North Chicago

Chicago Theatre

The Chicago Theatre was constructed in 1921 and designed by Cornelius Ward Rapp and George L. Rapp. It was the first lavish movie palace in the United States and was incredibly successful. 

This led to the owners (Balaban & Watz) constructing other theaters of its design throughout America. 

The whole design of the theater is based on luxury, which is clear just by taking a look at the grand lobby inside.

During your stay in the city, I’d recommend catching a show here to fully experience this incredible building. You can take your pick from comedy shows, live music performances, and theater productions.

However, if you don’t have time then simply head inside and go on a tour – trust me you won’t regret it!

Chicago Theatre

Chicago River Architecture Cruise 

If you’ve only got 3 days in Chicago, then going on a river cruise has to be at the top of your list. Chicago River architecture cruises usually last around 1.5 hours and typically start at DuSable Bridge. 

One of the best choices is this river cruise that will take you down the Chicago River and past some of the city’s most iconic buildings.

You’ll also learn all about the history and architecture of each building from your knowledgeable tour guide. Best of all, it allows you to skip the ticket office and board straight away!

Alternatively, this 1.5-hour river cruise is a great option as well.

If you’re a bit short on time or want to keep the children entertained, then this family-friendly river cruise is a great choice. It’s only 45 minutes long but will still show you the city’s most breathtaking landmarks.

Boat on a river in Chicago

Nature Boardwalk at Lincoln Park Zoo 

After your architecture cruise, make your way to the Nature Boardwalk at Lincoln Park Zoo. This is a great spot to unwind and take a break from all the hustle and bustle of the city.

The Nature Boardwalk is an oasis within the city with plenty of trees, flowers, and greenery. There’s also a pond where you can spot turtles, ducks, and other wildlife.

One of the unmissable sights within the Nature Boardwalk is the Educational Pavilion which is one of the most unique things you’ll see during this 3 day Chicago itinerary.

The honeycombed shaped pavilion is constructed of prefabricated wood elements and the arched structure forms a place to shelter during your exploration of the park.

If you have some extra time on your hands, I also recommend checking out the Lincoln Park Zoo. It’s one of the oldest zoos in the country and it’s completely free to visit!

visit chicago 3 days

Sunset at North Avenue Beach

There’s no better way to appreciate a new city than by admiring an epic sunset. Chicago has plenty of incredible opportunities for this but watching the sunset at North Avenue Beach just hits differently! 

It’s one of the city’s most popular beaches and is located within Lincoln Park so you won’t have to walk far after visiting the Zoo or the Nature Boardwalk. 

Not only is North Avenue Beach beautiful, but you’ll also find an awesome beach house here too. The building is inspired by an ocean liner and offers a top deck where you’ll get spectacular views – especially at sunset. 

Make sure to stay a bit longer after the sunset to see the city all lit up. It ’s truly an incredible experience!

Girl in yellow skirt running at the North Avenue Beach in Chicago

Dinner at Portillo ’s Hot Dogs

Chicago has endless options for dining, but you definitely need to try Portillo’s Hot Dogs during your 3 days in Chicago.

This Chicago-born chain is famous for its juicy hot dogs, tasty burgers, and delicious chocolate cake. Their Italian beef sandwiches are also a big hit. They even have vegan hot dogs so they cater to every dietary requirement. 

After a long day of exploring, eating at Portillo’s Hot Dogs is the best (and tastiest) way to refuel. 

visit chicago 3 days

Day 3 of Your 3 Days in Chicago

Skydeck chicago.

To truly make the most out of your 3 days in Chicago, you’ll want to head up to Skydeck Chicago during your visit. Located on the 103rd floor in the Willis Tower, Skydeck Chicago offers breathtaking views of the city.

If you head up there on a clear day you’re really in for a treat, as you’ll be able to see up to 50 miles (80 km) away including four American states! 

Are you feeling daring? If so, you should head out onto the ledge. The ledge is made up of four glass view boxes, and you’ll get a completely unobstructed view of Chicago. However, this probably isn’t suitable for people with a fear of heights, as it’s pretty daunting!

Since it ’s one of the most popular attractions in Chicago, I recommend heading there first thing in the morning right when it opens (usually around 8.30 am – 9 am). It ’s also advisable to book your tickets in advance so you don ’t waste any time waiting in line.

Chicago skyline view from Skydeck Chicago

Breakfast at Mojo Coffee

Mojo Coffee is a great place to fuel yourself for the last day of this 3 day Chicago itinerary.

You’ll find plenty of locations throughout the city but I’d recommend heading to this one as it ’s located right next to the Willis Tower. Plus, it ’s the very first cafe they ’ve opened in Chicago after their success in New Zealand!

Mojo Cafe offers plenty of tasty food options, including waffles, shakshuka, salads, poached eggs, and avocado on toast for starters.

They also have a delicious range of smoothies including ‘cold brew & chocolate’ and ‘pear, pineapple & spirulina’.

Also, if you ’re a coffee lover, grabbing a cup here is mandatory – and you can also take some freshly roasted coffee beans home with you.

Mojo Cafe in Chicago

Grant Park & Buckingham Fountain

After you’ve had your fill of the views from Skydeck Chicago and you ’re stomach is full, make your way to Grant Park. This is one of the most popular spots in the city and it’s easy to see why.

The park is huge (319 acres to be exact!) and there’s so much to see and do here. From gardens and sculptures to museums and fountains, there’s something for everyone in Grant Park.

One of the most popular attractions in the park is Buckingham Fountain. This iconic fountain is one of the largest in the world and uses around 15,000 gallons of water per minute.

The fountain also performs a water show hourly so make sure you time your visit right to witness it. You can also decide to come back after nightfall when you can enjoy a light and music display with the water show.

visit chicago 3 days

Museum Campus 

After you’ve explored Grant Park, make your way to Museum Campus. This 57-acre park is home to some of the best museums in the city including the Field Museum, the Shedd Aquarium, and the Adler Planetarium.

If you’re visiting with kids, they’ll definitely want to check out the Field Museum . This world-renowned museum is home to Sue, the largest and most complete Tyrannosaurus Rex fossil ever found.

Adults will appreciate the Shedd Aquarium which is one of the largest indoor aquariums in the world. And if you’re interested in space, the Adler Planetarium is a must-visit.

Visiting all 3 museums is pretty time-consuming so I would recommend choosing one or two that take your fancy, so you can take your time and not rush around. No matter which museum you choose to visit, you’re sure to have a great time at the Museum Campus!

TOP TIP: To make the most out of your visit and to save some cash, I’d recommend getting the Chicago CityPASS . It allows you to visit five of the city’s top attractions (including all 3 museums in Museum Campus) and you can save up to 48% off the normal ticket prices.

Chicago Skyline View from Museum Campus

Dinner at Lou Malnati’s Pizzeria 

After a day of exploring, you’re going to want a delicious dinner. And there’s no better place for that than Lou Malnati’s Pizzeria .

This iconic pizzeria has been serving up delicious deep dish pies since 1971 and is hands-down the best place to get pizza in the city. They use an exclusive sausage blend, vine-ripened plum tomatoes, and Wisconsin cheese to make the most delicious toppings. 

You can either create your own pizza here, or you can try one of their many tasty options including the ‘Malnati Chicago Classic’, ‘The Lou’, and the iconic pepperoni. 

Lou Malnati’s Pizzeria also has a wide variety of pasta dishes, salads, sandwiches, and desserts.

They have multiple locations throughout the city, this one is the closest to Millenium Park. There is no better way to end your 3 days in Chicago, than by dining here!

Deep dish pizza at Lou Malnati's Pizzeria in Chicago

Useful Info for Spending 3 Days in Chicago

Where to stay in chicago.

There are endless neighborhoods within the city so deciding where to stay in Chicago isn’t an easy decision. So, here is a quick guide to the main areas of the city: 

  • Downtown Chicago/The Loop  – perfect for first-time visitors
  • River North – the best place to stay for nightlife
  • Wicker Park – one of the coolest areas in Chicago
  • The Gold Coast – a beautiful area along Lake Michigan
  • Magnificent Mile – known for luxury stays and shopping

There are plenty of great areas to stay within the city, but these are just a few of the most popular ones. If you’re interested in knowing more about each neighborhood, make sure to read my detailed guide about the best areas to stay in Chicago .

If you ’re in a rush, here are my top recommendations for different budgets.

  • Luxury: Viceroy Chicago
  • Mid-range: Hotel EMC2, Autograph Collection
  • Budget: Central Loop Hotel

visit chicago 3 days

Best time to visit Chicago

Chicago’s high season runs from June to August, and temperatures range from 61°F (16°C) to 85°F (29°C) during this time. 

You’ll also find plenty of festivals and sports games to attend in the summer months, but be prepared to pay top prices for accommodation. 

If you’d prefer a quieter and cheaper experience, then visiting Chicago during the shoulder season is a great option.

The city’s shoulder season falls between April-May and September-October, and you’ll also find the tourist attractions to be much less crowded. 

Between April and May, temperatures range from 39°F (4°C) to 71°F (22°C) while during September and October, the temperature fluctuates between 45°F (7°C) to 76°F (24°C).

Although the weather is cooler and you’re likely to see more rain, you can get great bargains on accommodation and transport.

visit chicago 3 days

How to get around in Chicago

Chicago is super easy to get around as public transport is efficient and runs regularly. 

The best way to explore the city is by using the ‘L’ Train. There are 8 colored network lines that will take you to most of the areas and attractions in Chicago. Two of these run 24 hours a day, while the others typically operate between 4 am to 1 am. 

You can purchase single standard passes, but it’s cheaper to purchase a one-day or three-day pass depending on your itinerary. 

Buses are also a great way to get around as 129 routes run throughout the city. Some of these bus routes run on a 24-hour basis, while others operate until 11 pm or  2 am. 

If you’re looking to head out into the suburbs then you can take the Metra Rail. 

Taxis can also be found throughout the city but they aren’t cheap, although Uber and Lyft are available here. 

However, one of the coolest ways to get around the city is by water taxi. They offer a fast and affordable way to travel along the Chicago River, Lake Michigan, and between tourist attractions. 

They do only run between May and September/October though so you’ll need to keep this in mind. 

Although you can hire a car and drive around the city center, I wouldn’t recommend it – especially if you only have 3 days in Chicago. The traffic is a nightmare and parking is extremely limited (and very pricy).

visit chicago 3 days

Planning a trip to Chicago?

Then you might want to take a look at all our other travel guides about Chicago. I promise, they are just as awesome as this article was!

  • Top 7 Best Areas to Stay in Chicago
  • 15 Most Instagrammable Places in Chicago You Can’t Miss

Read about more US States: California | Massachusetts | Maine | Nevada | New Hampshire | New York | Vermont

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The Ultimate 3 Days in Chicago Itinerary

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3 Days in Chicago: The BEST Weekend Itinerary (By a Local!)

Planning 3 days in Chicago and seeking the perfect itinerary? I have lived in Chicago almost my entire life so I have created the perfect detailed Chicago 3 day itinerary with the best things to do, best places to eat, where you should stay, and all of my top tips, so that you can spend less time planning and more time enjoying the Windy City.

There is so much to do in Chicago but three days is enough to see most of Chicago’s top attractions . I have grouped each day by neighborhood so you don’t have to waste time getting around.

3 Days in Chicago Itinerary

3 Days in Chicago Itinerary Travel Blog

3 Days in Chicago – Day 1

Lets start Day 1 in Chicago by enjoying some of the best views Chicago has to offer.


For panoramic views of Chicago, head to 360 CHICAGO (formerly John Hancock Observatory), a public observatory on the 94th Floor of 875 N Michigan that offers breathtaking 360 degrees views of the city skyline and Lake Michigan.

The 360 Chicago observation deck is also home of TILT – Chicago’s highest thrill ride – an enclosed moving platform that literally tilts you out over Michigan Avenue from the 94th Floor.

Tip: 360 Chicago tends to be less busy and has shorter lines that the taller Willis Tower (on Day 2) but it is still best to visit in the morning to avoid crowds. (Click here to buy a skip the line ticket ).

Shop (or Window Shop) on the Magnificent Mile

After visiting 360 Chicago, walk south on Michigan Avenue and join the throngs of visitors and locals shopping (or window shopping) on The Magnificent Mile. The Magnificent Mile (or The Mag Mile), is an upscale section of Michigan Avenue, running from Oak Street to the Chicago River. Although some of the stores on Michigan Avenue are pricey, it is totally free to window shop. Landmarks on the Mag Mile include the historic Chicago Water Tower, the Tribune Tower and the Wrigley Building skyscraper.

Take an Architecture River Cruise

3 day weekend in chicago

Chicago has amazing architecture and the best way enjoy it is by taking an architecture river cruise . Because the water sometimes freezes, river cruises don’t usually run in the winter.

If you are visiting Chicago in the summer, you can do a longer combined architecture river and lake cruise to see the skyline from the lake as well.

best things to do chicago travel blog

An alternative to a river cruise is to take a walk along the Chicago Riverwalk . The Riverwalk is one of the best spots in Chicago for people watching and there are also restaurants , shops and places to sit along the way. You can see a map of attractions on the Riverwalk here .

Go on a Gangsters Tour

Chicago has a long  history of organized crime and is famous for being the home of mafia figure Al Capone. There are many mob tours for those that want to learn more about the history of organized crime.

Food or Drinks with a View

Chicago has several rooftop bars and restaurants with amazing views of Chicago.

Cindy’s (12 S Michigan Ave) is a restaurant and bar on the rooftop of the Chicago Athletic Association Hotel located across Millennium Park which offers panoramic instagram worthy views of Millennium Park and Lake Michigan. This is a popular spot and the wait for the elevator can be long but if you visit around the time it opens (10 am on the weekends and 11 am on some weekdays) you can enjoy the great views without the crowds.

LH ON 22 (85 East Wacker Drive) -Enjoy classic cocktails and small bites from the outdoor LH terrace of LondonHouse Chicago which offers great views of the Chicago River, Lake Michigan and the Magnificent Mile.

The J. Parker (1816 N Clark St) is a stylish bar and restaurant on the rooftop of the Hotel Lincoln with great views of Lincoln Park.

3 Days in Chicago – Day 2

From the highest vantage point of the city to the famous Bean, Day 2 in Chicago will take you to Chicago’s best and most famous attractions.

Skydeck at Willis Tower

The Skydeck at Willis Tower (formerly known as the Sears Tower and what locals still call it) is the most well known of Chicago’s two tall skyscrapers with public observatories. The Willis Tower is the tallest building in the Western Hemisphere and was the tallest building in the world from 1974 until 1998.

If you are not scared of heights, you can stand on the Ledge’s glass boxes that extend out over 4 feet from the Skydeck.

Tip:   Lines for the Skydeck can get very long (especially on weekends) so avoid the crowds it is best to visit first thing in the morning as soon as it opens or in the evening. (Click here to buy a skip the line ticket ).

See The Bean at Millennium Park

The Bean at Millenium Park is a must on any three day in Chicago itinerary

If you have seen photos of Chicago on social media, chances are you have seen photos of Cloud Gate (also called The Bean), the famous mirrored sculpture in Millennium Park.

Please note that due to construction, public access and views of Cloud Gate are limited through spring of 2024.

Although The Bean is very touristy, don’t skip it. It is one of the most instagrammable places in Chicago and it is a great spot to take photos to remember your trip to Chicago.  The Bean is usually crowded especially in the summer and on weekends so if you don’t want other people in your photos visit early in the morning.

The free Millennium Park is part of Grant Park and also includes the Jay Pritzker Pavilion, the Crown Fountain sculpture and Lurie Garden. In the winter, there is a free ice skating rink right in front of the park. On hot summer days, kids (and some adults) love to splash in the water from the Crown Fountain .

millenium park which includes crown fountain is a Chicago must do

If you are visiting Chicago with toddlers and young kids, you might want to also visit Maggie Daley Park , a large public park connected to Millennium Park that has play areas for kids of various ages, a fieldhouse, climbing wall and another ice-skating ribbon in the winter.

Art Institute of Chicago

Chicago has many great museums which are worth visiting but my top pick is the  Art Institute of Chicago conveniently located next to Millennium Park. It is one of the oldest and largest art museums in the United States and is frequently found on lists of the top museums in the world. (Click here to buy a skip the line ticket if you want to avoid long lines).

a perfect three day in Chicago itinerary includes Navy Pier

Some locals consider Navy Pier a bit of a tourist trap, but it is a not to missed attraction especially for those visiting Chicago with kids. Navy Pier is full of fun things to do including a large Ferris wheel, rides and games, the Chicago Children’s Museum and several shops, restaurants (including Giordano’s and Garrett Popcorn Shops) and bars. Navy Pier is also the starting point for various sightseeing cruises and boat rides.

Tip: If you are visiting Chicago in the summer, stay or come back for the free fireworks at Navy Pier every Wednesday at 9 pm and Saturday night at 10 pm. You can even watch the show from the water on a sightseeing cruise .

3 Days in Chicago – Day 3

Here are my suggestions for your third and final day sightseeing in Chicago. If you are visiting Chicago on a Sunday morning, head to Maxwell Street Market , one of the best places for Mexican food.

visit chicago 3 days

Visit One or More Museums

Chicago has many great museums which are worth visiting. The Field Museum , the  Shedd Aquarium and Adler Planetarium are all located close to each other on The Museum Campus. The Adler Planetarium Skyline Walk has one of the best skyline views of Chicago .

cherry blossoms in front of Museum of Science and Industry in Chicago

The Museum of Science and Industry is located in Hyde Park and is a bit out of the way from downtown Chicago but it is a really fun museum with hands-on activities and interactive exhibits. If the weather allows and you have extra time in Hyde Park, you might want to check neighboring Jackson Park . This park has cherry blossom trees in the spring and it also has a free Japanese garden.  Promontory Point is about a half mile away and has great skyline views of Chicago.

Tip:   If you are visiting a few museums and indoor attractions, consider purchasing a Chicago CityPASS or Go Chicago Card to save money on entrance fees.

Explore the Lakefront Trail and Beaches

people walking and relaxing on the Lakefront Trail in Chicago

Chicago’s Lakefront Trail is a paved path on a 18-mile-long stretch along Lake Michigan and it is a great spot to people watch and get some exercise.  In the summer and weekends, the lakefront is packed with locals and visitors walking, running and riding bikes.  You can find a map with the access points here .

Most people don’t think of Chicago as a beach destination but Chicago has many beaches on Lake Michigan.   Oak Street Beach and Ohio Street Beach are conveniently located close to the major tourist attractions. North Avenue Beach is more of a party beach and is located close to Lincoln Park.

More Things to Do in Chicago

If you have more time or not a fan of museums or tall buildings, here are some more fun things to do in Chicago:

Find Street Art

Moose Bubblegum Bubble by Jacob Watts one of the most famous street art murals in Chicago

Chicago is full of street art and there are always new murals popping up.  One of the most famous Chicago murals is “Moose Bubblegum Bubble” (pictured above) by Jacob Watts which located at 33 E. Ida B. Wells Drive (formerly 33 E. Congress Parkway). It is part of the Wabash Arts Corridor which is walking distance to Millennium Park, The Art Institute of Chicago and other well known tourist attractions. You can find more detailed mural walks in the Loop here .

Another famous mural is The Greetings From Chicago Mural at 2226 N Milwaukee Ave, in Chicago’s Logan Square neighborhood. You can see this mural and other street art on this street art tour .

Another neighborhood that has a high concentration of street art (as well as great Mexican food) is Pilsen.

Watch a Cubs Game at Wrigley Field (or attend another sporting event)

what to see in Chicago

Chicago is known for their love of their sports teams, so if you are visiting during the season you might want to attend a sporting event. To those unfamiliar, historic Wrigley Field is home to one of the city’s baseball teams – the Cubs.  Whether a fan of the Cubs, baseball in general or just a fun atmosphere, a day at the 100 year old ballpark is a must for locals and tourists alike.  You don’t need to enjoy baseball to enjoy a Cubs game – it is fun to just soak in the atmosphere while drinking and eating. (There are also tours of the stadium offered during the off season).

Enjoy One of Chicago’s Many Festivals

Chicago always has at least one or more festivals or events happening every weekend especially in the summer .  Some Chicago festivals are very well known and attract thousands of tourists, but there are many festivals and events in Chicago where you will mostly find locals. For great food, music and people watching, check to see if there are any festivals or events  going on while you are in town.

Walk The 606

The 606 is Chicago’s version of The Highline in NYC , an elevated trail goes through 2.7 miles of the city’s northwest side neighborhoods: Wicker Park, Bucktown, Humboldt Park, and Logan Square.  It is a bit off the beaten tourist path but it great place to walk, run or bike.  There are several access points so you can get off the trail to explore the various neighborhoods.

Where to Eat in Chicago

Chicago is known for its food so get ready to eat! Chicago is one of the best cities in the world for food and I could easily write a whole post just about the food! Although Chicago is famous for food like deep dish pizza and Chicago-style hot dogs – there is so much more great food in Chicago.  Don’t limit yourself to just deep dish pizza and hot dogs, but you should try those if you are visiting Chicago for the first time.

Lou Malnati’s and Giordano’s  are two of the best restaurants for deep dish pizza. Giordano’s can be found in several spots throughout the city including Navy Pier, near Michigan Avenue and near Millennium Park.

Many locals consider Pequods in Lincoln Park to have the best deep dish pizza in Chicago. Their version has a caramelized crust.

For Chicago style hot dogs (remember, no ketchup allowed) try Portillos , a popular chain.

Al’s Italian Beef (169 W Ontario St.) is famous for its Italian beef sandwiches.

For original Chicago-style popcorn head to Garrett Popcorn Shops, with a location near Millennium Park and Navy Pier.

To get an overview of the food scene consider a food tour:

Where to Stay in Chicago

Most people visiting Chicago stay in the downtown area including the Loop, River North, Gold Coast, Streeterville and Michigan Avenue since they are close to most of the major tourist attractions. If you are visiting during the weekend, the Loop is a great option as it is more quiet at night. River North (where I live) is close to nightlife and restaurants, but noise can be a problem especially during the weekends. Here are some of my top picks for the best hotels in Chicago :

The Peninsula Chicago.   If you are looking for a luxury hotel, The Peninsula Chicago is one of the best hotels in Chicago with a world renown spa and a half-Olympic length swimming pool overlooking the Chicago skyline. It has a central and convenient location right off the Magnificent Mile, close to shopping and less than a block from the Water Tower and 360 Chicago. Click here to see the latest prices and click here to read reviews .

Hilton Chicago/Magnificent Mile Suites.  Recently renovated all-suite hotel with fridge and microwave in room. Great location just steps from Michigan Avenue and one block from Lake Michigan.   Click here to see the latest prices and click here to read reviews .

ACME Hotel Company. This modern, stylish and unique hotel is located in downtown Chicago 2 ½ blocks from the Magnificent Mile in River North. Offers great value and great service. Click here to see the latest prices and click here to read reviews .

Best Western River North Hotel. Convenient located in the heart of River North close to the Chicago River as well as many restaurants and bars. Amenities include free high-speed Wi-Fi, deeply discounted parking, room service, fitness center, indoor pool and sun deck.  Click here to see the latest prices and click here to read reviews .

The Best Time to Visit Chicago

Chicago has plenty of things to do year round whatever the season. Summer is one of the best (and busiest) times to visit Chicago as the city comes alive and there are always outdoor festivals, concerts and events going on where you can take advantage of the warm weather. Restaurants and bars open their rooftops and sidewalk patios so you can dine outside. The temperature in the summer is usually hot but not unbearable (but some days can be very hot and muggy).

Winter can be very cold and snowy but some years can have mild winters with hardly any snow. Late November and December are busy with holiday events and festivities and the temperatures are usually still not that cold.  January and February tend to be the coldest months but attractions are less crowded. Even if you hate cold weather, there are enough indoor attractions to keep you entertained in Chicago during the winter .

Fall and spring are generally great times to visit Chicago – the popular attractions are not as busy as summer and the weather is usually more pleasant (but temperatures can be very unpredicable). The weekend before St. Patrick’s Day and the weeks during spring break can get very busy but the rest of spring is considered shoulder season.

Personally, I think the best time to visit Chicago is September and early October because students are back in school but temperatures are still warm but not as hot and humid as summer.

If you still need help deciding when to visit Chicago, check out The Best Time to Visit Chicago – A Month By Month Guide  for more details regarding weather and events by month.

Getting Around in Chicago

Chicago is an easy city to get around in with many public transportation options. Both Chicago airports – Chicago O’Hare (ORD) and Chicago Midway (MDW) – are connected to downtown Chicago by train.

For longer distances you can use public transportation , taxi, rideshare or rent bikes through Divvy (Chicago’s bike share program).

Taxis are plentiful and very easy to find downtown and at popular tourist attractions. You can also use the Curb app (for taxis) or ridesharing apps ( Lyft and Uber) to get around Chicago .

A hop on hop off bus is a great way to see all the attractions without having to figure out how to get around.

These are my top choices for the best things to do if you have 3 days in Chicago .

Planning a trip to Chicago? Check out more of my Chicago guides and itineraries:

  • Best Things to Do in Chicago in the Summer
  • 24 Hours in Chicago: A Perfect One Day Itinerary (From a Local)
  • Most Instagrammable Places in Chicago
  • Best Free Things to Do in Chicago
  • Best Day Trips From Chicago

3 Day Itinerary for Chicago From a Local

Related Posts

BEST Things to Do in Chicago This Weekend


One comment.

Hi, I have also lived in Chicago and yes, although Summer is great, the best time to visit I’d also say it’s Aug/Sept. This is one, if not THE one, of the best places on Earth. I’d even say, if you can stay longer than 3 days in Chicago, do so. You are not going to regret it, since the city offers so much to do year round. Lovely post!

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View of Chicago skyline from above with Lake Michigan visible to the right

3 Days in Chicago: The Ultimate Weekend in Chicago Itinerary

Chicago is a vibrant city that feels very alive, and with the perfect 3 days in Chicago itinerary, it’s possible to sample the best of the city over a long weekend!

The city is always on the move, and there isn’t an hour in the day that you won’t find at least 10 unique and adventurous things going on around town.

Music and food festivals pull out all the stops in Chicago, on top of the arts and cultural events that dot the city throughout the year.

Are you into food and drinks, lake views, and most of all, fun? Then Chicago is the place to be. There is enough here to explore for months, and we are going to pack all of the best events and activities into a 3 day long weekend itinerary to experience the essence of Chicago. 

Note: this Chicago blog post was written for Our Escape Clause by former Chicago locals Zach & Julie Ruhl, the travel couple behind Ruhls of the Road . Thanks for joining us, guys!

Table of Contents

Day 1 in Chicago Itinerary: The Bean, Skydeck & Great Chicago Food

Day 2 in chicago itinerary: lincoln park, wrigley field & beyond, day 3 in chicago itinerary: magnificent mile, navy pier & an afternoon adventure, where to stay for 3 days in chicago, where to eat during your chicago weekend getaway, getting around during 3 days in chicago, when to spend a long weekend in chicago.

Zach and Julie Ruhl of Ruhls of the Road dancing in a Chicago Park. They are the authors of this 3 days in Chicago itinerary

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Chicago is an enormous place. The city covers miles in each direction, with awesome things to do located all over the map. Therefore, this Chicago itinerary is going to thoughtfully take you from place to place, minimizing travel time and maximizing adventure.

Your first day in any new city should no doubt include some of the most signature sightseeing highlights there–and this Chicago itinerary is no exception, starting with a popular activity that is relatively new in Chicago: the Riverwalk. The current version of the Riverwalk was completed in 2017 and is an excellent place to start your Chicago weekend getaway.

Start your weekend in Chicago with a walk on the Chicago Riverwalk.

The Chicago Riverwalk starts at Wolf Point, near where the Chicago River turns from East/West to North/South. From there, the Riverwalk continues for over a mile, to the point where the Chicago River meets Lake Michigan.

Along this beautiful walk, you’ll pass a few awesome cafes and restaurants. This is a great place for a morning coffee, watching the morning hustle and bustle of America’s third-largest city. On top of that, the morning walk counts as your exercise for the day!

If you fall in love with the Riverwalk, then come back for a happy hour one evening. Riverside wineries and bars open up during the evening, complete with sets of outdoor games, live music, and some great entertainment! 

Photo of Chicago Riverwalk near a bridge that crosses the river, a great way to kick off your 3 days in Chicago itinerary

Check out Millennium Park.

At the end of the Chicago Riverwalk, you’ll reach Lake Michigan. Turn right here and head South to Millenium Park, where you’ll find an excellent location for soaking in the Chicago skyline from a beautiful park in the huge city center.

Millennium Park is an awesome Chicago sightseeing destination for two reasons. First off, it is just a great park full of fun things to do in Chicago !

There is an awesome playground for kids to play on, a great dog park for your four-legged friends, a huge green space to sprawl out for a picnic, a live music amphitheater, the Crown Fountain with a reflecting pool, endless gardens, and so much more!

You could spend a whole day at Millenium Park and not grow bored.

The second reason Millenium Park is so great is its proximity to everything. The park is great, but what makes it so impressive is that you are literally in a natural oasis amidst the concrete jungle of downtown Chicago.

Look around you while in the park, and you’ll see the towering structures of the Willis Tower, the Aon Center, and the rest of the enormous Chicago skyline.

Zach and Julie Ruhl at Millenium Park in Chicago Il, they are the authors of this long weekend in Chicago itinerary

Snap photos at The Bean.

At the edge of Millenium Park is The Bean, AKA Cloud Gate, Chicago’s most photographed (unofficial) monument.

The Bean is a huge monument, standing over 30 feet tall and 60 feet long, that is made of polished chrome and has no visible seams. This structure is truly unique and is an awesome downtown Chicago sight. 

The Bean is perfectly reflective, and due to its shape, the reflections can make for very fun images. It is essentially a gigantic magic mirror, placed in the middle of a bustling downtown environment.

Spend some time enjoying the fun reflections you can see as you walk in a circle around and under The Bean, then head for some food.

Downtown Chicago should have plenty of options on your way to your next stop: the Willis Tower. 

Chicago bean in Millenium Park at blue hour

Admire views of Chicago from the Willis Tower Skydeck.

The Willis Tower is Chicago’s tallest building and the second tallest in the United States. At one point, this skyscraper was even the tallest building in the whole world, and held that title for 25 years! There’s no doubt that this is a must-see spot on any 3 day Chicago itinerary.

When you visit the Willis Tower, there are really two things you need to do. First off, admire the size of this monstrosity from below. The building literally reaches into the sky, and from the bottom seems impossibly huge. Walk around it marveling upwards, just make sure to lose your attention and wander into the city streets!

The other way to see the Willis Tower is, of course, from the top. The Skydeck is at the very top of the building, where you can see Chicago stretch beneath you for miles and miles in each direction into the horizon.

If you have the stomach for it, there is even a glass-bottomed section where you can literally step out into the sky, or at least it looks that way. From the glass floor, you can see down over 1,000 feet to the streets beneath you. This is quite an incredible experience and one that you won’t get anywhere else in the United States!

Book your Skydeck tickets for the Willis Tower today!

View of Chicago IL skyline from willis tower skydeck, a must-see during a 3 day Chicago vacation

Finish your first day in Chicago in West Loop on Randolph.

The West Loop is an up-and-coming neighborhood in Chicago. This area seemingly has a great new restaurant pop up each week and has some of the most delicious food and one of the most fun atmospheres in the city.

Randolph Street in the West Loop is the culinary center of the neighborhood and is where you should head for dinner and drinks on your first day in Chicago. If you have the time and energy, the very best activity is to have a drink at a few different places, hopping from place to place and soaking up as much of this wonderful neighborhood as you can.

Each restaurant will have a unique vibe and atmosphere, so keep hopping around until you find the one you love best.

Want to make sure you experience the best food in the neighborhood? Add this popular West Loop Food Tour to your Chicago itinerary!

Macy Clock on Randolph and Street Street in Chicago Illinois

Close out your first night in Chicago at an Irish pub.

Chicago has a huge Irish population, and therefore quite a few Irish pubs located around the city. Our best recommendation is to find one close to your hotel and pop in for a Guinness as a night-cap. Enjoy the Chicago atmosphere, and then head to your hotel to get some sleep before heading off on your second day’s worth of fun things to do in Chicago!

Day 2 in Chicago is going to be a day full of exploring Chicago’s famous North Side. The North Side is awash with classic Chicago food options (Chicago loves its food…) as well as awesome sites to see and things to do. First up is the famous Lincoln Park.

Start the day with a stroll through Lincoln Park.

Lincoln Park is a huge and sprawling greenspace alongside Lake Michigan for 7 long miles. This is, in fact, the largest park in all of Chicago! And it also may very well be the most beautiful.

Alongside Lake Michigan, Lincoln Park has a few different beaches, as well as seemingly endless biking and walking trails. If you would rather bike than walk, then there are many bike rental options scattered all around the park, and around Chicago as a whole.

While strolling or biking through Lincoln Park, make sure to stop and see the Belmont Rocks, North Pond, and the Signal of Peace Monument. Along the way, admire the natural beauty and enjoy the sounds of birds singing as you bring on your second day in Chicago.

Chicago skyline as seen from Lincoln Park, one of the best places to visit in Chicago IL on a weekend in Chicago vacation

Soak up the sun at North Avenue Beach.

North Avenue Beach is one of Chicago’s largest and most popular beaches. Located right alongside Lake Michigan, this vast expanse of white sand makes for a great place to enjoy the beautiful Chicago summer sun.

If you are traveling with a group, then there are opportunities for some beach volleyball at North Avenue Beach! At the beach, you can rent a net and a ball (rentals are by the hour) and play some volleyball on the sand in view of the Chicago skyline!

While at North Avenue Beach, you must make a stop at the famous beach house that is shaped like a boat. This is also the location of Castaways, a bar and grill on the roof of the beach house serving yummy drinks with an incredible view. 

Head to Wrigley Field & Wrigleyville.

You can’t visit the North Side of Chicago and not see Wrigley Field. As one of the most famous baseball stadiums in existence, and the home of the Chicago Cubs, this is a must-see stadium, especially for sports fans.

Wrigley Field is located right in the heart of Wrigleyville on the North Side. Surrounded by residential areas and a huge bar and restaurant scene, this area is a magnet for good times, especially when the hometown Cubs are lacing up their cleats for a game.

If you are fortunate enough to be in Chicago while the Cubs are playing, head to Wrigley just for the experience of people watching and cheering on the hometown team. If you’d like, you could even try and buy some tickets, and usually, you can get a good deal on seats if you are okay purchasing them after the game is already in the 2nd or 3rd inning.

Wrigleyville, the neighborhood surrounding Wrigley Field, is an excellent place to hang out, have a drink, and hop around a few of the local establishments. Each of them has a great atmosphere, delicious, food, and of course a wide array of beers on tap.

Wrigley Field scoreboard in Chicago Illinois

Sample some Malort.

Malort is a Chicago specialty liquor and is something anyone over 21 should try when they visit the Windy City.

The liquor itself is not good because of taste, in fact, it tastes pretty bitter, and most people find it awful. However, it is all about the experience of trying something the locals love! If you’d like to experience the local culture of Chicago, then you have to try Malort at least once.

Finish the Day at the John Hancock Center Signature Lounge.

The John Hancock Center is the best building in Chicago. That may be a controversial opinion, but it is so true. The enormous slanted walls of the Hancock reach over 1,000 feet into the Chicago sky, with huge beams in a crisscrossing X pattern the entire way up. The building is an architectural masterpiece and is a wonder to see from the base.

The best place to experience the Hancock Center, however, is not from the base. It is from the Signature Room.

What is the Signature Room? It is an incredible 95th-floor bar and restaurant with an absolutely stunning view of Chicago. The Signature Room offers a 360-degree view of Chicago from above and is especially breathtaking as the sun sets and the sea of lights emerges beneath you.

Experiencing an evening at the Signature Room is a wonderful experience, and will be a highlight of your visit to Chicago. If you are visiting on a budget, just order a drink here, as dinner can be expensive!

Chicago Skyline at sunset--views like this are plentiful throughout this 3 day Chicago itinerary!

Day 3 is going to be spent exploring more awesome sites and destinations in downtown Chicago. It is going to be a day where you can see as much as you want, and take it all in at your own pace. Choose your own adventure and make today special as you finish up your long weekend in Chicago!

Walk down the Magnificent Mile.

Start the day with a trip down the Magnificent Mile. This is a section of Michigan Avenue that is the retail center of Chicago. The street is lined on both sides with tons and tons of flagship stores, boutiques, and shopping malls.

Along the Magnificent Mile, in addition to all of the premier shopping, there are a few awesome sights you’ll see during this part of your Chicago weekend getaway.

The Wrigley Building is an awesome structure located right where Michigan Avenue meets the Chicago River. The Tribune Tower and the Chicago Water Tower are also wonderful landmarks along this stretch.

Office buildings along Michigan Avenue in Chicago Illinois--don't miss a chance to walk down the Magnificent Mile during your 3 days in Chicago sightseeing trip

Explore Navy Pier.

Just a few blocks from the Magnificent Mile is Navy Pier, an absolute must-visit destination on any Chicago visit. The Navy Pier is, as the name suggests, a large pier, formerly used by the Navy, that extends straight out into Lake Michigan. 

These days, Navy Pier is an awesome destination that is used for a wide variety of attractions. First off, there is almost always some form of live entertainment or shows that are happening over a weekend at Navy Pier. On top of that, the pier is lined with awesome bars and restaurants, as well as shops and boutiques.

The view from the end of Navy Pier is excellent. First off, you’ll get to see the vast expanse of Lake Michigan on 3 sides of the pier. However, when you look back at the city, you’ll get a view of the full skyline including the Willis Tower and the Hancock Center. Do you want an even better view? Because there is one way to get it… There is a HUGE Ferris wheel that you can ride to get a stupendous view of the entire Chicago skyline and Lake Michigan!

Chicago Navy Pier with skyscrapers visible in the background and Lake Michigan in the foreground

Visit Buckingham Fountain in Grant Park.

After exploring Navy Pier, head to Grant Park, another of Chicago’s excellent downtown parks. Here you’ll have the chance to explore a huge area of green space, complete with monuments, statues, and a great lakeside walkway. At the heart of Grant Park, you’ll see Chicago’s most famous and beautiful fountain: Buckingham Fountain

Buckingham Fountain is at the center of Grant Park and is a great place to sit and enjoy a coffee or picnic. The fountain itself is beautiful, but it is made even better by the great Chicago skyline in front of you, and Lake Michigan behind.

Close up of Buckingham Fountain in Grant Park in Chicago Illinois

Further South in Grant Park you’ll find three other excellent Chicago sightseeing spots to consider adding to your 3 day Chicago itinerary:

Field Museum, Shedd Aquarium + Adler Planetarium

On the south side of Grant Park are 3 beautiful buildings, each of which houses an awesome adventure. The Field Museum is one of the largest natural history museums in the world and is home to some of the best exhibits you can possibly imagine. When we visited in the past, the dinosaur exhibit left us astounded, as they had a full-size Tyrannosaurus Rex named Sue!

The Shedd Aquarium is a world-class aquarium located just east of the Field Museum on Lake Michigan. This aquarium is stunning both from the outside and inside and offers hours of exploration as you make your way through the grounds.

Finally, the Adler Planetarium, America’s FIRST planetarium, is a wonderful place. This place offers the chance to explore things that are out of this world, literally. If you are at all interested in space, astronomy, or astrophysics, then you will have the time of your life at the Adler Planetarium.

Exterior of Field Museum in Chicago Il as seen from the front--consider paying a visit here during a Chicago weekend getaway!

Finish your long weekend in Chicago at River North.

River North is the area just north of the Chicago River. Whoever named it wasn’t very creative, but they were very accurate.

River North is absolutely FULL of awesome bar and restaurant destinations. As with many neighborhoods in Chicago, the best way to experience it is by hopping from place to place. When you find a place you love, stay as long as you’d like, then move along to the next place! That is the Chicago way of experiencing the nightlife.

Chicago is an enormous place, sprawling for miles and miles. The downtown area has many neighborhoods, each of which has pros and cons for visitors to the Windy City.

The best places to stay for 3 days in Chicago are near the Chicago River, specifically River North, Gold Coast, Streeterville, and The Loop.

In addition to those, a few more great neighborhoods are Lakeview, Lincoln Park, West Loop (which is home to great Chicago street art ), Near North, and Old Town.

Here are a few great hotel recommendations for budget, mid-range, and luxury travelers.

Classic Chicago Ilinois Theater sign

Godfrey Hotel — The Godfrey Hotel is in the River North neighborhood, and is right in the middle of many of the best activities on your 3 day Chicago itinerary. On top of the great location, the hotel is beautiful on the inside and gets excellent reviews. The Godfrey Hotel is a wonderful place to hang your hat while exploring Chicago.

Check rates & book your stay at The Godfrey Hotel today!

Hyatt Regency Chicago — The Hyatt Regency Chicago is located in The Loop neighborhood, right on the Chicago River.

Many of the rooms in the Hyatt Regency have beautiful views of the Chicago River, the skyline, and the city streets.

The rooms are wonderful, the price is good, and the location is excellent. Additionally, the fitness center, meeting rooms, an on-site bar and restaurant, and access to Chicago activities make the Hyatt Regency one of the best places to stay in Chicago.

Check rates & book your stay at the Hyatt Regency Chicago today!

The Langham — Now, to the creme de la creme. If you’re a luxury traveler looking for the best hotel in Chicago, look no further than The Langham.

First off, the location could not be better. Located right on the Chicago River in River North, you’ll be within walking distance of nearly everything on your itinerary.

Additionally, The Langham pulls out all the stops when it comes to amenities. The on-site spa, fitness center, pool, and deluxe bar and restaurant are all five stars. Of course, the rooms are wonderful as well, and nearly all have stunning views of the cityscape.

Check rates & book your stay at The Langham today!

Chicago Skyline with river filled with sailboats in the center, an excellent view to seek out during 3 days in Chicago

Chicago and food go hand in hand. You could explore a new food destination in Chicago every night for the rest of your life, and not eat at the same place twice. Not going to fact check that, but it is probably true. There are awesome restaurants on every corner, all across the city!

Here are four must-visit restaurants in Chicago that we love. 

Chicago-Style Pizza – Giordano’s

You can’t come to Chicago and not try some Chicago-style pizza. You literally can’t, it is impossible. The best Chicago-style pizza is at Giordano’s. The pizza here is absolutely LOADED with cheese and toppings, more than you have ever had, guaranteed. One slice and you’ll be satisfied, two slices and you’ll be stuffed. Be prepared to have leftovers!

Portillo’s is a Chicago institution. This started as The Dog House, a hot dog stand, and grew into Portillo’s, a delicious restaurant serving beef, burgers, and Chicago-style hot dogs all across the city. Portillo’s is yummy, quick, and is a Chicago must. Try the chocolate cake shake, you’ll be glad you did.

Chicago-style hot dog displayed on a red checkered napkin

Happy Camper

Happy Camper is an excellent classic pizza place located in the Near North neighborhood, which offers an excellent atmosphere. This is a great place to watch sports, meet friends, enjoy a happy hour, and of course, try some pizza!

The toppings are creative at Happy Camper, and the pizza is DELICIOUS. There is also a huge selection of local and imported beers to try.

Girl and the Goat

Girl and the Goat is an absolutely EXCELLENT restaurant located in the West Loop neighborhood on Randolph Street. T he food here is delicious and is very creatively and expertly prepared.

Call ahead for a reservation at Girl and the Goat, as there may be a long wait if you just show up asking for a table. If you do just show up, however, this is worth the wait.

And you can walk across the street to one of the many bars on Randolph while you wait for a table at Girl and the Goat!

Zach and Julie Ruhl at The Bean in Chicago

Bonus: take a Chicago food tour!

In a city as centered around food as Chicago, taking a food tour is one of the best ways to explore the city’s cuisine. 

Not only will you be able to sample a wide variety of classic dishes without committing to a whole portion, you’ll also learn plenty about Chicago’s history and culture along the way!

This popular food tour gets rave reviews and is an excellent addition to your long weekend in Chicago.

Book your food tour in Chicago today!

Deep Dish Pizza in Chicago being sliced and served, one of the most important foods to eat during your 3 day Chicago itinerary!

Getting around for 3 days in Chicago is in most ways easy, but can sometimes be challenging.

The public transport system is the easiest and most inexpensive way to get around, followed by cabs/Uber/Lyft, and finally driving yourself.

Much of the 3 days in Chicago itinerary laid out above, however, can all be completed by exploring on foot, especially from the recommended hotels. The awesome destinations and great parks are relatively close together and can be reached with a nice walk in the Chicago air.

Chicago has one of the best public transport systems in the US. The elevated train, AKA the ‘L’, brings people across Chicago east, west, north, and south. The ‘L’ stops at all of the amazing sites in the city, as well as O’Hare Airport, Midway Airport, and all the major thoroughfares.

If you would rather avoid public transportation, then the best way to travel around during this 3 day Chicago itinerary is with a cab/Uber/Lyft. Traveling this way is likely the fastest if you can avoid rush hour, and the most convenient. However, it will be more expensive than using the ‘L’ trains.

Finally, you, of course, have the option of driving yourself around town. In our opinion, this is the most stressful way to get around, as you’ll have to worry about parking in the busy downtown streets. This is a challenge and is made worse considering that many hotels offer parking fees.

Photo of Chicago train traveling on a bridge over car traffic--using Chicago's public transportation is the best way to get around on a Chicago weekend getaway!

The best time to plan a long weekend in Chicago is during the summer. The weather during the summer is absolutely perfect, and it’s definitely the easiest time to pack light for a Chicago vacation (if you visit during the blustery winter, be sure to carefully consider what to wear in Chicago !). This is also the best time to explore the awesome parks, beaches, and outdoor destinations in the Windy City.

Each year in the summer, Lollapalooza brings huge crowds looking for an awesome time and great music. Lollapalooza draws many of the best music acts in the world, so traveling to Chicago during the music festival is a great opportunity. On top of this festival, many great music artists perform regularly at Wrigley Field, Soldier Field, the United Center, and the other great venues across Chicago.

Coming in a close second to the Chicago summer is the spring when the city defrosts after its long Chicago winter and comes alive. There is nothing quite like spending 3 days in Chicago when the atmosphere is on the rise, as it is in spring.

Also during this time is St. Patrick’s Day, one of the largest holidays in Chicago. On St. Patrick’s Day the river is dyed bright green, and the partygoers are out in force.

4 photos of Chicago Illinois: skyline, beach, theater sign, deep dish. Black and red text on a white background reads "How to spend 3 days in Chicago"

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4 thoughts on “3 Days in Chicago: The Ultimate Weekend in Chicago Itinerary”

I’d like to follow for future information

Thanks for this comprehensive guide! It made planning a trip to Chicago so much easier!

As a frequent traveler to Chicago, who lives just a few hours away, I want to mention a few places that truly make Chicago iconic. The Palmer House Hotel is the best in the City. Right outside the doors of the Palmer House is a Chicago favorite, with a long history, called Miller’s Pub. Grab an Allagash White beer on tap – a local favorite. Don’t miss a food tour of Chinatown. There is so much history there, and the food is really amazing! Other amazing foodie spots in Chicago are Bongo Room for brunch and Cafe Babareba for Spanish style tapas (do not miss the baked goat cheese in tomato sauce). An architectural tour on the Chicago River is a lovely way to spend the day and if that isn’t your thing, the water taxis are a fun way to get around.

Agrred with the other poster–This itinerary is hugely missing the architecture tours! Best thing to do in the city. River north is fine, but kind bro-y for lack of a better descriptor. Bongo room is in Wicker Park which I describe as our Williamsburg. Not quite as artsy and cool as it was 5 years ago but still very fun!

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The perfect 3-day itinerary in Chicago

Karla Zimmerman

May 9, 2022 • 6 min read

Yellow tour boat cruising on the Chicago River through the skyscrapers of downtown Chicago, towards Lake Michigan. 

Only have three days? Chicago is the perfect city to visit © Mlenny / Getty Images

The nation’s third-largest city covers a lot of ground, but you can take in a good chunk of Chicago during a weekend if you have a plan. And we’ve got one with sky-high buildings and star art collections, along with dive bars and Route 66 diners.

Here's our guide to the perfect weekend itinerary in Chicago. 

Head to the docks beneath Michigan Avenue downtown and hop on a boat tour with the Chicago Architecture Center . Yes, it’s touristy, but it’s also marvelous. Grab a seat on deck and look up as the finest collection of buildings in the country glides by. Guides’ architecture lessons carry on the breeze, so you’ll know your Beaux Arts from International Style by journey’s end.

A mom lifts up a slice of Chicago deep dish pizza from a pie with spatula as two young children watch.

After stuffing your head with knowledge, it’s time to stuff your face with deep-dish pizza, Chicago’s premier local specialty. Giordano’s makes “stuffed” pie, which is a bigger, doughier version – like deep-dish on steroids. Loosen the belt, because each cheese-laden slice weighs a half-pound or so.

Next, motor north a few miles to catch a show at Second City , the launching pad of jokesters from Bill Murray to Tina Fey. The outlandish sketch revues are always high-quality laugh fests. They’re also popular, so book tickets well in advance.

Before the night ends, get a drink at the Old Town Ale House , across the avenue from Second City. It’s a wonderfully democratic institution (some might call it a dive bar), where beautiful people and seen-it-all regulars mingle on barstools under the nude celebrity paintings until last call at 4am. You might even see cast members from your show hanging out over a wee-hour brew.

An oxidized lion statue stands in front of the Art Institute of Chicago building, whose facade rises in the background; perfect weekend in Chicago

Start at downtown’s western edge and fuel up at Lou Mitchell’s , a diner from the days when Route 66 rolled by the area. The old-school waitresses call you “doll” while delivering fluffy omelets and plate-defying flapjacks to the table. Lines can be long, but Lou’s soothes the pain with free donut holes and Milk Duds as you wait for your table.

Walk a few blocks east to Willis Tower . Chicago’s tallest building pokes 1450ft into the heavens and its 103rd-floor Skydeck provides a panorama over four states. Brave souls can step onto the glass-floored Ledges to be suspended (almost) in stomach-lurching mid-air. Be sure to book tickets beforehand.

Stay downtown and mosey to the Art Institute of Chicago (advance reservations required). The second-largest art museum in the country hangs masterpieces aplenty, especially impressionist and post-impressionist pieces.

Georges Seurat’s pointillist A Sunday Afternoon on the Island of La Grande Jatte is here; so is Grant Wood’s American Gothic . Marc Chagall’s glowing stained glass America Windows fill a room, too.

When you’ve seen your fill, head to the Art Institute’s 3rd floor sculpture terrace, and step onto the silvery pedestrian bridge arching into Millennium Park . Make a beeline for the shiny “Bean” sculpture for the obligatory photo op. Splash around in Crown Fountain, where video images of locals spout gargoyle-style. Admire Frank Gehry’s swooping silver band shell. Then contemplate it all over a Nutella soufflé pancake and ginger tea at Hanabusa Cafe .

Take the Blue Line L train to Logan Square, a buzzy neighborhood 20 minutes northwest of downtown – prime for chowhounds and tipplers. Drop in at Revolution Brewing to knock back a Rosa hibiscus ale or other inventive beer with the local crowd.

Make your way a mile southwest to Giant , a small storefront cooking up big flavors in modern American comfort food. Advance reservations are essential. If you can’t score a seat, no worries: nearby Ground Control earns praise for its tofu fried chicken, beer-braised greens and other vegetarian dishes served with a side of local brews and budget cocktails.

From here it’s a stone’s throw to Rosa’s Lounge . The electric blues became Chicago’s tune when Muddy Waters, Howlin’ Wolf and friends plugged in their amps in the 1950s, and Rosa’s is an authentic spot to hear a fret-bending set.

The humble venue brings real-deal players to its arm’s-length-away stage where guitars wail into the night. It’s wise to buy tickets in advance, though you usually can walk up and get in after the first set (around 11pm). 

The iconic red and white sign on the Wrigley Field facade announces it as the home of the Chicago Cubs; Perfect weekend in Chicago

Chicagoans go gaga for brunch, and the West Loop provides loads of stylish hot spots to get your eggs on. The Publican delivers honey butter waffles, pork belly hash and hefty Bloody Marys, while Top Chef winner Stephanie Izard’s Little Goat shows how it’s done with cheesy hash browns and spiced apple pancakes. Roister makes chicken and waffles and biscuits and gravy that go way beyond the traditional versions.

If it’s baseball season and the Cubs are playing, hop on the Red Line train to Wrigley Field . The 1914 ballpark charms with retro touches like ivy-covered outfield walls and a hand-turned scoreboard. Shoveling down hot dogs and drinking beer in the raucous bleacher seats makes for an exceptional afternoon.

Otherwise, aim for the Pilsen neighborhood, a mash-up of Chicago’s Mexican community and hipster underground. Wild murals radiate off the buildings on practically every street.

A walkabout with Pilsen Public Art Tours is a good way to explore. Hungry? Bite into sublime pork tacos at Don Pedro Carnitas or complex, mole-rich dishes at 5 Rabanitos . The Pink Line L train to 18th Street gets you there.

In a long-exposure photograph, cars zoom through downtown Chicago leaving trails of light at night; Perfect weekend in Chicago

Where to stay

Downtown (aka the Loop): Cool boutique and architectural properties fill the core, where you’re steps away from Millennium Park, the Art Institute and other top sights. The playful Virgin Hotel offers large, cleverly conceived rooms in an old art deco bank tower, while the Silversmith flashes gem-inspired, vintage-cool rooms in a Gilded Age jewelers building.

West Loop: Chicago’s most trendsetting accommodations pop up in the West Loop, surrounded by heaps of fashionable bars and restaurants. The Publishing House Bed & Breakfast puts you in the thick of it, with 11 stylish rooms named after Chicago writers. The Hoxton Chicago brings mid-century-modern-inspired decor to its creative digs, along with free bicycles and a festive rooftop cafe.

How to get to Chicago 

O’Hare International Airport is on the city’s northwest side; it’s larger and where most international flights arrive. Smaller Midway International Airport is on the south side. Both have easy links to downtown via the L train, which costs $5 and takes 40 minutes from O’Hare, and $3 and 30 minutes from Midway. Amtrak arrives downtown at Union Station.

You might also like:

How to spend a perfect weekend in Chicago Out of the Loop: a tour of Chicago's off-the-beaten-path neighborhoods The best day trips from Chicago

This article was first published Sep 9, 2019 and updated May 9, 2022.

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The World Was Here First

The Perfect 3 to 4 Days in Chicago Itinerary

Published on April 10, 2024

by Olivia Ellis

Disclaimer: This article contains affiliate links. That means if you click a link and make a purchase, we may make a small commission. As an Amazon Associate we earn from qualifying purchases. For more information, see our privacy policy.

visit chicago 3 days

Chicago, standing as the third-largest city in the United States and the unofficial capital of the Midwest, is a blend of refinement, American industriousness, diversity, and a sincere, laid-back Midwest vibe. Whether you’re planning a 3 or 4 days in Chicago itinerary, this guide will offer you everything that creates the Windy City’s unique identity, from its classic foods, to the historic architecture lining the city.

Table of Contents

How Many Days in Chicago?

Chicago is a vast city and spending at least 3 days in the city is best to fully appreciate its diverse neighborhoods, iconic landmarks, and cultural institutions such as the Magnificent Mile, Millennium Park, and Lou Malnati’s Pizzeria.

Beyond this, 4 days or more in Chicago provide opportunities to dive deeper into Chicago’s neighborhoods such as Lincoln Park and Wrigleyville, or to explore at a more leisurely pace. Despite its size, Chicago is best enjoyed slowly, allowing you to get to know the city on a more intimate level.

Another component to factor in when deciding how long to spend in Chicago is the time of year. While winter in Chicago is famous for its blustery, snowy, and cold weather, the spring and summer open the city to an exciting atmosphere, with riverside events, beer gardens, and an abundance of outdoor activities such as city kayaking, or even swimming in Lake Michigan.

Because of this, I’d recommend spending more time in Chicago in the warmer weather vs a shorter trip in the winter unless you don’t mind spending time at your accommodation or your budget allows for time spent in a larger number of restaurants, or indoor sites/attractions.

Chicago Skyline from Lincoln Park

Getting To & Around Chicago

Chicago serves as a major transportation hub in the United States, offering convenient access for both domestic and international travel. Chicago O’Hare, as the primary airport for the city and the state of Illinois, is often the most common arrival airport.

Alternatively, if you’re visiting from destinations within the Americas (from East Coast cities like Boston or Philadelphia or western cities like Los Angeles or Phoenix ) or are flying with specific international carriers, you may also land at Chicago’s Midway Airport.

Both airports provide CTA Train services into downtown Chicago, making your journey into the city speedy and affordable compared to pricey taxi or ride-sharing services. From O’Hare, the journey takes approximately 45 minutes depending on your final destination.

If you need to reach downtown from Midway Airport, expect a shorter 25-minute train ride.

In addition to its airport accessibility, Chicago also boasts convenient train connections, particularly for travellers exploring the Midwest.

For those seeking to economize or are interested in exploring other Midwest cities like Indianapolis, Detroit, Cincinnati, or Milwaukee, Amtrak offers a comfortable Midwest route connecting these cities at a lower cost than air travel.

On a grid system layout, Chicago is renowned for its efficient public transportation and easy navigability, offering convenience and accessibility. Many central sites and downtown areas are conveniently within walking distance, making exploration of the city simple and convenient.

During the chilly winter weather, or if you just prefer to use public transportation, Chicago’s public transportation is excellent, providing a convenient means of moving around the city.

The Chicago Transit Authority (CTA) offers an extensive network of buses and trains, and even water taxis in the warmer months, allowing convenient access to Chicago’s diverse neighborhoods and sites.

Chicago CTA Train

3 to 4-Day Chicago Itinerary

Whether you’re keen to eat your way through Chicago, explore the city’s rich sports culture, admire its unique blend of architecture, or spend time wandering through its many cultural icons, there is a lot to do on a trip to Chicago.

Day 1 – Magnificent Mile, Willis Tower & More!

Magnificent mile.

Day 1 begins in the center of the city in the Magnificent Mile neighborhood of Chicago.

The Magnificent Mile is a prestigious and bustling neighborhood located along Michigan Avenue in central downtown Chicago. Stretching approximately 13 blocks from the Chicago River to Oak Street, the neighborhood is renowned for its upscale shopping, landmarks, and atmosphere. If you want to explore this area with a guide, you can book a walking tour.

I find this area to be a wonderful spot to explore in Chicago first, as it defines the energy of the city while also offering great breakfast spots and well-known Chicago spots such as Willis Tower.

The Magnificent Mile

Skydeck at Willis Tower

One of the iconic buildings worth visiting while in the Magnificent Mile is the Willis Tower. Built in 1970 and originally known (and still referred to by locals) as the Sears Tower, the Skydeck at Willis Tower offers possibly the best views of the entire city.

The most renowned feature of the Skydeck is the Ledge, located on the 103rd floor, allowing you to experience the sensation of being suspended over Chicago’s landscape while enjoying incredible views of the Midwest capital city.

On the ground floor, you can enjoy an interactive experience that educates you in Chicago’s culture and history, all while in a fun environment.

Tickets and time slots for the Skydeck must be booked in advance , and adult admission starts at $32.

If you’re interested in visiting multiple attractions/experiences in Chicago, the Chicago CityPass or the GoCity Pass is a great way to save money.

Looking down from the Skydeck

Starbucks Reserve Roastery

After experiencing Chicago at its highest point, head back to the city’s streets and make your way to the world’s largest Starbucks, here in Chicago.

Whether you’re a coffee drinker, prefer tea or you’re somewhere in the middle, the roastery is an attraction in itself, encompassing 5 floors of various interest, from coffee, bakeries and cocktail bars, to immersive roastery experiences and even a roof terrace.

Chicago Architecture River Cruise

The classic Chicago Architecture River Cruise is a quintessential experience for visitors to the city. Whether you’re an architecture enthusiast or simply enjoy learning about Chicago’s history while taking in its incredible scenery, this cruise offers the ideal opportunity.

As you wind along the Chicago River, you’ll have the chance to learn more about the city’s architectural landmarks while enjoying one of America’s most famous cityscapes.

Tours are available year-round, with multiple companies offering varying lengths of tours led by knowledgeable locals. These tours typically last between 60 and 90 minutes and provide amenities such as comfortable seating, bathrooms, and heating in the winter.

Some even offer a full-service bar onboard. Tickets can be purchased online and are typically priced around $40 for adults, though prices may vary depending on the provider and time of year or day.

Day 2 – Millennium Park, Art Institute & Deep Dish Pizza

Millennium park & cloud gate.

Start your second day in Chicago by visiting one of the city’s most iconic landmarks: Millennium Park and its famous attraction, Cloud Gate, unofficially known as “the bean.”

Situated in the heart of the city within Grant Park’s northwestern section, Millennium Park spans 25 acres and was established in 2004 to commemorate the third millennium.

Today, it stands as a symbol of Chicago, boasting an impressive collection of public art, panoramic views of Lake Michigan’s shoreline, and the Cloud Gate sculpture by Anish Kapoor.

Spend time wandering around one of Chicago’s most beloved green areas, taking in the park’s fountains, art, structures, the Chicago Cultural Center and even possibly enjoying a skating session in the wintertime.

Nearby, you could also pop by to see the iconic Chicago theatre to glimpse another of the city’s most famous landmarks.

The Cloud Gate in Millennium Park

Art Institute

By this point on your trip, you’ve likely noticed that Chicago is a city synonymous with art. One of the best ways to delve deeper into this aspect of the city’s culture is by visiting The Art Institute of Chicago.

As one of the oldest and largest art museums in the United States, the Art Institute houses nearly 300,000 pieces of art, including works by Pablo Picasso, Edward Hopper, Claude Monet, and a diverse array of sculptures, prints, and drawings from around the world.

During your visit, you can learn more about the museum and its installations through free guided tours offered daily at 1:00 PM and 3:00 PM.

The admission cost for adults is $32, with discounted tickets available for children and seniors. They can be purchased online or you can also organise a guided tour.

Additionally, admission to The Art Institute is included in the CityPass for those participating in the program.

Lion Statue in front of the Art Institute

Chicago Pizza at Lou Malnati’s

The first food that probably comes to mind when thinking about Chicago is Chicago deep dish pizza, and there’s no better place to eat it than at Lou Malnati’s Pizzeria , a Chicago institution founded by the oldest family name in Chicago Pizza.

Taking pride in the pizzeria’s use of fresh ingredients and vine-ripened tomatoes, anything on the menu will likely be delicious, but I suggest ordering the “Malnati Chicago Classic” with sausage, cheese, and tomato sauce or the “Lou”, a vegetarian option with spinach, mushrooms, tomato, and a tasty cheese blend.

With over 50 locations in the Chicago metropolitan area, you’ll be hard-pressed to not find a location nearby. Regardless of where you go, there’s no doubt that digging into a gooey, cheesy deep dish pizza is one of the best things to do in Chicago and if you’re really a pizza lover then you can also join a pizza tour!

Day 3 – Riverwalk, Museums & London House Rooftop

Chicago riverwalk.

On your third day in Chicago, explore the city riverside by strolling along the Chicago Riverwalk, a scenic pedestrian path that stretches for 1.25 miles along the Chicago River.

The Riverwalk comprises four distinct districts: The Confluence, The Arcade, The Civic, and The Esplanade.

Along this picturesque route, you’ll discover lush greenery, restaurants, cafés, art installations, and seasonal performances.

The Chicago Riverwalk provides an ideal setting to unwind, relax, and soak in the city’s ambiance, making it a favorite spot for both locals and visitors and a true example of how to take advantage of city space. You can also learn more about its darker past on this walking tour.

Chicago Riverwalk Sign

Navy Pier or Field Museum of Natural History

Chicago offers a diverse array of museums and attractions, ensuring there’s something for everyone in the City of Big Shoulders.

For those seeking an immersive experience, Navy Pier is a must-visit attraction. Originally built in 1916 as a dock for freight and passenger ships, Navy Pier has transformed into an exciting spot with restaurants, bars, shopping, and entertainment options for all ages. Admission is free, and the pier is open year-round.

Alternatively, for a more traditional museum experience, consider visiting the Field Museum of Natural History. As one of the world’s largest natural history museums, it houses a large collection of artifacts and exhibits exploring biodiversity and human cultures.

From dinosaur skeletons to ancient artifacts, the Field Museum offers an interesting journey through natural history and anthropology. Tickets can be purchased online.

View from Navy Pier

Drinks at London House Rooftop

Conclude your third day in Chicago at the renowned London House Rooftop bar. Perched atop the historic London House Hotel, this rooftop venue offers unparalleled nighttime views of the city’s iconic skyline.

Enjoy an elegant atmosphere and house cocktails as you take in the breathtaking vistas of the Chicago skyline. During the winter, cozy igloo capsules line the terrace, creating a festive atmosphere (reservations necessary).

Reservations are recommended in advance for popular times, and a smart casual dress code is in place.

Day 4 – Lincoln Park or Wrigleyville

Lincoln park.

If you’re spending 4 days in Chicago, consider exploring a neighborhood outside the downtown area.

Lincoln Park, located on the north side of the city, offers a leafy escape from the hustle and bustle of Downtown Chicago. Explore its residential streets lined with boutique shops and abundant food options.

Visit the neighborhood’s namesake, Lincoln Park, and learn more about various plant and flower species at the Lincoln Park Conservatory. Don’t forget to enjoy a lovely coffee or lunch at Floriole Cafe & Bakery.

Walking through Lincoln Park


For sports fans, spending a day in Wrigleyville is an exciting option for your last day in Chicago. This former working-class neighborhood, home to the Chicago Cubs, buzzes with activity, especially during baseball season.

During baseball season, the area offers an exciting atmosphere, boasting a wide array of sports bars and pubs.

Year-round, Wrigleyville offers a laid-back and friendly atmosphere with fun restaurants, seasonal outdoor concerts, film screenings, and even a farmers market.

And if you’re visiting during baseball season, be sure to buy tickets to a game to truly feel the soul of Chicago.

Where to Stay in Chicago

Moxy Chicago Downtown – Located in downtown Chicago, this hip, pet-friendly hotel is an excellent place to rest your head. It boasts 2 restaurants, air-conditioned rooms and an on-site fitness center.

The Hoxto n – This upscale, central hotel in the West Loop district is another great option in the windy city. There are on-site restaurants and beautiful rooms along with a great rooftop swimming pool – perfect for the warmer months!

Chicago Getaway Hostel – This cool hostel is a great budget option in the city. Offering lots of dorms and private rooms, there is a good social atmosphere. inviting common areas and a central location.

Not quite what you’re looking for? Click here to browse more Chicago hotels!

The Midwest is an entirely understated region of the United States, and a visit to its capital, Chicago, is the perfect way to find your way into the heart of its rich culture, warm hospitality, and urban landscape.

Are you planning to visit Chicago? Have any questions about this itinerary? Let us know in the comments!

visit chicago 3 days

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About Olivia Ellis

Olivia is a writer for The World Was Here First. Originally from Michigan, USA, she is currently living in Athens, Greece exploring Europe and filmmaking. When she’s not travelling or writing, Olivia can be found cooking delicious new recipes from around the world, reading, and spending time outdoors.

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Guided by Destiny

3 Days in Chicago: Discovering the Best of the Windy City

This post contains affiliate links which means that I will make a small commission if you purchase a product after clicking on any of them, at no extra cost to you.

Chicago is such an amazing bustling city! Just having 3 days in Chicago can feel overwhelming because there is so much to do and see. But let me assure you, you can accomplish quite a bit in 3 days.

Our Chicago trip took an unexpected turn due to various factors. From the haze caused by Canada’s wildfires to unexpected rain showers, and to top it off, a bustling holiday weekend coupled with a NASCAR event in town, which led to street closures and limited access to popular spots like The Bean.

Luckily growing up in the midwest I have already visited Chicago several times (plus I plan to return!), so I still feel confident I can help you create an epic 3 day Chicago itinerary!

View of Chicago city skyline at night from Lake Michigan

Table of Contents

When is the best time to visit Chicago ?

Chicago is a city that truly comes alive during the summer months from June to August. It’s a bustling time filled with festivals, outdoor concerts, and lively events that showcase the city’s vibrant energy. However, with the increased activity comes larger crowds, so be prepared for some busy streets and longer lines at popular attractions.

For a more relaxed visit, consider spring (April to May) and fall (September to October) as ideal times to explore Chicago. These seasons offer milder weather, fewer tourists, and beautiful natural scenery. Spring blooms and fall foliage add a touch of charm to the city, making it perfect for outdoor activities and sightseeing without the summer hustle.

Winter in Chicago, while cold, can be a magical experience with festive decorations, ice skating rinks, and holiday markets. The city transforms into a winter wonderland, offering unique opportunities to explore its architecture against a snowy backdrop. Plus, you can find great deals on accommodations during the off-peak season. Consider your preferences and priorities to choose the best time to visit Chicago.

Looking out at Chicago on the Shoreline Sightseeing Architecture River Tour

Chicago CityPASS

If you only have 3 days in Chicago and want to see some of the city’s top attractions, check out the Chicago CityPASS . It includes admission to some of the most popular Chicago activities at a discounted price, saving up to 48% off regular admission fees. We used this for our trip, and it was perfect!

The CityPASS includes admission to the Shedd Aquarium and Skydeck Chicago, plus three of the following attractions:

Field Museum

  • Art Institute of Chicago
  • Shoreline Sightseeing Architecture River Tour
  • Museum of Science and Industry

Adler Planetarium

  • 360 CHICAGO Observation Deck

Pointing at buildings from 360 Chicago

Best things to do if you have 3 days in Chicago

Chicago architecture river cruise.

The Chicago Architecture River Tour comes highly recommended by both locals and visitors, and for good reason! It’s a must-do experience that showcases the city’s stunning architecture and captivating skyline from a unique perspective.

Sit back and relax on a leisurely cruise as knowledgeable guides share fascinating historical and architectural insights about the iconic buildings that line the Chicago River.

Views of bridge and city during Shoreline Sightseeing Architecture River Tour in Chicago

Stroll along the scenic Riverwalk and immerse yourself in the vibrant atmosphere of Chicago. This 1.25-mile-long pedestrian-friendly pathway offers breathtaking views of the city skyline, charming cafes, restaurants, and plenty of outdoor seating areas where you can enjoy a meal or simply relax and take in the beauty of the surroundings!

View of the Chicago Riverwalk from boat tour

This one is a must for your 3 days in Chicago, especially if it’s your first time! Located in Millennium Park, the Cloud Gate sculpture, affectionately known as “The Bean,” is a beloved Chicago landmark.

Reflecting the city’s skyline in its polished, mirrored surface, this unique art installation offers a playful and interactive experience.

The Bean in Chicago

360 Chicago

Get ready for breathtaking panoramic views of the city skyline from the observation deck of 360 Chicago . Located in the iconic John Hancock Building, this attraction offers a unique perspective of Chicago from 1,000 feet above ground.

Views of city and Lake Michigan from 360 Chicago

Shedd Aquarium

The Shedd Aquarium is an aquatic wonderland! Dive into the fascinating world of marine life and explore a variety of mesmerizing exhibits.

Get up close and personal with graceful dolphins, playful otters, and majestic beluga whales. This educational and entertaining experience will leave you with a greater appreciation for the wonders of the ocean. It’s the perfect family-friendly Chicago activity!

The Shedd Aquarium in Chicago

Dine at some of the best restaurants in the country

Chicago is internationally renowned for its culinary scene, with SO MANY amazing dining options. From trendy gastropubs to fine dining establishments, the city offers a gastronomic adventure for every palate.

One of the stand-out restaurants from our trip was Sunda New Asian . From tempting sushi rolls to flavorful noodle dishes and innovative fusion creations, Sunda delivered consistently good dish after dish.

From the moment we took our first bite at Sunda New Asian’s Chicago location, it captured our hearts, so we were thrilled to find out they were opening a location in Midtown Tampa !

Sunda New Asian in Chicago cocktail

Nestled in the heart of downtown Chicago, Grant Park is an urban oasis. Known as “Chicago’s Front Yard,” this iconic park is home to numerous landmarks and attractions.

You’ll especially want to admire the Buckingham Fountain, a breathtaking architectural masterpiece. Inspired by the Latona Fountain at the Palace of Versailles, this iconic landmark is one of the largest fountains in the world!

If you love big cities, check out my NYC guide , 3-day LA itinerary , and fun Miami restaurants guide!

While in operation, the Fountain produces a major water display for 20 minutes every hour starting at 9 AM. Beginning at dusk, a special light and music display accompanies the major display, with the final major display beginning at 10:35 PM.

Buckingham Fountain at Grant Park

Skydeck Chicago

As you can see, between the gloomy weather and smog from the wildfires in Canada our views were a little dampened, but still impressive!

For Skydeck Chicago , you will ascend to the 103rd floor of the Willis Tower and experience the awe-inspiring views from the glass viewing platform known as “The Ledge.” Take in the sweeping views and test your courage on the thrilling Tilt experience (this is an additional $10 if you choose to experience it).

Epic views from Skydeck Chicago

Walk and shop the Magnificent Mile

Chicago’s Magnificent Mile is a shopper’s paradise! It offers a mix of luxury boutiques, flagship stores, and renowned department stores.

Make sure you take a break from shopping to admire the stunning architecture of the Magnificent Mile, with its towering skyscrapers and historic landmarks! This bustling avenue truly lives up to its name, providing an unparalleled retail experience.

Magnificent Mile in Chicago Illinois

Take yourself on a celestial journey at the Adler Planetarium , a hub of astronomical exploration and education. Engage in interactive exhibits that unravel the mysteries of the universe, from the history of space exploration to the captivating phenomena of black holes. Expand your knowledge of the cosmos and awaken your sense of wonder!

The Adler Planetarium in Chicago

The Field Museum is a renowned institution that houses an extensive collection of artifacts and specimens that tell the captivating stories of Earth’s past.

From the awe-inspiring Egyptian mummies to the fascinating Sue, the largest and most complete Tyrannosaurus rex skeleton ever discovered, the Field Museum offers a journey through time and an opportunity to deepen your understanding of the world around us!

The Field Museum in Chicago

Blue Man Group

See one of Chicago’s longest-running shows, The Blue Man Group ! It combines comedy, music, and multimedia theatrics into a mind-blowing performance that will leave you in awe. Watch as the energetic blue-faced performers captivate with their rhythmic drumming, enthralling visuals, and interactive antics.

This one-of-a-kind theatrical experience is a testament to the group’s innovative creativity and has made them a beloved staple of Chicago’s entertainment scene!

Check out a speakeasy

Chicago is certainly not short on speakeasies! With only 3 days in Chicago, we didn’t get to hit nearly as many as I would’ve liked, but what we lacked in quantity we made up for in quality.

Three Dots and a Dash was such a fun and tropical vibe! The drinks were fire, the vibes were immaculate, and it was within walking distance of our beloved Sunda New Asian! Making this the perfect pre or post-game spot for your dinner reservation.

Three Dots and a Dash speakeasy in Chicago

Have a Chicago-style hot dog

No visit to Chicago is complete without indulging in a classic Chicago-style hot dog. This iconic culinary creation features a poppy seed bun loaded with an all-beef hot dog, topped with mustard, onions, sweet pickle relish, tomatoes, pickles, sport peppers, and a sprinkle of celery salt.

We grabbed ours from a stand right outside of The Field Museum, and we loved it!

Chicago style hot dog in Chicago

Visit the largest Starbucks in the world

If you’re a fellow coffee lover, you simply can’t miss out on the grandeur of visiting the world’s largest Starbucks— Chicago’s Starbucks Reserve Roastery . This elevated Starbucks concept takes coffee appreciation to new heights, offering a curated selection of rare and small-batch coffees from around the globe as well as menu items you probably won’t recognize from your average Starbucks.

This coffee haven is spread across five floors, and each offers its own menu!

Starbucks Reserve in Chicago

Especially if you’re visiting Chicago in the summer, a boat day is a must! It’s the epitome of Chicago summers. Whether you do a Lake Michigan sunset cruise or a private boat rental , nothing beats a day out on the water!

Couple enjoying a boat day in Chicago

The Navy Pier offers plenty of attractions and activities for of all ages. From thrilling rides to the mesmerizing views of Lake Michigan and the city skyline, there’s never a dull moment here.

Make sure to catch the fireworks display that lights up the sky every Wednesday and Saturday night during the summer season, creating a magical ambiance that’s perfect for a romantic evening or a fun night out with friends and family.

Don’t forget to explore the various shops, restaurants, and entertainment options that make Navy Pier a must-visit destination in Chicago!

Fireworks at The Navy Pier in Chicago

Bonus things to do if you have time to spare during your 3 days in Chicago

  • Lincoln Park Conservatory — A stunning botanical haven that showcases a variety of plant species, from towering palms to rare orchids. It’s a great free thing to do in Chicago!
  • Jackson Park— An expansive park with lush greenery, scenic trails, and picturesque lagoons. Check out The Garden of the Phoenix, an exquisite Japanese garden within the park.
  • WNDR Museum — A fun museum full of multi-sensory, contemporary art installations.
  • Ice Cream Museum — Another fun museum! It’s immersive, interactive, and full of fun photo ops!
  • Lincoln Park Zoo— This free-admission zoo is the perfect family fun activity if you still have time to spare during your 3 days in Chicago.
  • Bike along the Lakefront trail— This scenic 18-mile trail offers stunning views of the lake and city skyline! Get a bike rental here.

Where to stay in Chicago

Chicago is a city brimming with diverse neighborhoods and a multitude of accommodation options . As you plan your Chicago itinerary, keep in mind the proximity of your chosen hotel to your planned activities and attractions. Here are some top picks for where to stay in Chicago, all located in the bustling Loop area where the main action happens:

  • The Blackstone Autograph Collection — The Blackstone offers a blend of historic charm and modern luxury. With stunning views of Lake Michigan and proximity to iconic landmarks like Millennium Park and Grant Park, this hotel is the perfect base for exploring the city.
  • Sentral Michigan Avenue — Situated along the vibrant Magnificent Mile, Sentral Michigan Avenue provides easy access to world-class shopping, dining, and entertainment. The hotel’s contemporary design, upscale amenities, and central location make it a popular choice for both leisure and business travelers.
  • Bluegreen Vacations Hotel Blake, Ascend Resort Collection — Experience boutique elegance at Hotel Blake. The hotel’s stylish rooms, personalized service, and convenient location make it a standout option if you’re seeking a memorable stay in Chicago.

For availability and rates for your specific dates check out available accommodation options here .

Are you ready for an epic 3 days in Chicago?!

I hope you’ve enjoyed this whirlwind tour of the city for your 3 days in Chicago! From exploring iconic landmarks to savoring delicious cuisine and soaking in the vibrant atmosphere, Chicago has so much to offer in a short time.

Whether you’re a first-time visitor or a returning traveler, there’s always something new to discover in this dynamic city. Here’s to more amazing travels and unforgettable experiences!

Before you go, be sure to follow me on Insta @guidedbydestiny and check out some of my other Midwest blog posts:

Fun things to do in the Twin Cities

Weekend in St. Louis

Perfect weekend in Chattanooga

fun things to do in chicago

Destiny Snyder is a passionate travel blogger and content creator based in the Tampa Bay area. Originally from a small town near Toledo, Ohio, Destiny's love for exploring new places began when she moved to Florida in 2017. She enjoys uncovering hidden gems, sharing insider tips on the best things to do, places to eat, and coffee shops to visit in every destination. With her blog Guided by Destiny and niche sites Sunkissed in Tampa and Sunkissed in St. Pete, Destiny aims to make trip planning stress-free and fun for her readers.

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visit chicago 3 days

Chicago   Travel Guide

Courtesy of jaskoomerovic | Getty Images

visit chicago 3 days

3-days Itinerary in Chicago

  • 3-Day Itinerary
  • All Things To Do
  • 1-Day Itinerary
  • 2-Day Itinerary

visit chicago 3 days

Art Institute of Chicago Art Institute of Chicago

Home to one of the country's most impressive collections of impressionist and post-impressionist art (plus works from numerous other genres), the expansive Art Institute of Chicago features nearly 300,000 works from all over the world in its permanent collection. You'll find pieces created in the Byzantine era, as well as paintings completed just a few decades ago.

Highlights include Jacob Lawrence's "The Wedding," Georgia O'Keeffe's "Sky above Clouds IV" and Grant Wood's "American Gothic." The Art Institute's exhibits also include all sorts of intriguing artifacts, from European armor to the Thorne Miniature Rooms, which showcase interior design and furnishings in Europe and America from the late 13th to early 20th centuries. In addition to the permanent collection, the Art Institute hosts traveling exhibitions covering a variety of subjects and showcasing a diverse array of artists and genres.

visit chicago 3 days

Millennium Park and Cloud Gate Millennium Park and Cloud Gate free

U.S. News Insider Tip: Construction around the Cloud Gate sculpture will limit the public's access to this top tourist attraction until spring 2024. While you might not be able to snag a selfie with "The Bean," many other attractions are available within the park. – Cortney Fries

A first-time visit to Chicago isn't complete without a stop at Millennium Park. Situated in the Loop just north of the Art Institute of Chicago , this 25-acre space is used to showcase cutting-edge art, architecture and landscaping; it also acts as a backdrop for concerts and festivals.

visit chicago 3 days

Chicago Architecture River Cruise Chicago Architecture River Cruise

A visit to 360 CHICAGO or Skydeck Chicago will give you a good overview of the city's layout. But if you want to learn more about Chicago's sky-high buildings, tag along on an architecture river cruise. During a river cruise, you'll gain great views and historical insight about well-known structures like the Wrigley Building, the Leo Burnett Building and the Fulton House.

Though several companies, including Wendella Sightseeing Co. and Chicago Line Cruises, offer architecture river cruises, most travelers recommend climbing aboard a Chicago's First Lady Cruises boat with a Chicago Architecture Center docent. You'll learn tons of information about the area's architecture, plus catch superb skyline photo-ops.

visit chicago 3 days

The Magnificent Mile The Magnificent Mile free

U.S. News Insider Tip: The Magnificent Mile, known for its world-class shopping, also has plenty to offer architecture buffs. Book a walking tour with the Chicago Architecture Center and hear the untold stories of North Michigan Avenue's architectural icons. Tours start at $30. – Sarah Estime

For shopping at more than 450 retailers within walking distance in downtown Chicago, make your way to The Magnificent Mile.

visit chicago 3 days

360 CHICAGO Observation Deck 360 CHICAGO Observation Deck

One of Chicago's most notable attractions is its skyline, and one of the best places to experience it is at the 360 CHICAGO Observation Deck.

Formerly known as the John Hancock Observatory, 360 CHICAGO towers 1,000 feet over The Magnificent Mile from its location on the 94th floor of the John Hancock Center (or 875 North Michigan Avenue as its more formally known). Encased by floor-to-ceiling windows, 360 CHICAGO boasts expansive views of the city; on a clear day, you can see four states. Meanwhile, the interactive screens will help you identify different landmarks that appear in your panorama.

visit chicago 3 days

Grant Park and Buckingham Fountain Grant Park and Buckingham Fountain free

U.S. News Insider Tip: If you're visiting Chicago Sept. 8 through 10, head to Grant Park early – around 11 a.m. to avoid the lines – for the Taste of Chicago. Enjoy the park and eat the best cuisine the city has to offer. Admission is free. – Sarah Estime

Often referred to as "Chicago's front yard," Grant Park is an approximately 313-acre swath of green space that starts at the eastern edge of the Loop and stretches down to the northern fringes of the Near South Side.

visit chicago 3 days

The Field Museum The Field Museum

U.S. News Insider Tip: After hours of museum hopping, grab a kid-approved lunch at Kim & Carlo's Hot Dog Cart. The no-frills stand offers everything from vegan dogs to the traditional Chicago hotdog. Enjoy your lunch on the water. – Sarah Estime

This extensive natural history museum occupies half an acre of Grant Park 's Museum Campus and houses exhibits that showcase artifacts from multiple eras and destinations, making it a must-see for kids (as well as any fans of the "Indiana Jones" movies).

visit chicago 3 days

Shedd Aquarium Shedd Aquarium

U.S. News Insider Tip: If you're visiting in the summer (June through August), check out Jazzin' at the Shedd. You can enjoy jazz music and drinks with incredible views from the terrace. Plus, the lights dim in the aquarium for a unique experience. – Elizabeth Von Tersch, Senior Editor

Shedd Aquarium is one of the world's largest indoor aquariums, housing around 32,000 creatures. While you're here, you can feel stingrays float beneath your fingers, listen to sea lions bark and learn all about a variety of turtles. A visit to Shedd Aquarium will lead you through a cornucopia of habitats, where you'll find additional animals like penguins, piranhas, sharks and beluga whales. Or, for an additional fee, you can participate in specialty experiences like animal encounters, feeding experiences and virtual reality.

visit chicago 3 days

Navy Pier Navy Pier free

Extending out onto Lake Michigan, Navy Pier offers plenty in the way of family-friendly entertainment.

The first thing you'll spot once you set foot on the pier is the towering Ferris wheel (which stands 196 feet tall); you'll also find a drop tower and a carousel. Once the kids have had their fill of thrill rides, you can spend some time cruising the Chicago River on a sightseeing or speedboat tour or spend a few hours exploring the Chicago Children's Museum , with hands-on exhibits ranging from treehouses to fire trucks.

visit chicago 3 days

Skydeck Chicago at the Willis Tower Skydeck Chicago at the Willis Tower

More than 1.7 million people make their way to Willis Tower's Skydeck Chicago each year, and it's easy to see why. Occupying the 103rd floor – that's nine floors higher than 360 CHICAGO – of the 110-story Willis Tower (the third-tallest building in North America after One World Trade Center and Central Park Tower), Skydeck Chicago boasts breathtaking views of the city. Visit on a sunny day and you may be able to see far beyond Chicago's borders to Indiana, Michigan, Wisconsin and other parts of Illinois.

The highlight for most visitors is the Ledge. Extending 4.3 feet beyond the building's exterior, this platform is made entirely of glass – even the floor. Travelers also liked the video screens that show what it would be like to stand 103 floors above other Chicago attractions, including Wrigley Field and Millennium Park . However, long lines quickly form for Skydeck Chicago, so plan on arriving early or purchasing a Chicago CityPASS, which covers expedited admission into the attraction. Or, simply pay extra for expedited entry, which features an express line to the elevators. For the best views, it's advised that you visit just after opening or after sunset. If you'd like to enjoy the sunset from the tower, plan on arriving 30 to 45 minutes before sunset to ensure you have enough time to get through the elevator line and up to the top.

visit chicago 3 days

The Chicago Theatre The Chicago Theatre

Aside from Cloud Gate and Buckingham Fountain , The Chicago Theatre's red and yellow marquee is perhaps one of the city's most recognizable landmarks. Illuminating North State Street at the northern edge of the Loop, The Chicago Theatre first opened its doors in 1921 as an extravagant movie theater and performance venue. Throughout its history, the theater has hosted such big names as Duke Ellington, Diana Ross and Prince, in addition to screening blockbuster flicks. Though the theater fell into disuse in the 1970s, new management and a full renovation in the 1980s helped return the venue to its former glory. Today, the theater is still used for a variety of comedic, theatrical and musical performances.

According to past patrons, the theater's historic appearance enhances the overall experience of catching an event here. Just remember, cameras and video cameras, including those on cell phones, cannot be used during tours or performances.

visit chicago 3 days

Lincoln Park Zoo Lincoln Park Zoo free

U.S. News Insider Tip: North Avenue Beach is a short walk over the North Avenue Bridge when you park at the southern end of the Lincoln Park Zoo lot. Explore the zoo, then stroll over to the beach for an afternoon in the sand. – Cortney Fries

Located 2 miles north of the Loop in the North Side neighborhood of Lincoln Park, the Lincoln Park Zoo is home to nearly 200 species, such as zebras, sloths and hippos. Visitors can view the zoo's furry (or scaly) friends in their natural habitats: Check out the gorillas in the sprawling, award-winning Regenstein Center for African Apes, or head to the Kovler Seal Pool to get up close and personal with harbor seals. Seal training and feeding occurs daily at 11:30 a.m. and 2 p.m.

visit chicago 3 days

Wrigley Field Wrigley Field

U.S. News Insider Tip: If you're visiting during the holiday season, don't miss Winterland at Gallagher Way for family-friendly rides and games inside and around the ballpark. Christkindlmarket Wrigleyville is free to enter. Enjoy festive shopping and international food and beverage selections. – Cortney Fries

Chicagoans take their love of sports very seriously. So, for a real taste of Chicago culture, head north of the Loop to Wrigley Field to watch the Chicago Cubs play ball at the Friendly Confines. History buffs will also appreciate this sports treasure, which first opened in 1914 and holds the honor of being the second-oldest Major League Baseball stadium in the country (after Fenway Park in Boston ).

visit chicago 3 days

Explore More of Chicago

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Travel, Hiking, Food

Long Weekend in Chicago: Essential 3 Days in Chicago Itinerary

Spending a long weekend (3 days) in chicago this 3 day chicago itinerary shows you the best places to go and eat in chicago. this itinerary also gives you many chicago planning tips if this is your first time in chicago..

Planning a trip to the Windy City for 3 days or a long weekend? You are in the right place!

From iconic architecture and world-class museums to deep-dish pizza and blues music, Chicago has something for everyone. Whether you’re a history buff, foodie, art lover, or just looking to soak up the urban energy, Chicago won’t disappoint.

I had been to Chicago previously in the winter and it was pretty miserable to be honest. But going there in the summer and early fall is a completely different (and amazing) experience.

In this 3 day long weekend Chicago itinerary I will show you the best places to see in Chicago and how to most efficiently spend 3 days in Chicago. I will also address practical information like how to get around Chicago, how to save money on attractions, where to eat and stay in Chicago for your perfect Chicago trip.

This blog contains occasional affiliate links, where I receive a small commission on sales of the products/hotels that are linked at no additional cost to you. In addition, as an Amazon Associate, I earn from qualifying purchases .

When’s the Best Time to Visit Chicago For A Long Weekend?

NOT in the winter! Ok I think we all know winter is brutal in Chicago so that’s the worst time to visit Chicago. I went to Chicago once in February and it was just pure misery.

Early Summer and early fall are the best time to visit Chicago with the warmer temperature and beautiful weather. In particular, the month of June, September, and October are great to visit Chicago because it does get quite hot and humid in July and August.

The shoulder seasons are generally cheaper and less crowded than the peak summer season and you can enjoy a lot of outdoor activities. Although if you do have to visit Chicago in the summer at least you can enjoy the beach near the city center.

Where to Stay in Chicago?

As a first time visitor, the best areas to stay in Chicago would be either near the Magnificent Mile or in the Loop . Other great areas to stay in Chicago include West Loop and Gold Coast.

The reason I suggest these two areas is because of the access to restaurants, museums, and other attractions. You can walk easily from place to place or take a local bus to get around. There are also a lot of accommodation options in these two touristy areas.

The Magnificent Mile

There are a ton of hotels near on Michigan Avenue as well as between Dearborn St. and Michigan Avenue.

I stayed at the Intercontinental which was very centrally located. Rooms were average size and service was good. I loved that I could walk everywhere, from 360 CHICAGO to Millennium Park, making it super convenient to explore.

Courtyard hotel Chicago | Where to stay in Chicago for a long weekend

Other hotels near the Magnificent Mile include Courtyard , Royal Sonesta or Hyatt . You will find a lot of chain hotels here so you know quality is guaranteed.

The Loop is a vibrant area where you will find the Bean at Millennium Park and all the famous museums in Chicago. You will inevitably spend a lot of time in the Loop area, so it’s a good area to stay.

Some of the best places to stay in the Loop include CitizenM , Arlo Chicago , the Blackstone .

West Loop & Fulton Market

If you want to stay somewhere close to good food, then you should consider Fulton Market and West Loop, an area west of the Loop. Formerly known as the meat-packing district, the West Loop is super walkable with industrial aesthetics and amazing restaurants.

In fact West Loop is one of my favorite areas in Chicago. I went there a few nights in a row just to try different restaurants and coffee shops.

So if you don’t mind walking or taking the bus to get around Chicago, then consider staying in the West Loop.

Some of the best places in the West Loop include the Hoxton , Nobu Hotel Chicago , and the Hyatt House .

If West Loop is my 2nd favorite area in Chicago, then Gold Coast is my absolutely favorite area in Chicago.

Gold Coast is north of the Loop and it is one of the most luxurious neighborhoods in Chicago. It is the home of beautiful mansions (like the original Playboy Mansion), upscale restaurants and stores (like RH).

You can easily walk to the beach and Lincoln Park and it is a short ride down to the Loop.

Some of the best hotels to stay at in Gold Coast include Ambassador Chicago and Viceroy Hotel .

Long Weekend (3 Day) Chicago Itinerary (With Maps)

Now you know some of the basics of how to get around and where to stay in Chicago, let’s talk about what you will actually do (and eat) in Chicago for a long weekend!

I am just so excited for you. Really, Chicago is such a nice place to visit when the weather is good (yeah don’t visit in the winter). With Lake Michigan to the east and tons of parks to relax and explore, Chicago really is beautiful when the weather is warm.

Coming from New York City, I am just so impressed with how clean and neat Chicago is and it also is not super crowded compared to New York City. So if you want a taste of Chicago as a first time visitor, you will love all the suggestions on this itinerary.

For your convenience, I mapped out all the major attractions and awesome restaurants in Chicago on this map below.

Day 1 : Famous Museums in the Loop + Skydeck (Orange Pins) Day 2 : Art Museum, Parks, Architectural Tour, 360 CHICAGO (Purple Pins) Day 3 : Magnificent Mile, Near North Side, Lincoln Park area (Green Pins) Where to Eat : Red pins

Day 1 in Chicago: Museums + Skydeck

Start your first day in Chicago with a bang! You will see some of the best museums in Chicago in what’s known as the Museum Campus.

Museum Campus is in the southern end of the Loop; it is an area that houses 3 of the most famous museums in Chicago: Adler Planetarium , Shedd Aquarium , and Field Museum .

It is also a beautiful area to walk around, with plenty of greens (and parks) and the view of Chicago skyline and Lake Michigan.

All 3 museums open at 9am, but I would actually recommend going to Shedd Aquarium first because it gets really crowded with school tours and just kids running around especially during the summer months.

So we will start our 3 day Chicago itinerary with Shedd Aquarium.

Shedd Aquarium

Hours of Operations : 9am – 9pm Ticket Price : $42-$45 (if not Chicago resident) with tax Time Needed : 2-3 hours at least

Shedd Aquarium is one of the largest and most renowned aquariums in the US.

The Shedd Aquarium shark tank | how to spend a long weekend in Chicago

It houses an impressive collection of marine life from around the globe. It features diverse exhibits that showcase a wide range of aquatic creatures, including fish, sharks, dolphins, sea turtles, penguins, and more. In fact it has over 32,000 animals representing 1,500 species; that number is just mind blowing to me.

One of the highlights of Shedd Aquarium is the Oceanarium, a massive exhibit that replicates a Pacific Northwest coastal environment. Here, visitors can observe majestic beluga whales, playful dolphins, sea otters, and a variety of marine birds as they interact.

Beluga Whale at Shedd | best things to do in Chicago

Funny story here : I was watching the “Animal Spotlights” program with the beluga whales when I visited. After the show finished as I was walking out, the beluga whales swam very close to me and jumped out of the water. Of course I couldn’t miss the opportunity to take photos of it. Little did I know he came over to splash me, so as you can imagine, I got super wet after taking that photo.

There are also other activities such as penguin encounters which require additional ticket.

Overall, if you want to avoid the crowd it’s best to visit Shedd Aquarium right at opening.

Shedd Aquarium is included in the Chicago Pass and Chicago CityPASS .

Adler Planetarium

Hours of Operations : 9am – 9pm (9am – 10pm on Wednesdays) Ticket Price : $35 (entry + 2 shows) Time Needed : 2-3 hours at least if you watch the shows

Adler Planetarium is the first planetarium in the western hemisphere!

This is a photo of the inside of Adler Planetarium

At Adler Planetarium, you can explore the wonders of the universe, learn about space science, and engage in immersive experience.

Adler Planetarium is perfect if you have kids traveling with you. Depending on the ticket you get, you can watch 1 or 2 planetarium shows.

This is a photo of the planetarium show at Adler Planetarium | Best 3 day Chicago itinerary

The reason I suggest going to Adler Planetarium after Shedd Aquarium is that many shows are in the early afternoon, so if you arrive at 9am when they open you will need to wait a long time before showtime.

Adler Planetarium is included in the Chicago Explorer Pass and Chicago CityPASS and it comes with 2 shows.

Field Museum

Hours of Operations : 9am – 5pm Ticket Price : $30 ( general admission ); $37 (3D movie or 1 of the 3 ticketed exhibitions) Time Needed : 2 hours at least

The Field Museum is a renowned natural history museum that lets you explore the wonders of our planet and its history.

Chicago Field Museum inside lobby | How to spend 3 days in Chicago

It has a vast collection of artifacts, specimens, and interactive exhibits as well as special temporary exhibits.

The Field Museum is home to an extensive range of exhibits that cover a wide array of topics, including anthropology, paleontology, geology, biology, and more. One of the museum’s most famous and beloved attractions is Sue, the largest and most complete Tyrannosaurus rex fossil ever discovered.

Field Museum House in Chicago | what to do and see in Chicago over a weekend

The museum also showcases exhibits that delve into human cultures and civilizations from around the globe, from ancient Egyptian mummies and artifacts to Native American artifacts and cultural displays.

Field Museum tickets are included in the Chicago Explorer Pass and Chicago CityPASS . Chicago CityPASS gives you all access rights to see all the ticketed exhibitions and 3D film; the Chicago Pass gives you access to 1 ticketed exhibition.

I forgot to mention that you can eat at the cafes inside the museums or planetarium or walk 10 minutes to get Chicago hot dogs at Devil Dawg (or eat at other restaurants).

Hours of Operations : 9am to 8 or 9pm depending on day and months. See official website . Ticket Price : $30+ ( general admission ); $55+ (expedited entry) Time Needed : 45 min – 1.5 hours

Skydeck is an iconic observation deck in Chicago. It was formerly known as the Sears Tower and now known as Willis Tower (the naming right will change in a few years so it might be called something else).

Skydeck panoramic view in Chicago for Chicago itinerary

The Skydeck is situated on the 103rd floor of the Willis Tower, making it one of the highest observation decks in the United States. It offers unparalleled panoramic views of the Chicago skyline, Lake Michigan, and the surrounding area.

On clear days, you can see for miles, taking in the beauty of the city’s architecture and the vastness of the landscape.

The most famous feature at Skydeck is “The Ledge” , which are 4 glass bottom “boxes” that extend out from the building. You can step onto the transparent surface suspended over 1300 feet in the air.

Skydeck ledge photo in Chicago

If you have a fear of heights like I am, you might get scared standing on it.

For different sized parties, there is a different time limit. For a party of 1-3 people, you have 1 minute to take photos/ videos after the official photos finish (they have cameras latched above the ledge to take photos of you and sell you the pictures).

For parties of 4 or more you get 90 seconds. The attendant will set an alarm and can help you take photos if you are traveling alone.

I highly recommend going to Skydeck around sunset time so you can see the colorful sky as well as all the lights come on in the city. So if you finished your museums early you can grab dinner first then go to Skydeck for sunset.

Skydeck is included in the Chicago Explorer Pass and Chicago CityPASS . CityPASS gives you expedited entry but I didn’t really need that when I went.

Day 2 in Chicago: Art Museum, Parks, Architectural Tour, 360 CHICAGO

After a whole day of touring the most famous museums in Chicago, you will spend day 2 doing a variety of things. This is going to be an action packed day so be prepared to walk.

Start your second day in Chicago by checking out the Bean and Crown Fountain for some photos. Proceed to walk through Millennium Park and Grant Park before heading back to the Art Institute of Chicago to see world famous artwork.

If time allows, stop by the Chicago Cultural Center for a quick (and free) self-guided tour to see the beautiful ceilings before heading back north to the Chicago River for a fun and educational architectural cruise . Finish your evening at 360 CHICAGO for another amazing view of Chicago at sunset.

The Bean and Crown Fountain at Millennium Park

The Bean, officially known as the Cloud Gate, is one of the most iconic symbols of Chicago. Located in Millennium Park (which is in Grant Park), it is a must-see attraction for all first-time visitors.

Chicago the Bean photo Chicago Pass vs. CityPass | How to save money in Chicago

Designed by renowned British artist Anish Kapoor, the Bean is a massive, highly polished stainless steel sculpture that reflects and distorts the surrounding cityscape.

You can walk around and under the sculpture and take some artistic photos with it. But be warned that the bean does get crowded so if you want an instagram worthy photo you will have to go fairly early.

Close to the Bean is another famous art installation called Crown Fountain.

Crown Fountain at Millennium Park in Chicago

Designed by Spanish artist Jaume Plensa, the fountain consists of two towering glass block towers facing each other across a shallow reflecting pool. The fountain uses digital technology within the glass block towers to display the ever-changing faces of Chicago residents.

Millennium Park & Grant Park

Chicago has no shortage of parks, in fact public parks make up around 9% of total Chicago land (according to my architectural guide).

During your second day in Chicago you will get a chance to see two of the most famous parks in Chicago, Millennium Park and Grant Park. Millennium Park is technically inside Grant Park.

BP Pedestrian Bridge in Millennium Park | How to spend a weekend in Chicago

The Bean and Crown Fountain are in Millennium Park, so you have already seen part of the park. As you explore the park, you will see some other highlights, such as the Jay Pritzker Pavilion , an outdoor concert venue, Lurie Garden , a tranquil oasis in the middle of Millennium Park, and the BP Pedestrian Bridge , a famous stainless steel bridge that connects Millennium Park with Maggie Daley Park.

As you continue to walk south, you will actually pass by The Art Institute of Chicago (we will go back to that in a second) and arrive at Grant Park.

Grant Park is often known as “Chicago’s front yard”.

Grant Park is right next to Lake Michigan, so you have an incredible view of the waterfront and the Chicago skyline.

Buckingham Fountain in Grant Park Chicago photo

Within Grant Park, you’ll find several notable landmarks and attractions. Buckingham Fountain , one of the park’s most iconic features, serves as a grand centerpiece with its majestic water displays and ornate design.

Fisher Boy Fountain in Grant Park Chicago photo

Other landmarks in Grant Park include MAGMA , an art installation, the Turtle Boy , Dove Girl , Fisher Boy and Crane Girl fountains , a farm and rose gardens .

Art Institute of Chicago (Closed Tue & Wed)

Hours of Operations : 11am – 5pm (8pm on Thursday) Ticket Price : $32 for general admissions; $10 extra for special admission; $40 to skip the line Time Needed : 2 hours at least

The Art Institute of Chicago is a world-renowned art museum and cultural institution. Founded in 1879, it is one of the oldest and largest art museums in the US.

Chicago Art Institute front with lion | best museums to visit in Chicago

There are over 300,000 works of art in the Art Institute’s collection, from ancient Egyptian artifacts to European and Asian masterpieces to contemporary arts and photography.

Art work at Art Institute of Chicago

The collection features renowned works by legendary artists such as Vincent van Gogh, Pablo Picasso, Claude Monet, Georgia O’Keeffe, and Grant Wood, among many others.

There are also temporary special exhibitions featured at the Art Institute that cost additional $10.

The Art Institute is included in the Chicago CityPASS only.

Chicago Cultural Center

Hours of Operations : 10am – 5pm Ticket Price : Free! Time Needed : 30 min – 1 hour

The Chicago Cultural Center is in a beautiful historical building right across from the Bean.

Chicago Cultural Center Dome photo G.A.R. Rotunda and Dome | Best free things to do in Chicago

Originally built in 1897 as the city’s first central public library, the Chicago Cultural Center is a stunning example of Beaux-Arts architecture. The building itself is a work of art, featuring grand marble staircases, intricately designed mosaics, and ornate decorative elements.

Chicago Cultural Center Preston Bradley Hall Tiffany Dome | what to do in Chicago for 3 days

There are 2 beautiful stained glass domes in the Cultural Center and an art gallery. There are also cultural events and programs that are hosted at the Cultural Center regularly.

Chicago Architectural Cruise

Hours of Operations : 9:30 – 8:45pm (see schedule here ) Ticket Price : $45-50 Time Needed : 75 min – 90 min

The Chicago Architectural Cruise tours are a popular and highly recommended way to explore the stunning architecture of the city. These boat tours take you along the Chicago River, providing a unique perspective and an in-depth look at the iconic buildings that define the city’s skyline.

Shoreline Cruise Chicago Architectural Tour

Led by knowledgeable guides, the architectural cruise tours offer fascinating insights into Chicago’s rich architectural history and the visionary architects who shaped the city. You’ll learn about the different architectural styles, from Beaux-Arts to Art Deco to modernist designs, and how they contribute to the unique character of Chicago’s skyline.

Shoreline Sightseeing Cruise Architecture Tour in Chicago

There are several different companies that offer architectural cruises. I took the Shoreline Cruise because it was covered by my Chicago Explorer Pass (and also Chicago CityPASS ) but you can also choose other ones like this one .


Hours of Operations : 9am – 11pm Ticket Price : $30+ for general admissions ; $39+ to Tilt & View; $46.5 for View & Sip Time Needed : 1-2 hours

360 CHICAGO, formerly known as the John Hancock Observatory is one of the two popular observation decks in Chicago.

360 CHICAGO observation Deck photo

Located on the 94th floor of this iconic building, it offers breathtaking panoramic views of the city’s skyline and Lake Michigan.

The main highlight of 360 CHICAGO is its observation deck, which provides visitors with an unparalleled 360-degree view of the cityscape.

One of the unique features of 360 CHICAGO is the TILT experience. This exhilarating attraction allows you to step into a glass-enclosed moving platform that tilts outward from the building, giving you a thrilling downward-facing perspective of the city below.

360 CHICAGO sunset view over Lake Michigan | Best observation deck in Chicago

There is also a bar and some seating areas at 360 CHICAGO so you can relax while enjoying the view.

I visited during sunset and I thought the view was amazing. This is why I suggest going to 360 CHICAGO before sunset time so you can grab an early dinner before visiting.

If you can only visit one observation deck in Chicago, you should check out my detailed comparison guide between 360 CHICAGO and the Skydeck to see which one is better for you.

360 CHICAGO general admission is included in the Chicago Explorer Pass and Chicago CityPASS .

Day 3 in Chicago: Magnificent Mile, Lincoln Park, Navy Pier, Food Tour

Your last day in Chicago is pretty chill. You have the option to do everything or just chill, eat, shop or check out some other museums.

You can start your day at the Starbucks Reserve Roastery to grab some coffee and pastries before window shopping on the Magnificent Mile to do some shopping (or window shopping). If you are visiting on a Friday or Saturday, you can do a tour inside the magnificent Chicago Theatre . If not, wander on the Riverwalk and take in all that Chicago has to offer.

Get lunch then take the bus over to Lincoln Park where you can check out the free Lincoln Park Zoo and Conservatory. Finish your day by having some fun at Navy Pier , check out the West Loop area for great food or have a fun night at a comedy club .

You can also take a food tour and try all the iconic food of Chicago.

Starbucks Reserve Roastery

Hours of Operations : 8am to 8pm M-Th; 8am to 9:30pm Fri – Sun

Starbucks Reserve Roastery in Chicago | best places to visit in Chicago for a 3 day long weekend

Located on the magnificent mile, the Chicago Starbucks Reserve Roastery is a fantastic place to stop by for some coffee and pastry early in the morning.

This is no ordinary Starbucks Reserve, in fact this particular location is the largest Starbucks in the world. It has 5 stories and each story has something different.

It also offers a bakery with a wide selection of freshly baked goods, artisanal bread, and delicious pastries.

Magnificent Mile

The Magnificent Mile, often referred to as “Mag Mile,” is a world-famous stretch of North Michigan Avenue. It is renowned for its upscale shopping and beautiful architecture.

Chicago Michigan Avenue Magnificent Mile

Stretching for approximately one mile, the Magnificent Mile is lined with a dazzling array of high-end boutiques, department stores, luxury brands, and flagship stores of renowned fashion designers. You can find brands like Burberry, Cartier, Rolex on Michigan Avenue.

Aside from shopping, the Magnificent Mile is also home to a plethora of renowned landmarks and architectural gems such as the Wrigley Building , the Tribute Tower , the John Hancock Center (where 360 CHICAGO is), and the Chicago Water Tower .

You will also see street performers, Architectural Cruise ticket booths, Chicago Riverwalk, theaters, and Museum of Ice Cream on the Mag Mile.

The Chicago Theatre

Marquee Tour Hours : 12pm Friday & Saturdays Ticket Price : $24 ( ticket link ) Time needed : 75 min

The Chicago Theatre is a famous landmark in downtown Chicago.

Chicago Theater Sign

Built in 1921, this theater is known for its grandeur, architectural beauty and its significance in Chicago’s cultural and entertainment scene.

If you are not watching a show in the theater, your only option to visit the inside of this magnificent building is to do the Marquee Tour.

The tour will lead you inside to see the grand lobby, sweeping staircase and beautiful auditorium. You will get a chance to stand on the stage and learn about the history of the building.

The Chicago Theater Marquee Tour is included with the Chicago Pass and Chicago Explorer Pass .

Chicago Riverwalk

If you are not doing the Chicago Theater Marquee Tour don’t worry, you can either spend more time shopping or check out the Chicago Riverwalk.

The Chicago Riverwalk is a scenic and vibrant promenade that runs along the south bank of the Chicago River. It stretches for 1.25 miles and you can stroll, relax, dine, and enjoy the stunning views of the city’s iconic architecture.

Lincoln Park Zoo

Hours of Operations : 8am – 5pm on weekdays; 8am – 7pm on Sat & Sun. See seasonal hours here . Ticket Price : Free! Time Needed : 1-2 hours

Located at Lincoln Park, the zoo is one of the oldest zoos in the US and it is completely free to visit!

Chicago Lincoln Park with view of Lincoln Park Conservatory

Spanning over 35 acres, the Lincoln Park Zoo is home to a diverse collection of animals, from gorillas to lions to exotic birds and reptiles.

The Farm-in-the-Zoo is a popular attraction where children can interact with farm animals, learn about agriculture, and engage in hands-on activities.

Lincoln Park Conservatory (Closed Monday and Tuesdays)

Hours of Operations : 10am – 5pm Wed – Sun Ticket Price : Free, but reservation needed . Time Needed : 45 min – 1 hour

Located right next to the Lincoln Park Zoo, the conservatory is a hidden gem that should not be missed.

Lincoln Park Conservatory

The conservatory, built in the late 1800s, showcases an impressive collection of tropical plants, flowers, and trees from around the world. As you step inside, you’ll be greeted by a lush and vibrant environment, with soaring palm trees, colorful blooms, and cascading vines that create a truly enchanting atmosphere.

The conservatory is divided into several distinct rooms, each with its own unique theme and plant life. The rooms include the Palm house, the Fern Room, the Orchid Room and the Show House.

Lincoln Park Conservatory photo of inside

If you are visiting the zoo you should definitely stop by the conservatory and enjoy the tranquility from the bustling city.

After an eventful day, you can either stop by Navy Pier to check out the Centennial Wheel , the ferris wheel that can be seen from all the observation decks and cruise tours or go to the West Loop to eat at some of the most iconic restaurants in Chicago.

long weekend in Chicago | Navy Pier Centennial Wheel

If you are into comedy shows , Chicago also has a number of comedy clubs such as The Comedy Bar, the Comedy Clubhouse, Zanies Comedy Night Club and many others.

Is 3 Days Enough For Chicago?

3 Days in Chicago is the perfect amount time for a first time visitor to see the highlights of Chicago.

From world class museums to renowned restaurants to beautiful parks, you can see the best of Chicago over a long weekend (3 days) in Chicago.

Of course you can always spend more time in Chicago to explore things a little further away from city center, such as Garfield Park Conservatory , the largest conservatory in the US, relax on a beach , check out Hyde Park and the Museum of Science and Industry , explore the trendy area of Wicker Park , or venture out to the beautiful Baha’i temple or the magnificent Hindu Temple of BAPS Shri Swaminarayan Mandir .

How to get to Chicago?

Unless you are traveling from nearby cities, most likely you will have to fly to Chicago.

Chicago is served by two major airports: O’Hare International Airport (ORD) and Midway International Airport (MDW).

O’Hare International Airport , located about 17 miles northwest of downtown Chicago, is one of the busiest airports in the world and serves as a major hub for domestic and international flights.

Chicago OHare Airport

Midway International Airport , situated about 10 miles southwest of downtown Chicago, primarily serves domestic flights and is known for its convenient location and smaller size compared to O’Hare. There are only a number of airlines that fly to Midway International Airport, such as Allegiant, Avelo, Delta, Frontier, Porter, Southwest and Volaris.

Besides flying, you can take the Amtrak train to Chicago to Union Station or take a long distance bus such as Greyhound to Chicago. Union Station, the city’s major train station, often serves as a hub for various bus services as well.

How to get around Chicago?

You can use a combination of public transportation, biking, walking and ride share apps to get around Chicago during your long weekend Chicago trip.

Chicago is a super walkable city if you are planning to stay in the downtown area and do touristy things! You can literally walk from museum to museum or just walk along Michigan Avenue.

I walked A LOT when I was in Chicago and when I got tired, I used other forms of transportation below.

Public Transportation in Chicago

Public transportation in Chicago includes the “L” (or the CTA trains), buses and the Metra Rail.

The CTA train, otherwise known as the “L” (short for “elevated”) is a convenient way to get around the city with over 140 stations located throughout Chicago and the surrounding areas.

Blue Line train in Chicago OHare airport | Best Chicago itinerary

The “L” has 8 lines, known by their colors (Blue Line, Red Line, Green Line, etc). The Blue Line and Red Line run 24 hours.

I was super confused when I was looking up directions in Chicago because some blogs would say take the “L” train but Google Maps was telling me to take the Blue Line and the airport sign says “CTA trains”. Well I am here to tell you that they all mean the same thing. L = CTA trains = whatever color Line .

Chicago L Trains on the Loop

The bus network is also expansive, with 129 bus routes covering places that may not necessarily be served by the L.

This is a photo of Chicago public bus | How to get around Chicago for your long weekend Chicago itinerary

The Metra Rail is a commuter rail train that goes from downtown Chicago to the suburbs. The closest Metra stop to downtown is at Millennium Park. You can see the Metra Rail system map .

Navigating & Paying for the public transportation station in Chicago

Google Maps and City Mapper both work well in Chicago when looking up directions with public transportation. You can also download the Ventra App which shows you public transportation information.

Paying for public transportation in Chicago is easy and there are a lot of options.

Apple Pay/ Google Pay/ Contactless Cards can be used to pay for the bus and L trains. You just have to tap your card and you are good to go. However I did notice that using contactless cards on buses costed me $5 for the full price (instead of $2.25) the first time I used it on a bus.

Ventra App : The Ventra App allows you to load money into the app and add the Ventra card to Apple Pay and Google Pay, then you can tap and pay on buses and L trains. I used this in Chicago and the bus fare was the $2.25 fare.

Chicago public transport Ventra Card screenshot | 3 days in Chicago itinerary - how to get around Chicago

CTA/Pace Pass : You can purchase a 1, 3, 7, or 30 day CTA/ Pace Pass from either the ticket machine or load onto your Ventra account.

photo of Chicago L train ticket machine at O'Hare airport | how to get from O'Hare International Airport to Downtown Chicago

For a full list of fares and options, see the official CTA website .

Taking Uber/ Lyft in Chicago

Uber and Lyft both operate in Chicago and you can easily get a car when it is too late or you simply do not want to bother with public transportation.

While I was in Chicago, I found Lyft to be a lot cheaper than Uber and the cars came faster. You may have a different experience but check both apps.

Biking in Chicago

When I was in Chicago I saw public bikes called Divvy Bikes all over Chicago.

How to get around Chicago | Divvy bikes in Chicago operated by Lyft

You can buy a Pass from Divvy, find an available bike, unlock the bike and take short rides. In fact Lyft operates the Divvy system in Chicago. When you look for cars on Lyft, you can actually see options for Divvy bikes.

For more information on Divvy Bike, see their official website .

Hop-on-hop-off bus in Chicago

If you just want to go to the main attractions in Chicago then a hop on hop off bus may be worth it.

Big Bus Hop on Hop Off Bus in Chicago

I saw a lot of people using Big Bus Tours when I was in Chicago and they are very conveniently located with stops at all the popular spots. They are also covered under the Chicago Pass and Chicago Explorer Pass if you want to save money.

Where to Eat in Chicago

Chicago is a food lover’s paradise, with a vibrant culinary scene that offers a diverse range of dining options. Whether you’re craving deep-dish pizza, sizzling steaks, ethnic cuisine, or innovative fine dining, the city has something to satisfy every palate.

If you are in Chicago you probably want to try the iconic Chicago hotdog, deep dish pizza, and Italian beef sandwiches.

Chicago hot dog photo | Best things to eat in Chicago

For Chicago hot dogs , I would recommend Superdawg Drive-in , the Wiener’s Circle , Portillo’s and Devil Dawg .

Chicago Deep Dish Pizza at Giordano's | Iconic things to eat in Chicago for a first time visitor

For deep dish pizza , the three most famous places are Lou Malnati’s Pizzeria , Giordano’s , and Pequod’s Pizza .

Chicago's Italian Beef Sandwich at Portillo's | Best food to eat in Chicago for a long weekend

When it comes to Italian beef sandwiches , be sure to check out Portillo’s or Al’s Italian Beef .

The Purple Pig Restaurant in Chicago | Best restaurants in Chicago for first time visitors

There are just so many amazing and famous restaurants in Chicago that I can’t list them all. Some of the most noteworthy restaurants include Alinea , Girl & the Goat , Au Cheval , XOCO , Grand Lux Cafe , and the Purple Pig . If you want a really beautiful restaurant then head to the RH store and eat in their 3 Arts Club Cafe (super overpriced though!).

Chicago itinerary - best places to eat in Chicago -Girl and the Goat appetizers

I bookmarked all of these restaurants (and more) on my Google Maps above. You should definitely aim to get reservation at least 2 weeks in advance for many of these restaurants (except Alinea, that’s a whole different story).

Alternatively you can just book a walking food tour and get a taste of everything famous and iconic.

Saving Money on Chicago Attractions

If you are planning to visit all the major attractions in Chicago, then the best way to save money is to get one of the Chicago discounted attraction passes.

The individual attractions do cost between $30 – $50, and they add up to quite a lot of money if you want to see all the famous ones.

With these Chicago discount passes you pay upfront for the pass then you can visit the available attractions for free (within a particular time period or with a particular number of attractions).

Using the first day of this 3 day Chicago itinerary as an example, visiting the 3 museums and Skydeck turn out to be about $144 but with a one day Chicago Pass you only pay $112 (after discount) so you can save quite a bit of money.

You can read this detailed Chicago pass comparison to see which pass is the best for you (hint: my favorite is the Chicago Explorer Pass because of its versatility).

Other ways to save money in Chicago is to take public transportation and walk instead of taking Uber everywhere unless it’s late night.

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Pinterest Pin 3 Days in Chicago Itinerary and Travel Guide with 4 photos. upper left: girl in front of tank at Shedd Aquarium; upper right: stained glass ceiling at the Chicago Cultural Center; lower left: girl standing on the ledge at skydeck; lower right: cloud gate in Chciago

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visit chicago 3 days

The Perfect 3 Days in Chicago Itinerary as per a Local

There is a really good chance that this post contains affiliate links. If you click through and make a purchase, I may receive a small commission (for which I am deeply grateful) at no additional cost to you.

Chicago is one of America’s most iconic cities . This 3 Day Chicago Itinerary will help you get the most out of your visit. On Day 1, you’ll visit Millennium Park and check out Chicago’s famous loop neighborhood. On Day 2, you’ll bike up the lakeshore and check out Navy Pier. On Day 3, check out some world-class museums and an observation deck. We’ll also guide you to the best restaurants and bars. This 3 days in Chicago itinerary is curated by a local. Let’s get started!

Chicago Itinerary - How to spend 3 days in Chicago (what to do and see)

Best time to visit Chicago

Chicago comes to life in the summertime! Although you can visit year-round, summer is best. Being situated on Lake Michigan makes Chicago vulnerable to dramatic, unpredictable, weather changes, strong winds, and chilling temperatures.

In the summertime, you’ll get to walk around freely, dine outside and visit rooftop bars. Springs in Chicago can be rainy and cold. Autumn tends to be nicer than Spring and would be the second-best time to visit. (Or the best time to visit if you don’t like muggy heat).

Where to stay in Chicago

If you’re looking for affordable luxury, I highly recommend the Chicago Athletic Association Hotel . It’s our top pick because it’s located right on Millennium park AND they have an incredible rooftop restaurant and bar — Cindy’s. Hotel guests get more exclusive access to Cindy’s and don’t have to wait in long lines to get in.

Budget friendly alternatives in the loop include the HI Chicago Hostel and Freehand Chicago. You can also opt-in for an Airbnb accommodation.

How to get around Chicago

Chicago is a big metropolitan city that’s well connected by public transportation. Mainly, buses and the “L” train. You can get an unlimited 3-Day CTA pass for $20. This would be the most economical way to get around the city. You can see quite a lot during your Chicago 3 day tour.

Otherwise, you can take taxis and Ubers. Expect to pay $10-15 for a 10-15 minute ride (depending on traffic of course).

If you do not love walking or prefer getting the main highlights in your first 24 hours, you can book a hop-on-hop-off tour .

A Quick Note on Traffic : Chicago has horrendous rush hours! Don’t get stuck in them if you can avoid it. It’s best to walk or avoid transit between 4:30 -6:30 PM on weekdays. Fridays are the worst, but summertime, in general, is pretty bad.

visit chicago 3 days

You might also like: How to spend the perfect 5 days in New York City


Chicago 3 day Itinerary

Chicago itinerary day 1, morning/afternoon.

Start your first day in Chicago with brunch at Cindy’s Rooftop. You can make a reservation in advance on their website. It’s a great place to sneak views of the stunning Millennium Park while you enjoy healthy, modern, breakfast favorites. I especially love the Avocado Toast. Also, the cocktails are amazing!

Next, head to Millennium Park. It’s across the street from Cindy’s Rooftop. Take your time exploring the park. Visit the Millennium Monument, Crown Fountain, the Lurie Garden and the Jay Pritzker Pavilion. Take selfies at “the Bean” or Cloud Gate.


Cross the BP Pedestrian Bridge and enter Maggie Daley Park. When you get to the end of the bridge, turn around. You’ll see stunning views of the skyline. Make sure to snap some photos here.

If you like guided tours, this is a great opportunity to join one of the popular Chicago Segway Tours . Another favorite tour of mine is the Chicago River Architecture Cruise . You can discover hidden architectural gems among the city’s renowned landmarks.

Head to Portillo’s for lunch. It’s a local Chicago fast food joint that’s made its mark across America. Still, Chicago is the best place to try Portillo’s. I always visit their huge Ohio Street location that has outdoor patio seating.

Try the Italian Beef Sandwich at Portillo’s. This is the most traditional Chicago style foodie fix. Add the cheese fries. Finish it off with a Chocolate Cake Shake… Is your mouth watering yet? In case you are looking for a healthier alternative, the Chopped Salad is another local favorite.

Traveling to Chicago with a partner? Here’s are some legendary Chicago date ideas .

USA-3-day-Chicago-itinerary-Crown Fountain

You can start your evening with a walk down Michigan Avenue. This is where you’ll find the city’s best shopping. Michigan Avenue runs North/South. Where Michigan crosses Delaware, this is where the luxury designers and high end retailers are clustered. For more luxury designers walk down (the nearby) State Street. Between Chestnut and Ohio Street are the more mid-level retail chains.

Have dinner on your first night in Chicago at Gilt Bar. You’ll want to make a reservation in advance. Request outdoor seating or ask if they can squeeze you into the Library. The Library is Gilt Bar’s ultra intimate speakeasy type bar. See more of Chicago’s top restaurants .

what to see in chicago in 3 days - USA-Chicago-Gilt Bar

Gilt Bar has been a staple of the Chicago Dining scene for years, and it hasn’t gone out of style. They serve decadent American comfort food alongside craft cocktails. I love the Orcchiette Pasta & Steamed Mussels. Don’t skip dessert! Get the Carrot Cake with Salted Caramel Ice Cream. You won’t regret it.

Finally, head to a rooftop bar for drinks. I recommend the J Parker at the Lincoln Hotel. It’s lively and fun. You’ll see a great panorama of Chicago. Drinks are top-notch.

Recommended: Fun things to do in Michigan

Chicago Itinerary Day 2

Start your second day in Chicago with Brunch at 3 Arts Cafe. This is one of Chicago’s most instagrammable restaurants! It’s located inside a posh furniture store which may sound weird… Trust me, it’s very cool. Glamorous chandeliers, exposed brick, fountains and fabulous food.

Then, head to Navy Pier. This is one of Chicago’s top tourist attractions. Taking a ride on the Centennial Wheel is a Chicago experience you can’t miss! Also, you’ll get to see amazing views of the city.

what to see in chicago in 3 days - USA-Navy Pier

If you want to skip the Centennial Wheel… there’s a low key skyline lookout spot that is completely free to visit. Head to the top floor of the Navy Pier Parking garage and you’ll find it!

After you’ve checked out Navy Pier, you’ll have to bike ride along the lakeshore. You can easily and affordably rent a Divvy bike at one of the many convenient locations. There’s a huge Divvy Station just outside Navy Pier.

what to do in chicago in 3 days - USA-Chicago-DuSable Bridge

Side Note About Biking in Chicago : Bike riding along the lakeshore is best! I don’t recommend tourists try to drive along any of the busy streets. It can be dangerous unless you know what you’re doing. Unfortunately, Chicago is not yet a very bike-friendly city. Also, don’t ride the Divvy bikes on the street sidewalks. People will yell at you! It’s not allowed, and it’s not proper etiquette.

You can choose to bike north towards Lincoln Park, or bike south toward the Planetarium and Museum Campus. Lincoln Park is a huge urban green space with many free attractions. You can visit the Lincoln Park Zoo, the cute Lily Pond and the Lincoln Park Conservatory at no cost!


If you chose to ride South towards the Museum Campus, you can visit one of Chicago’s fabulous museums:

  • The Field Museum
  • The Shedd Aquarium
  • The Adler Planetarium

Tip: You can save up to 55% on attractions with the Chicago Card.

If museums aren’t your thing, riding South along the lakeshore can still be fun. If you go to the area just outside the Adler Planetarium, you’ll be rewarded with spectacular views of the city! Arguably, the best view of Chicago’s panoramic skyline.

Another Favorite: A historical road trip from Tennessee to Virginia

Chicago-Itinerary-Lakefront by Planetarium-USA

You must try deep dish pizza while you’re in Chicago! This is Chicago’s most typical food. My favorite place to get deep dish is Lou Malnati’s. Unfortunately, you can’t make a reservation in advance. You might have to put your name down and wait for a while. Their Gold Coast Location is the best! While you wait, you can stroll through this cute neighborhood.

Another lesser-known, but uniquely famous, deep-dish pizza joint is the Chicago Oven Grinders. They make an extremely cheese dense pizza! They’ve even been featured on Food Network. This place also doesn’t take reservations but is worth the wait!

Check out another rooftop bar on your second night in Chicago! Visit Apogee Lounge for a more relaxed vibe, or Roof at the Witt Hotel for a party atmosphere.

Suggested: Best pizza in Manhattan, NY


Chicago Itinerary Day 3

For breakfast, you can head to the Nutella Café. Enjoy crepes, pastries and bold coffee.

If I could recommend one museum over all the others, I would highly suggest you visit the Art Institute of Chicago. It is Chicago’s most visited museum for a reason! The Art Institute is one of America’s oldest museums and contains one of the largest collections of art in the United States.

The Art Institute is located just south of Millennium Park. Make sure to stop by the Millennium Park Gardens –they’re a hidden gem. I especially love the South Garden. It’s one of the few places in downtown where you can get a break from the crowds.

After your visit, walk around Grant Park and check out Buckingham Fountain. There are always great art installations around.

Buckingham Fountain Chicago

A great place for a casual lunch and margaritas is Flaco’s Tacos in Steeleville. If you are looking for a more upscale experience, head to the NoMI Garden. It’s a secret (ish) rooftop bar adjacent to the upscale NoMI restaurant. Ask for the garden terrace!

Visit an Observation Deck around sunset. The two most popular places are:

  • John Hancock’s 360 Chicago – I would suggest getting the skip-the-line ticket in advance or there is a ticket for this observation deck , where you can Experience Chicago at different times of day/night with 2 visits in a 48-hour period.
  • Skydeck at the Willis (formerly Sears) Tower – This ticket includes The Willis Tower Skydeck + The Ledge Experience.

After you’ve seen Chicago from a rooftop, do the Riverwalk! First, I would suggest getting some photos on the DuSable Bridge or other nearby Bridges. Then, enjoy a leisurely stroll along the river.

You might also like: Where to find the best views of the Manhattan Skyline for free


Finish your last night in Chicago with dinner at one of Chicago’s most famous restaurants – Girl & the Goat. Make your reservations WAY in advance. It’s highly popular. If you can’t get into Girl & the Goat, try Little Goat or Duck Duck Goat instead.

These restaurants are located in Chicago’s up and coming Fulton Market neighborhood. It’s worthwhile to walk around here. Have ice cream at BomboBar ?

Discount Passes (CITYPASS)

The Chicago CityPASS offers a single pass for entrance into five of Chicago’s biggest attractions. When you do your math, the CityPASS does work out to save you some money.

I hope that this 3 days in Chicago itinerary helps you to cover all the must sees, dos and eats. As a long time local, I truly hope you enjoy Chicago to the maximum. Enjoy your travels!

This is a guest post by Valentina from Valentina’s Destinations

About Valentina’s Destinations: Valentina’s Destinations was born from my obsession with meticulously researching, organizing and planning my travel itineraries. I’m originally from Nis, Serbia. My family moved to the US when I was young, and I’ve been living in Chicago for the last decade. My passion is travelling the world with my boyfriend, Remigijus. When we’re not travelling, I work as a physician assistant in the psychiatry field. The mental health field is as rewarding as travelling can be. You can follow Valentina’s adventures on Instagram , Facebook , Twitter and Pinterest .

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The Ultimate Chicago 3 day itinerary according to a local

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visit chicago 3 days

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2 thoughts on “the perfect 3 days in chicago itinerary as per a local”.

visit chicago 3 days

Wow, what amazing beautiful places are in Chicago I guess 3 days is very less…I will do one thing I will plan for 1 week!

visit chicago 3 days

Yeah Joe, Chicago is amazing. There is so much to do. 3 days are good for the main highlights, but a week is always best to get a real feel of the place.

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How to Spend 3 Days in Chicago, IL: An Adventurous Chicago Weekend Trip Itinerary (from a local!)

Everyone knows that Chicago is one of the best destinations in the Midwest .  And with this 3-day Chicago itinerary, I’m sharing some of the best of the Windy City plus some hidden gems that you probably won’t find anywhere else.

Why?  I have lived here for decades and can open your eyes to more than The Bean in Millenium Park, Navy Pier, and the Magnificent Mile.

Save this article and share it with friends for the best way to spend 3-days in Chicago!

3 days in Chicago pin for pinterest.

This site contains affiliate links to products. I may receive a commission for purchases made through these links at no extra cost to you.  There are  only products included that I truly love. I APPRECIATE your support !

Side note:  The following post was written by Tanya, a local of Chicago. This way, you can be sure you are reading the best and most accurate weekend in Chicago itinerary. Locals know best! See the author’s bio at the end for more information.

Table of Contents

How do I get to Chicago?

To reach Chicago by air you’ll need to reserve a flight to either O’Hare International Airport (ORD) or Midway International Airport (MDW). 

Local Tip: Don’t rent a car, the public transportation system in Chicago is extensive and efficient. Most points of interest are within walking distance or near a train station and you will save dollars on parking which starts at $35 per day. 

Bus services like Greyhound and Megabus offer routes to Chicago. The bus journey is suitable for trips under 4 hours . It is a budget-friendly choice compared to flying.

Alternatively, you can opt for a train ride to Chicago . Amtrak runs long-distance train services to the city. Traveling by train is comfortable and eliminates the hassle of driving.

When is the best time to visit Chicago?

One Weekend in Chicago.

Chicago’s location in the Midwest gives you a fantastic chance to enjoy all four seasons to the fullest because of year-round activities.

Summer weather is hot and sometimes sticky. But there are lots of famous festivals like Lollapalooza, and the Taste of Chicago , as well as neighborhood events.

Spring and Fall are excellent times to visit, especially if you want to avoid the peak tourist crowds . You can often find great deals on hotels and activities during these shoulder seasons. Just be prepared for cooler or rainy climates and follow recommendations on how to dress in Chicago .

Where should I stay in Chicago?

Chicago is a melting pot and the various neighborhoods represent a diverse culture of people from around the globe.

If you truly want to experience the culture of Chicago, I recommend that you stay in a neighborhood like Old Town, Lincoln Park, Wrigleyville, or Ukrainian Village. 

However, if you want to be on the beaten path with proximity to the well-known iconic landmarks of Chicago, then you should stay closer to the Loop in neighborhoods like River North, Fulton Market, or the nearby South Loop.

Chicago has a range of hotels that make it affordable for any price point, from hostels to 5-star accommodations.

Chicago Hotel Recommendations: 

  • Budget-friendly Option:  Freehand Hotel is a mixture of private and shared spaces. The rooms are small with basic amenities, but they will make for a good night’s rest. 
  • Mid-range Option: Embassy Suites Magnificent Mile is one of my personal favorites and it is my first choice for a family staycation. If you are familiar with this brand of hotel, they offer free, made-to-order hot breakfasts and a manager’s reception with complimentary cocktails and snacks. This hotel is perfectly situated for popular attractions in Chicago. 
  • Luxury Option:  Four-Seasons Hotel Chicago has exceptional service as one would expect from lux accommodations. It’s a great option for celebrating special occasions or a romantic getaway.  
  • Dog-friendly Stay:  Stay Pineapple, The Loop Chicago- OK, I left out the part about this being an iconic hotel. But, not just the hotel, the entire building is a National Landmark! The hotel is in the Reliance Building which has great architectural significance in Chicago and they are fur-baby friendly.  
  • Unique Option:  The Palmer House – I personally love this hotel because it has a rich history and feels European. It’s also known as the place where brownies were invented. It’s one of the stops on the Chicago walking tour so even if you don’t stay, it’s worth taking a stroll through the lobby. 

3-Days in Chicago Weekend Itinerary

I am super thrilled to share this itinerary for you to see another side of Chicago through its neighborhoods! Here’s exactly how I would spend 3 days in Chicago.

Day 1: Touristy Fun

The Bean in millenium Park.

Although we are going to go off-the-beaten path during these 3 days in Chicago, I do believe some of the touristy stops are worth it for first-time visitors. Day 1 is the perfect time to check these off the list!

Start the morning with Chicago’s Hop On/Hop Off bus tour. You will get some incredible shots of the city, and you’ll see a ton of landmarks in a short amount of time. The bus tour starts at 98 E Wacker Dr and has 13 stops along the way. There’s an automated recording going during the tour to give you a bit of comedy and fun facts about the city.

Get off at the Millenium Park stop to check out the famous Bean . Take some time to wander around the park and people-watch a bit. Then hop back on the bus and continue along the route.

Book your Chicago Bus Tour Here!

Next, hop off the bus at the Chicago Museum Campus and walk to the Shedd Aquarium. This massive aquarium is home to over 30,000 different animals…including the beloved beluga whales!

Tip!! Admission to the Shedd is included in the Chicago City Pass. You can save up to 48 percent on 5 of the top attractions!

Alternatively, enjoy the afternoon at the Art Institute of Chicago. It is a number one tourism spot and we’re proud of that!  Or, if you’d rather shop, let your feet guide you along State Street or the Magnificent Mile. 

Now it’s time to relax a bit aboard a sunset cruise to enjoy the golden hour. This 90-minute architectural cruise takes you on a peaceful journey down the Chicago River while giving you a background of the design and construction of over 50 of the most famous buildings.

If you STILL have more energy, you can end your first night in Chicago with a trip to the Sky Deck for the best views of the night skyline. If you have it in the budget, you can even indulge in a Chicago-style pizza on the 103rd floor.

If a dinner in the sky is not in the budget, no worries! There are plenty of other options in the city to grab a deep dish! I recommend Lou Malnati’s Pizza on Wells Street.

Book your Chicago City Pass here!

Day 2: Explore Chinatown

Buildings in Chicago's Chinatown.

Ready for a cultural trip through Chicago? Grab a light breakfast to go and then catch the red line and head south to the Chinatown stop. The ride from the loop is less than 20 minutes.  

You may be stuffed from the tour, but don’t worry, there are plenty of opportunities to walk it off on Cermak Street, Wentworth Street, or the nearby square. There are tons of family-friendly activities in Chinatown . 

Be sure to check out the Nine Dragon Wall and then take a stroll around Ping Tom Memorial Park.

You can’t visit Chinatown and not sample some of the delicious foods and there’s no better way to do it than a Chinatown Food Tour. A guide will take you to all the best spots with samples at each!

Head back to Ping Tom Memorial Park to catch the water taxi at the pagoda back to the center of Chicago. It’s a great and inexpensive way to see Chicago from another perspective. Just note that the water taxi does not run year-round, it is closed in the winter season.

Then grab dinner at The Purple Pig. Although this spot is a bit pricey, it’s great for indulging in rich foods like pork belly, duck, and braised shoulder. This place is always buzzing because the dishes are that good!

Day 3: Take a Trip to Little India

Henna tattoo and Chicago Riverwalk entrance at night.

Today, I’ll show you how to explore Roger’s Park, a neighborhood on the north end of Chicago.  

After breakfast, take the CTA Red line north to the Loyola stop, walk 5 minutes south to Devon Avenue, then take the #155 bus to Western Avenue for a cultural immersion of “Little India”.  

The street is dotted with restaurants, boutiques, salons, markets, and places to shop for spices, snacks, jewelry, and souvenirs. It will take about two hours to peruse the stores .

Don’t miss the Tahoora Sweets & Bakery for some Indian treats. It will keep you fueled and pairs nicely with a mango smoothie from Annapurna.

If you have time to stop for lunch to enjoy Indian cuisine, it doesn’t get more authentic than this neighborhood. There are MANY choices to choose from.

After lunch, you can stop in one of the salons for a henna application.   Just be sure to make an appointment in advance.

Henna is used for its aesthetic value and as a form of artistic expression. Intricate henna designs on the hands or feet are considered beautiful and a way to show creativity. And if you are traveling with teens or younger ones, they will love it!

Then, head back to the Loyola train station (don’t forget to catch the bus on Devon).  

End your 3 days in Chicago with a stroll along the Chicago Riverwalk and finish your Indian-themed day experience with dinner at a downtown restaurant like Indian Garden Restaurant or Cumin Club. 

3 Days in Chicago Map

Here’s a quick recap and map to help you plan you Chicago weekend getaway!

  • Day 1: Hop on and off Bus tour, The Bean, Shedd Aquarium, Sunset Cruise, Skydeck
  • Day 2: Chinatown, food tour, dinner at The Purple Pig
  • Day 3: Roger’s Park, Henna Tattoo, Chicago Riverwalk

Other Things to do in Chicago:

Lakefront trail in Chicago.

It’s no secret that Chicago is jam-packed with exciting things to do. Although you won’t be able to fit in everything during your Chicago weekend trip, you may want to switch some things around in the above itinerary. Here are some fun ideas!

  • Explore The Art Institute of Chicago : One of the oldest and largest art museums in the United States, The Art Institute of Chicago houses an impressive collection of artworks spanning thousands of years and diverse cultures. From Van Gogh’s “The Bedroom” to Grant Wood’s “American Gothic,” art lovers will find plenty to admire here.
  • Catch a Show at The Second City : Experience the world-famous comedy scene at The Second City, where legendary comedians like Tina Fey, Steve Carell, and Bill Murray got their start. Enjoy improvisational comedy performances or take a comedy writing or improvisation class to tap into your comedic talents.
  • Visit The Field Museum : Delve into natural history and cultural artifacts at The Field Museum, where you can encounter Sue, the largest and most complete Tyrannosaurus rex skeleton ever discovered, as well as ancient Egyptian mummies, and exhibits on dinosaurs, Native American cultures, and more.
  • Take a Walk along the Lakefront Trail : Enjoy breathtaking views of Lake Michigan and the city skyline as you stroll, jog, or bike along the scenic Lakefront Trail. Stretching for miles along the lakefront, this picturesque path offers a refreshing escape from the hustle and bustle of the city.
  • Shop on the Magnificent Mile : Explore the upscale shops, boutiques, and department stores along North Michigan Avenue, known as the Magnificent Mile. From luxury brands to designer boutiques and flagship stores, this premier shopping destination offers something for every style and budget.
  • Experience Chicago’s Blues Scene : Immerse yourself in the soulful sounds of Chicago blues at legendary clubs like Buddy Guy’s Legends, Kingston Mines, or Rosa’s Lounge. Enjoy live performances by talented musicians and feel the rhythm of this quintessential Chicago music genre.
  • Three Dots and a Dash : Chicago has several speakeasies, so if you and your tribe are up for finding the front door, head over to this tiki bar. It’s tucked away in an alley and serves great food and drinks. 

Where to Eat in the City:

Revival food court in downtown Chicago.

It’s no surprise that Chicago is a foodie town. The city is filled with renowned Michelin-star restaurants as well as hole-in-the-wall spots that can draw crowds.  Here are some of my favorite places to eat in Chicago!

  • Gino’s East (Pizza)
  • Giordono’s (Pizza)
  • Pizano’s (Pizza) Psst: Die-hard pizza fans should sign up for a Chicago Pizza tour. 
  • Food Revival (Food Hall)
  • UrbanSpace (Food Hall)
  • TimeOut Market (Food Hall)
  • Chicago French Market (Food Hall)
  • Tank Noodle (Vietnamese)
  • Iyanze Bar and Cafe (West African)
  • Furama (Chinese)- I HIGHLY recommend this spot for some dim sum!

Other Tips to Know BEFORE Visiting Chicago:

  • Weather : Chicago’s weather can be unpredictable (it is the Midwest after all), with hot and humid summers and cold winters. Be prepared for sudden changes in weather by dressing in layers and checking the forecast before your visit.
  • Public Transportation : Chicago has an extensive public transportation system, including buses and the “L” train (elevated/subway). Consider using public transportation to navigate the city efficiently, especially during peak traffic times.
  • Explore Neighborhoods : As this 3-day Chicago itinerary suggests, Chicago is a city of diverse neighborhoods, each with its own unique character and attractions. Take the time to explore off the beaten path!
  • Safety Precautions : While Chicago is generally a safe city for tourists, it’s essential to exercise caution, especially in busy tourist areas and at night. Stay aware of your surroundings, avoid displaying valuables, and stick to well-lit and populated areas.
  • CityPass : Consider purchasing a CityPass to save money on admission to top attractions like the Shedd Aquarium, Skydeck Chicago, and the Field Museum. The CityPass also includes discounted public transportation options.
  • Festivals and Events : Check the city’s event calendar for festivals and events happening during your visit. From the Taste of Chicago food festival to the Chicago Jazz Festival, there’s always something exciting happening in the city.

Author’s Bio:

Tanya is a freelance writer and content creator of Travels & Treasures . She has lived in Chicago for over 30 years and has visited 43 of the 50 United States, France, Italy, Spain, Portugal, and the UK. She writes to guide your next adventure to hidden gems or top tourist sights in Chicago and abroad.

Hey hey! I'm Jordan, a full-time elementary teacher with a side of freelance writing/travel blogging. As much as I LOVE to travel, I also enjoy routine, being home, and sleeping in my own cozy bed. Anyone else?  Enter...weekend getaways! I'm hoping you find this to be your one-stop-shop to plan your next USA weekend trip (with or without your pup).

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3 Days in Chicago Itinerary How To Plan a Chicago Trip by

3 Days in Chicago: Best Itinerary For A Trip To Chicago

Welcome to JetSetting Fools, here you will find our best travel tips for destinations worldwide. Some of the links on this site are Affiliate Links and if you use them to make a purchase, we may earn a commission. For more information, read our Disclosure Policy .

Looking to plan the best trip to Chicago, Illinois? Don’t stress – we have it covered! After visiting the Windy City on numerous occasions, we have created the Ultimate 3 Days in Chicago Itinerary. Including the best sights, must-do activities and local eats, our Chicago trip planner is all you need for a fantastic visit to Chi-town!

How To Plan A Trip to Chicago, Illinois

Planning a Chicago trip can feel overwhelming, but we are here to help! Chicago is steeped in riveting history, decorated with dazzling architecture and is famous for its food scene. While Chicago is bordered on the east by Lake Michigan, the city sprawls in all other directions.

Many of the top Chicago attractions are found in the very walkable downtown loop, and a few must-see Chicago sights are scattered further afield. We are sharing our top tips in a day-by-day Chicago 3-Day Itinerary so that you can plan a Chicago trip without worry.

Pro Tip:  Get (and stay) organized for your vacation to Chicago using our Trip Planning Printables !

3 Days in Chicago

Chicago is one of the best weekend destinations in the United States ! Visiting Chicago in 3 days is just enough time to see the highlights and get a taste of the city – and we squeeze just about all that we can into our perfect Chicago 3 Day Itinerary.

In fact, our trip plan is designed for a long weekend in Chicago – based on the assumption that visitors will arrive on Friday or Saturday and stay until Sunday or Monday. That said, our Chicago in 3 Days Itinerary can be used for trips on any days of the week (with just a few minor adjustments).

While we think three days in Chicago is a perfect amount of time for a visit, we know not all travelers are planning a 3-day Chicago trip. Therefore, we offer alternate Chicago itineraries – for shorter and longer trips – at the end of this article. Whether you are planning a 2-Day Chicago Itinerary, making plans for 4 days in Chicago or devising a Chicago 5-Day Itinerary trip plan, you can use our suggestions for your vacation!

What To Eat & Drink during your Chicago 3 Day Itinerary

Eating is one of the top things to do in Chicago in 3 days. The city is home to numerous legendary eateries – far too many to fit into one fun weekend trip in Chicago. To help, we have narrowed it down to the best Chicago food options.

Throughout our Chicago Three Day Itinerary, we highlight the most famous Chicago restaurants. Our food recommendations include classic eateries, Chicago’s best hot dogs, and – of course – iconic Chicago deep-dish pizza. For drinks in the Windy City, we feature locally brewed beer, swanky cocktail lounges and famous jazz bars. 

You will find all of our recommendations for food and drink sprinkled throughout our 3 Days in Chicago Itinerary.

Our Chicago Itinerary for 3 Days

Our 3-Day Itinerary for Chicago features the best of the city in an easy to follow day-by-day plan. At the end of the post, you will also find our tips for how to get there, where to stay and what to pack.

Our Chicago three-day itinerary includes everything you need to plan your ultimate trip to the Windy City. Save, Bookmark or Pin this post for your Chicago trip!

Day 1 of Your 3 Day Chicago Itinerary: City View, Park, Beach and West Loop

On the first day of your 3-day trip to Chicago, get settled into your accommodations (recommendations below) – then get an overview of the area. Next, explore the city’s best park and beach before setting off for a fun night in Chicago’s West Loop.

Chicago Itinerary by

360 Chicago Observation Deck

Start your Weekend in Chicago Itinerary with the city’s best view! Zip to the top of 875 North Michigan Avenue – formerly the John Hancock Center  – to the 360 Observation Deck. The elevator ride only takes 40 seconds to travel 1,000 feet – so you should have no problem fitting the activity into your Chicago, Illinois trip plan!

Inside the 360 Observation Deck, visitors are greeted with incredible views of the Chicago skyline and Lake Michigan. Spend some time leisurely soaking in the view, sipping a drink at the bar or experiencing TILT – which claims to be the Highest Thrill Ride on the Planet. Buy your tickets now!

Historic Chicago Water Tower, Lincoln Park and North Avenue Beach

With your feet back on the ground, see some of the highlights of the City of Chicago. Walk to a historic landmark, through a beautiful park and along the shoreline on a Chicago beach.

The Chicago Water Tower still stands as a top Chicago landmark. Built in the 1860s, the tower is located on the famous Magnificent Mile. It is one of the few buildings that survived the 1871 Great Fire of Chicago. Although now in the shadow of skyscrapers, the tower is an important part of history and should not be missed by visitors to Chicago. 

Next up on your 3 Day Chicago Trip is the city’s best green space: Lincoln Park. Explore the myriad of paths that crisscross through the expansive lakeside Lincoln Park. If you are planning a trip to Chicago with kids, consider stopping at the Lincoln Zoo (it’s free!)! If the weather is cooperating, continue your walk on the sand at North Avenue Beach – and if it’s summertime, consider taking a swim in Lake Michigan!

Deep Dish Pizza for Lunch

For lunch, indulge in Chicago’s culinary creation: Deep Dish Pizza. Lou Malnati’s Pizzeria is a Windy City favorite known for their butter crust – and is a must-try during your 3 days in Chicago. The family-owned restaurant has several locations (including one just south of Lincoln Park).

That said, it’s not the only place to get gooey deep dish deliciousness on your weekend Chicago trip. There are dozens of highly acclaimed pizzerias serving up deep dish pies in Chicago. Giordano’s, Pizzeria Uno and Gino’s East are all good options for Chicago deep dish pizza. The Chicago Pizza and Oven Grinder Company, however, gets our vote and many rave reviews for their deep dish pizza and creative Pizza Pot Pies. 

Goose Island Fulton Street Brewery Tour

After lunch, continue to the next stop on your Three Days in Chicago Itinerary: The Chicago-born Goose Island Brewery. Established as a small city brewpub in 1988, Goose Island is now a globally recognized beer brand (thanks in no small part to it’s acquisition by Anheuser-Busch in 2011).

At the Fulton Street Brewery and Taproom, patrons are invited to take a brewery tour to witness the behind-the-scenes production process…and then sip delicious, fresh beer. Even if you skip the tour, this is a fun brewpub and should definitely be included on a beer-lovers three day Chicago Itinerary!

Time Out Market Chicago

We were first introduced to the concept of Time Out Markets in Lisbon, Portugal , where we were absolutely thrilled that they brought the best local chefs under one roof. At the Chicago Time Out Market, which is situated in the heart of the West Loop dining district, the idea is the same – and we think it’s a must for your Chicago Itinerary!

Visitors can order dishes from any of the carefully selected 18 Chicago chefs. The warehouse-style market encompasses 50,000 square feet of dining space – and includes 3 bars and a rooftop terrace.

The buzzing Time Out Market features Chicago classics, international fare and decadent desserts that are all well-recognized brands of the city.

A Night Out during Your 3 Day Itinerary Chicago

While patrons can linger at the Time Out Market bars, with only a weekend in Chicago, we recommend moving on to one of the hip bars in the West Loop (or beyond).

Best Bars for Day 1 of your 3 Days in Chicago

There is no shortage of hangouts in West Loop, so where you go depends on your taste. To help you decide, we’ve rounded up a short list of some of the fun bars you can add to Day 1 of your Chicago 3 Day Itinerary.

Blind Barber

Just a block west of the Time Out Market is Blind Barber, a barbershop by day…and a swank, 70s-style speakeasy by night.

Emporium Fulton Market

The fun Emporium Fulton Market is just down the street to the east – and features an array of arcade games and craft cocktails.

Lone Wolf Chicago

A favorite local neighborhood spot, the Lone Wolf is a classic and comfortable establishment to add to your Chicago night out.

Haymarket Brewery

If you are in search of Chicago craft beer, don’t miss Haymarket Pub and Brewery. They also feature live music on weekends.

Green Mill Cocktail Lounge

However, visitors who are planning a trip to Chicago and want to sip a cocktail inside a Chicago institution should leave the West Loop and head uptown to Green Mill Cocktail Lounge.

The iconic bar opened in 1907, was partly owned by Al Capone during Prohibition, has hosted famous singers – such as Billie Holiday – and now regularly features jazz and poetry nights. Just be prepared; it’s a bit north of the city, there is a cover charge, it’s cash only and seating is first come, first served.

Day 2 of Your Chicago Itinerary in 3 Days: The Loop, Architecture and Windy City Sports

On the second day of your Chicago in a Weekend Itinerary, explore top attractions on foot and by boat, then end the day in a classic northside neighborhood, maybe even watching a baseball game!

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Breakfast At The Famous Lou Mitchell’s

For breakfast on Day 2 of your Chicago trip, indulge in a hearty Midwest-style meal at the iconic Lou Mitchell’s. For a 100 years, the diner has been serving up omelets and pouring coffee for hungry patrons. Definitely old school and a little quirky (they hand out Milk Duds), eating at Lou Mitchell’s is a Chicago must!

Union Station Chicago

Ease into your full day of Chicago sightseeing at the landmark Union Station. Opened in 1925, the station serves Amtrak and Metra commuter lines – and ranks as the busiest rail station in the United States outside of New York City . Occupying an entire city block, the classic Great Hall waiting room is at the center – and is recognizable from many popular Hollywood films including The Untouchables and My Best Friend’s Wedding.

The Loop Walking Tour

Spend the rest of the morning walking off your Midwest breakfast on a self-guided walking tour of the Chicago downtown Loop. The district features historic architecture, lush parks and intriguing artworks. Exploring this area is an absolute must when visiting Chicago.

Trip Planner Chicago Loop

Begin your discovery at the well-recognized Willis Tower (formerly the Sears Tower), which ranked as the tallest building in the world when it was completed in 1973. Visitors can soar to the 103rd floor Skydeck Chicago (be sure to buy your ticket in advance !). After visiting the Willis Tower, continue on your tour of the Chicago Loop.

Explore the following Chicago Loop sights (in order) and use this link to Google Maps for locations.

  • Daley Plaza (and Picasso’s Untitled artwork)
  • Miro’s Statue
  • Chicago Theater (and famous Chicago sign)
  • Old Marshall Field Building (and legendary clocks)
  • Chicago Cultural Center (and Tiffany Dome)
  • Millennium Park and Grant Park (Cloud Gate mirrored sculpture a.k.a. The Bean , Crown Fountain – then detour out of the park to see the historic Route 66 Begin sign and go one block west to see the famed Palmer House Hilton Hotel – Chicago Stock Exchange Arch, Buckingham Fountain)
  • Queen’s Landing
  • Lakeshore Trail  
  • Chicago Riverwalk (view The Wrigley Building and Tribune Tower across the river)
  • DuSable Bridge

Billy Goat Tavern For Lunch 

End the tour by crossing the DuSable bridge and walking north on Michigan Avenue to the Plaza of the Americas – then have lunch at Billy Goat Tavern. This iconic eatery is surely a highlight of any weekend trip to Chicago. 

Established in 1934, the Billy Goat Tavern opened at the Lower Michigan Avenue location in 1964 and has been serving their famous “Cheezborgers” ever since. The original owner was the historic instigator of the Chicago Cubs’ Curse of the Billy Goat and the tavern was the inspiration for the Olympia Café in 1970s Saturday Night Live sketches .

Chicago Architecture River Cruise

After lunch, hop on a boat for a different perspective of the Chicago skyline – it’s an absolute must for a summer Chicago weekend itinerary. Enjoy an entertaining hour-long river cruise along the three branches of the Chicago River. The on-board tour guide shares the history of the city and more than 40 buildings that you will pass along the way. Book your seat now!

Wrigleyville (and a Cubs Game)

Home to the much-loved Chicago Cubs (unless you’re from the South Side or St. Louis), Wrigleyville is a north side neighborhood packed with lively bars and fantastic eateries. The historic Wrigley Field is at the heart of the neighborhood – and attending a baseball game (regardless of who you’re rooting for) is a highlight of any itinerary for Chicago.

If the Cubbies are not playing while you are vacationing in Chicago, it is still worth visiting the neighborhood for dinner and drinks. Visit one of the famous Clark Street sports bars – like the Cubby Bear or Sluggers – for simple grub and drinks (or go for a gastropub dinner at Mordecai).

If the Cubs are away and seeing a baseball game is at the top of your list of things to do in Chicago, then check the South Side White Sox schedule.

Outside of the summer baseball season, there are numerous pro sports events that you could add to your three days in Chicago trip plan. Check schedules for the world famous Chicago Bulls (basketball), Chicago Bears (football), Chicago Blackhawks (ice hockey) and Chicago Fire (soccer).

Day 3 of Your Weekend in Chicago Itinerary: Walking Trail, Hot Dogs & Navy Pier

Wrap up your 3 Days in Chicago Itinerary with more sightseeing, eating and walking it off! Start the day at a cool urban park, embark on a local food tour, get a birds’ eye view of the city and end your Chicago tour itinerary at tourist hotspot, Navy Pier.

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Walk Off the Food You’ve Eaten in Chicago in 3 Days

When we plan a trip to Chicago that includes gorging on the local fare, we also carve out time to walk it off. While our Weekend in Chicago Itinerary naturally includes a lot of walking between sights, there are two fabulous places to hit really stretch your legs: 606 Bloomingdale Trail and Lakefront Trail.

The 606 Bloomingdale Trail 

Similar to the New York City Highline and the Paris La Promenade Plantee, the Bloomingdale Trail at The 606  is a repurposed elevated train track-turned-public-park. Running three miles through four districts (Wicker Park, Bucktown, Humbolt Park and Logan Square) on Chicago’s northwest side, the walking trail features art installations and hosts local events.

We recommend walking The 606 from east to west. Churchill Field Park is a great place to hop on the trail. Pop into Mindy’s Bakery, run by famed Chicago chef Mindy Segal, for an incredible breakfast before starting your walk. Just be warned, there will likely be a line out the door – breakfast at Mindy’s is one of the top things to do in Chicago on a weekend – and it’s closed Monday – Wednesday.

Lakefront Trail

As the name suggests, the Lakefront Trail fronts Lake Michigan – and, for many visitors, walking along the shoreline is a highlight of a 3 Day Itinerary for Chicago. The trail stretches for 18 miles and can be used by bicyclists and pedestrians. From the path, there are fabulous views of Chicago and the shoreline. Hop on at any point and walk as far as you would like!

Famed Chicago-Style Hot Dogs

Your Chicago Trip Planner is not complete without consuming at least one hot dog. Chicago Dogs are noted for being ‘dragged through the garden’ – meaning, piled high with toppings that include mustard, onions, relish, tomatoes and a dill pickle spear sprinkled with celery salt (but never ketchup!). Unarguably, the place to get a Chicago Dog is at Portillo’s – a long-time, well-known chain that originated in the city (and has now expanded across the United States). 

In addition to hot dogs, Portillo’s also serves fabulous Italian Beef Sandwiches – another must-eat in Chicago! However, if you are just going after the beef, then go to Al’s #1 Italian Beef – an iconic Chicago eatery chain that was established in 1938.

Alternatively, Join a Chicago Food and Drink Tour

While we have included some of the top must-eat restaurants in our Chicago in a Weekend Itinerary, there is still more feasting to do! Rather than choosing one place for lunch on the last day of your 3 perfect days in Chicago, taste-test your way through the city. Join an expert guide in the local foodie scene to discover favorite haunts and classic fare including Deep Dish Pizza, Italian Beef, famous Chicago Hot Dogs and more. Get the details here!

Explore Navy Pier Chicago

Complete your Weekend in Chicago Itinerary with an afternoon at Navy Pier. Like Pier 39 in San Francisco , Navy Pier caters mostly to tourists, but a fun and enjoyable time is had by all. Featuring a wide array of restaurants, souvenir shops and art exhibitions, Navy Pier is a must-see in Chicago…and a great way to end your Chicago 3-Day trip!

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More Chicago Things To Do

We have outlined our best Chicago itinerary, including the top things to do when you visit Chicago in 3 days. Still, how to plan a trip to Chicago will depend on your specific interests. Therefore, we are sharing more fun things to do that you may want to add to your weekend trip to Chicago Itinerary.

Shopping on The Magnificent Mile

Visitors who want to go shopping in Chicago will find there is no shortage of stores! The best place to shop is on the famed Magnificent Mile, which is the section of Michigan Avenue that runs from the Chicago River north to Oak Street. The cosmopolitan street is lined with an astounding 460 retailers – from recognizable department stores to chic boutiques – and is a top destination for fashionistas planning a 3 Days in Chicago Itinerary.

Chicago Museums

With more than 65 museums in Chicago, there is certainly something for everyone. Whether it’s art, history or science that piques your interest, you can find a museum to include on your Chicago trip itinerary!

Chicago Trip Ideas: What Museums to Visit

When you plan trip to Chicago, it can be difficult to choose which museums to visit on your vacation. We are highlighting a few of the renowned museums to help you decide. 

Art Institute of Chicago: The city’s most famous art museum, the Art Institute is a top pick for 3 days in Chicago trips ( buy Skip-the-Line Tickets! ).

Museum of Science and Industry: The hands-on, family-friendly Museum of Science and Industry is a good museum to visit if you are planning trip to Chicago with kids. 

Museum of Contemporary Art: The fun and modern Museum of Contemporary Art is a fantastic museum to visit on a weekend getaway to Chicago. 

Shedd Aquarium: Whether you are planning a Chicago trip with family, as a couple or with a group of friends, the state-of-the-art Shedd Aquarium is a good addition to your Chicago vacation planner. 

The Field Museum: A fascinating museum of mummies and dinosaurs, the Field Museum is an excellent stop on a 3 day trip to Chicago. 

Adler Planetarium: If time permits in your itinerary, plan a day in Chicago that includes stargazing at the Adler Planetarium. 

Pro Tip : Save money and skip lines with a Chicago CityPass ! If you are planning on visiting more than one museum during your three days in Chicago, it will almost definitely save you money!

Go to a Theater Performance in Chicago

Need more ideas of what to see in Chicago in 3 days? Go to a show! Chicago has a vibrant theater district comprised of more than 250 theaters. From world-class productions to comedy acts, some of the best actors and comedians in the world have graced the stages in Chicago. 

Chicago Neighborhood Exploration

One of our favorite things to do in any city is explore the unique neighborhoods and districts. Throughout our Chicago weekend trip itinerary, we have featured some of the top Chicago districts – but we by no means covered them all. Some of the other places to explore in Chicago are Chinatown, Little Italy, Lincoln Park, Wicker Park, Boystown and Roscoe Village.

What To See Do Eat 3 Days in Chicago, Illinois USA by

How Many Days in Chicago?

We think 3 days in Chicago is the perfect amount of time to get acquainted with the city…but we would have no problem entertaining ourselves for a week in Chicago – or longer!

How many days you spend in Chicago will ultimately depend on your interests, budget and availability.

Sample Chicago Itineraries 

We have outlined a perfect plan for a long weekend in Chicago – but what if your trip plans include more (or fewer) days? No worries! Using our 3-Day Chicago Weekend Itinerary as a base, we are sharing our best suggestions for longer and shorter trips.

1-Day Chicago Itinerary

Planning a Chicago in One Day Itinerary is not easy. The city has so many iconic sights and delicious things to eat that it is difficult to pick and choose which ones to include in your Chicago trip plan. However, if one day is all you have, then we suggest making the absolute most of it!

Chicago 1 Day Itinerary Trip Plan

For us, an ideal One Day in Chicago Itinerary would follow Day 2 in our above plan of what to do in Chicago in three days. However, unless you are passionate about baseball, rather than going to Wrigleyville we would recommend spending the evening on Navy Pier or in West Loop.

Chicago Itinerary 2 Days

With 48 hours in Chicago, visitors can plan a Chicago 2-Day Itinerary that is succinct and hits almost all of the highlights.

Chicago 2 Day Itinerary Trip Plan

If you are planning a 2-Day Itinerary for Chicago, we suggest following Days 2 and 3 of our outlined plan for what to see in Chicago in 3 days. Again, if the Cubs were not playing, we would skip Wrigleyville and spend the evening in West Loop, even squeezing in the Goose Island Brewery Tour if possible.

Chicago Itinerary 4 Days

Planning a 4-Day Chicago Itinerary allows for a lot more sightseeing – including many of the museums that we skipped in favor of neighborhood exploration. 

Chicago 4 Day Itinerary Trip Plan

To organize an ideal 4 Days in Chicago Itinerary, we would follow our Chicago 3-Day Itinerary – then, on the last day, we would use the CityPass to visit the top museums, including The Art Institute, Field Museum, Shedd Aquarium and Museum of Science and Industry.

Chicago Itinerary 5 Days

Spending 5 days in Chicago allows for a lot more adventures at a somewhat leisurely pace.

Chicago 5 Day Itinerary Trip Plan

To plan a perfect 5-Day Chicago Itinerary, we recommend following the above outlined Chicago 4-Day Itinerary – then, on the last day, spend the morning discovering a new neighborhood, go shopping on the Magnificent Mile in the afternoon and attend a theater performance in the evening – then get a drink at the Lobby Bar in the posh Palmer House for a nightcap.

Tips For Planning Your Trip to Chicago

Now that you know what to do in Chicago in 3 days, we have a few more essential tips for your trip!

Organize your Chicago Travel Plan

There is a lot more to Chicago trip planning than determining what to see and do. Don’t worry – we share our top tips for planning a vacation in Chicago – from how to get there to what to pack – in the next sections. 

As you research Chicago vacation ideas and start making reservations, make sure you stay organized. A useful travel planner – like our Printable Travel Planner – will help you keep track of all the details of your perfect Chicago travel itinerary! 

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How To Plan Chicago Trip Budget

A trip to Chicago, Illinois can be expensive – but it doesn’t have to be. Travelers who are planning to spend a weekend in Chicago on a budget have many options for exciting entertainment. We suggest skipping sights with high-priced tickets and partaking in many of the cheap and free things to do in Chicago. 

Get our tips on how to plan the best budget trips – plus get our free Vacation Budget Planner – to help plan your budget Chicago, Illinois trip! 

How To Get to Chicago

An essential consideration for your Chicago trip itinerary is how to get there! Chicago can be reached by car, bus, train or plane. On our trips to Chicago, we have always arrived via plane.

Flying To Chicago

There are two major Chicago airports: O’Hare International (ORD) and Chicago Midway (MDW). Both airports have their pros and cons – O’Hare is an enormous airport serviced with flights from around the world ( London , Hong Kong , Tokyo , Munich , etc.), but is far from the city center. Alternatively, Midway dominated by Southwest Airlines and they service mostly US domestic destinations, but is much closer to downtown Chicago.

Both airports are connected to downtown Chicago via public transport (the Blue Line from ORD and the Orange Line from MDW), but visitors can also use taxis, Uber or private transport , too. 

Start your search for the best airfare and flight times on SkyScanner  – but first read our Top Tips for Finding Cheap Flights .

Trip To Chicago by Train

If you are traveling to Chicago from another city that is serviced by Amtrak, then you can also plan a Chicago 3 Days Itinerary with arrival by train. That said, the journey will likely take longer and could even be more expensive than flying – so bear that in mind as you make your trip plans! 

Getting Around Chicago

Downtown Chicago is very walkable – but getting to the districts outside the city center require transportation. Besides your own two feet, visitors have options when it comes to getting around Chicago – from the ‘L’ train to CTA buses to bikes to scooters to Uber and Lyft. 

Public Transportation

Chicago has one of the most extensive public transportation systems in America and makes getting around Chicago fairly easy. Both the ‘L’ train and buses have extensive networks. The affordable fares can be paid using a Ventra account – and both 1-Day and 3-Day flat fare tickets are available for your Chicago visit. Find Chicago Transit fare info here . 

More Ways to Get Around Chicago

That said, using Uber or Lyft is likely much more convenient – and if traveling in a group – not too expensive.

We do not recommend driving a car during your Chicago weekend itinerary; parking is a hassle and can cost a bundle.

Chicago Hop On Hop Off

The Chicago Big Bus provides an excellent service for travelers who want to easily get from one tourist site to the next. The Hop On Hop Off Chicago buses are double-decker, open-air vehicles that make stops at all top attractions – and include informative on-board commentary! Buy your ticket!

Where To Stay in Chicago

Although there are hundreds of places to stay in Chicago, for your Chicago vacation itinerary, we recommend choosing downtown accommodations.

Chicago Hotels

If you are going to splurge for 3 nights in Chicago, there is no better place than The Palmer House Hilton . The historic hotel, featuring a gorgeous lobby, is in a prime location within the Theater and Financial Districts near Millennium Park.

That said, there are hotels in Chicago that fit every budget and style. To find the perfect Chicago hotel for your stay, start your search on – like we do. Use the filters to select the hotel amenities that are most important to you – and use the map to find the best location. Be sure to read all of our best tips for booking hotels !

3 Day Trip Chicago Vacation Rentals

In our travels, we often use Airbnb to find affordable apartments in the places we visit. In fact, we have found that Airbnb is sometimes less expensive – and offers more space – than most hotel rooms.

However, this is not always true on short stays. Be sure to check the extra fees when booking a short trip – like 3 days in Chicago – before confirming your Airbnb stay.

What To Pack For Your Chicago Trip

We have a few final tips and packing hacks for what to pack for your 3 perfect days in Chicago. Need a packing checklist? Grab your FREE Printable Packing Checklist here !

Weather Appropriate Clothing for Your Chicago 3 Day Itinerary

What you pack in your suitcase for a trip to Chicago will depend on the season. Winters can be frigidly cold, summers are often unbearably humid, springtime is wet and autumn is likely to be brisk, hot or soggy. So yes, the frequent weather changes make planning what to pack for your trip a bit of a conundrum.

If you are taking a Chicago summer vacation, pack loose-fitting clothes, a wide-brimmed travel hat and sunscreen . In the wintertime, you will need a winter coat, cozy cap  and gloves . And, if traveling in the spring or fall, make sure to bring a packable raincoat and travel umbrella . Because the weather can fluctuate, it is best to pack clothing that can be layered and carry a great day bag for quick wardrobe changes and all your everyday essentials .

Walking Shoes for Your Itinerary for Chicago

Our Chicago 3-Day Trip Itinerary includes a ton of walking! We recommend wearing a pair of comfortable walking shoes for trekking around the city. I like to wear these lightweight shoes by Columbia and Kris prefers wearing his Merrell trail shoes for city walks.

Travel Camera

Chicago is incredibly photogenic – and, if you are anything like us, you will be snapping a lot of pictures during your three days in Chicago. Instead of using your cell phone camera to capture the sights, we recommend upgrading to a real camera . We travel with a DSLR Canon Rebel and use an everyday 18-135mm lens . The camera comes bundled with tons of accessories – so it is perfect budget camera for beginners!

US Travel Insurance for Your Chicago Itinerary 3 Days

Travel insurance can be useful on all kinds of trips – even a long weekend in Chicago. It can cover unfortunate situations, like cancelled trips, lost luggage and more. Check rates and coverage on World Nomads .

Start planning your trip to Chicago, Illinois ! Search for the lowest airfares , the best accommodations and fun things to do …then start packing !   Want more travel planning tips? Head over to our Travel Planning page for more information and tips on traveling – and for country-specific information, take a look at our Travel Guides page !

Visit More Top Destinations In The USA

Planning other trips in the United States? Use our detailed guides to discover the best of cities across America (and some Underrated US Destinations ). In fact, we wrap up our top picks for the best places to go in our guide, 22 Weekend Getaways in the US !

Best Weekend Getaways in USA Top 22 Destinations

Already have a destination in mind? We offer comprehensive guides for Phoenix , Columbus OH , Indy ,  Portland , Austin , Seattle , Boston , Denver and San Diego – to name a few! 

Up for a US road trip? Use the tips in our articles for the Oregon Coast , Columbia River Gorge , the California Coastline and through amazing Montana.

Find all of our tips for traveling in the United States on our USA Travel Destinations Page . 

We Want To Know: Do you have any advice on how to spend 3 days in Chicago? Is there anything you would add to our Chicago Itinerary? Give us your best tips on how to plan a Chicago trip in the comments below! 

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visit chicago 3 days

The Perfect 3 Days in Chicago Itinerary in 2024

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I’m fresh off the plane from a fantastic couple of days in Chicago. Visiting the ‘ Windy City ’ has been high on my USA bucket list for quite some time and it did not disappoint. With an even more impressive skyline than New York City, Chicago makes a perfect city break. Discover some of the best ways to spend 3 days in Chicago with this jam-packed itinerary.  

visit chicago 3 days

Chicago is one of those cities that is best explored on foot , and it’s effortless to navigate your way around. With skyscrapers that seemingly touch the skyline, you may end up with a crick in your neck, but it’s totally worth it. Even if you have no background or interest in architecture, you can’t help but admire the Chicago skyline. It’s breathtakingly beautiful and awe-inspiring. 

visit chicago 3 days

One of the most startling things about Chicago is how clean it is. During our visit, we often compared it to New York City which is dirty and grimy in comparison to Chicago. We failed to spot any trash on the streets, nor did we ever see any street sweepers, but it was spotless the entire time we were in the city.

Chicago Travel Tips

Getting around chicago.

Walking is honestly the best way for exploring Chicago. It’s an incredible city to walk around and you never know what you’ll stumble upon.

If you’d rather take the elevated train, ‘the L’ , that rumbles around the city above street level, you can buy a daily (or multi-day) Ventra ticket that provides you unlimited rides around Chicago on the CTA trains & buses network. 

If you are mobile, I highly recommend walking around downtown Chicago and experiencing the city. I never felt uncomfortable or unsafe. 

GoCity Pass Chicago

If you are planning on visiting a couple of museums, taking some tours and visiting a skyscraper or two then you should definitely think about getting the GoCity Pass Chicago . Like most cities, there is a lot to see in Chicago and purchasing tickets for a couple of activities can get expensive really quickly. 

visit chicago 3 days

I would highly recommend purchasing the GoCity Pass Chicago as it offers you access to the following attractions:

  • Hop-on/Hop-off Buses
  • Shedd Aquarium
  • 360 Chicago
  • Skydeck at Willis Tower

Museum of Science & Industry

  • Navy Pier rides & attractions
  • Architecture Cruise
  • & much more…

The GoCity Pass Chicago offers 1, 2, 3 & 5 day-passes for a selection of attractions across the city. We saved ourselves a small fortune by purchasing the 1-day GoCity Pass when we recently visited Chicago. In hindsight I wished we had purchased the 3-day GoCity Pass Chicago but oh well. 

visit chicago 3 days

Millennium Park & The Bean

On the first day of your 3 days in Chicago Itinerary it’s time to explore one of the most iconic sights in the city (& it’s not the skyline!). Visit Millennium Park , an enormous city park that runs parallel to Lake Michigan. The park is home to the Bean (aka the Cloud Gate) , which is one of the most photographed public art sights in Chicago. 

visit chicago 3 days

The Bean landed in Millennium Park in 2004 and was designed by Anish Kapoor. It draws millions of visitors each year, and during our visit at the end of winter, was covered in a light dusting of snow (the Snow Bean). 

visit chicago 3 days

Looking for an iconic and frame-worthy photo of your 3 days in Chicago then head down to Millennium Park and have your photo taken in front of the Bean. 

visit chicago 3 days

Explore the rest of the park (it stretches for a number of blocks), or head to the Art Insitute of Chicago which happens to be one of the largest art museums in the world. Use the GoCity Pass Chicago to bypass the lines and gain quick access to the art displays.

You can spend an entire day exploring the whole museum which houses iconic artworks such as Grant Wood’s ‘ American Gothic ’ (the farmer with a dour face holding a pitchfork, whilst his wife looks extraordinarily displeased with him), George Seurat’s ‘ A Sunday on La Grande Jatte ’, and Edward Hopper’s ‘ Nighthawks ’ (a painting of a moody late-night diner and its handful of patrons). 

Chicago Architecture Boat Tour

One of the best tours you can do in Chicago is an architecture boat tour on the Chicago River . Truly, this was one of my favorite activities that we did in Chicago on our vacation.

visit chicago 3 days

The Wendella Boats have a 90-minute Chicago Architecture Boat tour with excellent and knowledgeable guides who rapidly explain the architectural styles of the skyline, as well as the history of the city. 

You don’t need to be into architecture to appreciate the Wendella Boat tour, and the seating on the top deck allows for some of the most fantastic views of Chicago’s skyline.

visit chicago 3 days

Our tour guide was absolutely fantastic and during his break was happy to answer any questions that people had. His knowledge of the city was incredible and I loved his anecdotes.

visit chicago 3 days

Chicago Deep Dish Pizza

Plenty of research went into our Chicago trip as to where we could lay our hands (& mouths ) on the best Chicago Deep Dish Pizza . We studied forums, spoke to friends, and watched endless YouTube in preparation for our Chicago deep-dish pizza experience. 

visit chicago 3 days

If you’re not sure what a Chicago deep-dish pizza entails, it’s essentially a pie. The crust is fitted into a pizza pan, with the cheese on the bottom of the pizza crust and then the toppings are added. It’s baked in the oven for around 30-40 minutes and is an absolute feast.  

We ended up eating in the following restaurants in search of the best Chicago deep-dish pizza :

  • Lou Malnati’s (It came highly recommended but it wasn’t our favorite)
  • Uno Pizza (Our favorite)
  • Gino’s East 

visit chicago 3 days

The following places were mentioned in our research:

  • Pequod’s Pizza (we didn’t have a car, and it was too far for us to visit).

I’ll be completely honest with you, Chicago deep-dish pizza was not for me, however, I know that a ton of people will completely disagree with me. I gave it 3 chances, and I’m very happy to have crossed it off my travel bucket list.

It is one of those things in your 3 days in Chicago that you’ve simply got to try though. Form your own opinion on it. 

Spend your morning walking the beautiful Navy Pier that juts into Lake Michigan and admiring one of the best spots in the city for excellent Chicago Skyline views. Navy Pier is a great way to spend an afternoon or evening, dining in restaurants, hopping on the enormous Ferris wheel, or going on a cruise on Lake Michigan. You almost certainly spend an entire day of your 3 days in Chicago at Navy Pier. 

visit chicago 3 days

The Centennial Wheel lights up at night and is a great way of taking in the city as it starts to light up. Personally, I think this is a better place to take nighttime photos of the city, rather than the likes of the 360 Chicago Observation Tower.

visit chicago 3 days

You’ll also find a quaint carousel, tea cup rides, and one of those terrifying rides that swing you around in tiny seats (aka The Swinger). If you purchase the GoCity Pass Chicago you can use it on the 4 attractions at Navy Pier. 

Eat and drink your way through Navy Pier with a number of fast-food outlets such as McDonald’s, Garretts Popcorn, and a number of other restaurants and stalls. Or enjoy a laid-back cocktail or drink in the largest rooftop bar in Chicago (and apparently the US) – The Offshore Rooftop . 

visit chicago 3 days

Navy Pier is also just a great place to explore and walk around to take in the sights of the city and Lake Michigan. Hop on one of the many cruise boats that line the pier and explore the lake from a large 148-ft Schooner sailboat to lunch and dinner cruises. Sadly these tours do not operate in winter (when we visited) but are operational from April through early November. 

visit chicago 3 days

Magnificent Mile

A very short walk from Navy Pier is one of the premier shopping destinations in Chicago – Magnificent Mile. If you’re anything like me and love to shop, you’ll find this particular stretch to be absolutely incredible. Along the Magnificent Mile, you’ll find department stores such as Nordstrom, Neiman Marcus, and Saks 5th Avenue, as well as iconic stores such as Sephora, Burberry, Tiffany & Co, and countless others. 

visit chicago 3 days

We spent a morning checking our emails in the Starbucks Reserve Roastery which is a must when visiting the Magnificent Mile. Even if you deplore the coffee from Starbucks, a visit to this beautiful roastery is a must. With large open spaces and a pretty solid selection of pastries and coffees to choose from, this is not your typical Starbucks experience.

visit chicago 3 days

It also comes with a hefty price tag. Pictured is our order from Starbucks Reserve Roastery which includes two lattes, two croissants, and an apricot pastry for an eye-watering $48. We weren’t aware until our architecture tour later that afternoon that our coffees were in the region of $12-$15 each. I mean they were tasty and enormous, but not worth the price tag. 

visit chicago 3 days

You can easily spend days exploring the stores on the Magnificent Mile and all that it has to offer. 

360 Chicago John Hancock Building/Sky Deck at Willis Tower

I’m a sucker for an observation deck, I think mainly because I come from Ireland where our tallest building is something like 20 floors high. The opportunity to visit the 103rd floor of any building is always a treat.

visit chicago 3 days

We visited the 360 Chicago Observation Deck on the 94th floor of the John Hancock Building , where you can also participate in the thrilling ‘TILT’ experience. The building calls it a ride, but it’s a glass floor and window that extends out of the building and tilts you forward. 

visit chicago 3 days

The 360 Chicago Tilt is not for the faint of heart or those who suffer from a fear of heights (like myself). Watching the experience was enough to make me weak in the knees and you frankly couldn’t pay me enough money to do something like this! But much braver people will find this a lot of fun and something very different. 

visit chicago 3 days

The best time to visit either the 360 Chicago Observation Deck is just as the sun is setting and about to emerge into that beautiful dusky setting. Tickets are timed , so you will need to check the sunset schedule for your visit to time it just right. 

After visiting the 360 Chicago Observation Deck, I do wish we had decided to visit the Skydeck at Willis Tower (formerly known as the Sears Tower) which is the highest building in Chicago.  

visit chicago 3 days

The Skydeck at Willis Tower is on the 104th floor and has views across Lake Michigan and downtown Chicago. Apparently, you’re also able to see on a clear day up to 4 neighboring states. At the Skydeck, you’ll find the transparent ‘ The Ledge ’ that juts out from the building where you can look down 104 floors below. 

Today on the final day of your 3 days in Chicago itinerary you can spend an entire day at Museum Campus where you’ll find Field Natural History Museum, Adler Planetarium & Shedd Aquarium . If you purchase the GoCity Pass Chicago you can save a lot of money and use it on these superb museums. 

Field Natural History Museum

Rivaling New York’s Natural History Museum, the Field Natural History Museum if one of the largest in the United States. It also has the largest T-Rex on exhibit too. 

I’m not sure about you, but I absolutely love a good natural history museum. There’s something for everyone and in a world where humans like to hunt things into extinction, this can sometimes be the only way of seeing species that no longer exist. 

The Museum of Science & Industry is a must if you are looking for something entertaining for the kids on your 3 days in Chicago. There is so much to see and do in this incredible museum that will peak everyone’s imagination. 

visit chicago 3 days

Featuring incredible permanent exhibits such as a real U-Boat , the stunningly beautiful Zephyr train , and a tornado machine. Seriously there is so much to see and do in the Museum of Science & Industry that you could dedicate an entire day to seeing everything it has to offer. 

visit chicago 3 days

A great family-orientated museum , we probably weren’t the target crowd for this particular visit, but nonetheless, we enjoyed our time visiting the Museum of Science and Industry.

The Museum of Science & Industry is located a few miles from downtown Chicago, and if you are traveling without a car you can hop on a Metra train from Millennium Station and exit at the 55th/56th/57th stop . The station is less than a 5-minute walk from the Metra stop. 

visit chicago 3 days

If you want to visit the Museum of Science and Industry, you will need to purchase a Metra ticket (Ventra tickets aren’t accepted). The price for a Metra return ticket from the Museum of Science & Industry costs $4. 

visit chicago 3 days

Gangsters & Ghosts Tour in Chicago

A solid walking tour of the Loop in Chicago of one of the most famous gangsters in the United States – Al Capone. The Gangsters & Ghosts walking tour starts at the Chicago River and has some fascinating tidbits of Chicago history laced throughout the tour, as well as that of Al Capone and other notorious gangsters of the time. 

visit chicago 3 days

The ghost stories are pretty spooky but as a treat, halfway through the tour, you get to visit the Palmer Hotel where you can purchase a sampling of the infamous Brownie that was created during the Chicago fair in the 19th century on its premises. 

visit chicago 3 days

A little caveat to the Gangsters & Ghosts Tour in Chicago , you should have some knowledge of who Al Capone is and the Prohibition era of US History. You may end up slightly lost if you are unfamiliar with either. 

Cool places to eat in Chicago

We’re always on the lookout for cool places to eat in Chicago or wherever we travel to. Sometimes it’s a lot of hits, and then there are a lot of misses too. Chicago was one of those places where I think if we had an infinite amount of time we could have found some really cool places to eat in Chicago. 

visit chicago 3 days

The cool places to eat in Chicago that we did find and enjoy were through recommendations of friends who live in the city or have repeatedly visited. Google reviews and Tripadvisor reviews are always notoriously sketchy, so we try not to rely on them too much.

All the places listed below in the cool places to eat in Chicago were actually visited and enjoyed and you should consider adding them to your 3 days in Chicago itinerary too. 

Our hotel was just around the corner from Beatrix on North St. Clair Street (there are various locations around the city), so we lucked out with a really good breakfast and brunch spot . The food in Beatrix was seriously good. 

visit chicago 3 days

At this stage of the vacation, I needed a break from pancakes (I don’t eat eggs), so Beatrix had some excellent options such as Chia Pudding, and a delicious Granola Yogurt bowl . 

visit chicago 3 days

My partner B ordered the French Toast and it was absolutely life-changing . The breakfasts at Beatrix were fantastic and it would definitely be one of the cool places to eat in Chicago the next time you visit. 

Gibsons Bar & Steakhouse

We thoroughly enjoyed our fantastic fillet steaks in Gibsons Bar & Steakhouse in the Gold Coast part of Chicago. It’s an absolutely buzzing restaurant, that even on a Tuesday night was packed to the brim with patrons. It’s a short walk from 360 Chicago and serves seriously good value steaks. 

visit chicago 3 days

The food was so good here, I didn’t even take a picture of any of the food. Some tips for ordering:

If you are ordering the fries as a side to your steak or fish, there is enough food for 3-4 people. And ask for no salt, as they were slightly oversalted. 

On a separate note, I loved this part of Chicago and would have liked to have spent some more time exploring the area. It’s got a bougie village feel to it. 

Lil’ Ba-Ba-Reeba!

We fancied some Spanish tapas one evening and set our sights and stomachs on Lil’ Ba-Ba-Reeba! If you’re not familiar with Spanish Tapas then you are in for a treat. It’s essentially small dishes that range from h am croquettes (jamon croquettes), small cubed potatoes in a fiery tomato sauce ( patatas bravas ), grilled peppers with salt ( Padron peppers ), and lots of other deliciousness. 

visit chicago 3 days

This was definitely one of the cool places to eat in Chicago on a Monday night as they serve $20 pitchers of Sangria and the restaurant was packed. The food was delicious and we ordered 4 tapas to share. We could have definitely eaten more but we really wanted to try Garretts Popcorn on our way home. 

Cool places to eat in Chicago that I wish we’d had more time to try:

  • Au Cheval 
  • Girl & the Goat
  • Green Street Smoked Meats
  • The Purple Pig Restaurant
  • Bavette’s Bar & Boeuf
  • Time Out Market Chicago

Where to Stay in Chicago

There are a lot of really decent hotels in Chicago that are spread out across the city. When deciding where to stay in Chicago make sure you do some research for yourself and your needs. I’ve broken down 4 key areas that are worth looking into when deciding where to stay in Chicago here .

3 days in Chicago is just enough time to get a feel for the city and tick off some of the highlights that the city has to offer. There’s a lot to keep everyone entertained, whether that means shopping or visiting museums or hanging out on Lake Michigan.

visit chicago 3 days

Our visit at the end of winter meant that we couldn’t go out on a boat on Lake Michigan but everything else was operational. The weather was relatively mild (considering it was the end of February), and there were even 2 days that I walked around without a jacket. I believe this is very abnormal for that time of the year in Chicago.

Let me know what you thought of your 3 days in Chicago and what changes you would make to the itinerary. Fewer museums? More tours? More shopping?

visit chicago 3 days

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Le Travel Style

by Courtney Delfino • a San Diego based travel + lifestyle blog inspiring you to travel in style

Travel , Travel Guides , USA · Last Updated: February 17, 2024

How to Spend 3 Days in Chicago: a Chicago Itinerary

A full 3 days in chicago itinerary.

So you only have 3 days in Chicago? Well, that is the perfect amount of time to explore the Windy City. Chicago, also known as the “Windy City”, is one of the largest and most vibrant cities in the United States. This Midwestern metropolis has something for everyone, from world-class museums and stunning architecture to trendy neighborhoods and delicious food.

It’s one of my favorite cities because it has a little something for everyone to enjoy. The people are pure gold, the food is *chefs kiss*, and there are ample things to do in Chicago. In this “3 Days in Chicago Itinerary”, I’m sharing everything to know before visiting so you can truly enjoy all it has to offer!

Best Time to Visit Chicago

the chicago theatre marquee

They don’t call it the windy city for anything! The temperatures in Chicago can drop below zero in the winter so it’s best to travel to Chicago from May-July and September-November. Where the weather is mild and you’ll be able to enjoy walking around the city without freezing. Finally, St. Patricks Day is the most popular time to visit Chicago. The riverwalk turns green to celebrate the occasion and the entire city takes place in the festivities.

While all opinions and recommendations are always my own, my content on this blog post may contain affiliate links for hotels I’ve traveled to, tours I’ve completed, and products I recommend. This means I get a small commission (at no additional cost to you) if you book a stay or purchase a product after clicking one of these links. As always, I am so thankful for your support so I can continue to offer free resources.

Where to Stay in Chicago

Chicago has no shortage of beautiful hotels to choose from. If you’re like me and love a little luxury then I highly recommend these two hotels:

  • The Langham Chicago: luxury at its finest with the best views of the riverwalk. Make sure to take advantage of their club access when staying it includes breakfast, lunch, and dinner. Experiencing the Langham Club was incredible I think about those stunning views often. Book your stay here !
  • The Four Seasons: the ultimate 5-star hotel close to all the major shops. This hotel offers incredible service and rooms, beautiful views of the lake, and the tastiest in-house restaurant, Adorn. Book your stay here !

Mid-range hotels:

  • The Pendry: located right across from Millennium Park this hotel is in a prime location. Book your stay here !
  • Kimpton Gray Hotel: also located near millennium park this hotel offers packages that include food as well. Book your stay here !

Best Things to Do in Chicago

Millennium park.

Home to the infamous bean (which is properly named the Cloud Gate sculpture), Millennium Park is a must-see for every visitor. Take a stroll through the park and enjoy the public art and green spaces. The bean sculpture is the most famous landmark in this city and with the Chicago skyline in the background, it makes for the perfect photo opportunity.

Another popular feature of Millennium Park is the Jay Pritzker Pavilion, an outdoor concert venue that hosts concerts, festivals, and other events throughout the year. The pavilion is famous for its unique design, which includes a trellis made of stainless steel that curves over the stage and a sound system that provides excellent acoustics.

Millennium Park is open year-round and admission is free. It’s a popular destination for both tourists and locals, and there are always events and activities happening in the park. Whether you’re looking to take in some art, catch a concert, or simply enjoy a sunny day in the city, Millennium Park is a must-visit destination in Chicago. Finally, it’s magical to visit during the fall.

Architecture River Cruise

If you’ve seen “My Best Friends Wedding” then you’ll remember when Julia Roberts is dancing with Michael atop the Architecture River Cruise. It’s one of the most popular things to do in Chicago. A must-see for your 3 days in Chicago.

During the 90-minute tour, knowledgeable guides provide insight into the history and design of each building, offering a fascinating look at the city’s rich architectural heritage. Some of the highlights of the tour include the Wrigley Building, the Tribune Tower, the Marina City complex, and the Willis Tower (formerly known as the Sears Tower).

There is nothing like admiring architecture from the water. Overall, the Chicago Architecture Foundation River Cruise and walking tours are a must-do for anyone interested in architecture, history, or just taking in the stunning views of the city. There are ample architecture tours to choose from!

Walk the Chicago Riverwalk

The Chicago Riverwalk is a picturesque pedestrian walkway along the Chicago River that offers stunning views of the city skyline. Visitors can enjoy drinks at one of the waterfront bars, take a boat tour, or simply stroll along the river.

This 1.25-mile path is a treasured natural amenity for residents and tourists alike. You choose to walk, run, or just sit on a bench and admire you’ll experience the prettiest views of the city. It’s open from 6 am – 11 pm and is best experienced in the early morning while the city is still sleeping. Furthermore, you’ll recognize this spot from many movies including one of my personal favorites, While you Were Sleeping .

Visit the Art Institute of Chicago

Chicago is also home to several world-renowned museums, such as the Art Institute of Chicago, the Museum of Science and Industry, and the Field Museum. The Art Institute houses an impressive collection of art, including works by famous artists such as Monet, Van Gogh, and Picasso. The Museum of Science and Industry features fascinating exhibits on space exploration, genetics, and other scientific topics. The Field Museum is a natural history museum that has exhibits on dinosaurs, ancient cultures, and much more.

Depending on your preference either of those museums are a great way to spend an afternoon in Chicago. Book your tickets in advance!

Walk around Lincoln Park

Lincoln Park is Chicago’s largest park bordering the most affluent neighborhoods in the city. It’s an oasis to the locals from the bustling city of Chicago. One of the main attractions in Lincoln Park is the Lincoln Park Zoo, which is free to the public and open year-round. The zoo features a wide variety of animals, from big cats and primates to reptiles and birds. It also has a beautiful nature boardwalk that provides stunning views of the Chicago skyline.

Another popular attraction in Lincoln Park is the Honeycomb. This structure is unique and offers unique views of the chicago skyline. When visiting, you’ll be surrounded by nature while admiring the skyline from afar. Make sure to wear your walking shoes when exploring this beautiful part of the city. Finally, it’s especially pretty to visit in the fall to witness the changing leaves against the cityscape.

Willis Tower/Skydeck Chicago

The Skydeck Chicago is an observation deck located on the 103rd floor of the Willis Tower (formerly known as the Sears Tower) in downtown Chicago. It’s one of the city’s most popular attractions, offering stunning views of the city and Lake Michigan.

The Skydeck experience begins with a high-speed elevator ride to the top of the tower, which takes less than a minute. Once you arrive, you can step out onto the glass-floored Ledge, a series of glass boxes that extend out from the side of the building. The Ledge provides a unique and thrilling experience for visitors, as they can see the city from a completely different perspective, with nothing between them and the street below but a layer of glass.

Fun fact, you can see four states from the observation deck. It’s most definitely an experience everyone needs to try when visiting. Because of it’s popularity, it is extremely busy so make sure to book your time slots in advance!

The Chicago Theatre

An icon! The Chicago Theatre rivals “the bean” for the most photographed part of the city. This legend was built in 1921 and was America’s first large movie palace. Even if you’re not going to a show, you need to visit the famous marquee. Click here for a show schedule.

The Magnificent Mile

If you’re an avid shopper then The Magnificent Mile is the place for you. This street spans one mile of high-end luxury stores, beautiful architecture, and top-notch eateries. It’s the perfect place to spend an afternoon and grab lunch when you only have 3 days in Chicago.

Visit Milton Lee Olive Park

Located close to Navy Pier is Milton Lee Olive Park. It’s lesser known spot overlooking Lake Michigan featuring stunning views of the skyline. Finally, it’s a secluded spot to the city often with runners and locals taking their daily walk.

Other things to do in Chicago if you have time:

  • Visit Navy Pier
  • Catch a ball game at Wrigley Field
  • 360 Chicago Observation Deck
  • Garfield Park Conservatory
  • Admire the Architecture at the University of Chicago
  • Visit North Avenue Beach
  • Visit the Chicago Water Tower

3 Days in Chicago Itinerary

Here’s a summary of a suggested 3-day itinerary for exploring Chicago:

  • Visit the Sky Deck for panoramic views of the city
  • Walk the Chicago Riverwalk for waterfront views, drinks, and boat tours
  • Take an Architecture River Cruise
  • Dinner at Beatnik on The River
  • Visit Millennium Park
  • Explore the Art Institute of Chicago for impressive art collections
  • Shopping on the Magnificent Mile
  • Lunch at Three Arts Cafe
  • Walk around the Gold Coast Neighborhood
  • Stroll through Lincoln Park and visit the Honeycomb
  • Breakfast in the trendy River North neighborhood
  • Explore Navy Pier for entertainment, shopping, and dining
  • Check out Milton Lee Park for unique views
  • Have dinner at Pequod’s restaurant and catch a show at The Chicago Theatre

Where to Eat in Chicago

When it comes to food, Chicago is famous for its deep-dish pizza. There are several restaurants throughout the city where you can try this classic dish. However, Chicago is also home to a diverse range of cuisines, from hot dogs and Italian beef sandwiches to Korean BBQ and sushi. I’ve listed the top picks below:

  • Three Arts Cafe ($$$$): Did you really visit Chicago if you didn’t go to Three Arts Cafe? The prettiest restaurant in Chicago. Located inside the Restoration Hardware store this cafe is heaven. Don’t sleep on the burger, the best one I’ve ever had in my life!
  • Beatnik on the River ($$$): amazing views of the riverwalk and delicious Mediterranean-inspired foods.
  • Adorn ($$$$): located in the Four Season Hotel, Chef Jonathon Sawyer is cooking up award-winning dishes featuring global-inspired cuisine. Get the poutine and thank me later!
  • Pequod’s ($$): the locals love this spot for the most famous Chicago dish, deep-dish pizza. Being from New York, I’m a hard one to judge but this was surprisingly good. Chicago deep-dish pizza is not your average pizza and reminds me more of a casserole dish. But nonetheless, still tasty!
  • Portillo’s ($): when visiting Chicago you NEED to get a famous Chicago dog. Portillos is the most famous spot with locations all around the city. What makes Chicago Dogs special is its poppy seed bun.
  • Do-Rite Donuts & Chicken ($)
  • Girl & The Goat ($$$)

What to Pack for Chicago

  • If you’re traveling during the colder months make sure to have a warm coat. I’m talking about a puffer jacket. We all want to look cute but when walking around Chicago I highly suggest this puffer coat .
  • Warm socks to keep your feet warm
  • A comfortable but cute pair of booties . I love these chic ones, they’re comfortable for walking!
  • A warm beanie
  • A good scarf
  • My favorite leather leggings that pair nicely with the booties

Thank you for reading my 3 day Chicago itinerary. Chicago is a city that has something for everyone. Whether you’re interested in museums, food, architecture, or simply exploring unique neighborhoods, Chicago is a destination worth visiting.

I hope you have a fabulous time exploring the windy city. If you need more help packing you don’t want to miss my “ 22 Travel Essentials for your next trip ” post. Enjoy your trip!

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XX, Courtney

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visit chicago 3 days

February 21, 2023 at 7:41 am

Chicago during the fall is so gorgeous! These are all really great suggestions, especially all the pretty photo spots near Lincoln Park.

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3 Days in Chicago: The Best Weekend Itinerary

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3-Day Chicago Itinerary

Planning a trip to Chicago? Find out how to spend the perfect 3 days in Chicago with this weekend itinerary for first-timers.

With nearly 55 million visitors in 2017, it’s easy to see why Chicago is becoming a hot spot for domestic and international tourists alike.

If you’re visiting for the first time, this Chicago itinerary will show you how to spend the perfect 3 days in Chicago.

Whether you’re celebrating a birthday trip or a romantic trip, there is something for everyone in this Chicago weekend itinerary.

Table of Contents

What do I need to know about traveling to Chicago?

Best time to go : The best time to visit Chicago is in the spring, between April and June, or in the fall, between September and early November.

If you don’t mind the cold, December is also a beautiful time to visit and see the city lit up for the holidays.

Best area to stay : Magnificent Mile is the BEST neighborhood for first-timers. Other good neighborhoods to stay include The Loop , which is close to Cloud Gate and Millennium Park, River North , which is close to Navy Pier and the Tribune Tower, Gold Coast , which is perfect for luxury travellers, and South Loop , which is ideal for museum lovers.

Best way to get around : Public transport such as the metro (specially the L train) and bus is the fastest and easiest way to get around Chicago. The city is also very walkable.

If you prefer to be comfortable and relax, you can ride the  Hop-On Hop-Off Bus Tour , which is a great way to get familiar with Chicago for first-timers.

Top 5 things to do in Chicago : Willis Tower (Skydeck Chicago), Navy Pier , 360 Chicago (John Hancock Building), Architecture River Cruise (along the Chicago River), and the Art Institute of Chicago .

What’s Chicago known for? Nicknamed The Windy City, Chicago is known for its food (Chicago-style hot dogs, deep dish pizza, and Maxwell Street Polish Sausage), music (blues, jazz, and hip hop), history, and architecture (Sears Tower).

3-Day Chicago Itinerary

Top 10 things to do in Chicago

According to GetYourGuide , here are the top 10 things to do in Chicago. This can help give you some ideas of what to see and do during your 3 days in Chicago.

  • Willis Tower – This is where you’ll find one of Chicago’s most popular attractions, SkyDeck Chicago. Visit for FREE with the Chicago CityPASS .
  • Navy Pier – Such a fun place to hang out during the summer months.
  • 360 Chicago – One of my favorite places to visit at nighttime to see Chicago from above. Visit for FREE with the Chicago CityPASS .
  • Chicago River – Walk along the river or take this popular Architecture Boat Tour .
  • Art Institute of Chicago
  • Aqua at Lakeshore East
  • Lake Michigan
  • Field Museum of Natural History – Visit this popular museum for FREE with the Chicago CityPASS .
  • Centennial Wheel – Soar to heights of nearly 200 feet over Navy Pier with views of Chicago and Lake Michigan.
  • Lincoln Park

Save money on attractions with the Chicago CityPASS

Chicago a big city and there’s lots of fun things to do in Chicago. This can make it challenging to plan an itinerary and determine which attractions to spend your money on.

Getting the most bang for your buck is my #1 priority when planning a vacation and the Chicago CityPASS was rated the #1 Chicago tourism pass by TripAdvisor .

They’re also recommended by Expedia and Chicago CityPASS currently has a TrustScore rating of 4.8/5 on Trust Pilot .

With the Chicago CityPASS, you can save time, money, and enjoy stress-free sightseeing. But don’t just take my word for it. Check out this recent Google review.

chicago citypass reviews

PRO TIP:  Buy the pass online to save time and hassle. To buy the Chicago CityPASS, click here .

What’s included in the Chicago CityPASS ?

✓ Visit Chicago’s 5 top attractions ✓ Valid for up to 9 days ✓ Save 48%  on regular ticket prices ✓ Mobile or printable pass option

Chicago CityPASS   is a multi-attraction sightseeing card where you can choose to visit 5 top attractions all for ONE low price.

This includes free entry to:

  • Field Museum (VIP Entry and All-Access Pass)
  • Skydeck Chicago (Expedited Entry)
  • Shedd Aquarium (Priority Entry)

You’ll also get your choice of the following 2 places:

  • Art Institute of Chicago (Fast Pass)
  • Museum of Science & Industry
  • 360 Chicago Observation Deck
  • Adler Planetarium

The Chicago CityPASS was SO helpful for our weekend trip. This is the best way to visit Chicago. I didn’t have to worry about dealing with money and waiting in long ticket lines.

Simply show your mobile pass at each place to skip the long ticket lines and start your sightseeing adventure. We found the pass was an excellent value for our Chicago itinerary and made visiting attractions stress-free.

How to get your Chicago CityPASS:

Step 1:  Head to Chicago CityPASS to purchase your tickets.

When you purchase through GetYourGuide, you can cancel up to 24 hours in advance to receive a full refund . This can give you peace of mind just in case your plans change.

Step 2: You can use your mobile phone or print your voucher. With email, you’ll get instant access to your mobile tickets. Simply present your mobile admission at each place. .

Step 3: Now you have FREE access to any of the top 5 Chicago attractions included in the Chicago CityPASS. You can activate your pass anytime within 12 months from the date of purchase.

Once activated, your pass is valid for 9 consecutive days, so there’s no need to rush through each attraction.

Read Next: The cheapest way to see Chicago attractions

Plan ahead to avoid disappointment

Chicago can be busy during the summer months. If you have your heart set on visiting a certain place, seeing a particular show, or eating at a specific restaurant, you should book in advance .

Booking in advance is usually cheaper and saves you the hassle of having to wait in long line-ups when you’re in Chicago. Just skip the line and head straight to the attraction.

Even if you’re using the Chicago CityPASS , you’ll need to book some things in advance.

When you purchase the Chicago CityPASS, you can make reservations and book the time slot you wish through their website.

Below are some of the popular attractions and tours that you may want to consider booking in advance.

  • Shedd Aquarium (Advance reservations are required)
  • Skydeck Chicago (Advance reservations are required)
  • Museum of Science and Industry (Advance reservations are required)
  • 360 Chicago Observation Deck (Advance reservations are required)
  • Field Museum (Advance reservations are NOT required for CityPASS guests. Admission is on a timed-entry basis)

Where is the best part of Chicago to stay in?

After visiting Chicago several times and staying in different neighborhoods, I recommend staying in one of these 5 areas:

  • Magnificent Mile – The BEST neighborhood for first-timers
  • The Loop – Ideal for all travellers. See Cloud Gate and Millennium Park.
  • River North – Ideal for all travellers. See Navy Pier and the Tribune Tower.
  • Gold Coast – Ideal for luxury travellers.
  • South Loop – Ideal for all travellers, especially museum lovers.

Best Chicago hotels for every budget :

If you’re traveling on a budget, these are the best cheap hotels in Chicago:

  • La Quinta by Wyndam Chicago Downtown (Close to Willis Tower / Skydeck)
  • Hampton Inn Chicago Downtown/N Loop/Michigan Ave (Close to Cloud Gate)
  • Courtyard by Mariott Chicago Downtown/Magnificent Mile (Great for shopping)

If you have some more wiggle room in your budget, below are some of the best mid-range hotels in Chicago:

  • Fairfield Inn & Suites Chicago Downtown/River North
  • DoubleTree by Hilton Chicago Magnificent Mile
  • Springhill Suites Chicago Downtown/River North

If you want to splurge on your accommodations, below are Chicago’s top luxury hotels:

  • Waldorf Astoria Chicago
  • The Peninsula Chicago
  • Four Seasons Chicago

Best way to get around Chicago

For this downtown Chicago itinerary, I recommend using the city’s public transit . Chicago’s public transportation is excellent and will take you to all the landmarks and sights on your itinerary.

Once you get to the station, you have 3 options for paying your fare:

You can buy a Ventura ticket – This is good on CTA (Chicago Transit Authority). You can get a Single Ride Ticket, a 1-Day CTA Ticket (good for unlimited rides for 24 hours), or a 3-Day CTA Ticket (good for unlimited rides for 72 hours.

You can buy a Ventura Card – This is a rechargable card with money loaded to cover fare for up to seven people. You can get your pass at any Ventura Vending machine or Ventura retailer in Chicago.

If you have Apple Pay, Android Pay or Samsung Pay set up or have a contactless bankcard – Simply go straight into the gates and touch your card there.

Other great ways to get around the city

Walk – Chicago is a big city, but it’s very walkable. Just make sure to wear comfortable shoes – this is a must when visiting Chicago since you’ll be walking around a lot.

Hop-On Hop-Off bus tour – Yes, this is a bit touristy, but it’s a great way to see the city’s top attractions and learn more about local landmarks.

Ride the “L” train – This is the elevated public transit train in Chicago. It’s safe, cheap and one of the best ways to get to all the must-see spots on your Chicago itinerary.

Segway – Taking a segway tour can be another fun and exciting way to explore the city.

Cab or Uber – These are expensive, but it’s a convenient way to get around Chicago.

How to get to Chicago from the airport

Chicago has two airports you can choose to fly into: Midway or O’Hare International Airport . Both airports offer “L” trains that you can take to and from the airport to downtown.

The “L” train is a safe, cheap, and fast way to travel from the airport to your Chicago accommodations.

From O’Hare : The Blue Line “L” train will take you from O’Hare to downtown in about 45 minutes. It costs around $5.00.

From Midway International Airport: The Orange Line “L” train will take you from Midway International Airport to downtown in about 25 minutes. It costs around $2.50.

Related Posts:

  • Chicago CityPASS review: Is it worth it?
  • Quick guide to visiting Chicago on a budget
  • Chicago CityPASS vs. Chicago Explorer Pass – Which is better?
  • 10 reasons to visit Chicago in the winter

Chicago Itinerary: Day 1

Below are the highlights of Day 1 in Chicago:

Skydeck Chicago

  • Art Institute of Chicago or Adler Planetarium
  • Millennium Park
  • Chicago’s Riverwalk (Consider taking an Architecture Boat Cruise )
  • Deep dish pizza (for lunch or dinner)

3-Day Chicago Itinerary

Arrive at Skydeck Chicago  before it opens. This way you’ll be one of the first people in line to catch the elevator to the top.

Plan to spend at least one hour at the Skydeck (depending on how busy it is and how long you wish to stay).

Tips for visiting Skydeck Chicago :

The best time to visit is just after opening or after sunset .

If you want to catch a view of the sunset, plan to arrive at least 30-60 minutes before sunset time . This allows you to view the city in the daytime, twilight, and nighttime.

For those planning to take photos towards the windows, make sure to use the “blacklight” function of your camera if it’s an option. Also turn your flash off and polarizer filter for the best photos.

The Skydeck has implemented timed ticketing . You’ll need to reserve your spot in advance.

If you want to skip the long lines, consider getting Expedited Entry tickets . This will save you a ton of time with an express line to the elevators.

Expedited Entry admission is included when you purchase the Chicago CityPASS .

Interesting facts about Skydeck Chicago :

The Willis Tower (formerly known as Sears Tower) is 1,450 feet (443 meters) high. Including the twin antenna, it’s 1,730 feet (520 meters) high.

The Willis Tower is the 12th tallest building in the world, and the second tallest building in North America and the Western Hemisphere. It’s 110 stories tall.

The Willis Tower has the highest public veiwing area in the USA.

The Skydeck is 1,353 feet (412 meters) above the ground.

One a clear day, you can see four states – Illinois, Indiana, Wisconsin, and Michigan. The visibility from the Skydeck is approximately 40-50 miles (65-80 kilometers).

The Willis Tower elevators operate as fast as 1,600 feet (488 meters) per minute.

From here, take transit or walk over to the Art Institute of Chicago . Plan to spend at least two hours touring the galleries.

The Art Institute of Chicago was named the top art museums in the world. It’s also ranked as the #1 attraction in Chicago on TripAdvisor. You definitely don’t want to miss this when planning your Chicago itinerary.

Save time with the Chicago CityPASS

3-day Chicago itinerary for first time visitors

As you can see, getting the Chicago CityPASS is a good option if you want to visit the 5 top-rated attractions, save 48% off the regular ticket price, and maxmize your sightseeing time.

Tips for visiting the Art Institute of Chicago:

The best time to visit the Art Institute of Chicago is early on a weekday, between noon and 3:00PM.

Kids under 14 years old can visit the museum for FREE . Chicago teens under 18 years old can also visit for free.

If you want to skip the long lines , consider getting the Fast Pass . This allows you to bypass the general admission line at entrances AND offers expedited access to ticketed special exhibitions.

Fast Pass tickets are included when you buy the Chicago CityPASS .

If you’re short on time, the must-see things at the Art Institute of Chicago are the collections of Impressionist and Post-Impressionist art , which is considered some of the best in the world.

The most famous paintings at the Art Institute of Chicago include The Bedroom by Vincent van Gogh, A Sunday Afternoon on the Island of La Grande Jatte by Georges Seurat, Nighthawks by Edward Hopper, American Gothic by Grant Wood, Water Lilies by Claude Monet, and The Child’s Bath by Mary Cassatt.

If you’d prefer to learn about space, I recommend visiting the Adler Planetarium which is America’s first planetarium and a premiere resource for inspiring the next generation of space explorers.  

This is a fun museum to learn about astronomy and astrophysics.

Tips for visiting the Adler Planetarium:

This museum is not as busy as the other big museums in Chicago, so there’s no need to get there early to beat the crowds.

The best time to visit is in the summer months , especially if you want to observe the night sky.

The Adler Planetarium houses 3 full-size theatres and 2 full-size planetariums .

If you’re using the Chicago CityPASS , you’ll get FREE access to all of the exhibitions, plus TWO sky shows. Each show is 30-minutes long. Plan to spend at least 2-3 hours exploring Adler Planetarium.

The Adler Planetarium has Galileo’s Cafe , which offers fresh soups, flatbreads, sandwiches, salads, and desserts to enjoy while taking in a beautiful view of Chicago’s skyline.

Millennium Park & the Loop

Grab lunch at a nearby café and browse the shops in The Loop .

Make your way over to Millennium Park to see the famous the Cloud Gate sculpture (also known as “the bean”).

There is also a great spot to eat at the Plaza at Park Grill here. It features a walk-up bar, casual menu, and live music.

It’s usually busy during the day, but you might get lucky by going early in the morning before other tourists arrive.

Crown Fountain is another popular attraction in Millennium Park. This is an interactive work of public art and video sculpture that splashes water.

Chicago Architecture River Cruise

Walk up Michigan Avenue to the Chicago Riverwalk . This 1.25-mile long path includes four different districts: The Confluence, The Arcade, The Civic, and the Esplanade.

Chicago’s architecture is full of history which is why many people like to take an architecture boat cruise .

This is the most popular tour which takes you on a 60 (or 75-minute) tour to discover hidden architectural gems among the city’s renowned landmarks.

Chicago’s Riverwalk is one of the prettiest aspects about the city and the perfect area to be at sunset as the buildings light up the night.

More fun things to do in Chicago:

  • Navy Pier Centennial Wheel
  • Chicago: Lake Michigan Gourmet Brunch / Lunch / Dinner Cruise

3-day chicago itinerary

Eat deep dish pizza

Sit down for dinner at one of Chicago’s popular deep dish pizza restaurants. There are plenty of places to enjoy this but my favorites are Lou Malnati’s and Giordano.

The pizza takes at least 30 minutes to arrive at the table after ordering, so make sure to get a salad or appetizer if you’re hungry.

Dinner in West Loop

If deep dish pizza isn’t your thing, there are plenty of other great dining options to choose from in Chicago.

Head to the West Loop neighborhood, which has become a foodie’s paradise, especially along Randolph Street (also known as Restaurant Row).

After dinner, catch transit to Second City to see a show. This theatre specializes in sketch comedy and improv.

After opening its doors in 1959, it has become the most influential comedy theatre in the world.

Another popular nighttime activity is to head to Navy Pier to enjoy an up-close of the fireworks with a River Architecture Cruise . Don’t forget to bring your camera!

3-Day Chicago Itinerary

Prep for your trip to Chicago

visit chicago 3 days

Chicago Itinerary: Day 2

Below are the highlights of Day 2 in Chicago:

  • Shedd Aquarium
  • Field Museum
  • Magnificent Mile (Great for shopping and restaurants)
  • Museum of Science and Industry or 360 Chicago

3-Day Chicago Itinerary

Begin your morning at the Shedd Aquarium . Plan to get here when it opens, as it gets busy (depending on the time of year you decide to visit).

This is the largest indoor aquarium in the world and not to be missed when visiting Chicago. Housing more than 8,000 aquatic animals, you can easily spend two hours (or more) exploring all the exhibits.

Tips for visiting the Shedd Aquarium:

The best time to visit the Shedd Aqarium is early in the morning on weekdays , especially Wednesdays, Thursdays, Fridays.

Most visitors spend between 2 and 3.5 hours exploring the Shedd Aquarium.

If you want to see everything, get the All-Access Admission .

This allows you to get into ALL of the exhibits including seasonal Stringray Touch and a 4-D experience. All-Access Admission is included when you buy the Chicago CityPASS .

The Shedd Aquarium offers lockers for a small fee. Here you can store your bags and other personal belongings if you want.

After the aquarium, walk over to the Field Museum . This is my favorite natural history museum in the USA and one of my favorite hot spots in Chicago.

Here you can explore over 26 million biological specimens and cultural artifacts and learn about the story of our planet and its cultures. Depending on your interests, plan to spend a couple of hours here.

Tips for visiting the Field Museum:

The best time to visit the Field Museum is on weekdays or early weekend mornings right when they open.

The busiest time to visit is Saturday and Sunday between 11:00AM and 4:00PM. Fortunately the museum is large, so even on busy days, it won’t feel too crowded.

The museum’s exhibit space is almost half a million square feet! Be sure to wear comfortable shoes and plan to spend at least 3-4 hours exploring the museum.

If you want to see everything, get the All-Access Pass . This includes entry to all the permanent exhibits and regularly priced ticketed exhibitions, plus your choice of on digital 3D film.

All-Access Admission is included when you purchase the Chicago CityPASS .

The best things to see at the Field Museum are Sue the T-Rex , Evolving Planet , Inside Ancient Egypt , Underground Adventure , Grainger Hall of Gems , The Ancient Americas , McDonald’s Prep Lab , and Genghis Khan .

Grant Park, Magnificent Mile, and Navy Pier

3-day chicago itinerary for first-time visitors

If the weather is nice, grab lunch to-go and eat it in Grant Park (just above Museum Campus). This is a nice way to take a break, relax, and enjoy the scenery.

Grant Park is connected to Chicago’s Lakefront Trail. This is an 18-mile path that follows Lake Michigan shoreline on the city’s eastern edge. It’s an excellent place to check out skyline views, various beaches, walk or bike, and enjoy the outdoors.

In the middle of the park, you’ll see Chicago’s most famous fountain: Buckkingham Fountain. This beautiful fountain allows you to admire Chicago’s skyline in front of you and Lake Michigan behind.

Take transit (or walk) up Michigan Avenue north of the river to shop the Magnificent Mile .

Here you’ll see some of Chicago’s most popular skyscrapers, such as the Tribune Tower, Wrigley Building, and the Old Chicago Water Tower.

If it’s a rainy day, head indoors to Water Tower Place. This is a landmark on the Magnificent Mile with over 60 stores including the original American Girl Place.

If you’re not in the mood for shopping, check out Navy Pier which is a Chicago Landmark and offers a variety of attractions for all ages to enjoy.

I recommend riding the famous ferris wheel at Navy Pier (Centennial Wheel), which soars to heights of nearly 200 feet. This is a great way to get a 360-degree view of the Chicago skyline and lake Michigan.

  • Museum of Science and Industry

If you’re interested in learning about science, I recommend visiting Chicago’s Museum of Science and Industry , which is the largest science center in the Western Hemisphere.

Tips for visiting the Museum of Science and Industry:

The best time to visit MSI is right when it opens on weekdays. Weekends are the busiest, especially during the summer months when school is out.

MSI has over 400,000 square foot of exhibit space and is the largest science museum in the Western Hemisphere.

Before visiting, I recommend checking out their website first to look at the experiences, permanent exhibits and tours to think about what you want to see.

Admission to MSI is included for free when you purchase the Chicago CityPASS . This includes museum entry plus one timed-entry experience (Giant Dome theatre film or Motion Ride).

The most popular things to see at MSI include:

  • Coal Mine (descend into a coal miner’s world to learn about the machinery and mining methods)
  • U-505 Submarine (a 35,000 square foot exhibit that showcases the German submarine that was captured in World War II)
  • Whispering Gallery (where you can whisper to a friend from across the room and they’ll hear it)
  • Baby Chick Hackery (where you can watch real baby chicks hatch out of their shells)
  • Science Storms (where you can step into a control booth of a tornado)
  • Planes, Trains & Automobiles
  • Numbers in Nature (where you can check out a mirror maze).
  • 360 Chicago

3-day chicago itinerary for first time visitors

Make your way up Michigan Avenue to visit the top of the 360 Chicago Observation Deck.

Chicago is beautiful at night and I would highly suggest visiting the Skydeck during the day time, and the 360 Chicago at night to make the most of your Chicago itinerary.

Tips for visiting 360 Chicago:

The best time to visit 360 Chicago is before 10:00AM so you can beat the crowds. Make sure to check the weather beforehand so you can make the most of your experience by visiting on a clear day.

To check out the sunset, make sure to arrive one hour before sunset time .

If you’re feeling brave, check out Tilt which literally tilts you outward from the building. This allows you to see the city as if you were floating above it! (There’s an added $8 cost to experience Tilt).

If you don’t want to pay the extra fee to experience Tilt, consider checking out The Ledge at Skydeck Chicago. It’s free with your Skydeck ticket.

To save time and skip the long lines , get Express Entry tickets . This is included when you purchase the Chicago CityPASS .

If you’re feeling fancy, enjoy a delicious dinner at the Signature Room on the 95th floor with the best view of the city. Or if you prefer to just stop in for a drink, check out the Signature Lounge and watch the city lights glimmer in the night sky.

  • Chicago: Gangsters and Ghosts 2-Hour Walking Tour
  • Chicago Hop-On Hop-Off Bus Tour
  • Chicago 1.5-Hour Romantic Sunset Cruise

Chicago Itinerary: Day 3

Below are the highlights of Day 3 in Chicago:

  • Lincoln Park Zoo

Lincoln Park Conservatory

  • Wicker Park (Great neighborhood for shopping and restaurants)
  • Gold Coast (Beautiful neighborhood for shopping and restaurants)

Start your morning by visiting the Lincoln Park Zoo which has free admission and is one of the oldest zoos in the USA (opening in 1868). Plan to spend two hours exploring the zoo grounds.

If you have time, explore the South Pond Pavilion. This is a beautiul boardwalk where you can admire the views of Chicago’s skyscrapers.

Another free activity is to check out the Lincoln Park Conservatory, which is nearby the Lincoln Park Zoo.

This botanical garden is open year-round and is always lush and green. Here you’ll find over 1,000 different types of plants that are used in Chicago parks.

Explore Wicker Park

Hop on transit and head to Wicker Park to browse vintage shops and boutique stores in this trendy Chicago neighborhood. Grab a bite to eat for lunch at one of the many restaurants or cafes in the area.

3-Day Chicago Itinerary

S hop in the Gold Coast neighborhood

After exploring Wicker Park, take transit to the Gold Coast neighborhood which is nestled just north of downtown Chicago.

This is one of the country’s most affluent neighborhoods filled with historic homes, designer shops and one-of-a-kind boutiques.

If you’re looking to relax, sit down at one of the neighborhood cafes for a coffee or tea before heading down Rush Street towards Michigan Avenue.

A popular thing to do in Chicago is to take a food tour. Chicago has some of the best food in the world, so if you’re a foodie, I highly recommend checking out one of these fun tours:

  • Chicago: Lake Michigan Gourmet Brunch, Lunch or Dinner cruise
  • Chicago Secret food tour
  • Chicago: Bikes, Bites, and Brews biking tour

3-Day Chicago Itinerary

As your last evening on your vacation, you have a few options to add to your Chicago itinerary.

For sports lovers, check out a baseball game at Wrigley Field.

For music lovers , head to Andy’s Jazz Club or Blue Chicago to listen to some of the best blues musicians that Chicago has to offer.

For theatre lovers , check out a performance at The Chicago Theatre .

If you feel like doing an activity, head to 10pin Bowling Lounge under the Marina Towers north of the Chicago River. They offer a selection of beers and upscale snacks.

Chicago’s nightlife also offers a variety of lounges and bars to relax and unwind with a drink or two.

  • Amazing Lakefront Segway Tour of Chicago
  • Chicago: 45-Minute Private Helicopter Flight for 1-3 People
  • Chicago Food Tasting: 2.5-Hour Guided Walking Tour

travel planner printables

3 days in Chicago FAQs

How many days do you need in chicago.

3 to 4 days should be enough to see the top attractions in Chicago. However, depending on your interests and travel style, you can certainly spend a week in Chicago exploring the area and main tourist attractions.

What is the best time to visit Chicago?

The best time of year to visit Chicago is in the spring (April through May) and in the fall (September through October). This is when the temperatures are warm and comfortable.

Winters in Chicago can be very cold. But if you don’t mind the cold, Chicago is beautiful during the winter months (November through March). You’ll also find cheaper hotels rates.

Is 3 days enough to visit Chicago?

3 days is enough to see most of the top attractions in Chicago. If you want to take your time exploring the different neighborhoods, then you may want to consider staying 4 or 5 days in Chicago.

What can you see in Chicago in 3 days?

With this 3-day Chicago itinerary for first-timers, you can check out the city’s most popular attractions over a weekend. This includes the Art Institute of Chicago, Skydeck, 360 Chicago, Field Museum, Shedd Aquarium, Navy Pier, Adler Planetarium, Lincoln Park Zoo, and Museum of Science & Industry.

This itinerary also includes exploring the top neighborhoods in Chicago, including The Loop, Magnificent Mile, Gold Coast, Grant Park, and Wicker Park.

Is 2 days enough for Chicago?

With so many things to do, see and eat in Chicago — it’s impossible to do everything in just 2 days. However, 2 days is enough to see some of the city’s top attractions, such as Skydeck , the Art Institute of Chicago , 360 Chicago , and Navy Pier .

How can I spend 2 days in Chicago?

If you want to spend 2 days in Chicago, it’s easy to visit all the main tourist attractions and museums. Arrive the evening before, so you can have two full days to explore Chicago or you can arrive early in the morning.

For 2 days in Chicago, I recommend checking out the Shedd Aquarium , Field Museum , Magnificent Mile , 360 Chicago , Skydeck Chicago , Art Institute of Chicago , Millennium Park (Cloud Gate), Chicago’s Riverwalk (Consider taking an Architecture River Cruise ).

Is 4 days enough in Chicago?

Yes, 4 days in plenty of time to visit Chicago’s main attractions and landmarks. While you might feel rushed if you spend 3 days in the city, choosing to stay 4 days in Chicago allows you to see the top attractions and places.

What should I do in Chicago for a week?

Below are the best things to do in Chicago in a week for first-time visitors. You can check out these places for free with the GO City Chicago Pass .

  • Hop-On Hop-Off Bus Tour
  • Skydeck Chicago (Willis Tower)
  • Shoreline Architecture Boat Cruise
  • Millennium Park to see Cloud Gate
  • Robie House
  • Grant Park and Buckingham Fountain
  • The Magnificent Mile

Is Chicago expensive an expensive city to visit?

Chicago is slightly more affordable for tourists than other large cities in North America, such as New York City. You should plan to spend around $221 per day during your vacation to Chicago (per person).

According to BudgetYourTrip , a vacation to Chicago for one week will cost around $1,547 per person. This means a trip for two will usually cost $3,095 for one week.

Is December a good time to visit Chicago?

Yes, this is one of the best times to visit Chicago because it’s the least crowded and hotel prices are low in early December, January and February. My sister and I went to Chicago in mid-December and found it was a great time to see the city decorated for the holidays.

Is Skydeck better than 360 Chicago?

Both observatories are worth visiting if you have the time.

Skydeck Chicago admission is more expensive than 360 Chicago, but it also includes access to The Ledge for free. At 360 Chicago, you have to pay an extra $8 to check out the Tilt attraction.

Skydeck Chicago’s observatory is higher than 360 Chicago. The Skydeck is on the 103rd floor of the Willis Tower (1,353 feet / 412 meters). 360 Chicago in on the 94th floor of the John Hancock Building (1,000 feet / 305 meters).

Even though Skydeck Chicago’s observatory is slightly higher, it’s hard to tell the difference when you’re at 360 Chicago. Both observatories offer absolutely spectacular views of the city.

The wait times at Skydeck Chicago is twice as long as the wait times at 360 Chicago, especially during peak times. This is because Skydeck Chicago gets more visitors annually than 360 Chicago.

What is Chicago known for?

Chicago is famous for its deep-dish pizza, Chicago-style hot dogs, jazz music, Cloud Gate at Millennium Park, Navy Pier, its skyscrapers, Wrigley Field, Lincoln Park, the Chicago Loop, Garfield Park Conservatory, Chicago Riverwalk, Magnificent Mile, and 1920s gangsters.

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Reader Interactions

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January 31, 2017 at 7:23 pm

First, I’d like to say that I agree with most of your Chicago suggestions. It’s always fun to read what is suggested to outsiders as a resident of the Chicago area. I have a few suggestions of my own. Chicago is a great walking city in the warm months, but can be fairly miserable in the colder time of year. I would suggest grabbing a cab, Uber or public trans, as some of the distances between your suggested attractions can be vast. Your list takes people all over town, and seems a bit ambitious for walking. Also underutilized is the Pedway, which is nice in the winter or rainy weather (maps are available). I would advise NOT spending much time at Navy Pier. Many of us locals see it as a tacky, touristy attraction that is not the real Chicago. By all means, ride the Ferris wheel, visit the children’s museum, or take a boat ride, just don’t spend your whole day there. I also think that Uno’s, and Due’s deep dish pizza is far better than Malnati’s, but every Chicagoan will have a different opinion on that. If you want to see a show, Broadway in Chicago has almost as many quality shows as Broadway in NYC, while being less expensive. Some shows have discounted tickets, too. The Chicago Theater tends to have concerts, and miscellaneous shows, rather than plays. One last thing: the Adler planetarium is often eclipsed by it’s more flashy neighbors in the museum campus, but worth a look if you’re into astronomy and space.

Main Street  GalenaCountry-100.jpg

Three hours from the Loop, historic Galena maintains a charming Main Street with restaurants, hotels and shops. The annual Galena Brew Fest is July 20.

Courtesy of Galena Country Tourism

10 great day trips from Chicago that deliver nature, culture and superb food

This summer, ditch the urban routines of chicago for a slow-paced day trip or culture-rich overnight stay in the midwest..

Even if you live for summer in the greatest city on the planet, breaks are warranted. Whether you’re escaping big festivals that choke downtown or the Democratic National Convention’s swarm of lanyards, there are plenty of roads less traveled that are worth taking.

For this list, we narrowed travel time to under four hours and highlighted nature sojourns, tiny towns, architectural icons and more. Have a favorite spot that meets our criteria that isn’t on our list? Tell us at [email protected] and we may include your response in our weekly newsletter, the Green Room.

Indiana Dunes, Indiana

Less than 1 hour from the Loop

Need a break from the crowded city beaches? Jonesing to relive scenes from Dune ? Less than an hour’s drive from downtown, the Indiana Dunes beckon. Protected by state and national park designations alike, these epic mountains of sand hug 15 miles of lakeshore accessible through a handful of entry points along the way. The steep dunes are covered in trails bound to burn your glutes and calves, but the real draw in summer is the beaches .

Aptly named West Beach is the biggest and offers full-service amenities including a bathhouse and all-day lifeguard, but its popularity attracts big crowds on hot days. For a more chill Dunes beach experience, head further east to Kemil Beach, with picnic areas and access to the Dune Ridge Trail. For sustenance in nearby Chesterton, settle into a table for light Italian fare at the lovely Lucrezia Café or grab a spot at the bar at Craft House for local brews and pub grub.

BEVERLYSHORES-South Shore Ovenworks-3-courtesy South Shore Ovenworks.JPG

South Shore Ovenworks provides Neapolitan-style pizza and al fresco bench seating.

Courtesy of South Shore Ovenworks

Beverly Shores, Indiana

1 hour, 15 minutes from the Loop

Mid-century architecture buffs, this one’s for you. An easy drive from downtown (better yet, take Metra’s newly expanded South Shore Line ), Beverly Shores is a planned resort community that dates to the early 1900s, but features homes that look marvelously modern thanks to its Century of Progress Architectural District . This handful of private homes were originally built for the 1933 World’s Fair’s Homes of Tomorrow exhibition , and you can tour them on one single day in the fall — if you’re lucky enough to score tickets. Meanwhile, scenic drive-bys are complemented by sweet gift shops and vintage shops ; e-bike and golf cart rentals to take to the beach; and the Beverly Shores Depot & Gallery , which has exhibits throughout the summer.

Jan Parr, a longtime Chicago media editor who moved to Beverly Shores five years ago, says she stops by Goblin & The Grocer to catch up with neighbors over a glass of wine and also recommends checking out the South Shore Ovenworks pizza truck : a bright orange Studebaker parked next to the Camp Stop at Broadway and Highway 12, with al fresco bench seating (grab craft beer or a bottle of wine at Hobgoblin next door). “The pizza maker trained at Eataly in Chicago and uses imported, top-notch ingredients for his wood-fired Neapolitan-style pizza,” Parr says. “All our return visitors want to go the ‘pizza truck.’ ”

  • Will hike for beer! Seven Midwest hikes with taprooms nearby.

Harbor Country, Michigan

About 1 hour, 15 minutes from the Loop

It’s difficult to pick a favorite town in this charming corner of southwest Michigan. Collectively known as “Harbor Country,” eight distinct hamlets straddle 94 from the Michigan border to Warren Dunes State Park, each with its own personality and attractions. The proverbial heart of the “Hamptons of the Midwest” is New Buffalo, whose handful of wineries, upscale shopping and lodging, and galleries lend it a slightly more cosmopolitan air than its neighboring towns. Melissa Lewis, principal at Melissa Lewis Interiors, recommends starting or ending your journey at the Whistle Stop : a must-stop for delectable sandwiches, snacks and baked goods. “Whether we are in the area with friends or commuting to and from camp drop-offs, my kids always demand a stop for a sandwich and mini-cookies galore,” she says. “They’ve also got fabulously curated items from local artisans which are perfect for a last-minute host or hostess gift.”

Just up the road is Union Pier, where more wineries (including St. Julian , Michigan’s oldest), fine dining restaurants and antiques are complemented by posh inns.

A quick drive inland leads to the village of Three Oaks, the arts and cultural hub of Harbor Country. The Acorn Center for the Performing Arts hosts concerts, events and festivals year-round, and around the corner the Vickers Theatre shows new movies and old favorites. For lunch, grab a table at Froehlich’s and peruse the vast provisions shop while you wait. Don’t forget to pick up some award-winning whiskey at Journeyman before heading back to the city.


Black Point Estate in Lake Geneva, Wisconsin is one of the largest mansions in the area.

Courtesy of Kristina Lorraine

Lake Geneva, Wisconsin

1 hour, 45 minutes from the Loop

There’s a reason why so many wealthy Chicagoans of the Gilded Age sought to build holiday homes on Geneva Lake. The vast lake’s crystal-clear water, gentle breeze and rolling hills offered a welcome respite from the crowded city — and little has changed since. The so-called “Newport of the West” is still home to many of those tony mansions, which are visible from any number of pleasure cruises on the lake. ( Black Point Estate , one of the biggest, is also open for house tours.)

Beyond the mansions circling the shore, Lake Geneva is a quintessential resort town with a sweet little pier, lakeside walking trails, a smattering of ice cream parlors (check out Scoops just off Main Street), decent antiquing and a range of places to dine, drink and snack. There’s also a magic theater hosted by “master illusionist” Tristan Crist (you can’t miss his cheesy billboards on the way into town), and the truly beautiful Victorian-era Yerkes Observatory .

While en route from Chicago, don’t miss all the produce and provisions from surrounding farms. “When I’m driving up to [nearby] Elkhorn, I stop at River Valley Ranch for produce and miscellaneous pantry items, Lake Geneva Meats and Simple Bakery for the best seeded sourdough,” says Heidi Coudal, owner and culinary director at Big Delicious Planet, who frequently passes through Lake Geneva en route to her family’s vacation home on the nearby Sugar Creek Preserve. “And every weekend, we drive over to Rushing Waters Fisheries for fresh trout,” which supplies fish to several restaurants in Chicago.

Starved Rock State Park, Illinois

Two hours from the Loop

Looking to cool off from city life without braving the crowded beaches? Consider piling into the car for an easy drive to this vast state park, most of which is lushly shaded. Bring your boots or nonslip water sandals: Many of the park’s best walks and hikes weave around pretty waterfalls and moss-covered canyons (18 of them!), and wooden bridges carry greenery-starved pedestrians through about 13 miles of trails.

Fawn Julsaint, owner of the cleaning service My Deer Cleaner, visits Starved Rock with her daughter a few times a year for day and weekend trips. “We like doing the Wildcat Canyon trail,” she says. “It’s a 2-mile, moderate loop hike where you walk to several canyons and waterfalls and loop back along the Illinois River. It’s great for kids and families who aren’t prepared for a more adventurous 3-4 mile hike. The paths are well marked with colors on the posts and signs so you know where to go along the route.”

Beyond hiking, when’s the last time you visited a state park with its own concert series? The Veranda , located at the Starved Rock Lodge & Conference Center, features al fresco dining and live music every Friday and Saturday night. So go ahead: Book a cabin or campsite, or stay in the beautifully historic lodge proper . Julsaint notes that overnighting also positions you to spend time at the neighboring Matthiessen State Park or stop at Jamie’s Outpost in nearby Utica for dinner and live music or karaoke. “And,” she says, “the trip is never complete without ice cream or sweets from Roxie’s Sweet Confections .”

Douglas and Saugatuck, Michigan

Two hours, 15 minutes from the Loop

If you’re looking to slow down a little — to appreciate a James Beard–worthy meal, to indulge in a beachside stroll, to ponder deeply meaningful creative interpretations of Lake Michigan and beyond — check out what’s referred to as the Art Coast of Michigan. This pair of small, neighboring towns began building a reputation as a creative hub back in the late 19th century’s Arts and Crafts movement. The most famous institution is the Ox-Bow School of Art , whose roots go back as far as 1910 and whose programming peaks in summer with Friday Night Open Studios , glorious al fresco monthly Culinary Events and Sunday Sojourns that pair tours of the vast campus with a laid-back brunch.

Oval Beach is the main sandy strip here (there are several others), but there’s more to the waterfront than Lake Michigan. Anne Godwin, an interior design and sales manager at home furnishings brand Ebanista, says she and her husband “fell in love with the Saugatuck/Douglas/Fennville area years ago and hope to own property there at some point — and this is coming from a Wisconsinite.” Among the draws: an LGBTQ+ artist presence, top-tier establishments and a “super-friendly” vibe, Godwin says.

For a farm-to-table lunch or dinner, Godwin recommends Penny Royal Cafe & Provisions . “The owner used to be a chef in Chicago,” she says. “They made the move to Michigan and created such a gem. It’s cool to see the hard work this couple had invested.” (Plus, she adds, it’s very Instagrammable.) For dinner, head to Phil’s for pad Thai and finish the night singing karaoke with the locals at the Corner Bar (Coral Gables) , a “super-chill, no frills dive bar on the water.” Godwin says she could name 50 other things, “but this is a great start for a day trip or short weekend. Plus,” she says, “you gain an hour on the way home.”


Kohler is the original company town synonymous with the famous plumbing and bath fixture manufacturer, but also has intriguing destinations like the John Michael Kohler Arts Center.

Courtesy of Durston Saylor/Kohler Arts Center and Art Preserve

Kohler, Wisconsin

Three hours from the Loop

No, it’s not a toilet museum — though there are more than a few on display at the John Michael Kohler Arts Center . More broadly, Kohler is the original company town synonymous with the famous plumbing and bath fixture manufacturer. The traditional tudor workers’ dormitory, opened as the American Club in the early 1900s, now operates as one of the most luxurious resorts in the Midwest. It’s almost a 3-hour drive, so consider saving up and booking an overnight visit to experience all the fine dining and monied recreation (think: fly fishing, golf, skeet shooting) — or, at the very least, the Kohler Waters Spa . This mecca of hydrotherapy spa treatments is closed for renovations this summer, but you can still pop in for nail services to sneak a peek.

Beyond the resort, nearby Sheboygan offers small-town charm. Lizz Kannenberg, senior creative director at Chicago tech company Sprout Social, has collected favorites while spending time at her family’s lakehouse. “ Majerley’s Black River Grill is the greatest of all supper clubs,” she says, noting a recent $22 bar tab for six old fashioneds. For caffeine and light bites, there’s Paradigm Coffee , a queer-friendly haven for great coffee, food and art. She also recommends That Place on 8th , a dive bar with a “pay what the owner (who goes by Tequila Kat) feels like” policy. “My last trip there was with six ladies and we paid $16 for our first round, and she gave us the second round for free because she ‘liked the look of [us],’ ” Kannenberg says, noting that it also has an incredible selection of posters for charity brat frys.

Finally, don’t miss the region’s signature Sheboygan Hard Rolls: a type of roll made only in the Sheboygan/Kohler area. With butter and jam or cheese, they’re a Wisconsin classic, and Kannenberg says Johnston’s or West Side bakeries are the best. Down the road, Kohler Park Dunes offers front-row seats to the Lake Michigan shoreline, and the little Tellen Woodland Sculpture Garden makes for a whimsical stop on the way up or back.


Galena features an architecturally award-winning main street nicknamed the “Helluva Half Mile.”

Galena, Illinois

Want to get a sense of what Chicago might have looked like if its historic 1800s buildings had survived the Great Chicago Fire? Spend the day — or a night — in Galena. Largely populated in the 1820s by settlers seeking out the area’s namesake ore, this truly charming small town features an architecturally award-winning main street nicknamed the “Helluva Half Mile.”

As one of the first streets in Illinois to require architectural reviews of its exterior building plans, Galena’s mid-1800s main street — which was given a facelift in the 2010s — is so aesthetically cohesive, it looks like a movie set. The town is equally renowned as a home to numerous Civil War generals (eight!), most famously Ulysses S. Grant, whose nationally landmarked home is a must-visit. The city’s tourism bureau maintains a vibrant list of summer events, from concerts to tours, and one highlight is the city’s annual Brew Fest on July 20. There are plenty of spots around town to grab a bite: Modern delis and sushi joints mixed in with throwback steakhouses , or splurge on dinner theater tickets to Amelia’s .

Travel-Trip Wisconsin Mineral Point

Hilly steep streets, little log buildings and stone cottages lend Mineral Point olden fairytale vibes.

Courtesy of Helen O’Neill/AP

Mineral Point, Wisconsin

Settled around the same time as Galena, and for the same reason (a wealth of Galena ore), aptly named Mineral Point is a sweet spot in Wisconsin’s southwest region. Hilly steep streets, little log buildings and stone cottages lend Mineral Point olden fairytale vibes, but its cultural touchstones are timeless: artisan crafts, architecture and beer.

The community’s Shake Rag Alley nonprofit arts center is as beloved for its arts as its tidy acreage of gardens and stone paths, which come alive with pollinators in the summer months. The town’s original 1915 opera house was restored in 2008 as a “theatre for all the people,” which is reflected in its programming, from Eagles tributes to Loudon Wainwright III to screenings of current blockbuster movies. Joel Reese, vice president of marketing and communications for the Chicagoland Chamber of Commerce, counts Mineral Point as one of his favorite places in Wisconsin, especially thanks to its bike-friendly rural roads and well-maintained trails. (“Shout-out to the perfectly named Cheese County Recreation Trail ,” he says.) Reese’s visits start with browsing the town’s number of interesting shops including Brewery Pottery , which is just a little out of town. Then, a long bike ride to tire himself out, followed by a delicious meal with some home-crafted beers and fried cheese curds at Commerce Street Brewery (“How can you pass up a place that made several beers in honor of Betty White ?” he jokes). It’s been around since the 1990s and has rooms for let upstairs in its beautifully restored 1854 warehouse.

As Reese says, “The quiet town and country air means you’ll never get a deeper night’s sleep.” Plus, it’s worth staying the night just to have a legit Cornish breakfast pasty at Red Rooster on High Street. There’s no website, but you can’t miss it.

Travel Wisconsin Frank Lloyd Wright

Spring Green is home to Frank Lloyd Wright’s infamous Taliesin.

Courtesy of Beth J. Harpaz/AP

Spring Green, Wisconsin

Three-and-a-half hours from the Loop

Though it’s a longer trek, this is one of the most rewarding drives on the list thanks to the increasing number of glorious green hills and barren blue skies once you’re past Madison. This deceptively sleepy Midwestern hamlet is home to Frank Lloyd Wright’s infamous Taliesin : the so-called love nest he shared with a mistress before it was burned to the ground, murdering his love and her children. The architect’s gravestone is down the road but his body isn’t. (His remains are at the other Taliesin, in Arizona.)

For lighter drama, grab tickets to the American Players Theatre a few miles east: a truly lovely amphitheater with exceptional theater productions and free concerts during summer weekdays. Even more bizarre than Taliesin’s history is House on the Rock: a literal house built onto the chimney of a rock. For a cozy breakfast or lunch, “I love the Spring Green General Store !” says City Lit Books owner Stephanie Kitchen, who often passes through while visiting extended family in the Driftless region. “There is a cute downtown area that includes a great local bookstore/cafe, Arcadia Books . I’d be remiss if I didn’t mention it!”

Lauren Viera has covered Chicago’s arts and cultural scenes for more than 20 years. She is the author of The 500 Hidden Secrets of Chicago (Luster) and lives in Logan Square.

Summer performances collage

19 killed, 86 wounded in shootings during extended Fourth of July weekend in Chicago

Of those shot, 24 were in mass shootings in greater grand crossing, the near west side, douglas and austin..

Chicago Fire Department vehicle

At least 19 people have been killed and 86 others wounded by gunfire in Chicago over the extended Fourth of July holiday weekend.

Sun-Times file

More than 100 people were shot, including 19 who were killed, during shooting attacks in Chicago over the extended Fourth of July weekend.

By the end of Friday, the tally of shootings — six people shot Thursday and 62 shot Friday, 12 killed over both days — surpassed the numbers for last year’s entire holiday weekend. Last year , 11 people were killed and 62 wounded over the holiday weekend, which stretched over four days, July 1-4.

This year’s holiday violence includes four mass shootings. In all, 24 people were shot, four fatally, in the mass attacks.

Chicago Police Supt. Larry Snelling will join Mayor Brandon Johnson at 9 a.m. to address the shootings during a meeting at Public Safety Headquarters, 3510 S. Michigan Ave.

“We are devastated by the recent violence that has left our city in a state of grief, and we extend our heartfelt condolences to the families and communities impacted by these recent events,” Mayor Johnson’s office said in an earlier statement.

Chicago Mayor Brandon Johnson reacts to gun violence during the long Fourth of July weekend.

Fatal attacks:

  • About 11:50 p.m. Sunday, two teens, 18 and 16, were arguing with someone in the 700 block of East 89th Place when the person they were arguing with opened fire, striking them both, police said. The 18-year-old was shot twice in his chest and taken to the University of Chicago where he died, police said. The teen boy was shot in both of his thighs and taken to the same hospital in fair condition, officials said.
  • Just before 11:30 p.m. Sunday, officers conducted a well-being check in the 200 block of North Central Avenue and found Melvin Hill, 36, on the kitchen floor bleeding and unresponsive, police and the medical examiner’s office said. He had suffered a gunshot wound to his head and was dead at the scene, police said.
  • About 11:55 p.m. Saturday, a 25-year-old motorist was found unresponsive with multiple gunshot wounds to his torso after he struck a viaduct in the 5800 block of South Elizabeth Street, police said. He was dead at the scene, police said.
  • About 11:15 p.m. Saturday, a man and woman, 26 and 25, were walking in the 100 block of East 21st Street when a white SUV approached and someone inside opened fire, police said. The man was shot multiple times in his body and taken to Northwestern Memorial Hospital where he died, police said. The woman was shot in her left leg and was taken to the same hospital, where she was in good condition, officials said.
  • About 10:35 p.m. Saturday, a 47-year-old man was driving in the 10600 block of South State Street when he was struck in his left armpit area by gunfire, police said. The man then struck three vehicles before coming to a complete stop, officials said. He was taken to Christ Medical Center in Oak Lawn where he died, police said.
  • Saturday night, a man died after exchanging gunfire with two people along train tracks in South Shore. He suffered multiple gunshot wounds about 8:50 p.m. near the 1700 block of East 71st Street and was pronounced dead at University of Chicago Medical Center, police said.
  • About 2:10 a.m. Friday, officers responding to calls of a person shot in the 1200 block of West Washburne Avenue found Demetrius Dorn, 43, with multiple gunshot wounds, officials said. He was pronounced dead at Stroger Hospital.
  • A man and woman were found shot about 7 a.m. Friday in the 3400 block of East 87th Street , police said. They were dead at the scene.
  • A 30-year-old man identified as Leontrey Taylor by the Cook County medical examiner’s office was shot and killed in the 700 block of South Cicero Avenue in Austin about 2 a.m. Friday, police said.
  • Kendall Richardson was killed and six others were wounded about 1 a.m. Friday in the 100 block of South Menard Avenue when two people exchanged gunfire and fled, officials said. Richardson, 40, was shot in his buttocks and took himself to Stroger Hospital, where he died. The other victims — three men, two women and a 15-year-old boy — did not suffer life-threatening injuries.
  • Two women, 59 and 29, were shot about 11:50 p.m. Thursday in the 900 block of North Leclaire Avenue . The older woman was shot in her hip and head and taken to Stroger Hospital, where she later died. The younger woman was shot in her torso and also taken to Stroger, where she was listed in fair condition, police said.
  • About the same time Thursday, a 35-year-old man was arguing with someone in the 6000 block of South Winchester Avenue when the person shot him multiple times. The 35-year-old was pronounced dead at St. Bernard Hospital, police said.
  • Around 11 p.m. Thursday, a 30-year-old man was standing in the street with a crowd in the 8400 block of South Kerfoot Avenue in Auburn Gresham when he was shot in his torso. He was taken to University of Chicago Medical Center where he died, officials said.
  • A man was found shot to death about 2:10 p.m. Thursday in Roseland on the Far South Side. Officers responding to a ShotSpotter alert found the man, 24, unresponsive in the 9300 block of South Lafayette Avenue . He had been shot in his chest and flank and was taken to Roseland Community Hospital, where he was pronounced dead, police said.
  • An 8-year-old boy and two women were killed, and two young boys were critically injured in a shooting about 6:15 a.m. Thursday. Multiple people fired into a home in the 7100 block of South Woodlawn Avenue in Greater Grand Crossing on the South Side.
  • Around 1 a.m. Thursday, Dion Butler, 34, was shot in his neck in the 6200 block of South Laflin Street in Englewood, according to police and the medical examiner’s office. He was taken to University of Chicago Medical Center, where he died.

Nonfatal shootings:

  • About 12:15 a.m. Friday, eight people were wounded during an exchange of gunfire in the 1300 block of West Hastings Street on the Near West Side, police said. The wounded included five women, ages 74, 31, 19 and two who are 18. Three men, ages 36, 28 and 23 also were injured. None of the victims suffered wounds considered to be life-threatening.
  • A 16-year-old girl was shot in her head and critically wounded about 1:40 a.m. Friday in the 1200 block of South Central Park Avenue in North Lawndale, police said.
  • Another 16-year-old girl was wounded in a shooting early Saturday in Brighton Park on the Southwest Side. She was walking about 2 a.m. in the 3500 block of South California Avenue when shots were fired and she suffered a graze wound to her leg, police said. She was hospitalized in good condition.
  • Saturday evening, a 15-year-old boy was shot and critically wounded in the 100 block of North Lavergne Avenue in Austin, police said.

Early Sunday, a white truck approached a group of people on the street in the 3700 block of South State Street and there was an exchange of gunfire, leaving four people shot, police said. A 41-year-old man was shot in his lower back and was in critical condition, police said. A 31-year-old man was shot in his abdomen and left hip and was also in critical condition. A 35-year-old woman was shot in her buttocks and was listed in good condition, and a third man, 30, was shot in his left thigh and also listed in good condition, police said. All four were taken to University of Chicago Medical Center, authorities said.

Besides the gunshot victims noted above, 60 other people were wounded by gunfire between11 p.m. Wednesday and 5 a.m. Monday, the span of time the Sun-Times is using to define the start of this year’s four-day holiday weekend.


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July Fourth violence nationwide kills at least 33, Chicago ‘in state of grief,’ mayor says

Police say two people were killed and three others injured in Independence Day violence in Huntington Beach, California.


The temporary memorial for the Highland Park shooting victims, Katie Goldstein, Irina McCarthy, Kevin Michael McCarthy, Stephen Straus, Jacki Lovi Sundheim, Nicolás Toledo and Eduardo Uvaldo, is seen near 1707 St. Johns Avenue in Highland Park, Ill., Thursday, July 4, 2024, two years after a mass shooting at the parade. (Pat Nabong/Chicago Sun-Times via AP)

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Paradegoers with Moms Demand Action march during the Independence Day Parade along Central Avenue in Highland Park, Ill., Thursday, July 4, 2024, two years after a mass shooting at the parade. (Pat Nabong/Chicago Sun-Times via AP)

Erin Cartwright Weinstein, clerk of the circuit court of Lake County, receives a hug during the Independence Day Parade along Central Avenue in Highland Park, Ill., Thursday, July 4, 2024. (Pat Nabong/Chicago Sun-Times via AP)

Shootings and other violence during the extended Fourth of July weekend have left at least 33 people dead, including 11 in Chicago, and injured dozens more nationwide, authorities said.

The Fourth of July historically is one of the nation’s deadliest days of the year. A flurry of shootings around the holiday a year ago left more than a dozen people dead and over 60 wounded. And a year before that, seven people died in a mass shooting at a Fourth of July parade near Chicago.

Violence and mass shootings often increase in the summer months , with more people gathering for social events, teens out of school and hotter temperatures.

Chicago ‘in state of grief’

In Chicago alone, 11 people had been killed and 55 wounded in shootings as of Friday morning during the extended July Fourth weekend, the Chicago Sun-Times reported. The violence included a mass shooting on Thursday that killed two women and an 8-year-old boy.

The recent violence “has left our city in a state of grief,” Mayor Brandon Johnson said.

A community rally was planned for Friday evening, and the city will beef up police presence over the weekend, Johnson said in a statement.


“We are devastated by the recent violence that has left our city in a state of grief and we extend our heartfelt condolences to the families and communities impacted by these recent events,” Johnson said.

Eight people were wounded in Chicago’s Little Italy neighborhood shortly after midnight Friday. About 90 minutes later, a shooting in the city’s Austin neighborhood injured six. Police said preliminary findings suggest the separate shootings involved an exchange of gunfire between two people who then fled.

Recent violence at a popular Lake Michigan beach in Chicago prompted officials to close it early each night through the holiday weekend as a precaution. The 31st Street Beach has been the scene of recent stabbings and shootings.

Southern California violence

In Huntington Beach, California, two people were killed and three others injured in an Independence Day attack less than two hours after a fireworks show ended, police said. Authorities arrested a suspect after responding to reports of an assault with a deadly weapon Thursday night.

15-year-old boy arrested in Niles, Ohio, shooting, 10-year-old girl dies in Cleveland

In the northeastern Ohio community of Niles, Police Chief Jay Holland said a 15-year-old male was in custody after a 23-year-old man was fatally shot Thursday night at a Fourth of July party at a residence.

A 10-year-old girl, identified as Gracie Griffin, was fatally shot in a Cleveland neighborhood, police said. It is not yet known what sparked the shooting or if she was targeted.

Fatal drive-by shooting in Philadelphia

A 19-year-old man was killed and six others were wounded in a drive-by shooting in Philadelphia on Thursday night.

The wounded, which included four juveniles, were being treated at hospitals for various injuries that were not considered life-threatening. It is not known yet what prompted the shooting.

Boston-area shootings leave 1 dead, 5 wounded

Three shootings occurred in the Boston area following the city’s Fourth of July celebrations, leaving one man dead. The fatal shooting occurred about 1:30 a.m. Friday in a park near Boston’s South End neighborhood. At about the same time, three other people were wounded in the city’s Jamaica Plain neighborhood. A third shooting at a gas station later left a victim with life-threatening injuries.

A 17-year-old male suffered a stomach wound in another shooting Thursday night in a condominium parking lot in East Bridgewater, Massachusetts.

Connecticut woman fatally shot in car

In Connecticut, a woman was found shot in her car early Friday and was pronounced dead at a hospital. Police identified her as Shamyria Williams, 23, of Hartford. Relatives told reporters they believed she had just left a Fourth of July party.

Six teens shot at home in Albany, New York

Police in Albany, New York, said six males ranging in age from 16 to 19 were being treated at a hospital for injuries that were not considered life-threatening after a shooting at a large gathering.

Police responded to reports of a shooting at a home around 12:15 a.m. Friday. None of the victims were found at the scene but police said they located evidence consistent with gunfire in the yard behind the residence and in the street.

One teenager who had been shot flagged down officers along a street a short time later, police said.

Five teens shot during party in suburban Detroit

Five teens were wounded when shots were fired into a crowd following a fight at a party early Friday morning in Pontiac, about 30 miles (48.2 kilometers) northwest of Detroit.

Three of the victims are 14 years old. The other two are 15 years old. All are males. Authorities said they were taken to hospitals with wounds not considered to be life-threatening.

Tampa nightclub shooting wounds 4

Four people were wounded in a shooting early Friday outside a Tampa adult nightclub after an altercation between the club’s security guard and two men, police said.

The two men drove their car to the front of the Pink Pussycat Lounge and one of them shot the security guard with a handgun, police said. The security guard underwent surgery at a hospital and was in stable condition. Three other men suffered unspecified minor injuries. Police said both suspects were arrested and charged with several crimes.

Violence elsewhere

In the Queens section of New York, an 8-year-old boy was fatally stabbed in an apartment in what police described as a domestic dispute. Police said officers later fatally shot a 20-year-old man who held a knife to his 43-year-old father’s throat and refused commands to drop the weapon.

In High Point, North Carolina, a shooting at an unofficial fireworks display left one person dead after a large crowd had gathered in the parking lot of the city about 90 miles (145 kilometers) west of Raleigh, police said. The victim was identified as Keith S. Lynch, 32, of High Point.

Shootings at two St. Louis-area Fourth of July gatherings left two men dead and five others injured, two critically, police said.

In West Virginia, Charles Speer, 42, of Kermit, died early Friday after being shot multiple times following a physical altercation at the home of another man, state police said.

And a road-rage incident led to the fatal shooting of a 36-year-old man in Taneytown, Maryland, according to the Carroll County Sheriff’s Office.

Earlier Thursday, a police officer serving a warrant in Cleveland and an armed person making threats in Yellowstone National Park were among those killed in other shootings .

Associated Press reporters Rick Callahan in Indianapolis; Bruce Shipkowski in Trenton, New Jersey; Susan Haigh in Hartford, Connecticut; Steve LeBlanc in Boston; Curt Anderson in St. Petersburg, Florida; Jonathan Drew in Raleigh, North Carolina; Jim Salter in St. Louis; and Karen Matthews in New York City contributed to this report.

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  • WEATHER ALERT Flood Watch Full Story

2024 NASCAR Chicago Street Race: Live updates

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CHICAGO (WLS) -- The NASCAR Chicago Street Race for 2024 is being held in and around Grant Park on July 6 and 7. Along with two banner races, the event features a family-friendly festival with with live music, including performances by The Black Keys, The Chainsmokers and Keith Urban.

Extensive street closures and re-routes are now in place as the city constructs the winding race course, and fans are flocking to the city over the long Fourth of July holiday weekend.

Chicago, start your engines...

Everything you need to know about NASCAR Chicago Street Race 2024

2024 NASCAR Chicago Street Race guide: Start time, where to watch, how to get here, tickets and more

2024 NASCAR Chicago Street Race weekend schedule, live concerts and festival information

Chicago NASCAR race course route map, street closures, parking restrictions

Clean up underway after NASCAR race

Crews picked up fencing and barriers this morning around Grant Park re-opening some roads after NASCAR took Chicago literally by storm.

Johnny Sha lives nearby. He likes to see the event come, but he's also glad to see it go.

"Sure I mean people like the event to be here, but we also like to see all this set up to be gone yeah," Sha said.

Chopper 7 showing northbound DuSable Lake Shore Drive reopened Monday morning between McFetridge Drive and Randolph Street.

Meanwhile Michigan Avenue between Roosevelt and Jackson should re-open by noon.

While the event moves out, so are the fans. Roger Thomas from Cleveland said he had a great weekend.

"We goofed off and went to Wrigley Field and came back," Thomas said. "We took the bikes and zipped around. we stayed in the Congress Hotel and had a perfect view of the race. we didn't have to leave the hotel room."

Tyler Dawes came from Noblesville, Indiana for the race and headed home Monday morning with his rain poncho stuffed in his backpack, giving Chicago a big thumbs up.

"I thought it was great," Dawes said. "I thought it was great. Again I saw a lot of very excited fans just come out and kind of see the magic of the racing world. I wish it was a little earlier just so they didn't encounter the same rain delay."

While many streets around Grant Park are re-opening Monday, it will take many days to pick all of this up. Clean up is expected to last well into next week.

Streets in downtown Chicago closed for NASCAR race begin to reopen Monday

Select streets will begin reopening following the conclusion of the event. All street closures are expected to remain in effect as demobilization of the track wall, fence, and viewing structures takes place.

Chicago OEMC issued the following street reopening schedule:

  • The northbound section of DuSable Lake Shore Drive is set to reopen on Monday, July 8 at 6 a.m.
  • The southbound section of DuSable Lake Shore Drive is set to reopen on Tuesday, July 9 at 11 p.m.
  • Northbound and southbound Michigan Avenue between Roosevelt Road and Monroe Street is set to reopen on Monday, July 8 by noon. Northbound Michigan Avenue between Van Buren and Jackson will have one travel lane closed.

READ MORE | Chicago NASCAR street closures, reopenings guide

The priority streets to reopen are DuSable Lake Shore Drive, Michigan Avenue, and Columbus Drive.

Other street closures will remain in effect as demobilization of the track wall, fence, and viewing structures takes place.

Northbound DuSable Lake Shore Dr. will begin reopening Monday, July 8 at 6 a.m., with all NASCAR-related demobilization activity expected to conclude by end of day July 18th.

Streets with local access are only for residents, businesses and their employees.

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2024 NASCAR Chicago Street Race weekend wraps up

NASCAR can't seem to escape the rain in Chicago as downpours shortened the race for a second year in a row.

Many fans were braving the weather though and staying until the checkered flag to see Alex Bowman win the race.

"I knew it was gonna be a great ending... it's been really close, so I just had to stick it through," Chicago resident James Chaplin said.

Fans adjusted to the weather quickly with ponchos and rain gear as they said the atmosphere was worth it.

"Rainy, but this is the energy, it doesn't matter... the energy is awesome... people are happy and we're right here loving NASCAR in Chicago," Chicago resident Jorge Azpeitia said.

It was a jam packed weekend of action with all sorts of live entertainment.

Motor cross bringing the tricks and flips before the race, as well as some concerts with Laura Alaina and Keith Urban stealing the show.

"It's pretty neat actually to see the big names coming out for these... and the Chainsmokers yesterday, that was a fantastic concert," NASCAR fan Jennifer Decker said.

"I love how the concerts got screens everywhere so you don't feel like you're glued in this sunny place where you'll burn... so I love this atmosphere," said Pam Schoeffling from Milwaukee.

Despite the rain impacting the race in back-to-back years, fans said it was an enjoyable weekend that they hope NASCAR will continue to bring to Chicago.

"We've had great food... great talent playing... great race... great city. Hope to have it back," said Cam Arnold from Nashville.

Alex Bowman wins 2024 NASCAR Chicago Street Race Cup Series race

After a long rain delay, NASCAR driver Alex Bowman took home the win in the Grant Park Cup Series race in the second-annual NASCAR Chicago Street Race.

Tyler Reddick, who drives for Michael Jordan's 23XI race team, attempted a comeback in the final lap. His attempt did not success and he took 2nd place.

The race was shortened after a rain delay, and did not go for the full 75 laps. NASCAR announced the race needed to be completed around 8:20 p.m.

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