road trip planner from chicago

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19 Awesome Road Trips from Chicago (with Timings)

Keeping your introduction to road trips from Chicago short and simple, let’s take a look at the summer, winter and weekend favourites!

The city of Chicago is awesome and all, but it’s also a great starting point for some great Chicago road trips. The city’s prime location acts as a portal to the Midwest – from historical cities to sprawling state parks and urban-stress-relieving beer. 

Best Chicago Road Trips in Summer

If you’re looking for one of the longest Chicago road trips, how about driving from Chicago to New Orleans ? If you’re thinking a little shorter, then read on…

Distance: as far as you can go

No American road trip is complete without covering some part of classic Road 66 – of which, lucky for us, kicks off in Chicago!

Snap a selfie at the official sign between East Adams and South Michigan Avenue then check-off stops such as the Gemini Giant, the Pontiac murals, Lincoln Presidential Library and more. If you can spare a month, make it all the way down to the Pacific Ocean.

2. Illinois’ Great River Road

Distance: 3.5-hour drive

In a seemingly never-ending chain of historical sites and activities, the drive along Mississippi River to East Dubuque is one of the best road trips from Chicago.

Moline and Rock Island are two cool detours but you can head straight for East Dubuque for its Chicago Great Western Railway Depot Museum. John Deere Pavilion lets you hop from car to farm machines, while the city Nauvoo shows off many historic homes. 

3. Lake Michigan to South Haven

Distance: 2.5-hour drive

Escape the heat by packing your car with beach gear and setting off for a nice drive around Lake Michigan and towards South Haven.

There are plenty of berry farms along the way so you can stain your hands with blueberries; or maybe you prefer to climb up a lighthouse?

To take your road trip even further, bring a bike! Cruise along the water front; take a dip or two. 

Do you have a favourite road trip quote? Click for the best long drive quotes to inspir e your next adventure!

4. Shawnee National Forest

Distance: 6-hour drive

One of the longest Chicago road trips on the list, it’s more than worth it to visit Shawnee National Forest. In fact, plan to camp amidst the spectacular range of landscapes for one of the best driving trips from Chicago!

Local favourites include the Garden of the Gods – you’ll find super special rock formations like Anvil Rock. Little Grand Canyon and Bell Smith Springs feature moderate hikes; Inspiration Point offers panoramic views over the prairie, Mississippi River and the forest.

Not convinced? Shawnee Hills Wine Trail is a brilliant drive that links up vineyards and wineries in the area – a great stop on a road trip from Chicago.

How about driving from Chicago to Atlanta? Here’s my guide to the best stops on a Chicago to Atlanta road trip , just for you.

Best Chicago road trips in Winter

If you want the best road trips from Chicago when it’s colder and darker, then these are the best ones for you.

5. Grand Rapids

Distance: 3-hour drive

After just long enough of a drive, pull into Grand Rapids for a nice sweep of activities. The Beer City Ale Trail will keep you road-tripping on foot (or car, if you have a Designated Driver); or wander through Downtown Market for food adventures instead.

Warmed by booze, drop by the 158-acre Frederik Meijer Gardens & Sculpture Park where their installations are bright pops of colour against an all-white backdrop. 

6. Muskegon

Speaking of unusual winter activities, I’ve heard so much about Muskegon Winter Sports Complex. Just an hour from Grand Rapids, it’s a great next stop on your Chicago road trip.

Their Olympian-designed ice-luge course is perfect for beginners, spanning 850 feet of forested speed racing. Muskegon is also home to USS Silversides Submarine Museum if you’re into marine vehicles, and there’s a great pier and lighthouse too.

7. Indianapolis

When temperatures are cold, cold, cold – you might opt for staying indoors. The city of Indianapolis is one of the best road trips from Chicago during winter because of its incredible indoor entertainment: museums.

From the Indianapolis Museum of Art to the Indianapolis Children’s Museum to quirky Indiana Medical History Museum, you can escape the cold all day!

Of course, drop by famous City Market for great eats and then maybe go on a catacombs tour underground too. This makes for one of the best road trips from Chicago.

8. Boyne Mountain Resort

Distance: 5-hour drive

Michigan winters are best captured with the ski resort of Boyne. Drive past snowy landscapes to reach 850 acres of skiing, snowmobiling, dogsledding and photography escapades.

While the forested grounds offer romantic snow-covered views, don’t miss out on the epic zip lines that take you through the trees and slopes. 

If you like your road trips from Chicago with a bit of snow and ski thrown in, then this is a great option for you.

Your ESTA for the USA

Before you go to the USA make sure you have your ESTA organised. You can find help with this on this link: https://www.application-esta.co.uk/ESTA-guide . It doesn’t take long and organising it beforehand will make things go that bit smoother at the airport.

9. Apostle Islands

Distance: 7-hour drive

Does driving over ice count as going off-road?

It’s an unforgettable journey to Apostle Islands National Lakeshore as winter ice freezes thickly to transform water into road, ending with stunning ice caves!

Make sure to visit the only inhabited Madeline Island as well for a cool wind sled experience and hot tub stay. 

Day Road Trips from Chicago

10. lake geneva.

Distance: 1.5-hour drive

Chicago’s number one when it comes to day trips, Lake Geneva is one of the best lake town’s in the US.

Downtown boasts all the food and drinks you need for the inevitable food baby; you might even land a booze cruise.

Hot air balloon rides, Lake Shore Path, ziplines and even ski slopes make it a year-round place to visit. It’s a multi-visit destination for sure!

11. Harbor Country

Distance: 1-hour drive

Wind between the towns of Michiana, Grand Beach, Three Oaks, New Buffalo, Lakeside, Union Pier, Harbert and Sawyer. This Chicago road trip will have you hopping between wineries and breweries, not to mention the beach.

It’s so close to the city, but the sand dunes and soft grasses make it a wholly different world. 

12. Starved Rock State Park

Distance: 2-hour drive

Families and romantics will love Starved Rock State Park for reasons that include: 13 miles of hiking, 18 canyons, free entry and nature-surround lodge.

It’s a great location to unplug for a day as you hunt down natural rock pools, waterfalls and incredible moss-strewn glades. You can even visit in the winter for cross-country skiing and cuddles in front of expansive mountain views. 

13. Saugatuck 

Making up Lake Michigan’s “art coast of Michigan”, Saugatuck and its neighbours (Fennville and Douglas) are house dozens of art galleries!

Unique and LGBTQ+-friendly shops feature alongside artsy hubs to make it a super welcoming town. Of course, famous Oval Beach appeals with soft dunes and paddleboat rides too. From craft booze tours to fruit picking and corn mazes, it’s one of Chicago’s best road trips.

14. Elkhart Lake

I won’t spoil it for you but this 292-acre lake and nearby Kettle Moraine State Forest is truly a place to unwind from the crowds.

You can hike the epic Ice Age National Scenic Trail or bike down Old Plank Road Trail. Pumpkin patches, race-tracking and fishing are all inclusive!

Want a charming hideaway? This is it.

Road Trips 4 hours from Chicago

Want your road trips from Chicago for a special weekend? Then these Chicago road trips are only 4 hours away.

15. Ann Arbor

If you’re looking for an all-season destination, Ann Arbor is the perfect road trip from Chicago.

Huron River entertains with kayaking, paddle-boarding, tubing and swimming; Matthaei Botanical Gardens and Nichols Arboretum displaying beautiful foliage. Definitely spare some time for Kerrytown Market and Shops for all their indie offerings! 

16. Door Country

Also called ‘Cape Cod of the Midwest’, Door Country is a 70-miles-long basket of fun!

You’ll never get tired of exploring its orchards, coves, lighthouses and wineries. Away from the light pollution, Newport State Park offers stunning starlit skies while Ephraim is all the small-town charm you need. Just imagine – 300 miles of coastline.

You can reach Galena under 4 hours but I recommend taking your time. Pull up through scenic rolling hills to go back in time because the Galena Historic District is made up of cobblestone streets and over 1,000 buildings from the 19 th century.

For those non-history buffs, Chestnut Mountain opens as a ski resort in the winter; Stagecoach Trail and Apple River Canyon State Park are open year-round. 

18. Richland County

To really escape from people, Richland County is a rural road trip destination where you can bunk for the night. But away from the isolated and lush property of Candlewood Cabins are fields and hills that keep you outdoors all day.

The Ridge Road and Pine River Recreation Trail fulfils all your adventurous needs – where else would you find wildlife while biking over abandoned railroads?

You also have three rivers and five state parks within an hour’s distance, and the lovely 100-mile Lower Wisconsin River Scenic Byway for more driving way. 

19. Huron-Manistee National Forest

Michigan really surprises us again and again!

Along the peninsula is the expansive Huron-Manistee National Forest, one of the best road trips from Chicago if you are a nature enthusiast. A single paved road takes you through dense forest (beautiful in the fall) to parking areas so you can hike your way through the serene space or canoe on the rivers. 

Road trips from Chicago

Of course there are loads of great things to do in Chicago but visiting Chicago really opens up a world of opportunities when it comes to road trips.

Whether you’re taking the car out for an hour-long spin or you’re willing to buckle down for a few hours, you won’t be disappointed by the scenery along your journey or the fantastic destinations ahead. 

Related Posts:

• 7 Ways to Make the Most of Your Road Trip Budget
• Planning a Road Trip in the USA: 13 Best Routes!
• 57 Coolest Things to Do in Chicago for 2023
• Christmas Things to Do in Chicago in Winter: 21+…
• 14 Awesome Stops on a Chicago to New Orleans Road Trip
• 11 Unique Stops on the Drive from Chicago to Atlanta

Hi, I'm Vicky! I wrote this. You can find me on all the social media @VickyFlipFlop. I love a bit of adventure, will try anything once, and have a strong passion for the local food and drink, whatever it may be. I'm here to help inspire you to travel to places a little out of your comfort zone, or at least to explore the usual destinations in a different way. Stay, have a look around, and if you have any questions – let me know below.

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Best Road Trips From Chicago

Top road trip destinations from chicago.

Wisconsin Dells

🚗 200 miles ⏱️ 3 hours

The best place for family fun and outdoor adventures is Wisconsin Dells, known as the "Waterpark Capital of the World." Here, you will enjoy thrilling water rides, scenic boat tours, and picturesque hiking trails amidst natural beauty.

On this drive to Wisconsin Dells, we recommend putting aside some time to visit Rockford and Madison .

Mackinac Island

🚗 470 miles ⏱️ 6 hours, 20 minutes

Imagine an idyllic getaway where horse-drawn carriages and bicycles replace cars. On Mackinac Island, you will also enjoy breathtaking views of Lake Huron and treat yourself to the island's famous fudge.

On this scenic drive, you can also visit Benton Harbor and Grand Rapids en route.

Niagara Falls

🚗 555 miles ⏱️ 8 hours, 30 minutes

Niagara Falls is one of the most famous natural wonders on the planet and rightfully so. The awe-inspiring beauty and sheer power of its waterfalls, along with its dramatic scenery make it one of the most beautiful panoramas in the world.

En route, you can add visiting beautiful Lake Erie cities such as Cleveland and Erie to your road trip plans.

Indiana Dunes

🚗 50 miles ⏱️ 1 hour

Perfect for a day trip, this drive to Indiana Dunes will take you to a magical landscape where beautiful beaches and stunning dunes await. While enjoying the scenery, you will also have opportunities for outdoor activities by Lake Michigan.

On your way, you can take a stroll on Wolf Lake Boardwalk and visit Gary Aquatorium , a great destination for the entire family.

New York City

🚗 805 miles ⏱️ 12 hours

Whether you are looking for sightseeing, amazing shopping experiences or some of the best museums in the country, Big Apple has it all! Here, you can visit iconic landmarks like the Statue of Liberty, watch Broadway shows and stroll through Central Park.

Don't miss out on visiting Cleveland and Pittsburgh en route, and make a detour to Philadelphia if you have time.

🚗 470 miles ⏱️ 7 hours, 10 minutes

This is the ultimate road trip for any music lover. "Music City" is famously home to amazing live performances, important historic sites and some of the best BBQ restaurants in the area.

If you are an urban adventurer, don't forget to add Indianapolis and Louisville to your itinerary en route.

Badlands National Park

🚗 940 miles ⏱️ 14 hours

A drive through Badlands National Park's rugged beauty will stay with you forever. Here, you can admire dramatic landscapes and unique geological formations, hike through otherworldly terrain, and enjoy the stunning vistas.

If you have more time, why not stop at Minneapolis and Sioux Falls on the way to Badlands?

Washington DC

🚗 670 miles ⏱️ 11 hours

If you want to tick some iconic landmarks off of your bucket list, then Washington DC is one of the best destinations from Chicago. Some of the amazing places you can visit include the White House, National Mall, and the Smithsonian Museums.

Some of the big cities you can visit en route are Indianapolis and Columbus , Ohio.

Philadelphia

🚗 760 miles ⏱️ 11 hours, 30 minutes

Step back in time in Philadelphia, where the founding of the United States comes to life. Explore historic sites like Independence Hall and the Liberty Bell, and don't forget to try Philly's famous cheesesteaks.

We recommend putting aside some time to visit Cleveland and Pittsburgh on the way to Philly.

Great Smoky Mountains National Park

🚗 600 miles ⏱️ 9 hours, 30 minutes

There is no place as scenic and brooding as the Great Smoky Mountains with its majestic and hazy landscape. This national park is also home to fascinating wildlife, green forests, scenic hikes and cascading waterfalls.

Before you lose yourself in the stunning scenery of the Great Smoky Mountains, you can visit Indianapolis and Louisville en route.

New Orleans

🚗 940 miles ⏱️ 14 hours, 10 minutes

A road trip that will satisfy any kind of road tripper from foodies to music lovers, New Orleans is an amazing destination to visit from Chicago. Check out the live jazz gigs, enjoy delicious Creole cuisine and explore the famous French Quarter.

On this drive towards the Gulf of Mexico, you will also get to visit St Louis and Memphis for a taste of the charming South.

🚗 560 miles ⏱️ 8 hours, 30 minutes

Discover the soulful music and rich history of Memphis, the birthplace of blues, soul, and rock 'n' roll. Visit iconic attractions like Graceland, Beale Street, and Sun Studio, and don't forget to sample city's famous barbecue cuisine.

On your way to Memphis, we recommend stopping at St Louis to visit the famous Gateway Arch .

🚗 650 miles ⏱️ 10 hours

For a stark contrast in scenery, travel from Lake Michigan's shores towards the Blue Ridge Mountains and visit Asheville. This beautiful city is surrounded by gorgeous scenery, and is a great gateway to the beloved Blue Ridge Parkway.

Before you reach Asheville, you can stop at Knoxville and even make a detour to the Great Smoky Mountains National Park .

Minneapolis

🚗 415 miles ⏱️ 6 hours, 15 minutes

From one big city to another, this drive to Minneapolis will take you to the banks of the Mississippi River. Take some time to explore art galleries, bike trails, and world-class dining in this dynamic Midwestern city.

Madison , Wisconsin Dells and Eau Claire are only a few of the amazing places you can discover en route.

🚗 650 miles ⏱️ 10 hours, 10 minutes

Getting to Canada from Chicago is easier than you might think and Toronto is one of the closest big cities you can visit across the border. Here, make sure to add the famous CN Tower to your list of must-see places.

Before you cross the border, you can explore Lansing and Port Huron if you'd like to extend your road trip.

🚗 460 miles ⏱️ 7 hours

Cleveland sits by the shores of Lake Erie, and is known for its world-class museums and scenic waterfront. Take some time to explore the Rock and Roll Hall of Fame while here; the perfect stop for any music lover.

This route will allow you to make detours to charming small towns such as South Bend and Findley on your way to the big city.

🚗 300 miles ⏱️ 4 hours, 30 minutes

Unleash your inner urban adventurer and visit Louisville, famous for its Southern charm and historic landmarks. This riverside city is also well known for its great restaurants serving delicious Southern cuisine.

Indianapolis is located directly on this route, and we recommend spending some time here to visit Indianapolis Zoo .

🚗 95 miles ⏱️ 1 hour, 30 minutes

This short road trip to Milwaukee is a great idea for a day's adventure. Here, you can enjoy a meal by the waterfront, and take a brewery tour or two. There are plenty of different neighborhoods to explore in this historic city on Lake Michigan's shores.

On the way, you can spend some time at Six Flags Great America Amusement Park in Gurnee , a great stop for families!

🚗 250 miles ⏱️ 4 hours

Toledo sits on the banks of the scenic Maumee River and is a destination where you can enjoy both city vibes and laid-back small-town charm in a single place. Spend some time in the downtown area and visit the city's amazing museums.

This drive is dotted with lovely towns such as South Bend and Elkhart , just short detours from the route.

🚗 147 miles ⏱️ 2 hours, 30 minutes

For a relatively short drive, Madison is a great destination to visit from Chicago with a perfect combination of colorful neighborhoods and outdoor adventures. You will also find some great dining options in the capital city of Wisconsin.

If you have time, we recommend also visiting the cute towns of Rockton and Janesville en route.

🚗 130 miles ⏱️ 2 hours, 20 minutes

Visit Switzerland right in the heart of Wisconsin. Monroe in Wisconsin boasts a proud Swiss heritage, and is home to cheese factories and a charming downtown. Take a walk along its quaint streets and taste the award-winning cheeses of this pretty town.

This is a relatively short drive so you can easily make a detour to Rockford to visit Anderson Japanese Gardens .

Great River Road

🚗 300 miles ⏱️ 6 hours

The scenery you will get to enjoy on this drive along the Great River Road will take your breath away. Think of the beautiful river views, charming river towns, and historic landmarks you will see following the banks of the Mississippi River!

For the best scenery and to enjoy a meal, we recommend stopping at Galena and continuing your journey until La Crosse .

Grand Rapids

🚗 186 miles ⏱️ 2 hours, 45 minutes

This road trip to Grand Rapids is a beautiful drive on the shores of Lake Michigan before you head inland to Grand Rapids, where you can visit craft breweries and explore the city's museums and dine at local eateries.

Why not spend some time on the lakeshore if you have some time and visit Benton Harbor and Saugatuck ?

Harbor Country

🚗 80 miles ⏱️ 1 hour, 20 minutes

A short road trip from Chicago will take you to Harbor Country where you can visit beautiful beach towns, gawk at scenic vistas and have fun outdoors. This destination sits right on the scenic shores of Lake Michigan.

To enjoy the coastal scenery, you can make stops at Indiana Dunes National Park and Warren Dunes State Park en route.

Branson, Missouri

🚗 550 miles ⏱️ 8 hours, 10 minutes

Branson is nicknamed the entertainment capital of the Midwest, where live shows, family attractions, and outdoor adventures abound. From music theaters to theme parks, Branson offers fun for all ages.

On the way, you can also visit Springfield , Illinois, and the Lake of the Ozarks for a fabulous getaway.

🚗 145 miles ⏱️ 2 hours, 20 minutes

Fennville, Michigan is known for its picturesque orchards, fabulous vineyards, and beautiful countryside. Explore the scenic beauty of Southwest Michigan and sample the local flavors of this idyllic destination.

As you drive hugging the coast of Lake Michigan, we recommend checking out Benton Harbor and South Haven .

New Glarus, Wisconsin

🚗 145 miles ⏱️ 2 hours, 40 minutes

You don't need to travel to Europe for the perfect Swiss experience, you can find it nearby at New Glarus in Wisconsin. Treat yourself to a genuine Swiss meal, hop on a scenic drive in the New Glarus Woods State Park and enjoy a laid-back getaway in this picturesque town.

If you'd like to expand this relatively short drive, you can make detours to Rockford and Monroe .

🚗 112 miles ⏱️ 2 hours

Cedarburg, Wisconsin is a lovely small town where you will find the perfect balance of historic charm, local artisans, and scenic beauty. Make sure to explore the quaint streets lined with shops and galleries and experience the welcoming atmosphere firsthand.

On your way to Cedarburg, you can stop at Milwaukee for a taste of the big city before your small-town experience.

🚗 100 miles ⏱️ 1 hour, 30 minutes

For the perfect small-town experience, enjoy a short and scenic drive from Chicago to Utica, Illinois. This laid-back town is just a short distance from the beautiful Starved Rock State Park.

You can make detours to Joliet and LaSalle on this short drive, and enjoy the scenery of Illinois River if you have time.

Longer road trips from Chicago

Yellowstone National Park

🚗 1,450 miles ⏱️ 21 hours, 30 minutes

Yellowstone National Park is home to impressive geysers, beautiful hot springs, majestic waterfalls, fascinating wildlife, and stunning landscapes.

🚗 1,750 miles ⏱️ 26 hours

Experience the dazzling lights and non-stop entertainment of Las Vegas, and enjoy world-class casinos, extravagant shows, and vibrant nightlife.

Yosemite National Park

🚗 2,140 miles ⏱️ 33 hours

The stunning Yosemite National Park is famous for its towering granite cliffs, cascading waterfalls, and ancient sequoia trees.

Myrtle Beach

🚗 1,060 miles ⏱️ 16 hours, 20 minutes

Escape to the sunny shores of Myrtle Beach, where miles of sandy beaches, thrilling attractions, and world-class golf courses await.

🚗 1,000 miles ⏱️ 14 hours, 30 minutes

Explore the Mile High City of Denver, surrounded by the stunning Rocky Mountains and discover outdoor adventures and craft breweries.

Zion National Park

🚗 1,740 miles ⏱️ 25 hours

The breathtaking landscapes of Zion National Park are home to red rock cliffs and narrow slot canyons where you can hike iconic trails.

Los Angeles

🚗 2,020 miles ⏱️ 29 hours

Los Angeles is famously home to Hollywood, as well as beautiful beaches, amazing theme parks and world-class museums waiting for you to explore.

Grand Canyon

🚗 1,700 miles ⏱️ 25 hours

Grand Canyon is one of the world's most breathtaking natural wonders and the vast expanse of the canyon is dotted with scenic viewpoints and hiking trails.

Acadia National Park

🚗 1,260 miles ⏱️ 19 hours, 20 minutes

Acadia National Park is where rocky shorelines, forested trails, and scenic vistas come together for the perfect outdoor adventure.

🚗 1,180 miles ⏱️ 14 hours, 30 minutes

Savannah is a charming and historic city with cobblestone streets, historic squares, museums and antebellum architecture.

🚗 1,330 miles ⏱️ 20 minutes

As you drive to Austin from Chicago, you can explore the heartland of America and the vibrant culture of Texas along the way.

🚗 1,080 miles ⏱️ 17 minutes

Boston is a beautiful New England city with historic streets, and is home to some of the most prestigious universities in the country.

🚗 1,385 miles ⏱️ 21 minutes

For the ultimate beach road trip, head to Miami, where you can enjoy the sunshine, swimming in the Atlantic Ocean and amazing nightlife.

🚗 1,320 miles ⏱️ 22 minutes

Welcome to "The Themepark Capital of the World!" In Orlando you can visit some of the best amusement parks like the Walt Disney World Resort.

🚗 2,200 miles ⏱️ 36 hours

The sunshine and beaches you will get to enjoy in San Diego will be worth the long mileage of this epic road trip from Chicago.

San Francisco

🚗 2,470 miles ⏱️ 38 hours

Visit the City by the Bay and soak in the beauty of the California sunshine. You will admire stunning coastal vistas and iconic landmarks here.

🚗 2,100 miles ⏱️ 30 hours

Admire the iconic skyline of Seattle, explore its great museums, and enjoy a cup of coffee at one of its many Third-Wave Coffee shops.

🚗 1,230 miles ⏱️ 19 minutes

Enjoy the famous Florida sunshine in Tampa and relax by the beach with Gulf Coast's beautiful scenery right in front of you in this tropical paradise.

🚗 1,750 miles ⏱️ 25 hours

Explore the beauty of the American Southwest and discover Tucson and its famous desert landscapes, especially in Saguaro National Park.

30 Delightful Road Trips from Chicago

If you’re looking to get away from the city, here are the best destinations for day trips and weekend road trips from Chicago.

Chicago’s location makes it an ideal place to get in the car and go, whether you live in the city or you make it your home base for some Midwestern exploration.

I’ve lived in Chicago and its suburbs for twenty years, and in the Midwest my entire life (except for a brief four years in my early twenties).

Let’s just say I’ve been to a LOT of towns, villages, cities, parks, etc., that are within easy driving distance from the Windy City.

And while I love Chicago (I even wrote a book about it ) and The Local Tourist began as a guide to the city’s River North neighborhood, sometimes even I just need to get away.

I’ve hand-picked some of my favorite Midwest road trips from Chicago. If you’re looking for delightful towns with delicious food and drink, boutiques and artisan shops, intriguing history, outdoor adventures, natural beauty, and so much more, you’re sure to find your perfect road trip from Chicago.

Road trips are the equivalent of human wings. Ask me to go on one, anywhere. We’ll stop in every small town and learn the history and stories, feel the ground and capture the spirit. Then we’ll turn it into our own story that will live inside our history. Victoria Erickson

Love travel quotes? Here you go!

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Road Trips from Chicago

How to choose the best road trips from chicago.

How far will you drive for a weekend trip?

I asked that question of members of The Local Tourist Facebook group and their answers surprised me. The winning time was five hours, and second place was four hours.

Several of these road trippers would even drive eight hours for a weekend vacation!

Based on their input, and my own obsession with road trips, I’ve included some destinations that require a few hours behind the wheel.

I’ve also included places that are much closer. In fact, there are a few towns and cities that are technically suburbs of Chicago. Depending on your starting point, these destinations may provide more of a staycation than a vacation.

But hey – that’s what being a Local Tourist is all about, right?

I’m only including destinations that I’ve personally visited and enjoyed. Clearly, I need to spend more time in Ohio and Michigan.

For each road trip destination, I’ve included driving time. This assumes you’ll be driving interstates and won’t be avoiding toll roads. It also assumes no traffic.

Depending on when you leave for your weekend road trips from Chicago, traffic could increase times by at least an hour, so check Google maps or Waze before you go.

I’ve also included suggestions for places to stay, as well as links to each destination’s official Convention and Visitors Bureau, or CVB. These local resources are my travel planning not-so-secret weapon .

Ready to plan your road trips from Chicago? Let’s go!

Related: before you go, check out all my tips for planning a road trip .

10 Day Trips from Chicago

If you’re looking for a quick getaway or even a day trip, these locations are short road trips from Chicago and all within two hours of the Windy City.

Elgin, Illinois

Driving time: 1 hour

Known as the City in the Suburbs, Elgin, Illinois, is a relatively quick drive or an easy train ride from downtown Chicago. Its proximity makes it perfect for a day trip, but there’s enough to do that you’ll want to make a weekend of it.

A good place to start is downtown Elgin. Located right on the Fox River, it’s filled with public art and historic buildings.

Get the history of the area at the Elgin History Museum (pictured above).

You can also take a free self-guided walking tour of the Elgin Historic District.

Since that walking will make you hungry, grab a sandwich at Blue Box Café or head up to West Dundee for a burger and a pint at Emmett’s Brewing Co., an award-winning brewery.

Another one of the great things to do in Elgin is visit Lords Park and Zoo. On its grounds is the Elgin Public Museum, the only natural history museum in the Fox Valley.

Where to stay in Elgin, Illinois: Most of the hotels in Elgin are along the I-90 corridor. The Holiday Inn & Suites is one of the most highly rated accommodations near Elgin.

CVB: Explore Elgin Area, exploreelginarea.com

Indiana Dunes National Park, Indiana

One of our newest national parks is a short drive or train ride from Chicago. Established in 2019 , Indiana Dunes National Park is 15,000 acres along the southern shores of Lake Michigan.

There are over fifty miles of trails, making hiking Indiana Dunes National Park one of its top attractions. Hikers can traverse dunes, wetlands, prairies, rivers, and forests, all in one park.

There’s a fee to access the park: $15 per person (up to $25 per family group) and $25 per carload.

You could spend the entire weekend at the park. However, if you want a break, drive a little further east to Michigan City.

While the town is known for Lighthouse Place Premium Outlets, it’s also home to several museums, including the Old Lighthouse Museum.

Where to stay near Indiana Dunes State Park: Camping is available within the park itself, and there are several hotel chains in Michigan City .

CVA: South Shore Indiana, southshorecva.com

Harbor Country, Michigan

Driving time: 1 hour 15 minutes

Just across the border from Michigan City, Indiana, is Harbor Country.

The Red Arrow Highway takes you through eight small towns, each unique, each charming in its own away. Think boutique instead of big box, locally owned versus chain.

Outdoor enthusiasts will find everything from kayaking and paddle boating to fishing, surfing, and golf. Of course, you can also spend the day at the beach.

One of the biggest attractions is the number of Southwest Michigan wineries and breweries. The climate is very similar to Napa Valley, and the area’s known for its award-winning wines.

Where to stay in Harbor Country: You can find inexpensive hotels as well as private homes in New Buffalo, Michigan .

CVB: Harbor Country Chamber of Commerce, harborcountry.org

Kenosha, Wisconsin

Driving time: 1 hour 20 minutes

Kenosha is the fourth largest metro area in Wisconsin, as well as the fourth-largest city on the shores of Lake Michigan, and there are TONS of things to do.

It’s the home of the oldest operating velodrome in the country, a free dinosaur museum, historic restaurants, not one but two lighthouses, and you can still ride an electric trolley.

Start your visit at the Kenosha History Center for an overview of the area’s past. Then don’t miss the Dinosaur Discovery Museum or Kenosha Public Museum, both of which are free.

The Civil War Museum is an impressive look at Wisconsin’s role in the war.

A must-visit restaurant is House of Gerhard, featuring traditional German specialties. Another favorite is Franks Diner. Guy Fieri featured it on  Diners, Drive-ins, and Dives and it serves up tasty American cuisine with a side of sass.

Check out more reasons you should visit Kenosha, Wisconsin .

Where to stay in Kenosha: you can stay in Kenosha hotels that are conveniently located off I-94, or you can choose an historic inn like The Stella Hotel and Ballroom. For a great view, check out Wyndham Garden Kenosha, right on the harbor.

CVB: Visit Kenosha Wisconsin, visitkenosha.com

McHenry County, Illinois

Driving time: 1 hour 30 minutes

I lived in McHenry County, whose northern border is shared with Wisconsin, for five years and still found new things to do.

One of the most surprising aspects of the area is the sheer number of parks. The McHenry County Conservation District manages more than thirty conservation areas, and most of them have hiking trails.

There are also city and village parks, as well as two state parks within the county.

Another great thing about the area is the food. Oh, the food! There’s farm-to-table at 1776 Restaurant and Duke’s Alehouse and Kitchen, incredible Italian at 750° Cucina Rustica, rich encased meats at Richmond Brathaus, and the best custard anywhere at Julie Ann’s Frozen Custard.

All are local; all are family-owned; all are delicious.

McHenry County’s county seat is Woodstock, which you might recognize. It’s where Groundhog Day was filmed, and the town celebrates with their very own groundhog, Woodstock Willie.

You can even stay in the same bed and breakfast where Bill Murray’s character woke up again, and again, and again.

With the mouthwatering breakfasts served each morning at Cherry Tree Inn Bed and Breakfast, though, you won’t mind if the same thing happens to you.

Read more about why I love being a Local Tourist in McHenry County , and you will, too!

Where to stay in McHenry County: Cherry Tree Inn Bed and Breakfast , of course! Since there are only four rooms, if they’re full, you can find hotels in Crystal Lake , the largest town in the county.

CVB: Visit McHenry County, visitmchenrycounty.com

Starved Rock State Park

Head to Starved Rock State Park for a day of fresh air, physical fun, and outdoor adventure.

Located just 94 miles southwest of Chicago, the landscape is an unexpected tableau of bluffs, steep trails, and waterfalls. Since it’s on the Illinois River, there’s also fishing and boating.

You can bring a lunch to enjoy at the waterfront picnic area, or grab a bite to eat at the historic lodge.

Nearby Ottawa is a charming town with lots of creative chefs, so you can have the best of both worlds.

Where to stay in Starved Rock State Park: There’s a lodge at the park itself, but I personally prefer camping. Starved Rock has one of the best campgrounds in the Midwest .

Janesville, Wisconsin

Driving time: 1 hour 45 minutes

Located right off I-90, Janesville is an ideal weekend road trip from Chicago, especially if you like the great outdoors, art, and history.

The town’s tagline is “Wisconsin’s Great Outside,” and there are thirty miles of trails in Janesville, including a portion of Wisconsin’s Ice Age Trail. One of the most scenic treks is the mile and a half hike to Devil’s Staircase.

The Rotary Botanical Gardens is a non-profit garden covering twenty acres. You won’t want to miss their Holiday Light Show.

From Thanksgiving weekend through December, the gardens become a magical winter wonderland strewn with hundreds of thousands of lights.

History buffs will get a kick out of exploring Janesville’s thirteen historic districts. One of the highlights of any visit to Janesville would be the Lincoln-Tallman House.

Built in 1857, it’s been a museum since 1951. Eighty-five percent of the furnishings in the house are original, including the bed that Lincoln slept in when he was a guest.

Janesville’s dining scene is relatively new, but with restaurants like Genisa Wine Bar and the Sandwich Bar, it’s gaining steam and there are enough unique spots to keep your palate happy.

I definitely recommend bellying up to the 1933 Art Deco bar at O’Riley and Conway’s Irish Pub for some Scotch eggs.

Combine history and beer at Gray Brewing Co. They’ve been brewing beer since 1856, except during that pesky Prohibition when they turned to sodas. It’s one of the oldest family-owned breweries, not just in Wisconsin, but in the United States.

When you visit Janesville, make sure you’ve got your walking shoes and plenty of room on your SD card, because the town is filled with vibrant and colorful murals.

Where to stay in Janesville, Wisconsin: Renovated in 2019, the Hampton Inn provides comfortable rooms with modern décor. Breakfast is included, and it’s one of the better spreads I’ve seen.

When I stayed, the hot items were frequently replenished and there were several options including both waffles and mini-waffles.

CVB: Janesville Area Convention and Visitors Bureau, janesvillecvb.com

Lake Geneva, Wisconsin

Located just 75 miles northwest of Chicago on the other side of the Wisconsin border, Lake Geneva provides a year-round escape from hectic city life and is a short day trip from Chicago or great weekend destination.

One attraction with a direct tie to Chicago is the Yerkes Observatory (pictured above).

Yerkes is considered the birthplace of modern astrophysics and was funded by Charles Yerkes, who had a huge role in developing Chicago’s public transportation.

Lake Geneva has long been a playground for Chicagoans. In the late 1800s and early 1900s, it seemed that every wealthy Chicagoan built a mansion on the shores of the lake. Today, many of those mansions still stand.

The best way to see them is to take a boat tour, especially if you can ride along when they’re delivering the mail. Lake Geneva is one of the few places left in the country where mail is delivered by boat.

Another way to see the mansions is to walk the path that surrounds the lake. Like Chicago’s lakefront with its public beaches, Geneva Lake is surrounded by a trail that’s open to everyone.

The lakefront path is one of the most popular things to do in Lake Geneva .

One place you can only visit from a boat, unless you have physical limitations and can’t climb the many stairs from the dock, is Black Point Estate. This historic mansion has many ties to Chicago, including Jane Addams .

For something completely different, feed an ostrich. Safari Lake Geneva is a drive-through experience that allows you to feed giraffes, alpacas, elands, and emus.

An experience that’s both fun and tasty is taking a class at Lake Geneva Cooking School. Chef John teaches you how to make dishes you might never attempt on your own, and he pairs them with stellar wines.

Like many, during lockdowns he pivoted and fulfilled his dream of publishing a cookbook . I’ve made several recipes from it, and highly recommend it.

Golf is one of Lake Geneva’s biggest draws. During the winter months, you can ski, snowboard, snowshoe, and ice fish.

Where to stay in Lake Geneva: Technically located in Fontana on the west side of Geneva Lake, The Abbey Resort is a sprawling complex with beautiful rooms overlooking a marina.

They also have multiple pools and there’s often live music, either in the bar or outside during the summer.

CVB: Visit Lake Geneva, visitlakegeneva.com

Milwaukee, Wisconsin

Milwaukee, Wisconsin, is an urban getaway filled with culture and outdoor fun.

The instantly recognizable Milwaukee Art Museum is definitely worth visiting, and after you’ve browsed its collections you can take a walk along the lakefront.

For more art, book a room at Saint Kate The Arts Hotel . This astounding hotel is like staying in a work of art – because you are. It’s right downtown, providing easy access to the river walk.

Beer lovers will have a blast exploring Milwaukee’s breweries. Lakefront Brewery is known for its fun tours. Milwaukee Brewing Company and Mobcraft are also great places to visit.

There’s no beer at the Pabst Mansion, but you’ll still want to see Captain Frederick Pabst’s house, built in 1892. It’s a gorgeous Flemish Renaissance Revival mansion that’s on the National Register of Historic Places.

Fun fact: Captain Pabst earned his stripes with the Goodrich Line of steamships, which was based out of Chicago.

Another nautical stop is North Point Lighthouse. Built in 1888 high on a bluff, Frederick Law Olmsted himself designed the grounds. Chicagoans will recognize the famous landscaper’s name from the 1893 World’s Columbian Exposition and the University of Chicago, among others.

Olmsted also landscaped Lake Geneva’s Yerkes Observatory, which was part of the University until recently.

The Harley-Davidson Museum is another must-stop and be sure to dine at Motor, the on-site restaurant.

During the summer there are festivals just about every weekend, so check Visit Milwaukee’s events calendar to find out what’s happening.

And of course, make sure you have some cheese curds, brats, and beer.

Where to stay in Milwaukee: Saint Kate The Arts Hotel for a modern art experience, The Pfister Hotel for a dose of history, and Iron Horse for more industrial décor and easy access to the Harley-Davidson Museum.

CVB: Visit Milwaukee, visitmilwaukee.org

Lafayette, Indiana

Driving time: 2 hours

My grandparents lived in West Lafayette, Indiana, so I grew up visiting. However, it wasn’t until a few years ago that I actually explored the town. Boy, had I been missing out on a lot.

Known as the home of Purdue University, West Lafayette, and its sister city Lafayette, have history, art, culture, delicious food and drink, and a vital sense of community.

There are several places that make this a great place for a road trip from Chicago. One is the Haan Mansion Museum of American Art.

The mansion was originally built for the 1904 World’s Fair in Saint Louis. Now it’s in West Lafayette and is filled with impressionist paintings and historic furniture.

Another is SAMARA. Designed inside and out by Frank Lloyd Wright for Dr. John and Catherine Christian, it’s a nearly perfectly preserved example of Wright’s Usonian architecture.

Another fascinating spot is Prophetstown State Park, combining a landscape that’s distinctly Indiana with the history of the Native Americans who fought the settlers’ encroachment, and the farmers who eventually tilled the land. While there, visit the nearby Tippecanoe Battlefield.

I’ve got even more places to visit in Lafayette. These include not only places I’ve been, but also spots recommended by students at Purdue University. I’ve partnered with a 400-level travel-writing class since 2018, and many of their submissions are local to the college town.

See why you should visit Lafayette and West Lafayette Indiana

Where to stay in Lafayette, Indiana: Mr. TLT and I loved the cozy intimacy of Black Blanket Farms Bed and Breakfast . If they’re booked, Lafayette has a gazillion hotel options since it’s a college town.

CVB: Visit Lafayette-West Lafayette, homeofpurdue.com

9 Weekend Road Trips from Chicago between 2 and 3 hours

Shipshewana, indiana.

Driving time: 2 hours 15 minutes

If you’re looking for a slower pace, yet still want plenty to do, add Shipshewana to your weekend adventures.

Shipshewana is in LaGrange County, also known as Indiana Amish Country. You’ll know when you get close because you’ll start seeing horse-drawn buggies and bicyclists everywhere.

With the third largest Amish population in the world, this area is a definite departure from the hustle and bustle of city life. Instead, it’s antiques and hand-crafted furniture, delicious food, and fun entertainment.

One of Shipshewana’s most well-known attractions is the Shipshewana Flea Market . Begun in 1922 with a livestock auction, this family-owned business is the largest flea market in the Midwest.

Learn what it’s like to attend the Shipshewana Misc & Antique Auction .

You also don’t want to miss the Davis Mercantile . Another family affair, it’s a destination for dining, shopping, and riding the carousel.

If you plan your trip in advance, you might be able to dine in an Amish home, which is a real treat (and the best mashed potatoes ever). If it’s a last-minute getaway, The Blue Gate Restaurant is always a favorite. After dinner, head upstairs for a show at the theater.

Other fun things to do in Shipshewana include touring Cook’s Bison Ranch, exploring one of the many county parks, having dinner in an Amish home , canoeing or kayaking on the Pigeon River, and taking a driving tour on a hunt for barn quilts.

Where to stay in Shipshewana: The Blue Gate Garden Inn is a comfortable hotel that’s filled with amenities, including outdoor fire pits and an ice cream shop.

CVB: Visit Shipshewana, visitshipshewana.com

Sheboygan, Wisconsin

Driving time: 2 hours 30 minutes

When people ask me the destination that surprised me the most, Sheboygan, Wisconsin, tops the list.

I visited in August 2021, and it was my first press trip post-cancer. It was exactly the experience I needed: waves, beaches, amazing food, brilliant art, and a community that preserves its past.

Your first stop should be the Sheboygan Visitor Center. It is absolutely the coolest visitor center I’ve ever seen – and I’ve been to a lot.

Sheboygan’s known as the Malibu of the Midwest, so of course I had to get out on the water. One of my favorite things to do was take a first sailing lesson in Lake Michigan. That’s right – you can learn how to sail on a weekend trip to Sheboygan.

The Kohler name is prominent in the area. In addition to the manufacturing company and a nearby resort, there’s also the Kohler Arts Center and the Kohler Art Preserve, which opened in 2021.

Kohler also manages the James Tellen Woodland Sculpture Garden, one of several artist-built environments throughout the state.

History geeks will want to stop at Sheboygan Indian Mound Park and the Sheboygan County Historical Society and Museum.

For dining, don’t miss Black Pig, Il Ritrovo, and BoMallies. Breakfast should absolutely begin at Paradigm Coffee and Music. Best. bagel. sandwich. ever.

Check out my piece about this surprising place, and I’ve even included the perfect 3-day Sheboygan itinerary .

Where to stay in Sheboygan: Blue Harbor Resort offers gorgeous rooms and an even better view. They’ve also got a whole water park, on-site dining, and easy access to the beach.

CVB: Visit Sheboygan, visitsheboygan.com

Elkhart Lake, Wisconsin

About twenty minutes from Sheboygan is another delightful road trip from Chicago.

Elkhart Lake has all the feelings of a resort town. There are historic accommodations, unique boutiques, and delicious dining.

The eponymous lake is gorgeous, with crystal clear water. You can take a pontoon boat ride, or go kayaking or paddle boarding.

The village is also right by the Ice Age Scenic Trail and Kettle Moraine State Forest – Northern Unit, providing lots of opportunity for outdoor activities.

Racing fans won’t want to miss Road America. This four-mile road course is considered the best in the United States and one of the top in the world.

Not only can you watch racing, you can also take a spin around the track yourself. They offer both motorcycle and automobile driving schools.

Where to stay in Elkhart Lake, Wisconsin: Osthoff Resort is an historic inn that offers a variety of room options, including suites and villas, and features amenities such as an indoor and outdoor pool, spa, and fitness center.

The resort also has several dining options on-site, including a fine-dining restaurant and a casual bistro.

CVB: Elkhart Lake, visit website

Galena, Illinois

Driving time: 3 hours

Galena, Illinois, is located near the Mississippi River on the opposite side of the state from Chicago. Surrounded by the rolling hills and bluffs of the Driftless Region, it’s an area dotted with wineries and golf courses.

There are many reasons nearly a million people visit the former mining mecca each year. From shopping along its historic main street to the many wineries in the area, it’s a great spot for a romantic weekend or a girls getaway.

A stroll down Main Street feels like a step back in time. Be sure to stop into Galena Canning Company for a taste of salsas and jams, and Galena Brewing Company offers a lineup of tasty beers.

Thrill-seekers will love a visit to Long Hollow Canopy Tours , a zipline adventure through the woods.

Nature lovers can explore trails along the nearby Mississippi River, and golfers will love a few rounds at Eagle Ridge Resort & Spa.

There are also several historic buildings, and the Ulysses S. Grant Home is one of the most popular places to visit for a look into the past.

Where to stay in Galena, Illinois: While there are hotels that are closer to Galena’s historic Main Street, two of my favorites are a short drive from downtown. Goldmoor Inn Bed and Breakfast is an elegant getaway overlooking the Mississippi River.

Eagle Ridge Resort and Spa is my home away from home when I’m in Galena. I’ve stayed there at least five times. I love the variety of accommodations, activities, and the delicious food.

CVB: Visit Galena, visitgalena.org

Hendricks County, Indiana

My first visit to Hendricks County, Indiana, was in 2017, and since then I’ve returned four? five? times. You might say I like it. I even taught the first writing workshop for Midwest Travel Network (I’ve now taught three) at Natural Valley Ranch, a cabin with that private pond out its back door.

There are also horses, that you can ride. Squeee!

It’s a large county comprised of several towns. Some are large, like Plainfield and Avon, and others are small, like the tiny Lizton, which is home to the best barbecue – and pecan pie – in Indiana (and possibly the Midwest).

Race fans not only have easy access to the Indianapolis Motor Speedway, they can also see the NHRA Finals at the Lucas Oil Raceway within Hendricks County.

The only Doctor Who Museum and Store is in Hendricks County, as is the Tie-Dye Lab, where you can make your own tie-dye apparel. Beasley’s Orchard has the best apple cider. Oasis Diner is the only diner on the National Road and it’s got one of the best pork tenderloin sandwiches anywhere.

Basically, go to Hendricks County . There’s so much to do I bet you’ll want to go back again and again, just like I do.

Where to stay in Hendricks County: Natural Valley Ranch is great if there’s a big group of you exploring the area. If not, then I’m a fan of Staybridge Suites . Each room includes a kitchenette, plus they offer free breakfast and weekday happy hours.

CVB: Visit Hendricks County, visithendrickscounty.com

More Road Trips from Chicago between 2 and 3 hours

• Madison, Wisconsin; 2 hours 45 minutes
• New Glarus, Wisconsin; 2 hours 45 minutes
• Indianapolis, Indiana; 3 hours
• Quad Cities, Illinois/Iowa; 3 hours

11 Weekend Road Trips from Chicago between 3 and 5 hours

Fort wayne, indiana.

Driving time: 3 hours 10 minutes

When you go to Fort Wayne, go hungry. And thirsty. This northeastern Indiana town has a thriving food and beer scene that will have you coming back for more.

This All-American City is located at the confluence of three rivers, and that riparian location has fed its personality since it was founded when General “Mad” Anthony Wayne built a fort there in 1794. That fort didn’t last long, and by 1815 the town was on its third fort, built by Major John Whistler.

Chicagoans might recognize that name: he built Fort Dearborn when he was a Captain. You can visit a replica of Whistler’s fort, and they often have events.

One of the best things to do in Fort Wayne is visit the YLNI Farmers Market. This bustling marketplace features everything from handmade chocolates to hot sauces that’ll blow your top off to candles that smell like Fort Wayne (and Montana, Chicago, and everywhere else Simple Nature‘s creative creator has been). 

But what about that food, you ask? A few favorites include Club Soda, for white tablecloth dining with a side of live music, Birdie’s for shared plates in an airy rooftop, and Hall’s Prime Rib for down-home diner cooking.

Beer fans will want to belly up at Junk Ditch, The Hoppy Gnome, and Hop River Brewing Company.

Where to stay in Fort Wayne, Indiana: Courtyard Fort Wayne Downtown at Grand Wayne Convention Center is in a great location; across from the convention center and in between Parkview Field and Embassy Theatre.

CVB: Visit Fort Wayne, visitfortwayne.com

Green Bay, Wisconsin

Driving time: 3 hours 15 minutes

While it may seem blasphemous to some to suggest driving to the home of the Packers from the home of the Bears, I guarantee there’s a lot more going on than gridiron battles.

Auto enthusiasts will love The Automobile Gallery. Opened in 2016, this collection of pristine vehicles span over a century of automotive history.

From the iconic 1908 Cadillac Model T to the sleek 1960 Chevrolet Corvette, every car enthusiast will find something to admire.

The museum also features a rotating selection of vehicles, ensuring that there is always something new and exciting to discover.

For transportation of another kind, visit the National Railroad Museum. The museum began in 1956 and now covers a sprawling 33-acre campus.

Not only can you see locomotives like the iconic “Big Boy” No. 4017, you can step inside a Pullman sleeper car and learn about the porters who worked America’s rail lines.

Ready for a drink? From Captain’s Walk Winery to Zambaldi Beer, you’ll find something to whet your whistle.

And if you’re hungry, Green Bay will keep you fat and happy. (Speaking from experience here.) Don’t miss the authentic kringles at Uncle Mike’s Bake Shoppe or a cup of Booyah, a hearty Belgium chicken stew.

Where to stay in Green Bay, Wisconsin: Stay in the heart of Green Bay at the historic Hotel Northland . The hotel’s especially great for a romantic getaway.

CVB: Discover Green Bay, website

Dubuque, Iowa

Driving time: 3 hours 20 minutes

You’ll be glad Dubuque Iowa is one of these easy road trips from Chicago, because there’s so much to do you’ll want to return again and again.

Dubuque’s location on the Mississippi means it’s filled with river lore. Begin your visit at the Mines of Spain, a National Historic Landmark and Iowa State Recreation Area. It’s named for the mines that Julien Dubuque, the town’s founder, worked with permission from first the Mesquakie and then the Spanish. The Julien Dubuque Monument resembles a rook and overlooks the Mississippi; Dubuque is buried on the site.

Get an in-depth introduction to the river and the region at the National Mississippi River Museum and Aquarium, then go on the river itself. You can take a steamboat tour or an American Lady River Cruise aboard a yacht.

Like Janesville, Dubuque’s downtown is also covered with murals, and it’s a fun afternoon to walk the streets and find your favorite.

Dubuque’s most unusual attraction is the Fenelon Place Elevator. It’s the shortest, steepest railroad and a ride to the top provides some of the best views in the city.

Another spot for great views is Eagle Point Park. You’ll get a birds eye view of Lock and Dam #11 and can see into both Wisconsin and Illinois.

One of the most famous attractions is in nearby Dyer. The Field of Dreams Movie Site is surprisingly moving, especially now that you can tour the house. Inside you’ll discover stories behind the filming of this beloved classic.

I think the food scene in Dubuque will surprise you. It certainly surprised me to discover several innovative chefs serving quality cuisine. Make reservations for both Brazen Open Kitchen and Pepper Sprout and you’ll be one happy diner.

Where to stay in Dubuque, Iowa: since it’s right downtown, you can’t get much more convenient than Hotel Julien Dubuque . Plus, it’s a gorgeous hotel with oodles of history, including stories about Mr. and Mrs. Lincoln and a certain gangster from Chicago.

CVB: Travel Dubuque, traveldubuque.com

Brown County, Indiana

Driving time: 4 hours

Brown County, Indiana, is known for its beauty when the leaves change colors, but that doesn’t mean you can only visit in the fall. The rolling hills are beautiful year round.

While the area is easy to get to now, that wasn’t always the case. Its relative isolation fostered a vibrant artists community, which thrives to this day.

Visit Brown County and you can see the home and studio of one of the founding artists T.C. Steele. He was one of the five members of the acclaimed Hoosier Group. In the late 1800s, that group put Indiana’s art scene on the map, and Brown County in particular.

Browse the galleries of Nashville, Indiana, and you’ll see works of art from those early painters as well as artists of today.

Get a two-for-one cultural experience at Country Heritage Winery. Not only can you taste wines, when you take a weekend road trip from Chicago, you can do so while listening to live music.

Another favorite is Hard Truth Hills. Inspired by Sierra Nevada’s set-up in Asheville, North Carolina, this is a multi-purpose destination with a brewery, a distillery, a restaurant, and an outdoor stage. Pro tip: get the to-die-for pulled pork nachos.

Brown County is one of those places where you can choose to go-go-go, or you can kick back and relax. Either way, it’s definitely worth the drive.

Learn more about Brown County and how it became the tourist destination it is today.

Where to stay in Brown County: Abe Martin Lodge is located within Brown County State Park. Bring the kids and your swimsuits; they’ve got an indoors water park. Want something more secluded? There are cabins, too.

CVB: Brown County, browncounty.com

Sandusky, Ohio

Driving time: 4 hours 45 minutes

Sandusky is most famous for being the home of Cedar Point amusement park, but this city on the shores of Lake Erie is much more than roller coasters and funnel cakes.

A fun way to get an overview is to take a Segway tour. Sandusky Segwave offers guided tours through the historic downtown. Perched atop your personal transporter, you’ll glide past historic sites, through city parks, along the lakefront, and past the Merry-Go-Round Museum. You’ll learn about the town’s very beginnings, as well as its role in the Underground Railroad.

Another reason to visit Sandusky is Kelleys Island. Take a high-speed ferry to the largest American island in Lake Erie for a day of art, shopping, and wine.

While you’re on the island, don’t miss Glacial Grooves State Memorial. This National Natural Landmark protects the largest easily accessible grooves in the world. To see them is to witness the power of the glaciers that shaped North America.

Before you go back to Sandusky, get a scoop of Lake Erie Cookie Island Monster. It’s the official ice cream of Ohio’s Lake Erie Shores and Islands , Sandusky’s visitors bureau.

Warning: it will turn your tongue blue!

Check out my guide to see many more things to do on Kelleys Island .

Where to stay in Sandusky, Ohio: Hotel Kilbourne . This place puts the boutique in boutique hotel. In addition to being the only Sandusky hotel that’s on the water, it’s also got a rooftop bar and an on-site restaurant.

CVB: Ohio’s Lake Erie Shores and Islands, shoresandislands.com

Driving time: 5 hours, or as long as you’d like!

Route 66 epitomizes the freedom of the open road, and it begins in Chicago. The route became official in 1926, providing many small towns access to significant national roadways for the first time. Although it was decertified in 1985, the Mother Road lives on.

This scenic byway changed course over the years, and these alignments are well marked in Illinois. If you’re short on time, I-55 will take you from one attraction to the next, but the fun of driving one of the country’s most historic byways is in following its original path.

Some of the most popular roadside attractions include Buckingham Fountain (not technically on Route 66, but you’re so close!), the Gemini Giant, Bunyon’s Statue, and Carlinville’s Million Dollar Courthouse.

Route 66 in Illinois is only 301 miles, but it’s nearly a century of Illinois history, so take your time.

More road trips from Chicago between 3 and 5 hours:

• Iowa City, Iowa; 3 hours 45 minutes
• Door County, Wisconsin ; 3 hours 50 minutes
• Bloomington, Indiana ; 4 hours
• Spencer, Indiana : 4 hours
• Collinsville, Illinois and Cahokia Mounds State Historic Site : 4 hours 45 minutes
• Traverse City, Michigan; 4 hours 55 minutes

Want an epic trip from Chicago but don’t feel like driving? Consider a train to Seattle – here’s what it’s really like to ride the Amtrak Empire Builder !

Map of Road Trips from Chicago

I hope these delightful road trips from Chicago will help you find someplace wonderful to visit for your weekend getaways. Each place is special and offers unique experiences. When you go, I’d love it if you’d share your photos in our Facebook group .

Oh, and be sure to bookmark this page, because I’ve got more destinations to add!

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Your Family Will Love These 30 Road Trips Near Chicago

• Updated: 04/03/2024

Chicago and US Midwest families, we feel you. Airplane tickets are pricier than ever. Though, your need for a getaway has never been greater. 

You want to get out of town with minimal effort and do not want to spend a small fortune to do it. 

To help, I share my favorite short to medium-distance driving destinations and those recommended by regional experts—other travel bloggers and planners passionate about places in the Midwest. 

Together, we came up with this list of the 30 best road trip destinations for the summer and the fall, from big cities to small charming towns to blow-you-away natural wonders, all within a five-hour drive of Chicago.

Table Of Contents

Check out our destination recommendations by state below. 

• Michigan & Ontario

Or view all 30+ places we recommend going in the map below.

How to use this map:  In the map header, click the square tab to the left of my logo or click the enlarge frame to the right to view detail. You can save the map to “Your Places” on Google Maps by clicking the star next to the map name. Or you can share it by clicking the share icon.

Wisconsin: Top Road Trips Within 5 Hours of Chicago

Welcome to Wisconsin, or the “Dairyland State,” loved by visitors for its rich dairy heritage, delicious cheeses, and beautiful landscapes, including miles upon miles of lakeshore coastline.

Check out these six Wisconsin destinations shared in more detail below.

• Madison, WI
• Milwaukee, WI
• Sheboygan, WI
• Door County, WI
• Wisconsin Dells, WI
• Lake Geneva, WI

Also, consider adding Green Bay (a 4-hour drive) and the lake-perfect Northwoods towns of Manitowish Waters and Boulder Junction (a 5.5-hour drive) to your driving trip wishlists.

Madison, Wisconsin

Approximate drive time from Chicago: 2.5 to 3 hours

Recommended by: Rebecca Gade Sawicki of VeggiesAbroad.com

At just two and a half hours from Chicago, Madison is the perfect destination for a quick day trip or a weekend away . This sustainability-focused college town offers families tons of outdoor activities, diverse dining, and art and culture.

If you’re a family that loves the outdoors, visiting Madison during the summer is best. This is the prime time to enjoy the city’s prized lake life (five lakes surround it) and over 200 miles of paved bike trails. Madisonians love to bike (even in the winter), which is one of the best ways to see the city.

Another great activity to see Madison’s unique and eco-friendly side is to explore the independent boutiques that line Willy Street. You’ll find plenty of vintage shops, locally created art, zero-waste products, and clothing that’s been ethically produced and sourced.

While you’re in the area, don’t miss an iconic Madison treat, Nutkrack — this sweet and salty snack was actually created by accident! And, around the corner from Nutkrack is Madison’s oldest vegetarian restaurant , Green Owl Café — don’t miss their loaded vegan cheese fries.

When deciding where to stay in the city, the best place is downtown. This will put you within easy walking distance of many shops, restaurants, and events.

The Hyatt Madison/Downtown offers spacious rooms and suites, perfect for families, along with continental breakfast, and has multiple sustainability initiatives to reduce its and its guest’s carbon footprint. Or search for more Madison lodging options here .

Sign up for my monthly Discovery Newsletter & get a free Trip Budget Calculator !

Milwaukee, Wisconsin

Approximate drive time from Chicago: 1.5 hours

Recommended by: Lisa of WavesandCobblestones.com

Milwaukee, Wisconsin , is the perfect city to visit on a family road trip from Chicago. Milwaukee is an easy 1.5-hour drive from Chicago, located to the north along the banks of Lake Michigan.

There are plenty of great things to do in Milwaukee to keep your family entertained! Rent kayaks and paddle along the Milwaukee Riverfront for some fresh air and exercise. Or show some team spirit and take the family to a ball game and watch the Brewers play baseball at the American Family Field or the Bucks on the basketball court at the Fiserv Forum.

There are many fun museums to visit in Milwaukee with your family, such as the Milwaukee Art Museum , a top-notch fine arts museum, where admission is free for children 12 years and younger. Or Discovery World , Milwaukee’s science museum, and Reiman Aquarium. Or the National Bobblehead Hall of Fame and Museum—a one-of-a-kind museum with over 10,000 bobbleheads from across the globe!

Stay at the Plaza Hotel , centrally located in Milwaukee’s historic Lower East Side, with suites that include a pull-out sofa and accommodate up to four people. The Plaza rooms have full kitchens, and with a large grocery store just a block away, you can save money on meals and snacks during your stay.

Or search for more Milwaukee lodging options here .

Sheboygan, Wisconsin

Approximate drive time from Chicago: 2.5 hours

Recommended by: Theresa Goodrich of TheLocalTourist.com

Sheboygan, Wisconsin, is a surprising destination only two and a half hours away from Chicago and a great road trip for families because of the variety of things to do. Begin your visit at the Visit Sheboygan Visitors Center and see Science on a Sphere , a suspended globe that acts as a projector screen displaying programs provided by the National Oceanic and Atmospheric Administration. You can also get tips for places to visit and pick up brochures and souvenirs.

One of the best things to do in Sheboygan for families is Bookworm Gardens. This whimsical garden is a haven for book lovers and children alike, where literature comes to life through vibrant displays and interactive exhibits. Another must-stop for families is the Above and Beyond Children’s Museum . You can’t miss it—there is a ship’s hull sticking out of the building! While downtown, stroll 8th Street for delicious pizza at Il Ritrovo , and don’t miss the Victorian Chocolate Shoppe . Since Sheboygan is on the shores of Lake Michigan, it is also a great summer vacation spot, with sandy beaches and lakefront parks .

Make Blue Harbor Resort your base camp. With its own waterpark, an arcade, mini-golf, a beach, and outdoor games—the kids will love staying at this resort. Or search for more Sheboygan lodging options here . 

Door County, Wisconsin

Approximate drive time from Chicago: 4 to 5 hours

Recommended by: Janice Moskoff of GatherandGoTravel.com

This Wisconsin peninsula just north of Green Bay, surrounded by Lake Michigan, boasts beautiful beaches, scenic hiking trails, and family-friendly activities that will keep everyone pleased for days. 

We visited Door County in the fall , and it was gorgeous. The leaves had not quite fully changed, though we took full advantage of the pretty outdoors to bike and hike at several of the peninsula’s five state parks . 

We even visited Cave Point County Park , one of the Door’s nearly 20 county parks, and were treated to an easy-to-access spectacular scene of Lake Michigan waves crashing against a stunning rocky coastline on a windy day. The beauty of this experience blew us away. Expect the Door to do the same to you.

In the summer, the Door truly shines. Families flock here for the beaches, events, and the abundance of outdoor activities. 

With over 300 miles of shoreline , you can swim, kayak, and fish in the crystal-clear waters of Lake Michigan, especially gorgeous on a sunny day.  Plus, the towns dotting the peninsula are charming, full of shops, galleries, and many restaurants.

Visit or stay on the west or bayside of the peninsula, where you can catch sunsets in towns like Fish Creek or Sister Bay . Or opt for the eastside—where we stayed—and catch the sunrises in or around Bailey’s Harbor . Top family-friendly resorts include Newport Resort , Ephraim Shores Resort , and Scandinavian Lodge . Though, know that the Door books early. So, if you plan your trip last minute, grab the best lodging you can get from Sturgeon Bay or further north and use it as a base to drive around and explore the Door. 

Search all family-friendly Door County lodging options on VRBO or Booking.com .

Wisconsin Dells, Wisconsin

Approx drive time from Chicago: 3 hours

Recommended by: Hannah & Adam Lukaszewicz of GettingStamped.com

The Wisconsin Dells is the ideal road trip destination from Chicago as it is known as the Waterpark Capital of the World . The driving distance from Chicago to Wisconsin Dells is just under three hours, making it the perfect length for a weekend getaway . Kids love to splash and play in the water, so why not visit multiple waterparks in one road trip?

The Wisconsin Dells is home to the first-ever indoor waterpark and currently has the largest concentration of waterparks in the world. No matter if you are visiting in the summer or the winter, you will find an amazing waterpark for your family to visit and enjoy, as the area is home to 12 different indoor water parks and over 20 water parks in total.

The best place to stay in Wisconsin Dells is one of the Waterpark Hotels . Our favorite waterpark hotel is Great Wolf Lodge as not only does it have a fantastic waterpark with a 6000 ft outdoor pool, 1000 gallon tipping bucket, a wave pool with three-foot-tall waves, a toddler pool, and a variety of slides for kids of all ages.

The Great Wolf Lodge has unique themed rooms and fun activities, including magi-quest, live shows, and an arcade, making it a kid paradise!

Lake Geneva, Wisconsin

Approximate drive time from Chicago: 2 hours

Recommended by: Diana of TravelsinPoland.com

With an approximate driving time of 2 hours, Lake Geneva is a short drive from Chicago and one of the best cities to visit in Wisconsin. The small-town atmosphere combined with a variety of activities make it a perfect choice for families with children of all ages.

Families can enjoy a day on the water, renting boats, kayaks, or paddle boards, or opt for a scenic boat tour around the lake. Or walk along a portion of the Lake Geneva Shore Path , a 21-mile trail that offers stunning views of grand estates and natural beauty. Spending time on the lake is the best way to experience the area, particularly during warmer months. Shopping in downtown Lake Geneva can keep families occupied for hours. The shops along the main roads have unique items such as art and handcrafted goods. There are also mom-and-pop cafes, ice cream, and candy shops in town.

For accommodation, The Abbey Resort , located in the heart of town, offers a great choice. It is a full-service family-friendly resort offering spacious rooms, indoor and outdoor pools, a game room for the kids, and a full-service spa for the adults. Or search for more Lake Geneva lodging options here .

Michigan & Ontario: Top Road Trips Within 5 Hours of Chicago

Experience the best of the Mitten State , a northern gem and a truly ideal destination for vacationing families. The Michigan coastlines—particularly to the west, with sandy beaches, spectacular sunsets, and towering dunes —will wow you with their beauty. Plus, the vibrant cities and small towns in Michigan will offer enough activities and culinary delights to keep you busy and satisfied for days.

Check out these four Michigan & Ontario destinations shared in more detail below.

• Saugatuck, MI
• Ann Arbor, MI
• Detroit, MI, into Ontario, Canada (a loop driving trip)
• Traverse City, MI (with a day trip to Sleeping Bear Dunes National Lakeshore)

To expand your options—consider adding these Michigan Southwest coastal towns to your road-trip-and-relax lists, like New Buffalo, St. Joseph/Benton Harbor, South Haven, Holland, and Grand Haven. Or spend time exploring more urban centers like Detroit or Grand Rapids .

Saugatuck, Michigan

Approximate drive time from Chicago: 3 hours

We love Saugatuck. We have visited for weekend trips several times in the fall and keep returning for more.  What draws us? The unbelievably beautiful beaches and dunes, the quaint downtown area filled with art galleries and boutiques, and the concentration of seriously elevated cuisine.

Our favorite beaches are Oval Beach , which consistently ranks as one of the top beaches in the country, and offers soft sand, clear water, and stunning views of Lake Michigan.  Additionally, we love the nearby and dog-friendly Saugatuck Dunes State Park , which is perfect for hiking and exploring, with over 1,000 acres of dunes, forests, and beaches.

When not visiting the beaches or getting ice cream, or shopping the galleries on Butler Street, Saugatuck’s main thoroughfare, we spend our time apple picking (in the fall), boating on the Kalamazoo River, or dining at one of the truly fantastic eateries in and around town. I share more things we love to do in Fall Trip: 10 Wonderful Family Things to Do in Saugatuck, MI “

Visiting families also love going on Saugatuck Dune Rides . This thrilling ride takes you on a tour of the dunes, with steep climbs and drops, which the kids will love. And bonus! The knowledgeable guides will share the history and ecology of the area, making it both fun and educational. 

For meals, you cannot go wrong nearly anywhere you choose to eat, but our favorites include The Southerner , where the biscuits alone are worth repeat visits, Pennyroyal Cafe & Provisions , and a short 15-minute drive to enjoy drinks and snacks at Virtue Cider .

Booking a stay in Saugatuck can be surprisingly pricey, so I share helpful information on where you can stay in the surrounding areas for less in “ Saugatuck, MI: 8 Amazing Areas to Search for Lodging .” Then, and especially because many local inns do not allow children as guests, I detail my top choices for family lodging in “ Roundup of the Best Family-Friendly Places to Stay in Saugatuck .”

Ann Arbor, Michigan

Approximate drive time from Chicago: 4 hours

Whether you’re a University of Michigan sports enthusiast or just looking for a hip town surrounded by gorgeous natural beauty, Ann Arbor is the ideal Michigan town to visit!  From Chicago, the trip via car or train (Amtrak offers service from Chicago’s Union Station to Ann Arbor) is just under four hours , making it a perfect road trip for a few days away!

Ann Arbor is well known for its thriving arts and culture scene . Year-round, it hosts a variety of art, music, and film festivals, including one of the largest outdoor art fairs in the nation, The Ann Arbor Art Fair . The Art Fair takes over Ann Arbor every July and spans 30 city blocks with over 1,000 artists! You’ll also find food and music throughout the fair.

For families who enjoy outdoor activities, you’re in luck! Ann Arbor is surrounded by natural beauty, with parks, nature reserves, and the Huron River flowing through it. Head to the Argo Livery during the summer and rent a canoe, kayak, or stand-up paddle board. You can go out on your own, or Argo offers multiple group river trips that range in time and distance from just under 4 miles and 1.5 hours to almost 6 miles and 2.5 hours.

When it comes to dining, you’re in for a treat — the city is well-known for its eclectic mix of cafes and restaurants. From the famous and funky sandwiches at Zingerman’s Delicatessen to the veggie eats at Ann Arbor’s best vegan restaurant, Detroit Street Filling Station.

When choosing a place to stay, it’s best to stay right in the heart of the city (especially if it’s your first visit). Two terrific family options include the Residence Inn by Marriott Ann Arbor Downtown and The Graduate Ann Arbor . Or search for more Ann Arbor lodging options here .

Detroit to Southwestern Ontario Loop Trip (a 5 Day, 4 Night Itinerary)

Approximate drive time from Chicago to Detroit: 4.5 hours

Recommended by: Erie Conners of EverywhereOntario.com

For a unique road trip that takes you into another country, consider making the trip from Chicago to Southwestern Ontario , Canada.  This southernmost region of Canada is filled with quaint small towns, sandy beaches , an abundance of fruit farms and wineries , and incredible historic sites that tell important stories from the Underground Railroad that delivered many slaves to freedom in the 1800s. 

From Chicago, you’ll drive 4 hours to the Detroit-Windsor border. In Detroit, you’ll cross the Ambassador Bridge or take the Detroit-Windsor Tunnel to get into Canada. 

Depending on how long you’ll be staying in Canada, here are the sites I recommend according to a path that takes you from the Detroit-Windsor border to the Sarnia-Port Huron border , where you’ll loop back to Chicago:

• Optional overnight at Caesar’s Windsor Hotel , or search for other Windsor lodging .
• Or, Pelee Island : Take the ferry to Canada’s southernmost landmass, Pelee Island. Visit Pelee Island Winery and bike around the island before taking the ferry home. Overnight in Leamington at a beautiful B&B , or other lodging . 
• Grand Bend Beach : Visit one of Ontario’s top beaches in the summer months. Lounge on the beach, participate in water sports, or walk along the Grand Bend Strip for boutique shopping.
• Sarnia: Walk along the waterfront to see Port Huron from the Canadian side. Overnight at The Insignia Hotel , in Sarnia . Or stay search for other nearby lodging .
• Cross the Bluewater Bridge back to Port Huron and drive 5 hours back to Chicago.

Traverse City, Michigan

Approximate drive time from Chicago: 5 to 5.5 hours

We visited vibrant Traverse City, MI , picturesquely nestled at the southern u-shaped end of Grand Traverse Bay , for five days in the heart of summer with our family dog and loved every minute of our trip. 

In addition to enjoying the lakeshore views that front the length of the town and strolling the shops and restaurants of bustling Front Street, our favorite activities were biking along the wooded TART trails—especially the Leelanau Trail, and hiking. 

We walked the paths in Grand Traverse Commons Natural Area , located behind the outdoor shopping plaza, making our way to the Hippie Tree, a massive old willow tree at the center of the trail network. Painted in bright colors by locals representing living artwork, the tree is rumored to have a haunted history that we only learned about after our visit. 

On another day, we drove out to the Old Mission Point Peninsula to spend the day enjoying the sweeping lake views from the lighthouse, hiking the trails in the adjacent Old Mision Point Park , stopping to buy fresh farmstand cherries, picking blueberries with the kids, and to enjoy a late al fresco lakeside lunch at the Jolly Pumpkin Restaurant & Brewery .

Another highlight was taking a day to visit the Sleeping Dunes National Lakeshore (a 40-minute drive), where we climbed dunes, hiked the Empire Bluff Trail , one of many in the area , and relaxed and picnicked on dog-friendly Esch beach. 

In addition to the outdoor activities, which could also include boat trips on Lake Michigan or kayaking on local lakes or rivers, your family will love the varied collection of breweries and wineries with outdoor dining areas ideal for families. When visiting, you can stay at a centrally located and family-friendly hotel, like the Bayshore Resort . Or search for a rental in the area. Find more available Traverse City hotels and lodging here . 

Indiana: Top Road Trips Within 5-Hours of Chicago

Hang out in the Hoosier State in one of these two top destinations:

• Indiana Dunes National Park, IN
• Indianapolis, IN

Additionally, consider staying in French Lick, IN, at the French Lick Resort  (a 5-hour drive), located in the hills of Indiana’s Hoosier National Forest. It is a classic family-friendly Americana resort offering loads of activities including, golf, biking, hiking, spa treatments, and supervised drop-off kid activities.

Indiana Dunes National Park, Indiana

Approximate drive time from Chicago: 45 minutes

Recommended by: Caitlin Dismore of TwinFamilyTravels.com

If you are in the Chicago area and looking for a family-friendly trip nearby, definitely consider visiting Indiana Dunes National Park and the surrounding area. Just 45 minutes outside of the city, the park offers a beautiful setting with plenty of beach access points and hiking trails.

In addition to the fabulous activities within the park, the surrounding towns offer a variety of attractions, shopping, and dining to keep the whole family entertained. West Beach is the perfect place for a family outing. It’s the largest beach in Indiana Dunes National Park and is great for swimming, sunbathing, or just relaxing. The Lake Michigan water is clean and clear, and there’s plenty of sand for kids to play with.

Hiking is another popular activity while in the park. Explore Indiana Dune’s biodiversity by hiking along the boardwalks, past historic homes, and even through marsh areas. If you are up for it, complete the 3 Dune Challenge at the nearby Indiana Dunes State Park .

If you are traveling with young children, consider staying at the Country Inn & Suites By Carlson Portage . The hotel has both a standard indoor pool and a shallow pool specifically designed for children, complete with a frog slide. Or search for other lodging options in the nearby Portage, Indiana area.

Indianapolis, Indiana

Approximate drive time from Chicago: 3 to 3.5 hours

This lively Midwestern city offers a wide range of activities and attractions ideal for families. From world-class museums to racetracks , expect a visit to Indy will be a memory-making trip your kids will love.

Top spots include the Indianapolis Children’s Museum , which has 472,900 square feet and five halls of exhibit space, making it the largest children’s museum in the world!  While there, kids can explore science, history, and art exhibits. Or they can ride a carousel, board a train, or climb a giant treehouse.

Prefer outdoor activities?  Be sure to visit the Indianapolis Zoo and White River Gardens , where the kids can roam, see amazing things, and do fun activities. In addition to seeing tigers, dolphins, and orangutans, the kids can visit the petting zoo, ride trains, join for animal feedings, or watch cheetah racing. 

For families who love cars and racing, include a visit to the Indianapolis Motor Speedway . Known as the “Racing Capital of the World,” the speedway is home to the famous Indianapolis 500 race and offers tours of the track and museum. When in the area, stop for burgers and root beers at the Mug ‘n Bun, a nearby vintage drive-in.

On where to stay, consider booking a room at the five-star Conrad Indianapolis tops the list with its spacious rooms and prime downtown location. Prefer something less splurgy? The more budget-friendly Homewood Suites by Hilton Downtown Indianapolis , with a complimentary breakfast, makes for an excellent alternative. Or search for other lodging options in the Indy area here .

Illinois: Top Road Trips Within 5-Hours of Chicago

Check out these top locations in the Land of Lincoln: 

• Starved Rock State Park, IL
• Shawnee National Forest, IL

Also, consider a visit to Galena (a 2.5 to 3-hour drive) with a historic downtown full of shops and restaurants, nearby outdoor activities like walking and biking along the Galena River, and lots of family-friendly lodging , some with pools.

Starved Rock State Park, Illinois

Recommended by: Alyssa of AnAppleaPlane.com

Only 1.5 hours by car outside the bustling city of Chicago, Starved Rock State Park transports visitors into another world. Dramatic canyons and cascading waterfalls are not the first things you picture when you think of the Midwest!  

If you do not plan to drive your own car, renting one will be most effective for your time and budget. Or, you can get to the area by taking a train from Chicago’s Union Station to Mendota Amtrak Station and hailing a 30-minute cab to the park. A huge draw to Starved Rock is its easy-to-access features . Many of Starved Rock’s most famous waterfalls provide drive-up parking lots, so the walk to the waterfall is only a couple of minutes.

Alternatively, consider parking at the main visitor center lot and hiking to your waterfalls of choice. Waterfalls at Starved Rock flow after rainfall or snow melt, so be mindful that these will not be here year-round. The longest-lasting waterfalls are at St. Louis Canyon and La Salle Canyon.

Other top features of the park include hiking, boat tours, and camping . And perhaps the park’s biggest draw—the entrance is free !

Consider staying in the highly-rated Starved Rock Lodge for either cabin or hotel room options. Or search for other nearby family-friendly lodging options here .

Shawnee National Forest, Illinois

Approximate drive time from Chicago: 5 hours

Recommended by: Melissa of HelloWanderlustFamily.com

Located in southern Illinois, Shawnee National Forest is about a 5-hour drive from Chicago, making it an easy and accessible destination for families. 

One of the best things about Shawnee National Forest is its variety of activities , such as hiking, fishing, ziplining, or just relaxing in nature—it offers something for everyone.  Two must-see attractions are Cave in Rock and Little Grand Canyon Trail. Cave in Rock is a 55-foot-wide cave formed over thousands of years by the forces of the Ohio River and the wind, and a highlight of Little Grand Canyon Trail is you get to hike in and around a series of waterfalls that cascade down the rocky cliffs. 

When looking for a place to stay, consider the location of your planned activities . Shawnee National Forest is huge, with some attractions only 15 minutes away, while others may take an hour to reach. Because of this, choose accommodation closer to the area where most of your activities will be. One excellent lodging option for families is Home2 Suites in Carbondale , which not only provides larger room sizes and access to a pool but is in a city that offers plenty of amenities. Or search for more Carbondale lodging options here . Alternatively, for a more unique and memorable experience, consider staying at the Timber Ridge Outpost & Cabins , which offers cozy treehouses perfect for families seeking a one-of-a-kind stay.

Gurnee, Illinois

Approximate drive time from Chicago: 45 minutes to 1 hour

Recommended by: Lisa of PlanningAway.com

If you are looking for a fun short road trip from Chicago, Gurnee Illinois is just the place! There are lots of fun things to do in Gurnee, Illinois !  Gurnee is about 45 minutes north of the city. Home to Six Flags Great America and Great Wolf Lodge , it is the perfect place to spend a fun weekend.   

Six Flags Great America is the highlight of a trip to Gurnee. There are over 30 roller coasters and rides to explore. There is also a water park inside Six Flags called Hurricane Harbor. Six Flags has great shows and entertainment options for all ages.  

To relax after a fun day at Six Flags, stay nearby at Great Wolf Lodge , where you can enjoy many activities, including an indoor water park, Magiquest game, rock climbing, ropes course, arcade, bowling, and mini golf.  Kids will also love character meet and greets, dance parties, and many other fun activities by Great Wolf Lodge, and included in your stay. The lodge is perfect for kids under the age of 12 . 

There are some places to eat inside Great Wolf Lodge, but if you want to really experience Gurnee, you will want to venture out and try some local favorites. Kaiser Pizza is delicious, and Oberweis Ice Cream is a must. Gurnee Mills shopping and outlet mall is a good stop for families too. Shop at the Bass Pro, eat at the Rainforest Cafe, and enjoy many more fun shopping options. If you do not want to stay overnight—Gurnee also makes for a great day trip from Chicago.

Missouri: Top Road Trips Within 5-Hours of Chicago

Saint louis, missouri.

Approximate drive time from Chicago: 4 hours 30 minutes

Recommended by: Lynli Roman of Wanderbig.com

With less than five hours between cities, Saint Louis is a family getaway that feels far away but is easy to drive from Chicago in a half-day! Book a room at the railroad depot turned hotel , Union Station , and spend your time exploring the many family-focused activities that Saint Louis offers.  First, take your family to explore the City Museum . Described as “weirdly wonderful,” the City Museum is the crown jewel of family-friendly fun in St Louis. Housed in an old shoe factory, the City Museum boasts a huge network of slides, tunnels, and caves for all ages. All ages love the rooftop, where you can ride the Ferris wheel or climb a giant praying mantis for perfect views of the St Louis skyline. 

Next, wander through Soulard Farmers Market and taste your way through the city. The Soulard Farmers Market is one of the oldest markets in the United States, with roots dating back to 1779! Most alive during the weekends, you’ll find 147 stalls filled with unique vendors selling everything from local Missouri produce to handmade gifts. Nearby grounds include a playground and plenty of space for an impromptu picnic with your market spoils. 

No family road trip to St Louis is complete without a trip to Forest Park— one of the nation’s largest and most-visited urban parks. The park is home to the Saint Louis Art Museum , the Saint Louis Science Center , the Missouri History Museum , an outdoor theater, and the Saint Louis Zoo . Entrance fees vary, but many amenities, including general admission to the zoo, are free!

Want to see more St. Louis lodging options ? Search for other family-friendly accommodation options here .

Ohio: Top Road Trips Within 5-Hours of Chicago

From city trips to world-class amusement parks to under-the-radar natural gems, Ohio regularly delights visitors , and especially families, with all it offers as a vacation destination.

Four Buckeye State destinations to consider for your next road trip include:

• Cincinnati, OH
• Cleveland, OH
• Cuyahoga Valley National Park, OH
• Cedar Point Amusement Park, OH

Cincinnati, Ohio

Approximate drive time from Chicago: 4.5 to 4.75 hours

Recommended by: Linda of MidwestExplored.com

If you’re looking for one of the best family road trips near Chicago—you can’t beat Cincinnati, Ohio.  After all, this underrated city is located just four and a half hours, or 297 miles, away from Chicago and is a well-priced, family-friendly destination brimming over with fun Cincinnati things to do that everyone will love.

So, start your visit with a trip to The Cincinnati Art Museum , founded in 1881, and in the Eden Park area.  Not only is the museum free to visit, but there are over 67,000 works that cover 6,000 years, ensuring there is something for everyone at this incredible institution. 

Next, grab a picnic lunch and explore Ault Park , which spans an impressive 220 acres of land and is the city’s fourth-largest park, and features a wealth of picnic areas, playgrounds, and walking trails that will help keep energetic kids busy. Finally, learn more about the Underground Railroad at the National Underground Railroad Freedom Center before taking in the electric hue of the cool signs on display at the American Sign Museum.

Then, when you’re ready to call it a day, return to your room at the Hyatt Regency Cincinnati , where you can take advantage of their family-friendly suites, indoor pool and catch up on laundry at their on-site facility. Or search for more Cincinnati lodging options here .

Cleveland, Ohio

A visit to Cleveland truly offers the best of all worlds—thrills at nearby Cedar Point Amusement Park (1-hour drive), cultural chills, and hills made for hiking at Cuyahoga Valley National Park (30-minute drive).  Stay in town at a place like centrally located and highly-rated Roost Cleveland , which offers fully furnished apartments with hotel-like perks,  and use it as a base to explore the area. 

The city, on the shores of Lake Erie, is home to the Rock and Roll Hall of Fame, the Cleveland Museum of Art, and the Cleveland Orchestra—great destinations and cultural institutions for families to experience and explore.  And when your crew gets hungry, head to the historic West Side Market to grab a bite from local food vendors and souvenir shop for artisanal products.

For families with outdoor enthusiasts, pair a visit to Cleveland with a day trip to Cuyahoga Valley National Park , a 30-minute drive away, where you can hike one of many highly rated wooded or waterfall trails.

Want to see more Cleveland lodging options ? Search for other family-friendly accommodation options here .

Cuyahoga Valley National Park, Ohio

Another must-see destination for families visiting Ohio is Cuyahoga Valley National Park .  Located just outside Cleveland (a 30-minute drive), this park offers over 33,000 acres of natural beauty and outdoor activities. 

Families can explore the park’s hiking trails , go fishing or kayaking on the Cuyahoga River, or even take a scenic train ride.  With its pretty waterfalls, wooded paths, and diverse wildlife, Cuyahoga Valley National Park is a perfect destination for families looking to get outside, get moving, and enjoy the best of what nature and national parks offer.  

If you do not plan on staying in Cleveland, consider booking rental lodging in tiny and historic Peninsula Village , a private island of town surrounded by Cuyahoga Valley National Park.  Top rental picks in Peninsula, OH, for families include a few three and four-bedroom homes that can sleep up to ten. Search “Peninsula, OH” on VRBO  to find them.

Cedar Point Amusement Park, Ohio

Approximate drive time from Chicago: 4.5 hours

Cedar Point Amusement Park , located on a peninsula extending into Lake Erie near Sandusky, Ohio, is surrounded by water and overflowing with family-style fun. 

Known as the “ Roller Coaster Capital of the World ” with over 70 rides, including 18 roller coasters—thrill-seeking families will love it. The park also features a water park, live entertainment, and plenty of family-friendly dining.  Take at least two days to enjoy all it has to offer.

Stay on-site at one of the Cedar Point resorts like the beachfront Hotel Breakers , Lighthouse Point offering cottages and campgrounds, Castaway Bay with an indoor water park, or the budget-friendly Cedar Points Express Hotel .

Kentucky: Top Road Trips Within 5-Hours of Chicago

Louisville, ky.

Need a reason to visit Louisville, KY? How about six? Your family will love visiting the Louisville Zoo or strolling along Waterfront Park facing the Ohio River and adjacent to downtown Louisville, stopping to play in playgrounds or cool down in hot summers at the splash park. 

While in the area, catch a ride on a riverboat like the Belle of Louisville , which offers several different types of cruises, including historic narrated ones to picnic lunch cruises . Or your whole crew might love the Hometown Music Kids Cruise , designed especially for families.

Kids and parents who love baseball—or love to see how things how are made—will enjoy a visit to the Louisville Slugger Museum & Factory , conveniently located downtown. Your tickets give you access to the museum and a tour of the factory—kids even get a free mini-bat at the end of the tour.

Need an indoor day activity? Explore the Mega Cavern , a former limestone quarry, now an underground adventure park offering ziplining, ropes courses, and a bike park, just a 15-minute drive from downtown and near the Zoo.  Or visit the downtown Kentucky Science Center , where your kids can engage with exhibits about the human body and outer space.

For places to stay, The Grady Hotel and Homewood Suites by Hilton Louisville Downtown are great choices. Both hotels are centrally located downtown and highly rated. Or search for more Louisville lodging options here . 

Related Reading

For traveling families, check out my related articles below for more trip ideas and tips that will help smooth your travels and get out the door with less hassle.

• Need An Itinerary For A Spring Trip To Europe? Here Are 25 Amazing Ideas
• 31 Warm Winter Break Vacation Ideas Your Family Will Love
• Enjoy the Ride: 12 Tips for Better Family Road Trips
• 15 Tips on How to Raise the Bar on Rental Cars
• Pack Faster & Better With This Universal Printable Packing List
• 25 Expert Packing Tips to Help You Travel Better
• Pre-Trip: A Practical Checklist to Close the House & Pack

Additional Trip Planning Resources

To further help you with travel planning, I share my go-to resources for every trip below. 

Google Flights. My first research stop for affordable flights for every trip. Learn why here . 

Google Hotels . Use its “ Where to stay ” button to discover the best neighborhoods to base your visit.

Booking.com. For hotel and rental bookings, I appreciate its flexible cancellation, candid user reviews, discounts, loyalty program, and easy-to-use interface.

Viator , Get Your Guide , & Airbnb Experiences . Quickly find and book highly-rated tours and activities on these sites.

Google Travel Things to Do & Google Maps . Find more things to do in your destination on Google Travel, then record where you want to visit on a custom Google Maps list. 

AllTrails . Love to hike? Me too. I religiously use AllTrails to discover hiking and biking trails and download its offline maps to manage my hikes.

Guide Along . 5-star self-guided audio tours that are GPS-compatible for US road trips and national parks. We loved the Glacier National Park tour .

Insure My Trip. I never travel internationally without trip insurance. Learn why here . My preferred place to shop and compare policies is InsureMyTrip.com . 

Plus, check out the 15 travel apps I use on trips, my preferred guidebooks , and my free customizable travel itinerary template , downloadable in four file formats.

About the author:  Janice Moskoff is a travel writer and blogger who loves hiking, exploring the world, and reading. She writes to inspire travel-loving families, adult friends, and couples on her blog,  Gather and Go Travel . Check out  her bio , learn how she became  a blogger , and discover how to  work with her . Sign up for her monthly  Discovery Newsletter  to get her latest travel recommendations and  how-to’s .

Love to travel? Sign up for m y monthly Gather & Go Travel Discovery Newsletter and get a free trip budget calculator .

Affiliate Disclosure: Some of the links on this page may be affiliate links, and at no additional cost to you, I earn a commission if you make a purchase. I only recommend products and companies I use. And the income goes to keeping the site community-supported and ads minimal.

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Welcome to Gather and Go Travel , a blog inspiring families, adult friends, and couples to explore US and international destinations and to get outdoors. I am Janice, an experienced traveler to over 50 countries and a travel writer, book lover, and blogger. Learn more about me , read our story , and how to work with me .

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The 17 best road trips from Chicago

Need a change of scenery? Load up the car and embark on one of the best road trips from Chicago.

No coast? No problem. Chicago can sometimes feel like a Midwest oasis, but there's plenty to see just a scenic road trip away. With summer quickly approaching, you can spend a few weekends sipping bourbon in Louisville, hiking  in Eau Claire or sunbathing in Door County. So if you're not sure where to start, check out our list of unique nearby destinations , load up the car, turn up "Life is a Highway" and hit the road—one of these routes from Chicago could quickly become your preferred weekend getaway . 

RECOMMENDED: The best day trips from Chicago

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Best road trips from Chicago

1.  St Louis, MO

Driving time from Chicago:  Four and a half hours

While beer, blues and BBQ are likely on the top of your St Louis bucket list (and rightfuly so), there's a lot more to discover in the Gateway to the West—like custard from Ted Drewes and a walk around Forest Park. There's also a ton to see on the five-hour drive from Chicago: Stop off in Springfield to see attractions like the Illinois State Capitol, or in Atlanta, IL to take a photo with Paul Bunyon holding a massive hotdog. 

2.  Eau Claire, WI

Driving time from Chicago:  Five hours

Folks head to the Chippewa Valley in northern Wisconsin for its rolling hills and colorful foliage (plus plenty of beer and cheese to smuggle back to Chicago), but there are some worthy sights along the road as well. Snap a selfie with Pinkie the Elephant in DeForest, WI and sample cranberry-flavored everything at the Wisconsin Cranberry Discovery Center   in Warrens, WI. Once you're in Eau Claire, trade in the car for a kayak:  Riverside Bike & Skate   in downtown Eau Claire rents canoes and kayaks and has shuttles that will drive you upstream so you can hit the Chippewa River. 

3.  Traverse City, MI

The charming resort town of Traverse City, located at Michigan’s northern tip, offers plenty to do for nature enthusiasts. Clinch Park and Bryant Park have gorgeous, popular beaches while the more remote Haserot and North Bar Lake beaches offer the chance for a secluded getaway. You’re also within a stones throw of the coastal M-22, one of the most scenic drives in America, as well photo-ops at the Grand Traverse and Little Sable lighthouses. 

4.  Detroit, MI

Driving time from Chicago:  Four and a half hours

Despite what Blackhawks fans may chant, there is plenty about Detroit that doesn’t suck. You could easily spend a day or two on art alone, thanks to world-class museums like the Detroit Institute of Arts and the Museum of Contemporary Art Detroit ; powerful, immersive public art like the Heidelberg Project and colorful, whimsical folk art like Hamtramck Disneyland . Enjoy a leisurely morning browsing at Eastern Market showcasing dozens of artisan food producers, makers and crafters, and then check out the tempting restaurant and bar options nearby. On the way home, stop in neighboring Dearborn, home to the largest and most diverse Arab community in the U.S., for delicious food at spots like Al-Ameer , Sheeba and Shatila Bakery . 

5.  Galena, IL

Driving time from Chicago : Three hours

At the top of many Chicagoans city escape must-visit list is Galena, Illinois. This charming town just under three hours from the city is known for its history, 19th-century architecture and resorts. There are hundreds of unique and antique shops in the city center to add some vintage pizzazz to your living room. History buffs can head over to the  Ulysses S. Grant Home  to tour the city’s proudest attraction. Once you’ve worked up an appetite, stop into  Log Cabin Steakhouse , which has been in operation since 1937. During the third weekend of June, tourists and locals alike gather for the annual  Great Galena Balloon Race .

6.  Door County, WI

The road trip doesn't end when you reach Door County; There's plenty to navigate by car as you wander the series of small towns located on a beautiful 75-mile peninsula surrounded by Lake Michigan and Green Bay. There are also 53 public beaches, five state parks, and 300 miles of shoreline so get ready to put some miles on your car. Need a pit stop? Milwaukee is a little less than half way. 

7.  Louisville, KY

Kentucky’s largest city, located just across the Ohio River from southern Indiana, is steeped in bourbon and long on charm. The home of the old fashioned and mint julep embraces its role as the gateway to Bourbon Country. The city now has over 10 tourable distilleries, including   Evan Williams,   Angel’s Envy   and  Old Forester . If bourbon and honkytonk aren't for you, downtown Louisville has an incredible art scene and is booming with independent businesses and charming shops. 

Discover the best things to do in Louisville

8.  Madison, WI

Driving time from Chicago: Three hours

Sure the Midwest loves its college towns, but Madison's proximity to five surrounding lakes make it one of the more of the scenic ones. The abundance of waterways make kayaking, rafting and canoeing especially popular—you can book them directly through Madison Boats . For those averse to using their sea legs, there's the 16-acre Olbrich Botanical Gardens for all ages or the National Mustard Museum (yes, you read that correctly). It wouldn't be a trip to Wisconsin without trying blocks and blocks of cheese, so make sure to stop by the "Capital of Cheese" known as Fromagination in downtown Madison. 

9.  Cincinnati, OH

If Skyline Chili is not your bag, don’t worry—there’s a whole lot more to the Queen City than its most famous tourist foodstuff. Cincy has been undergoing a major glow-up over the past decade or so, from the ever-evolving Smale Riverfront Park, which offers lots to do and gorgeous views of the skyline and the Ohio River to the revitalization of the historic Over-the-Rhine neighborhood. There, you'll find a number of must-visit spots, including the popular Rhinegeist Brewery, the vibrant Findlay Market , the stunning Music Hall and Washington Park , which sports a sweet playground and community events throughout the year. Plus, the Cincinnati Zoo is one of the best in the country, and the only place you can see Internet icon Fiona the Hippo in person. That in itself is worth the trip.

10.  Shawnee Hills Wine Trail, IL

Driving time from Chicago:  Six hours

Not going to make it to Napa this year? Opt for the just-as-beautiful Shawnee Hills Wine Trail instead. The 3 5-mile scenic drive meanders through Shawnee National Forest in southern Illinois and features over 10  award-winning wineries in cute towns like Cobden, Alto Pass, and Pomona. If you need more than wine to prompt a trip, there's plenty of nature in the vicinity and the nearby town of Murphysboro is home to some of the finest BBQ in the Midwest at 17th Street Barbecue . 

11.  Bloomington, IN

Driving time from Chicago:  Four hours

This cozy college town offers some big-city amenities, but it's the surrounding hills, forests and lakes that make it special. A short itinerary could look like: Hike the Deam Wilderness trails ; s ee the Morgan-Monroe State Forest wildflowers; admire the Cedar Bluffs Nature Preserve limestone bluffs; g o fishing at the reservoir lakes. Just don't forget to leave room for a meal at  Feast Market & Cellar , a family-owned kitchen with a lovely corner porch where everything is made from scratch daily. 

12.  Saugatuck, MI

Driving time from Chicago:  Two and a half hours

This dreamy lakeside town (and next-door neighbor Douglas) has long been a favorite of Chicagoans looking to spend time on the water, whether it’s a boat on the Kalamazoo River or a relaxing day on one of the area’s six clean, inviting beaches. From hiking the Saugatuck Dunes to window shopping on Butler Street to enjoying dinner and drinks alfresco, there are many ways to get some much-needed fresh air here. It’s also one of the Midwest’s best queer-friendly vacation destinations, home to more than 100 LGBTQ-owned and friendly businesses. 

13.  Ann Arbor, MI

Driving time from Chicago:  Four hours

If you'd rather stick to less-crowded cities, skip Detroit and opt for Ann Arbor instead. Foodies and beer nerds will love this low-key vacation spot for its plethora of good restaurants and breweries. Home to the renowned University of Michigan, this city’s quaint downtown is full of unique shops, spots to eat and so much more (make sure Blank Slate Creamery is on your list). 

14.  Toledo, OH

The road from Chicago to Ohio is filled with worthwhile attractions, including Indiana Dunes State Park and the Hall of Heroes Super Hero Museum in Elkhart, Indiana. Once you arrive in Toledo, you'll be greeted with picturesque churches, wild urban parks, a trendy jazz culture and plenty of microbreweries to keep you busy. Just outside the city you'll also find fall-harvest overload in the way of apple and pumpkin farms where you can pick your own fruits and veggies and gorge on baked treats.

15.  Shipshewana, IN

Driving time from Chicago:  Two hours

OK, just hear us out. The heart of Indiana Amish country is a great option for a convenient road trip perfect for families, history buffs and, most of all, antiquers. The Shipshewana Trading Place Flea Market is a bargain-hunter’s dream—the largest flea market in the Midwest, with lively auctions Wednesday mornings. After a morning of browsing and bargaining, you’ll work up an appetite for some Amish home cooking, which you can even sample in a  literal Amish home . For outdoorsy types, nearby Mongo offers canoe and kayak rentals for a relaxing day on the water. 

16.  Des Moines, IA

Driving time from Chicago: Five hours

There's a surprising amount to explore over a weekend in Des Moines, from more than 20 breweries in the metro area to the six-mile Art Route , which showcases 87 public art pieces from sculptures to murals. But what really makes Des Moines worth visiting are its summer events, like the eclectic 80/35 music festival, and, of course, the festive juggernaut that is the Iowa State Fair , where you can get 69 different food-on-a-stick creations (nice). When you're heading back on I-80, don't miss the World's Largest Truck Stop in Walcott, truly a site to behold.

17.  Columbus, IN

Driving time from Chicago : Three and a half hours

In the heart of Southern Indiana, Columbus is an unexpected center for boundary-pushing architecture—in fact, the American Institute of Architects ranked the city sixth in the nation for architectural innovation. Roughly 70 different constructions sprinkled around the city and county make this city an architectural wonder. Take an  Architectural Highlights Tour  of more than 30 of Columbus' structures and learn how this city became the state's award-winning arts and design destination. Make another pit stop of striking constructions with a stroll through Mill Race Park , an 85-acre riverfront park near the city's center. Once you’ve worked up an appetite, stop by  Columbus Bar , the oldest bar and restaurant in town.

Need more travel inspiration?

The best weekend getaways from Chicago for families

Take a break from the city and find family-friendly activities throughout the Midwest on these weekend getaways.

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The Ultimate Road Trip Itinerary from Chicago to Florida

by Cheryl | Sep 6, 2018 | destinations we EXPLORE , places we EAT , places we PLAY , places we STAY | 5 comments

If you know our family, we love going on adventures and long road trips. On our latest road trip, we made our way from Chicago to Florida. If there’s one thing I’ve learned from road tripping, it’s that the kids are much happier if we add in stops (and snacks — lots and lots of snacks.) Plus, it’s much more fun to explore than sit around in the car, right?

So if you’re thinking of planning a trip (yes, go for it!) to Florida, here’s a rundown of our complete road trip itinerary from Chicago to Florida. Keep checking back for updates as I’ll have full details for you!

Disclosure: Some of the links below are affiliate links, meaning, at no additional cost to you, I will earn a commission if you click through and make a purchase.

Day 1: Chicago to Glasgow, Kentucky

Pit stop : Whenever we are on I-65, we always, always stop at Fair Oaks Farm for a potty break (clean bathrooms!), food, ice cream, or samples. (exit 220) If you have more time, I’d even suggest hanging out and seeing how this modern dairy farm operates. See what else you can do at Fair Oaks Farm .

Worthy Road Trip Stop:  Our first major stop to stretch our legs was at Columbus, Indiana about an hour south of Indianapolis. The small Midwest town of Columbus, Indiana is known for their modern architecture. We had ice cream at an old-time ice cream parlor, Zaharakos , then let the kids unleash their energy at the playground at the Commons with the awesome Luckey Climber. We had fun in Columbus and hopefully will return again to check out more of the architecture around the city.

We hopped on the road again and reached our final destination of the day:  Glasgow, Kentucky.

Where to eat:  We wanted something close to our hotel, and El Mazatlan was just down the hotel. After quick research, we also found out it was a local favorite. The Mexican food was pretty good, but we were impressed with the large (and strong) 16 oz. margaritas for $4. Yes, you heard that right!

Where to Stay:  Holiday Inn Express Hotel & Suites Glasgow

If you have more time:   Take time to explore Mammoth Cave National Park, the largest cave system in the world. Gary from Everything Everywhere shares his experience at Mammoth Cave.

Days 2 to 4: Chattanooga, Tennessee

  View this post on Instagram   I can’t get enough of the beauty at #RockCity especially Lover’s Leap and the waterfall. Why Is it called Lover’s Leap? Legend says that a woman and a man from feuding tribes fell in love and eloped. The man was captured and thrown off the cliff. Eventually the woman followed after. . . . #instatravel #travelwithkids #travelbloggers #discovertheroad #travel #familytravel #postcardplaces #instago #instatravel #wonderlust #instapassport #travelwithme #roadtrip #familytravelblogger #bestintravel #trekarooing #roadtrip #travelmom #otheplaceswego #ChattanoogaFun @Chattanooga_Fun #Tennessee #visittennessee #visitchattanooga @SeeRockCity #waterfalls #myviewtoday #scenicview #instawaterfall #loversleap A post shared by O the Places We Go (@oplaceswego) on Aug 6, 2018 at 6:46pm PDT

If there’s one thing you need to know about Chattanooga, it’s that there’s so much to do!

Things to Do:

• Lookout Mountain’s legendary attractions – Ruby Falls  for the tallest underground waterfall, Rock City’s incredible vistas , and Incline Railway’s one-mile trek up the mountain.
• Explore the river and ocean at the Tennessee Aquarium. If you have time, definitely schedule a backstage tour.
• Learn about Chattanooga aboard a Chattanooga Duck , an amphibious vehicle that goes on the road and water.
• Try a moon pie (or 12) at the Moon Pie General Store .
• Walk on the  Walnut Bridge , the world’s longest pedestrian bridge.

Where to eat:

• At Champy’s Fried Chicken, f ried chicken is king here along with fried catfish and fried pickles.
• Try  Purple Daisy Café for finger-lickin’ BBQ and an insane banana pudding
• Delightful BBQ (small portions) at  Puckett’s Grocery located just a short walk from the Tennessee Aquarium.
• Treat yourself to any of the amazing flavors at Clumpie’s. 
• Looking for amazing burritos? MoJo’s by the base of Lookout Mountain is calling your name.
• Try unique flavored donuts at Julie Darling Donuts .

Where to stay: SpringHill Suites by Marriott Downtown Chattanooga/Cameron Harbor

Related: Read all about our #ChattanoogaFun.

Day 4: Chattanooga, TN to Gainesville, FL

Worthy Road Trip Stops :

• Since we passed by Georgia, known for their peaches, we just had to grab some peaches at Lane Southern Orchards. We were pleasantly surprised to find a peach tour on-site and was also able to try their homemade peach cobbler topped with their homemade peach ice cream. Yummy!  Read more about this worthy road trip stop at Lane Southern Orchards.
• Georgia is also known for pecans, so we also had to make a pit stop for pecan. Located right off the highway,  Ellis Brothers Pecans,  has pecans in every flavor. Imagine aisles and aisles of pecans (and samples). It was awesome! Plus, their restrooms were clean.
• We couldn’t get enough of BBQ so we stopped by Smok n’ Pig BBQ . If you’re ever in the area, we highly recommend. Huge portions, great value (entrees includes salad bar AND dessert!), plenty of seating.

Where to stay: Holiday Inn Express & Suites Alachua – Gainesville Area

If you have more time:   If you happen to visit on a Saturday, stop by the Retirement Home for Horses at Mill Creek Farm . As the name suggests, 140 horses call Mill Creek Farm home. The admission is two carrots – a fabulous deal.

Day 5: Gainesville, FL to Winter Haven, FL

  View this post on Instagram   A post shared by O the Places We Go (@oplaceswego) on Aug 11, 2018 at 7:54am PDT

We actually wanted to visit a natural spring today, but we were told there was a brown out due to rain. It was a hot and steamy day so we made our way to Gainesville.

Worthy stop: If the weather is on your side, make sure to bring bathing suits to the Depot Park’s splash pad. The park is pretty fantastic, too! We were all pretty famished and at the suggestion of Visit Gainesville tried out a BBQ spot in a convenience store. Pearl’s Country BBQ may have been the best BBQ we’ve had the entire time.

We drove a couple hours and made it to Central Florida . Yay!

Things to do: Kids loved exploring Hammock Hollow, the children’s garden at Bok Tower Gardens . The singing carillon is not to be missed!

Where to eat: Another local favorite, Harry’s Old Place, serves delicious seafood along with my kids’ personal favorite, gator bites!

Where to Stay: Hampton Inn Winter Haven

Related: Read all about our visit in Central Florida’s Polk County.

Day 6: LEGOLAND at Winter Haven, FL

Things to do:

What can I say? Any LEGO lovers will love this place. The kids could not get enough of the fun at Legoland Florida. We saw a Miniland on steroids, went on rides, found out that roller coasters are not going to happen anytime soon, ate apple fries, got wet at Legoland Waterpark, and then eventually rained out. It was a blast!

What to eat:  Food at Legoland Florida and delivery from MJ’s pizza

Day 7: Tallahassee, FL

  View this post on Instagram   A post shared by O the Places We Go (@oplaceswego) on Aug 14, 2018 at 10:43am PDT

We visited the Sunshine State’s capital, Tallahassee. and immediately wished we had more time to explore.

Things to Do: Explore Old Florida fauna, the zoo, and have a fun treetop adventure at Tallahassee Museum .

• Burger concoctions at Midtown Caboose.
• Ice cream at Lofty Pursuits .
• Delectable donuts from Donut Kingdom .

Where to stay: The super hip and trendy (and pet-friendly) Aloft Tallahassee Downtown

If we had more time: I think we would have enjoyed seeing the Capitol, as well as seeing wild manatees at Wakulla State Park. Learn more about the Capitol from Perceptive Travel .  Travel with Sara talks about exploring Tallahassee by Segway. Fun!

Read all about our visit to Tallahassee here.

Days 8-10: Destin, Fort Walton Beach, and Okaloosa Island, FL (The Heart of the Emerald Coast)

Oh, the beautiful Emerald Coast. Whether you want to fill your time with activities, lounging on the beach, or both, the Emerald Coast is fantastic.

• Walk along the Okaloosa Boardwalk and Okaloosa Island Pier for fantastic views of the emerald green waters.
• Golf with dinosaurs at Wild Willy’s Adventure Zone , then cool off in the arcade.
• Find dolphins on Southern Star Dolphin Cruises .
• Get to know the area’s animals at the Gulfarium . Say hi to their albino alligator.
• Bowl under the sea at Uncle Buck’s Fish Bowl , while sipping your fishbowl drink, of course.
• Catch some rays at the beach . Kids can build sand castles with the white, soft sand.

Where to Eat:

• Enjoy the atmosphere and awesome views of the beach and ocean at Al’s Burger and Beach Club on The Boardwalk. Don’t miss the blackened tuna salad or ahi tuna burger.
• Have lunch at The Cowhead for amazing burgers.
• Head a few doors down for snow cones at KC’s Sandbar and Grille . Whatever flavor you choose make sure to get it with ice cream and topped with homemade sweet cream.
• Eat and bowl at Uncle Buck’s Fish Bowl. Try their gator bites here too.

Where to Stay: The Island by Hotel RL, a beachfront hotel

Day 11: Emerald Coast, FL to Huntsville, AL

We said goodbye to Florida and made our way back to Chicago. But not without checking out more places, of course. Unfortunately, since we were on running out of time, we didn’t get a chance to explore Rocket City.

If we had more time: Space exploration at U.S. Space & Rocket Center and food at Supper Heroes. Read about all the fun you can have at the U.S. Space & Rocket Center from Travel with Sara  and Traveling Adventures of a Farm Girl .  Find out about all the family fun in Huntsville from  Thrifty Jinxy, and yes, there’s more to explore than space as told by Litte Family Adventure . Hint: You must try Cotton Row Restaurant.

Day 12-13: St. Louis, Missouri

  View this post on Instagram   A post shared by O the Places We Go (@oplaceswego) on Aug 19, 2018 at 2:54pm PDT

We made the drive to St. Louis with just one quick fast food stop. We wanted to get to our final overnight stay of our trip, and still have time to explore a little of the city of St. Louis.

Suggested stop:   If you need to stretch your legs, The  Paducah  Riverfront in Paducah, Kentucky is a great place to walk while looking at historical murals. [ Read about our side trip to Paducah here.]

Suggested stop : The hometown of Superman, Metropolis, IL, has plenty of photo ops including a huge statue of the man himself and a museum dedicated to all things Superman. [ Read about our super trip to Metropolis, Illinois . ]

Things to do In St. Louis:

• The revitalized area around the Gateway Arch is finally complete! Check out the new museum, tour, and the surrounding areas.
• Try the free Saint Louis Science Museum with dinosaurs and space exhibits. Don’t miss the outdoor area with rain garden and chickens.
• If the St. Louis Cardinals are playing, you shouldn’t miss a game at Busch Stadium.
• Get lost with the kids at the super cool City Museum.
• Try toasted ravioli and St. Louis style pizza from Imo’s pizza.
• Get your ice cream fix at Clementine’s Naughty and Nice Creamery .
• Try Afghan food at St. Louis’ first Afghani Restaurant at Sameem’s Afghan Restaurant in The Grove. Emperor Plate large enough for two people or one very, very hungry husband.

Where to stay:  Drury Plaza Hotel St. Louis at the Arch

Day 13: Casey, IL

Time to head back home, but before doing we had to check out the collection of world’s largest things in Casey, Illinois.

Suggested Stop:  If you’re looking for a wonderful farm to table place to eat, look no further than Firefly Grill in Effingham, Illinois. Make a stop at a Corvette museum. If you love to cook, then you’ll want an authentic John Boos cutting board . [ Read more about our Effingham, Illinois. ]

Yes, it may have been a little out of the way (shhh, don’t tell my husband!) but visiting Casey, Illinois was totally worth the small detour! The small town has 8 of the World’s Largest items, and also some other big items.

Find out what other big things you can see on the ultimate road trip stop at Casey, Illinois.

Have you driven to Florida before? What were some of your favorite things to do on the way there?

More about our Chicago to Florida road trip:

Chattanooga, Tennesee

Georgia Road Trip Stops

Central Florida’s Polk County

12 Hours in Tallahassee with the Family

St. Louis, Missouri

Casey, Illinois

Road Trip Survival

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I have a Florida trip scheduled for June and I was just wondering aloud how many days I’d need to allow for a road trip from North Dakota when your post caught my eye. It gave me a frame of reference and some great ideas for what to see on the way. Thanks for inspiring me to start planning!

Yes, please let me know if you have any other questions or suggestions. Do you know which route you’ll be taking?

Would love to have and see some road landscapes – we don’t get much road trip here in San Diego! Beautiful scenery, as usual!

Last year, we stopped in Louisville at toured the Louisville Slugger Museum. Everyone leaves with a free (small) bat!

I’d also highly recommend Legoland in Florida. My boys LOVED it when we were there 2 years ago (age 7 and 5), and we are thinking about going back in March.

Thanks For given us experience about road trip to chicago to florida

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The Best Road Trips From Chicago To Take This Spring

The best is yet to come, especially when you're going on an adventure. It's time to load up the car and head to one of these vibrant Midwest states for spectacular culture, art, and a culinary scene.

Fall is here, so it’s time to get away! While we adore our beloved Chicago, the Midwest is sprawling with beautiful and scenic cities within just a few hours of the city. Whether you want to get away to explore a stunning hiking trail or just spend the weekend roaming a charming town with cobblestone streets, there are tons of amazing things you can experience, so check out the best road trips from Chicago!

1. Madison, Wisconsin

First on our list is where Wisconsin’s capital is located, and it happens to be the second largest city in the state. Madison lies in the south-central part of the state and is centered on an isthmus between Lakes Mendota and Monona.

The proximity to the lakes makes waterside adventures a must; there are endless activities to participate in, between boating, kayaking, and swimming. After, take a stroll through the charming streets and head to one of the many breweries, or for an evening filled with serenity, head to the Olbrich Botanical Gardens , where Oblrich’s Thai Pavilion is located and is the only one in the US, and the only one outside of Thailand surrounded by a garden.

🚗 Distance from Chicago : 148 miles

🕐 Arrival Time: 2 hr and 23 mi

2. Holland, Michigan

When people think of Holland, what usually comes to mind is the Keukenhof Tulip Gardens in Amsterdam, Holland. However, you don’t need to buy an international plane ticket when another Holland is only a few hours away. This road trip from Chicago will be your new favorite getaway.

While in Holland, you’ll be able to indulge in Dutch experiences such as sprawling tulip gardens , cobblestone streets, and the picturesque Tunnel Park. With over 100 specialty shops, breweries, and restaurants, this is the perfect place to head on a road trip.

🚗 Distance from Chicago : 150.8 miles

🕐 Arrival Tim e : 2 hr 25 min

3. Traverse City, Michigan

One of our favorite Chicago trips, known as the “Cherry Capital” of the world, it’s easy to get lost in the beauty of Traverse City. Stroll along the shoreline at Grand Traverse Ba y and glance at the fluid waves as you take in a majestic sunset.

While there are many things to do in Traverse City, some of our highlights include touring the wineries, scaling a dune at the Sleeping Bear Dunes National Lakeshores, picking out some blum cherries, and immersing yourself in the beautiful lakeside town.

🚗 Distance from Chicago : 318.6 miles

🕐 Arrival Time : 4 hr 55 min

4. St. Louis, Missouri

One of the major cities in Missouri, St. Louis, lies along the Mississippi River and displays an iconic 630-foot Gateway Arch built in the 1960s. St. Louis is a quintessential city to visit, with a vibrant arts and culture scene, lively bars, and acclaimed restaurants.

This is also one of the best road trips from Chicago if you’re a fan of Chicago baseball. With Busch Stadium nearby, schedule your road trip for a game between the Cardinals and the Cubs, one of the best rivalries.

🚗 Distance from Chicago : 298.8 miles

🕐 Arrival Time: 4 hr 28 min

5. Bloomington, Indiana

Bloomington is most notably known as the home for students of Indiana University . Nestled in the rolling hills of southern Indiana, the city has spectacular foliage surrounding the town as you drive in.

Along with the visually stunning scenery , there is vibrant art, spectacular shopping, and notable restaurants—all of which support the thriving local business scene. However, it wouldn’t be right to mention Bloomington without mentioning sports. With the Big Ten, rowdy football and basketball games are an innate part of the town.

🚗 Distance from Chicago : 232.3 miles

🕐 Arrival Time : 3 hr 48 min

6. Columbus, Ohio

Along with Bloomington, Columbus is a celebrated city with a younger population due to the booming tech industry and innovative arts scene. As Ohio’s state capital , it’s one of the largest college campuses in the country.

This is one of the best road trips from Chicago if you’re looking for lively nightlife . Walking down High Street, you’ll be surrounded by reverberating music and packed patios, especially if the Buckeyes are playing.

🚗 Distance from Chicago : 356.5 miles

🕐Arrival Time: 5 hr 27 min

7. Wisconsin Dells, Wisconsin

Situated in southern Wisconsin, the Dells lies on the Wisconsin River in a region of glacier-carved sandstone formation and might be one of the most exhilarating cities on this lift. This is the best road trip near Chicago for any family planning an adventure-filled weekend .

There are numerous theme parks and entertainment centers, including Noah’s Ark Water Park and Mt. Olympus Water and Theme Park, both indoor and outdoor, spanned with waterslides, lazy rivers, rafts, and more! It’s one of the ideal road trips from Chicago for a family outing.

🚗 Distance from Chicago : 193.5 miles

🕐 Arrival Time : 2 hr 59 min

8. Saugatuck, MI

If you’re looking for award-winning beaches , scenic waterways, and verdant dunes, take a road trip to Saugatuck, Michigan. This is the ultimate escape for a quiet, luxurious weekend, with an animated art scene and renowned culinary restaurants. It’s a place that seamlessly switches from exploration to recreation for people visiting—making it one of the best road trips from Chicago.

🚗 Distance from Chicago : 145.8 miles

🕐 Arrival Time : 2 hr 19 min

9. Ann Arbor, MI

While many of the Michigan cities listed here are located along Lake Michigan, Ann Arbor is one the few recognized as an urban oasis in the middle of the state. The downtown scene is from a storybook with a red-brick main street filled with independent bookstores, locally-made candle shops, home goods, and more.

While there’s a lot to do downtown, head outside the city to explore the nature parks surrounding the town, which have some of the most scenic hiking trails.

🚗 Distance from Chicago : 241.3 miles

🕐 Arrival Time : 3 hr 45 min

10. Sheboygan, Wisconsin

Deemed the “Malibu of the Midwest, ” Sheboygan, Michigan, might not have five-foot waves like the West Coast. Still, it’s a freshwater haven for anyone who loves fishing, sailing, and surfing, from outdoor recreational activities like golfing and biking to events and festivals that highlight the art scene, cultural heritage, and vibrant music, it’s no wonder it’s one of the best road trips from Chicago.

🚗 Distance from Chicago : 147.6 miles

🕐 Arrival Tim e: 2 hr 24 min

11. Cincinnati, Ohio

Cincinnati is a beloved Midwestern city—right on the border of Northern Kentucky—some say it’s where metropolitan vibrancy meets Kentucky’s southern flair . From a wild sports fandom, you can catch Joe Burrow throwing a football or Joey Votto singing his bat, all less than a 1/2 mile from each other. However, besides athletics, there are splendid places to explore within Cincinnati, and it’s one of the ideal road trips from Chicago.

🚗 Distance from Chicago : 295.4 mi

🕐 Arrival Tim e: 4 hr 32 min

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Minneapolis to Chicago drive

Minneapolis to chicago road trip planner.

Here's a sample itinerary for a drive from Minneapolis to Chicago. If you're planning a road trip to Chicago, you can research locations to stop along the way. Make sure you check road conditions to double check the weather. Traveling with a dog or cat? Find pet-friendly stops . Camping along the way? Search for RV campgrounds . Find the best hotels, restaurants, and attractions based on the most talked about places recommended by Trippy members.

10:00 am  start in Minneapolis drive for about 1.5 hours

11:33 am   Eau Claire (Wisconsin) stay for about 1 hour and leave at 12:33 pm drive for about 1 hour

1:39 pm   Neillsville stay for about 1 hour and leave at 2:39 pm drive for about 1 hour

3:43 pm   Oakdale (Wisconsin) stay for about 1 hour and leave at 4:43 pm drive for about 42 minutes

day 1 driving ≈ 4.5 hours find more stops

10:00 am  leave from Wisconsin Dells drive for about 1 hour

11:00 am   Madison (Wisconsin) eat at The Old Fashioned stay for about 1 hour and leave at 12:00 pm drive for about 1.5 hours

1:26 pm   Rockford (Illinois) stay for about 1 hour and leave at 2:26 pm drive for about 1.5 hours

3:47 pm   Arlington Heights (Illinois) stay for about 1 hour and leave at 4:47 pm drive for about 39 minutes

5:26 pm  arrive in Chicago eat at Lou Malnati's Pizzeria stay at The James Chicago Hotel

day 2 driving ≈ 4.5 hours find more stops

Where should I stop along the way?

Eau Claire (Wisconsin)   (4 answers) Neillsville Oakdale (Wisconsin) Wisconsin Dells   (16 answers)     Noah's Ark   (3 mentions)     questions about Wisconsin Dells:         Best free things to do in Wisconsin Dells? Madison (Wisconsin)   (41 answers)     Wisconsin State Capitol   (3 mentions)     restaurants around Madison (Wisconsin):         The Old Fashioned         Great Dane Pub & Brewing Co         L'Etoile         Ha Long Bay     questions about Madison (Wisconsin):         What is your favorite restaurant in Madison?         Family-friendly campsites near Madison for large groups         Where is there a good Japanese restaurant?         One day trip, looking for a good time under $100         Catholic Easter Vigil Mass with good music in Madison? Rockford (Illinois)   (5 answers) Arlington Heights (Illinois)   (4 answers)

Where's the best place to stay in Chicago?

Are you going straight to a hotel, or looking for a vacation rental or Airbnb?

The best resource on neighborhoods, areas, and hotels is the Trippy page on where to stay in Chicago .

You can also see most people recommend as the best amount of time to visit. Find out how many days in Chicago to stay.

If you're looking for a quick answer, you can check out The James Chicago Hotel , which was mentioned 12 times on Trippy.

Here are some more hotels people talk about:

Want to research more popular hotels in Chicago? Click the blue button below.

Where's the best place to eat in Chicago?

Need some recommendations on somewhere to get food?

Trippy members suggest Lou Malnati's Pizzeria , which was mentioned 36 times.

Here are some more restaurants people talk about:

Want to research more popular restaurants in Chicago? Click the blue button below.

What are some things to do in Chicago?

This section could be endless, so rather than trying to suggest every local activity or attraction, we'll leave it open-ended.

These are some of the places people talk about on Trippy:

Of course, Trippy is the perfect place to ask questions because there's an entire community of travelers talking to each other and sharing tips and advice. Trippy is where you can get answers personalized for your tastes, budgets, trip dates & more!

For example, here are some questions people have asked about Chicago. Click on any question to see answers from the community!

Click the button below to explore more questions and answers related to Chicago.

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Yes, even this step is optional, because if you're on vacation who wants the trip to end? It's okay, you can start planning your next trip!

Want to plan the trip back? Get the reverse directions for a Chicago to Minneapolis drive , or go to the main page to plan a new road trip .

You can also compare the travel time if you're flying or driving by calculating the distance from Minneapolis to Chicago . Or get a full Minneapolis to Chicago flight plan .

Don't forget about exploring your own hometown with a staycation. You can also find some cool day trips or get away for a weekend. Maybe try typing in a faraway location like London, Hong Kong, or Sydney, and get inspired for your dream trip around the world.

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Travels & Treasures

A Complete Guide for a Chicago Road Trip

Packing for a Chicago road trip is a great way to explore the metropolis, scout the neighborhoods, soak in the breathtaking views, and create memorable experiences. 

If you’re planning a road trip to Chicago, the Windy City, it’s essential to be well-prepared to make the most of your adventure. 

Since I have lived and driven in the Chicago area for over 30 years, you can use this guide that I created to help you through the essential items to pack, tips for driving in Chicago, road safety tips, and more. 

So, fasten your seatbelts and get ready for an exciting journey!

Table of Contents

Essential Items for a Chicago Road Trip

Firstly, let’s get the obvious items out of the way. Although they apply to just about any road trip, I think it’s important to keep this in mind for Chicago too.  

• Comfortable Clothing : When starting your road trip, opt for comfortable clothes that are suitable for long hours of sitting. Choose breathable fabrics, such as cotton, and consider layering to adapt to changing temperatures during your road adventure.
• Weather-appropriate Gear : Depending on the time of year, Chicago’s weather can be unpredictable, so pack accordingly. In spring and fall, you will want to layer your clothing. Bring a light jacket or sweater, a raincoat or umbrella, and hats and gloves for colder seasons.
• Snacks and Drinks : Keep yourself fueled during the drive with a variety of snacks like granola bars, fruits, nuts, and bottled water. During summer, bring a cooler for the trip to stay hydrated and to store perishable items. It will also save you time and money so that you don’t have to stop and spend extra dollars at pricey convenience stores. 
• Navigation Tools : Ensure a smooth journey by bringing a GPS device or using a reliable navigation app on your smartphone. For your road trip, you could have a physical map or printed directions that serve as backup.
• Entertainment Options : Long road trips can be tiresome, so pack entertainment options like books, podcasts, or audiobooks. Prepare playlists with your favorite music to keep the atmosphere lively. Also, pack some games and movies or have a list of engaging car games prepared for the little ones when traveling on a road trip. 
• Roadside Emergency Kit : Prepare for unexpected situations by carrying a roadside kit. It’s always wise to be prepared for any emergencies on the road. Put together a roadside emergency kit that includes a spare tire, jack, jumper cables, flashlight, first aid kit, basic tools, and a roadside assistance contact number. Additionally, consider adding a portable phone charger and extra batteries to stay connected.

Tips for Driving in Chicago

When it comes to driving in Chicago, there are a few things that people might not know. First and foremost, be prepared for the notorious traffic congestion, especially during peak hours.

Chicago has a public transportation system. I advise that you use it as much as possible because it will save you time and money especially during peak season , while visiting the city.

Peak Traffic Hours

The morning peak hours going into Chicago are between 6 AM and 9 AM. The peak hours leaving Chicago are between 3 PM and 7 PM.

The evening hours extend just a bit because some like to visit happy hour events, so the peak period is a tad longer.

Anytime outside of these hours are generally OK for driving except for popular sports events like a Bulls or Bears game, a concert, or other city-hosted events like parades and large festivals.

Also, note that Chicago is a bustling city that does a lot of business, so you will have to contend with semi-trucks, delivery vans, and heavy-duty trucks.

Construction

There is a saying in Chicago that “There are two seasons of the year, winter and construction.”

Plan your driving around the peak traffic hours and look for alternate routes via GPS. Even if you have extra time, don’t take it for granted.

Delays during construction are inevitable (and frustrating when the traffic is reduced from 4 to 1 lane)! There may also be delays caused by unexpected accidents or slowdowns caused by emergency vehicles.

Parking is always a challenge in the city and it’s very expensive and fees for parking violations are hefty. The best way to locate a garage is via SpotHero.com. You can find discounted fees for early arrivals (before 7 AM) but the hours you are allowed to stay for the discounted price is usually limited.

If you are staying in the downtown area and have a parking spot, I suggest you leave the car and use public transportation during your stay. Getting around Chicago is very easy, and you will save more money by avoiding the expense of additional parking.

If you do need to use a car, familiarize yourself with street parking regulations. There is rarely free street parking and just about every parking space downtown is metered. Look for the meter posts near the end of each block to pay for parking. The machines accept cash and credit cards.

When parking in neighborhoods, you will find that some require a permit or vehicle sticker. In winter, the lack of snow removal makes it difficult to find parking so residents will “reserve” spots with chairs, cones, or anything they can find. My advice is to avoid using these spots or you may risk retaliation.

Lastly, if driving in Chicago intimidates you, stay in the right-most lane or use the side streets. Avoid the road rage caused by speeding drivers who don’t use good driving etiquette. Try not to block cars who are trying to cross the main road from alleys, parking lots, or turning lanes.

Keeping these lesser-known aspects in mind will help ensure a smoother and stress-free driving experience in the bustling streets of Chicago.

Road Trip Safety Tips

While embarking on a road trip to Chicago, it’s crucial to prioritize safety. Read further for some essential safety tips to ensure a smooth and secure road trip.

Check Your Vehicle Condition

Before hitting the road, inspect your vehicle’s tires, brakes, lights, and fluids. Ensure everything is in good working order and consider getting a professional mechanic to perform a thorough inspection.

Plan the Route

Plan your route in advance, considering traffic conditions and any road closures. Utilize GPS navigation or maps to avoid getting lost and save time.

Share Your Itinerary with Family and Friends

Inform a trusted friend or family member about your road trip itinerary. Provide them with details of your planned route, accommodation, and expected arrival times. This way, someone will be aware of your whereabouts. Looking for more to do? Review some recommendations in our ultimate guide to Chicago .

Take Regular Breaks

Long drives can be tiring, so take regular breaks to stretch your legs, have a snack, and rest. Fatigue can impair your driving abilities, so it’s essential to stay alert and well-rested.

Stay Alert and Avoid Distractions

Keep your focus on the road and avoid distractions such as texting, eating, or adjusting the radio while driving. Remember, safety should always be your top priority.

Follow Traffic Laws

Observe and follow all traffic laws and regulations, including speed limits, seatbelt usage, and traffic signals. Be mindful of other drivers and pedestrians to ensure everyone’s safety on the road. When in doubt, review the rules of the road for Illinois .

Itineraries by Car: Scenic Drives in Chicago

Once you’ve reached Chicago, there are several iconic attractions you shouldn’t miss. Here are some must-see places that will make your road trip unforgettable.

Lake Shore Drive

Take a leisurely drive along Lake Shore Drive, which stretches along the beautiful shoreline of Lake Michigan. Enjoy stunning views of the lake, the city skyline, and iconic landmarks like Navy Pier and Grant Park.

Lake Shore Drive is about 16 miles long. You can start at 67th Street in the South Shore neighborhood and goes north to Hollywood Avenue.

The Magnificent Mile

Cruise along North Michigan Avenue, known as the Magnificent Mile. Marvel at the impressive architecture, luxury boutiques, and iconic landmarks as you drive through this bustling shopping district.

The Magnificent Mile is one mile long and starts at the Chicago River and extends north to Oak Street Beach .

The Outer Drive

The Outer Drive is also known as South Lake Shore Drive. This scenic route takes you through the southern part of the city, offering picturesque views of the lake, harbors, and the Museum Campus which consists of The Field Museum, the John G. Shedd Aquarium , and the Adler Planetarium.

The Outer Drive starts at East Jackson Drive and extends south to East 67th Street. It is in the southern part of Lake Shore Drive.

Green Bay Road

Head north of the city and take a drive on Green Bay Road. This road offers a scenic journey through the charming suburbs, lined with beautiful homes, parks, and quaint downtown areas.

Green Bay Road extends through the northern Chicago community and multiple northern suburbs including Evanston, Skokie, Wilmette, Winnetka, Glencoe, Highland Park, Lake Forest, Waukegan, and Zion. These are great towns to explore outside of Chicago during your road trip.

Sheridan Road

Embark on a drive along Sheridan Road, which runs parallel to Lake Michigan. This picturesque route takes you through charming neighborhoods, historic mansions, and scenic lakefront parks.

Sheridan Road extends through the northern Chicago community and multiple northern suburbs including Evanston, Wilmette, Kenilworth, Winnetka, Glencoe, Highland Park, Lake Bluff, Lake Forest, North Chicago, and Waukegan. You make want to include a visit to some of these towns during your Chicago road trip.

Chicago Skyway

Experience a unique perspective of the city by driving on the Chicago Skyway. This elevated toll road offers fantastic views of the downtown area and provides a smooth route to the neighboring state of Indiana for a day drive.

FAQs for a Chicago Road Trip

What is the driving distance to chicago.

The driving distance to Chicago varies depending on your starting point. Use a reliable navigation tool or map application to get the most accurate distance information.

Are there any tolls on the way to Chicago?

Yes, there are tolls on some highways leading to Chicago. Make sure to carry cash or have an electronic tolling device like an I-PASS or E-ZPass for seamless travel.

How many days should I plan for a Chicago road trip?

The ideal duration for a Chicago road trip depends on your interests and the attractions you want to explore. A minimum of 3-4 days is recommended to cover the major highlights, but extending your stay allows for a more immersive experience.

Can I find parking easily in downtown Chicago?

Parking in downtown Chicago can be challenging, especially during peak hours. It’s advisable to research parking options in advance of your road trip and consider using public transportation or ride-sharing services to navigate the city.

What are some offbeat attractions in Chicago?

Apart from the popular landmarks, you can explore offbeat attractions like the Garfield Park Conservatory , and 360 Chicago Observation Deck, or take a street art tour in neighborhoods like Pilsen and Wicker Park.

Final Thoughts on a Chicago Road Trip

A road trip offers an incredible adventure filled with iconic Chicago attractions , delicious food, vibrant culture, and memorable experiences.

By packing essential items, following safety tips, and planning your itinerary, you can make the most of your journey.

Don’t forget to create your Chicago road-trip itinerary or read some of our recommendations for a perfect blend of vacation activities , iconic sights, cozy accommodations, and unique experiences.

Explore Millennium Park and Navy Pier, dive into the city’s vibrant culture, and immerse yourself in art at the Art Institute of Chicago .

When it comes to accommodations, choose from downtown hotels for convenience or boutique options for a personalized touch. Experiencing one of the best neighborhoods in Chicago will also create a memorable stay.

Indulge in deep-dish pizza (don’t forget to invite me), take an architecture boat tour , and catch a thrilling sports event. Chicago offers a road trip experience like no other, where every moment can be filled with excitement and discovery.

Tanya, a travel writer and content creator who has lived in Chicago for over 30 years, is your go-to local expert for Chicago's hidden treasures. Tanya's deep knowledge of various cities and attractions is acquired through personal exploration, making her articles a treasure trove for travelers and families. She has visited 43 of the 50 United States, France, Italy, Spain, Portugal, Japan, and the UK.

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4 Phenomenal Road trips to Chicago inc Interactive Maps!

Hit the road with our guide on 4 incredible Chicago road trips, complete with interactive maps and itineraries. Perfect for travelers craving scenic routes and tasty stops!

The Windy City, Chicago, Illinois is a large metropolis on the scenic Lake Michigan. The Skyline is punctuated with vast skyscrapers, such as the  Willis Tower (Former Sears Tower)  and the Legendary John Hancock Center at over 1,451ft high.

Chicago is also known for its tasty foods from Chicago style pizza (Deep dish) & mouth watering Chicago hot dogs. In addition, Chicago is know for its Jazz and of course the Notorious 1920s gangster Al Capone!

In this post i'm going to run through my top 4 most life changing road trips I've taken to or from Chicago! I've also included an interactive road trip map for each & Itinerary! So lets Dive right in!

4. New York City to Chicago Road Trip!

New York City and Chicago have always had a rivalry. Some say New York is just Bigger & Badder, while others point out that the Chicago people are just more friendly & laid back!

Me & my girlfriend were having this same dispute…so to settle any arguments we decided to to a road trip between New York City & Chicago and of course head past some great cities on the way!

New York TO Chicago Road Trip

New York City to Chicago Road Trip Itinerary:

• New York City
• Philadelphia
• Washington D.C

You can also head to Chicago via Finger Lakes & Niagara Falls which is a great option!

See:  New York City to Niagara falls Road trip!

Interactive Map (New York to Chicago Road Trip):

Dive into our Interactive map below!

User Guide:   Simply Click the +/- buttons to zoom in & out,  Click on a favourite attraction, and click directions symbol to give you the driving or walking route directly there!

(Many visitors choose to share our map on facebook by clicking the link below:

[social_warfare]

Webmasters:  Why not embed this map on your website to help your readers? Feel free by clicking the link in the top right corner.

But remember to credit us at:  townandtourist.com/new-york-chicago-road-trip/

How far is Chicago from New York?

There are  795 miles  between New York & Chicago. Driving direct it would take you  13hr, 7 mins.. .but where is the fun in that!

Road Trips  are about the journey and the amazing places to stop along the way!

Related Read:   Best Time to Visit Chicago

Is it cheaper to fly or drive?

It’s not always cheaper to drive, but in many cases it be less than half the cost of flying to drive and alot more fun!

new york road trip hammock girl

Which is the best method of transport from New York to Chicago?

From the Table below we evaluated which is the best method of transport between New York and Chicago. Now this all depends on personal preference.

However, from the data it’s clear that the  Bus is the cheapest method of transport between New York and Chicago.

So if your a real Backpacker and don’t want to  rent a car  then this is a great option for you. However, there are a couple of negatives against taking the Bus.

There is not as much comfort and space as the train and you can’t stop off as many times as you could in a car!

For more on Public transport to Chicago check out:  New York to Chicago on Public Transport: Is it worth it?

Dive into our helpful comparison table below!

Should I take the train between New York & Chicago?

The Amtrak train takes you up through Connecticut, Massachusetts before traveling along the coast of New York state.

This is a really Scenic train ride and an experience in itself. For more info see:  Ultimate Guide to the USA by Amtrak Trains

Buffalo New York train journey

For our full New York to Chicago Road Trip Itinerary

check out: New York City to Chicago Road Trip: Itinerary/Map

3. Chicago to Iowa: wild west road trip!

A Chicago to Iowa Road Trip is a short but sweet mid america road trip! Along the way you will drive through authentic Americana.  Line of sight you can travel the 236 miles  between Chicago & Iowa in approximately 4 hours! However, we prefer to take the more scenic route to really experience old americana.

freight-house-farmers market. Iowa.

Chicago to Iowa Road Trip Itinerary

Here are our Stops along the way.

• Iowa City, Iowa
• Bonus: Amana Colonies

Interactive map (New York to Chicago Road Trip):

Dive into our Interactive Map below, for the best attractions to see on a road trip between Chicago & Iowa.

User Guide:   Simply Click the +/- buttons to zoom in & out, (Zoom out to see Blowing rock).

Click on a favourite restaurant, and click directions symbol to give you the driving or walking route directly there!

(Many visitors choose to  share our map on facebook  by clicking the link below!)

Be sure to visit Galena!

Galena is a historic small town in northwest Illinois. This little town down is old school Americana at its best! Here you will find a host of 19th century buildings such as the 1826 Dowling House and Hourseshoe Mount which offers views of THREE STATES!

You can check out other ancient ceremonial sites at Casper Bluff.

Things to do in Galena:

• Home of Ulysses S Grant
• Chicago Atheneum
• The Dowling House
• Galena Grant Park
• Galena Ghost Tours.
• Galena Trolley Tours

For the full Itinerary be sure to check out this post here:  Chicago to Iowa Road Trip: Wicked Mid West!

2. Atlanta to Chicago Road Trip

Atlanta is known for it’s southern hospitality, diverse musical heritage and number of world records!

It also has the busiest passenger airport in the United States of America the  Harts-field Jackson Atlanta International Airport , which draws over 50 million people annually!

This makes it a popular starting point for many great US road trips!

Atlanta to Chicago Road Trip Itinerary:

• Atlanta, Georgia
• Chattanooga, TN
• Nashville, TN
• Louisville, Kentucky
• Indianapolis, Indiana
• Chicago, Illinois

Interactive map (Atlanta to Chicago Road Trip)

Dive into our interactive Map below!

User Guide:  Use the +/- arrows to zoom in an out of the landmarks. Many users choose to  share the post on facebook  and access the map that way.

Tip:  Turn your phone sideways for easier use. Click the directions button top right to be routed to attraction.

Visit the worlds largest drive inn Restaurant!

Be sure to visit this record breaking institution, covering over two acres in Downtown Atlanta,  Varsity  is the worlds largest drive inn Restaurant and can accommodate up to  600 cars outside  and over  800 people inside . The venue is especially popular when Georgia Tech plays at home.

Fun Fact:  Varsity makes over  two miles of Hot Dogs, 5000 fried pies and 300 gallons of Chilli daily!

Varsity worlds largest food drive in

1. Chicago to San Francisco: The Ultimate Road Trip!

San Francisco is know for its diverse cultures from the Chinatown area to its incredible food scene, iconic landmarks (golden gate bridge, Alcatraz prison island) and hipster vibe.

A road trip between Chicago and San Francisco is the ultimate road trip!

Related Read:   15 Best Waterfalls Near Chicago

How far is San Francisco to Chicago?

San Francisco is 2,132 miles from Chicago! Driving direct with no stops it would take you  31 hours!

You will cross 7 states and numerous cities of the USA! From Iowa to Nevada!

Welcome to San Francisco

Chicago to San Francisco Road Trip Itinerary:

Me & a few friends have actually taken this road trip twice! The first time we went the fastest route via Americas mid west! (Route 2).

Visiting places such as Iowa city and Denver, Colorado.

The second time we took a  longer route  but visited some iconic cities such a Las Vegas and LA.

We even got to see the  World Largest Hot Balloon Festival in Albuquerque , New Mexico!

Wonderful Instagrammable Balloon Photos. See:  20 Golden Reasons to go Albuquerque Balloon Festival?

From LA we hopped onto the Pacific coast highway 1 which is one the  25 Most Epic Driving Roads in the U.S.A: Road Trip Ideas!

Route 1 - Las Vegas & LA Road Trip Itinerary:

• Chicago, IL
• St Louis, MO
• Oklahoma City, OK
• Albuquerque , New Mexico
• Las Vegas , NV
• Los Angeles , CA
• San Jose , CA
• San Francisco , CA

Las-Vegas-Road Trip

Route 2 - Mid West Road Trip Itinerary:

• Iowa city , IA
• Kansas  City, KA
• Denver , CO
• Salt Lake City, UT
• Sacramento, CA

Winter Camping at Grand Sand Dunes Colorado is a incredible experience. Source: theknow.denverpost.com

For more info check out:  20 Incredible Winter Camping Destinations: USA

Interactive Map (Chicago to San Francisco Road Trip):

(The Road Trip Map outlines the two different routes mentioned above)

Route 1: Via St Louis, Albuquerque, Las Vegas and Los Angeles

Route 2: Via Iowa City, Denver, Salt Lake City and Reno.

Related Read:   25 Best Hiking Trails Near Chicago

Should I take the California Zephyr?

The California Zephyr Amtrak train first hit the rails in was 1949. Since then it has taken rail enthusiasts on one of the most scenic train rides in the USA! Which runs between Chicago & San Francisco.

The Scenery on the California Zephyr is world renowned.  On this journey you will cross the farmlands of Nebraska, the  Colorado  Rockies, through the Sierra Nevada mountains before arriving at  San Francisco .

California Zephyr train

The Dome Car:

The Dome Car offers seats facing out of the windows offering panoramic views of the scenery.

The Dome cars are common on scenic routes but do fill up quickly, especially on trains like the California Zephyr which passes through the untouched areas of the Colorado Rockies. So get to the carriage early to avoid disappointment.

Related Read:   15 BEST Boozy Bottomless Brunch in Chicago

Insider Tip:

Listen out for the Commentary of the most significant section of the California Zephyr route and try some classic american eggs and Bacon for breakfast in the diner carriage.

For our full guide check out our Ultimate Guide to the  California Zephyr: Chicago to San Francisco

Where to Stay in San Francisco?

For a recommended list of my favourite places to stay in San Franscisco, follow the link  HERE.

Vital Road Trip Tips:

• Make sure you have all your  Travel Essentials
• Make sure you have all your  Travel Accessories
• Bring a  Great Travel Camera  to capture some scenic shots.

Make sure you are equip with some great Photography Gear!

• Bring some High Quality Hiking boots: See Recommended  Hiking Gear
• Check our recommended  Camping Gear
• Avoid gigantic $15,000 Medical Bills see:  Why you NEED Travel Insurance in 2020?
• Make sure your Car is serviced, with a spare tire or alternatively rent a fully reliable car.

How to get the best car rental Deals?

Check out:  Ultimate Car Rental Travel Hacks!

For RV Rentals we always use:  RV Share

Bring your RV to Tiden Park.

73 Basic Dutch Phrases for Your Next Trip to Netherlands 🇳🇱

Learn essential Dutch phrases for a smooth trip to the Netherlands. Perfect for travelers looking to connect with locals and enrich their experience.

Win a $500 Flight!

Embark on the adventure of a lifetime! Enter our Dream Journey Sweepstakes for a chance to win a $500 travel voucher, redeemable with any major US airline. Whether it's sandy beaches, bustling cities, or tranquil mountains, your dream destination is just an email away!*

Is Sun Country Airlines Safe? Discover How They Prioritize Your Safety

When you're planning your next getaway, the safety of your chosen airline is probably at the top of your list. You've likely heard of Sun Country Airlines, a budget-friendly option that's been gaining popularity. But the big question on your mind is, "Is Sun Country Airlines safe?"

Is Delta Air Lines Safe? Unveiling the Truth for Nervous Flyers

When you're planning your next trip, safety is likely at the top of your list. And if Delta Air Lines is on your radar, you're probably wondering just how safe it is to fly with them. Let's face it, in today's world, the safety of an airline can make or break your travel plans.

Is American Airlines Safe? Uncovering the Truth for Nervous Flyers

When you're planning your next trip, safety is probably at the top of your mind. And if you're considering flying with American Airlines, you're likely wondering just how safe it really is. It's a valid concern—after all, you're cruising at 35,000 feet!

Is Biman Bangladesh Airlines Safe? Unveiling the Truth for Anxious Flyers

When you're planning a trip, especially one that takes you across borders, the safety of your chosen airline is a top priority. You've probably come across Biman Bangladesh Airlines in your search for flights, and it's natural to wonder about its safety record. After all, you're entrusting them with your most precious cargo: you and your loved ones.

Is Arkia Israeli Airlines Safe? Unveiling the Truth That Every Traveler Must Know

When planning a trip, you're likely to ponder over which airline to choose, especially when it comes to safety. If you've got your eyes set on Israel, Arkia Israeli Airlines might have popped up in your search. It's Israel's second-largest airline, but how does it stack up in terms of safety?

Is Air Albania Safe? Unveiling the Truth About Your Next Flight's Security

When planning your next trip, you might wonder about the safety of your chosen airline. It's a valid concern, especially if you're considering flying with a relatively new player like Air Albania. Founded in 2018, it's the flag carrier of Albania, but how does it stack up in terms of safety?

Is Jeju Air Safe? Unveiling the Truth Behind Your Flight Fears

When planning a trip, especially by air, safety is always at the top of your mind. You've probably come across Jeju Air, a popular low-cost carrier in South Korea, and wondered, "Is Jeju Air safe?" It's a valid question, considering the budget-friendly tickets and the airline's growing network across Asia.

Is Air Tahiti Nui Safe? Unveiling What Every Traveler Needs to Know

When planning a trip to the enchanting islands of Tahiti, you're likely considering Air Tahiti Nui for your journey. It's the flagship carrier that promises an exotic travel experience, whisking you away to paradise. But amidst the excitement, a crucial question pops up: Is Air Tahiti Nui safe?

Is Avelo Airlines Safe? Unveiling the Truth for Anxious Flyers

When you're planning your next trip, safety is always at the top of your mind, right? You're probably wondering if Avelo Airlines, the new kid on the block in the aviation world, ticks all the boxes for a safe journey. It's a valid question, especially with so many options out there.

Is PenAir Safe? Unveiling the Truth for Nervous and Aspiring Travelers

When you're planning your next flight, safety is probably at the top of your list. You've likely come across PenAir in your search for regional flights, but you're wondering: is PenAir safe? It's a valid question, especially when flying to some of the more remote locations PenAir serves.

Is Ravn Alaska Safe? Unveiling Truths Behind Your Flight's Reliability

When planning a trip to the Last Frontier, you might wonder about the best way to hop between its vast landscapes. Ravn Alaska pops up as a popular option, but there's a big question on your mind: Is Ravn Alaska safe? Let's dive into what makes an airline tick in terms of safety and see how Ravn stacks up.

Is Breeze Airways Safe? Unveiling the Truth for Anxious & Aspiring Travelers

When you're eyeing those tempting deals from Breeze Airways for your next trip, it's only natural to wonder about their safety record. After all, who doesn't want a smooth and secure journey to their dream destination? Breeze Airways, a newcomer in the sky, has sparked curiosity among travelers seeking both value and peace of mind.

Is Cape Air Safe? Unveiling the Truth Behind Pilot Training and Fleet Safety

When planning your next adventure or business trip, you're likely to ponder over the safety of your chosen airline. If Cape Air's on your radar, you're probably asking, "Is Cape Air safe?" It's a valid question that deserves a closer look, especially when your comfort and peace of mind are at stake.

Is Silver Airways Safe? Unveiling the Truth for Anxious Flyers

When planning your next trip, you're likely juggling a lot of decisions. Where to stay, what to pack, and, crucially, which airline to trust with your safety in the skies. If you're considering Silver Airways for your journey, you might be wondering just how safe it is. After all, flying can be nerve-wracking enough without worrying about the reliability of your chosen airline.

Is GoJet Airlines Safe? The Truth Behind Passenger Reviews and Safety Concerns

When you're planning your next trip and considering flying with GoJet Airlines, one question might pop into your mind: "Is GoJet Airlines safe?" It's a valid concern, especially in today's world where safety is paramount. Let's dive into what makes an airline safe and see how GoJet stacks up.

Is Endeavor Air Safe? Unveiling the Truth Behind Your Secure Journey

When you're planning your next trip and considering flying with Endeavor Air, it's natural to wonder about safety. After all, you want your journey to be as smooth and worry-free as possible. Safety is a top priority for any airline, but how does Endeavor Air stack up?

Is Trans States Airlines Safe? Unveiling the Truth Behind Pilot Training & Safety

When you're planning your next trip and considering flying with Trans States Airlines, it's natural to wonder about their safety record. After all, ensuring a safe journey is at the top of everyone's list. You're not alone in your curiosity, and the good news is, we've got the scoop for you.

Is Air Wisconsin Safe? Unveiling the Truth Behind Your Flight's Safety

When you're planning your next trip and considering flying with Air Wisconsin, safety is likely one of your top concerns. It's a big deal choosing an airline, especially with the myriad of options and opinions floating around.

Is Envoy Air Safe? Unveiling the Truth Behind Your Next Flight

When you're planning your next trip and considering flying with Envoy Air, it's natural to wonder about the airline's safety record. After all, your safety is paramount, and you want to ensure you're making the best choice for your travel.

Is Mesa Airlines Safe? Discover What Passengers Aren't Telling You

When you're planning your next trip and considering flying with Mesa Airlines, safety is likely at the top of your mind. It's a big world out there, and knowing you're in good hands while jetting off to your next adventure can make all the difference.

Is Compass Airlines Safe? Uncovering What Every Traveler Must Know

When you're planning your next trip and considering flying with Compass Airlines, it's natural to wonder about their safety record. After all, ensuring a safe journey is at the top of everyone's list. But diving into the world of airline safety can feel like navigating through a maze. Don't worry; we've got you covered.

Is Republic Airways Safe? Insights That Every Nervous Flyer Must Read

When you're planning your next trip and considering flying with Republic Airways, it's natural to wonder about their safety record. After all, ensuring you're in good hands while thousands of feet up in the air is pretty crucial. You're not alone in your concerns; it's a question on the minds of many travelers.

Is SkyWest Airlines Safe? Unveiling the Truth That Every Traveler Must Know

When planning your next trip, you might be wondering about the best airline options out there. Safety, no doubt, tops your list of concerns. You've probably heard of SkyWest Airlines, a major player in the regional airline sector. But the burning question remains: Is SkyWest Airlines safe?

Is Icelandair Safe? Discover Why Flyers Trust Their Journey With Us

When you're planning a trip that involves flying, safety naturally tops your list of concerns. And if Iceland's stunning landscapes are calling your name, you're probably considering Icelandair for your journey. But how safe is this airline, really?

Is Luxair Safe? Unveiling What Really Matters to Nervous Flyers

When planning your next trip, you're likely scrolling through countless options, wondering which airline will get you there safely and comfortably. Luxair, Luxembourg's flag carrier, often pops up as a top choice for European destinations. But in the sea of airlines, you might ask yourself, "Is Luxair safe?"

Is SpiceJet Safe? Uncovering the Truth Behind Passenger Reviews

When you're planning your next trip, safety is always at the top of your mind. And if you're considering flying with SpiceJet, you might be wondering just how safe it is. After all, flying can be daunting, and choosing the right airline is crucial for a worry-free journey.

Is El Al Safe? Debunking Myths & Unveiling the Truth for Nervous Flyers

When you're planning a trip, especially an international one, safety is likely at the top of your list. And if your travels are taking you to or from Israel, you've probably heard of El Al. It's Israel's national airline and has a reputation that precedes it. But what's behind the buzz? Is El Al really as safe as they say?

Is China Eastern Safe? Unveiling the Truth Behind Your Flight Fears

When you're planning a trip, especially one that spans continents, safety is likely at the top of your list. You've probably come across China Eastern Airlines in your search for flights, and it's natural to wonder about their safety record. After all, you're entrusting them with your most precious cargo - yourself and your loved ones.

Is China Southern Safe? Unveiling the Truth Behind Your Flight Concerns

When it comes to air travel, safety is always at the forefront of everyone's mind. You might be planning your next trip and wondering, "Is China Southern safe?" It's a valid question, especially when venturing far from home.

Is Malaysia Airlines Safe? Unveiling the Truth for Anxious Travelers

When you're planning your next adventure or business trip, the airline you choose is a big deal. You want comfort, good service, and most importantly, safety. Malaysia Airlines often pops up as a tempting option with its attractive routes and competitive prices. But there's that nagging question in the back of your mind: Is Malaysia Airlines safe?

Is Japan Airlines Safe? Unveiling the Truth for Anxious Flyers

When planning your next trip, safety is likely at the top of your list, especially when it comes to choosing an airline. You might be wondering, "Is Japan Airlines safe?" Well, you're in the right place to find out. Japan Airlines, known for its impeccable service, also prides itself on its safety record.

Is ANA Safe? Discover How They Ensure Your Peace of Mind in the Skies

When you're planning a trip, especially one that involves flying, safety is likely at the top of your mind. You might be wondering about All Nippon Airways, commonly known as ANA, and its safety record. Is it a reliable choice for your next journey?

Is Singapore Airlines Safe? Unveiling the Secrets Behind Their Flawless Safety Record

When you're jetting off to exotic locales or crucial business meetings, the last thing you want to worry about is your safety in the sky. That's where Singapore Airlines comes into play. Known for its impeccable service, it's natural to wonder about its safety record too.

Is Emirates Safe? Unveiling What Happy Travelers Really Think

When you're planning your next journey, safety is likely at the top of your list. You've probably heard a lot about Emirates, known for its luxurious experience, but how does it stack up in terms of safety? Let's dive into what makes an airline safe and see where Emirates lands.

Is LOT Safe? Unveiling the Truth Behind Your Flight's Safety

When you're planning a trip, the safety of the airline you choose is a top priority. You might've heard about LOT Polish Airlines and wondered, "Is LOT safe?" Well, you're not alone in asking. Safety concerns are valid, especially when it's about flying thousands of feet above the ground.

Is Aeromexico Safe? Unveiling What Every Traveler Needs to Know

When you're planning your next trip and considering flying with Aeromexico, safety might be at the top of your mind. It's natural to wonder about the safety records of airlines these days, especially with the amount of travel we all do. Aeromexico, as one of the leading carriers in Latin America, often comes under scrutiny.

Is Norwegian Safe? Discover Why Travelers Trust Its Skies

When you're planning your next adventure, safety is always at the top of your list. And if Norway's on your radar, you're probably wondering, "Is Norwegian safe?" Let's dive into what makes this Nordic country a destination worth considering from a safety perspective.

Is Allegiant Air Safe? Unveiling the Truth About Your Flight's Safety

When you're planning a trip, the safety of the airline you choose is a top priority. You've probably heard mixed reviews about budget airlines, and Allegiant Air often comes up in those conversations. It's natural to wonder, "Is Allegiant Air safe?"

Is Hawaiian Airlines Safe? Discover Why Flyers Trust This Paradise Airline

When you're planning a tropical getaway, the last thing you want to stress over is whether your flight will be a smooth sail or a turbulent ride. Enter Hawaiian Airlines, a name that's almost synonymous with the aloha spirit and island hopping. But beyond the lei greetings and in-flight POG juice, you're probably wondering, "Is Hawaiian Airlines safe?"

Is Frontier Airlines Safe? Unveiling the Truth Behind Your Flight Fears

When you're planning your next adventure or business trip, the airline you choose can make all the difference. You've probably heard about Frontier Airlines, known for its budget-friendly fares, but you might be wondering, "Is Frontier Airlines safe?" It's a valid question that deserves a closer look, especially in today's travel climate.

Is Spirit Airlines Safe? Unveiling the Truth Behind Your Flight Fears

When you're planning a trip and looking for budget-friendly options, Spirit Airlines often pops up as a tempting choice. But amidst the excitement of snagging a great deal, you might pause and wonder, "Is Spirit Airlines safe?" It's a valid question, especially when you're about to trust them with your most precious cargo—yourself!

Is JetBlue Safe? Uncovering the Truth Behind Their Safety Measures

When you're planning your next trip, the airline you choose is as crucial as your destination. You've probably heard a lot about JetBlue, known for its comfy seats and ample legroom, but how does it stack up in terms of safety? It's a question worth asking, especially in today's travel climate.

Is Alaska Airlines Safe? Discover Why Flyers Trust Their Journey With Them

When you're planning your next trip, safety is likely at the top of your list. You're not just looking for a smooth flight; you want peace of mind from takeoff to touchdown. That's where Alaska Airlines comes into play. It's a name you've probably heard tossed around when talking about reliable air travel, but how safe is it really?

Is Southwest Airlines Safe? Uncovering What Every Traveler Needs to Know

When you're planning your next trip, safety is always at the top of your mind. And if you're considering flying with Southwest Airlines, you might be wondering just how safe your journey will be. It's a valid concern, especially in today's world where travel safety has become more important than ever.

Is United Airlines Safe? Real Passengers Share Their Experiences

When you're planning your next trip, safety is probably at the top of your list, especially when it comes to choosing an airline. You've likely come across United Airlines, a major player in the aviation industry, and wondered, "Is United Airlines safe?" It's a valid question that deserves a closer look.

Ultimate Guide: Best Places to Live in Hawaii for Every Lifestyle

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Ultimate Guide: Best Places to Live in Minnesota for All Lifestyles

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Ultimate Guide: Best Places to Live in Alaska for Everyone - From Retirees to Families

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Ultimate Guide: Top Places to Live in West Virginia for Every Lifestyle

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Ultimate Guide: Top Vermont Havens for Everyone - From Retirees to Young Families

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Ultimate Guide: Best Places to Live in Arkansas for Everyone (2024)

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Idaho's Top Living Spots: The Ultimate Guide for Everyone - From Retirees to Families

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Ultimate Guide: Best Places to Live in Wyoming for Everyone

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Ultimate Guide: Top Spots in South Carolina for Young Adults - Live, Work & Play

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Ultimate Guide: Best Places to Live in Washington State for Everyone

Thinking about making a move to the Evergreen State? You're in for a treat! Washington's got a bit of everything, from bustling city life to quiet, cozy towns. Whether you're after the techy vibes of Seattle or the serene landscapes of the Olympic Peninsula, there's a spot just for you.

Ultimate Guide: Top Places to Live in Montana for Everyone – From Retirees to Families

Thinking about calling Montana home? You're not alone. With its breathtaking landscapes and wide-open spaces, it's a place that calls to the heart of adventurers and peace-seekers alike. But with so many amazing spots, picking the best place to plant roots can feel overwhelming.

Ultimate Guide: Best Places to Live in Virginia for Every Lifestyle

Thinking about making a move to Virginia? You're in for a treat! This state's got everything from bustling cities to quiet, cozy towns. Whether you're after top-notch schools, job opportunities, or just a beautiful place to call home, Virginia's got you covered.

Ultimate Guide: Top Places to Live in North Carolina for Happiness, Weather & More

Thinking about making a move to North Carolina? You're in for a treat! From the bustling streets of Charlotte to the serene beaches of the Outer Banks, North Carolina's got a little something for everyone. Whether you're after the hustle and bustle of city life or the quiet charm of small-town living, you'll find your perfect spot here.

Ultimate Guide: The Best Places to Live in Georgia for Everyone—from Retirees to Families

Thinking about making a move to Georgia? You're not alone. With its warm climate, rich culture, and booming job market, it's no wonder people are flocking to the Peach State. But with so many great places to choose from, where do you even start?

Ultimate Guide: Best Places to Live in Florida for Every Lifestyle

Thinking about moving to Florida? You're not alone! The Sunshine State is a magnet for folks seeking sunshine, beaches, and that laid-back lifestyle. But with so many awesome spots, picking the best place to plant your roots can feel overwhelming.

Ultimate Guide: Best Places to Live in Indianapolis for Everyone

Thinking about moving to Indianapolis? Great choice! Indy's got a lot to offer, from vibrant neighborhoods to bustling city life. But with so many spots to choose from, finding the perfect place to call home can feel like looking for a needle in a haystack.

Ultimate Guide: Best Places to Live in Orlando for Families & More

Orlando's not just about theme parks and tourist spots; it's a fantastic place to plant roots, especially if you've got a family in tow. With its sunny weather, great schools, and endless activities, it's no wonder families flock here. But with so many neighborhoods, choosing where to live can feel like finding a needle in a haystack.

Ultimate Guide: Top Places in Oregon for Young Adults - Live, Play, Thrive

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San Antonio's got a vibe that's hard to beat, with its rich history, vibrant culture, and killer food scene. If you're thinking about making the move or just curious, you're in the right spot. Finding the perfect neighborhood in this sprawling city can be a bit like searching for a needle in a haystack—but a whole lot more fun.

Ultimate Guide: Best Places to Live in Kentucky for Everyone

Thinking about calling Kentucky home? You're onto something special. Known for its rolling hills, horse farms, and friendly communities, the Bluegrass State offers a unique blend of natural beauty and welcoming neighborhoods.

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Thinking about moving to Maryland? You're in for a treat! This state's got a mix of everything - from bustling city vibes in Baltimore to the laid-back, scenic beauty of its coastal towns.

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Thinking about making Portland your new home? You're in for a treat! This city's got a vibe like no other, with its quirky culture, amazing food, and stunning nature spots. But with so many cool neighborhoods, picking the perfect spot can be a bit of a head-scratcher.

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Thinking about making a move to Austin? You're not alone. This vibrant city has been pulling folks in with its unique charm, incredible music scene, and mouth-watering BBQ. But with so many cool neighborhoods, picking the right spot can feel like finding a needle in a haystack.

Ultimate Guide: Best Places to Live on East Coast for Everyone – From Retirees to Families

Dreaming about moving to the East Coast? You're not alone. With its charming towns, bustling cities, and stunning beaches, the East Coast offers a little something for everyone. Whether you're after the vibrant city life or a quiet seaside retreat, you'll find your perfect spot here.

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So, you're thinking about moving to Washington, DC? Great choice! The city's not just about politics and monuments. It's got neighborhoods that'll make you wanna stay forever. From trendy spots buzzing with cafes and galleries to quiet, leafy streets perfect for Sunday strolls, DC's got a bit of everything.

Ultimate Guide: Best Affordable Places to Live in North Carolina for Every Lifestyle

Looking for a spot in North Carolina that's easy on your wallet but still ticks all the boxes for a great place to live? You're in luck. North Carolina's got a bunch of hidden gems that offer a fantastic quality of life without breaking the bank.

Ultimate Guide: Top Family-Friendly California Locales for Every Lifestyle

California's got it all for families looking for their next home sweet home. From the sunny beaches to the scenic mountains and bustling cities, there's a spot for every family's taste and budget.

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Thinking about calling the Midwest home? You're in for a treat! This heartland is chock-full of hidden gems, each offering its unique blend of charm, community, and comfort. From bustling cities with all the modern amenities to quiet towns where everyone knows your name, there's a perfect spot for everyone.

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Looking for the perfect spot in Georgia to call home? You're in luck! Georgia's got a little bit of everything, from bustling city vibes in Atlanta to the laid-back coastal charm of Savannah. It's a place where you can find your niche, whether you're after top-notch schools, thriving job markets, or just a great community feel.

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Looking to move close to Orlando but not sure where to start? You're in luck! Orlando's surrounding areas offer a mix of vibrant communities, each with its own unique charm. Whether you're after the buzz of city life or the tranquility of suburbia, there's a spot near Orlando that's perfect for you.

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Dreaming of a spot with sandy beaches, cozy neighborhoods, and endless bagels? Long Island's got you covered. It's not just about the stunning coastline; this place is a melting pot of cultures, cuisines, and communities. Whether you're a city escapee, a nature lover, or somewhere in between, there's a perfect corner here for you.

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Thinking about making a move to Arizona? You're not alone. With its stunning landscapes, booming job market, and vibrant culture, it's no wonder young adults are flocking to the Grand Canyon State. But with so many cool spots to choose from, where should you set up camp?

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Looking for a spot in Washington State that won't break the bank? You're in luck! We've got the scoop on the best affordable places that still offer that amazing Pacific Northwest vibe. Whether you're dreaming of cozy mountain towns or vibrant city life, Washington's got a little something for everyone.

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Soccer Scores

Sunday, june 9, 2024.

• T Chawinga - 28', 47' , 
• Lauren - 45'+2' , 
• V DiBernardo - 46' , 
• L LaBonta - 67' Pen
• J Huitema - 24', 41'

International Friendly

Italy beat bosnia in final euro 2024 warmup.

Italy edged Bosnia 1-0 on Sunday as midfielder Davide Frattesi scored a stunning ...

• D Frattesi - 38'
• J Kucka - 44' , 
• R Bozeník - 56' , 
• E Ampadu - 60' OG , 
• L Bénes - 90'

France held 0-0 by Canada despite Mbappé sub

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• Á Di María - 40'

FIFA World Cup Qualifying - Concacaf

• J George - 82' , 
• T Jules - 88'
• S Nicholson - 30', 79' Pen , 
• K Dixon - 42'
• O Anderson - 43'
• J Henríquez - 10' , 
• R Tejada - 60' , 
• N Bonilla - 83'
• N Reid-Stephen - 73'
• L Deedson - 12' , 
• D Lacroix - 45'+1' , 
• B Labissiere - 84'
• M Ugalde - 9' , 
• Á Zamora - 34' , 
• G Taylor - 70'
• Z Lewis - 45'+4' Pen
• K Arriaga - 14' , 
• D Ruiz - 49' , 
• E Rodriguez - 53' , 
• L Vega - 56' , 
• A Najar - 62' , 
• B Róchez - 90'+1'

FIFA World Cup Qualifying - CAF

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• M Elia - 6'
• G Dadzie - 29'
• M Wondimu - 31'
• H Diallo - 27'

Spanish Liga F

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• P Comendador - 69'
• C Pina - 26' , 
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• C Graham Hansen - 75' , 
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• J Aguado - 45'
• Granada ( 7-3-19 ) 0
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USL Championship

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USL Jägermeister Cup

• A Wehner - 13'
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Spanish LALIGA 2

• J Puado - 88'
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Argentine Nacional B

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Argentine Primera B

Argentine primera c, brazilian serie a.

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Ghanaian Premier League

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• Bibiani Gold Stars ( 12-10-11 ) 2
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Choose United Airlines to fly to more than 210 destinations in the U.S. and more than 120 destinations internationally — every day we operate more than 4,500 flights across five continents. Our comprehensive route network means you can book a direct or connecting flight to and from airports all over the world. Our main U.S. hubs are located in the major cities of Chicago, Denver, Houston, New York/Newark, Los Angeles, San Francisco and Washington, D.C. United is a founding member of Star Alliance™, whose entire network provides service to nearly 200 countries.

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From Chicago

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From San Francisco

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• Basic Economy - Ideal for travelers on a budget or looking for a quick getaway. This fare option gives you the opportunity to enjoy most benefits of United Economy® but at a lower fare with some restrictions. It is available only on select routes.
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• Economy Plus® - A great option if you need more space to relax, follow up on work, or if you prefer to sit closer to the cabin. Upgrade to Economy Plus for your next flight or opt to upgrade for an entire year on all available flights.
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Easily check in online at united.com/checkin or by using the United app up to 24 hours prior to your departure. For travel outside of the United States, you can even scan your passport using the app.

At your departure airport, you can check in at a self-service kiosk or United check-in counter.

Please review our full check-in information page for more information.

Review all baggage details here , or use our handy baggage calculator .

On all mainline aircraft and two-cabin regional aircraft, enjoy inflight Wi-Fi . On select routes, personal device entertainment is also available, so you can stream TV shows and movies from our extensive library directly to your laptop or mobile device.

United offers a variety of food and drink selections, depending on the route and duration of your flight. For more information on United Economy dining, see additional details about United’s meal service .

Make the most of your travel by enrolling in MileagePlus, United’s award-winning frequent flyer program. This membership allows you to earn miles to book United award travel, earn travel benefits and much more. Learn all about the advantages of our MileagePlus program .

MileagePlus members can also earn and use miles when they travel with Star Alliance member airlines.

Browse destinations and flight offers on  united.com  and book your flight today.

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• Houston - Monterrey
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Security Alert May 17, 2024

Worldwide caution, update may 10, 2024, information for u.s. citizens in the middle east.

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Our passport agencies and centers :

• Process all applications we receive from acceptance facilities and by mail, and
• Serve customers by appointment only who have urgent travel to a foreign country in the next 14 calendar days, or need a foreign visa in the next 28 calendar days

The U.S. Department of State runs each passport agency and center. An agency and center is different than acceptance facilities which may include post offices, libraries, and local government offices.

Avoid the stress of needing to visit a passport agency or center for urgent travel. Apply early at an  acceptance facility  or  renew by mail .

Steps to Make an Appointment for Urgent Travel

I have not yet applied.

Follow these steps to make an appointment:

• Go to our  Online Passport Appointment System .
• Enter information about your travel plans to see if you qualify for an appointment. You may make an appointment for up to seven members of your household.
• Enter your email address. We will email you a code which you must enter to continue making an appointment. Check your junk or spam folder if you do not see the code in your inbox.
• Enter your mobile phone number. We will send you a text message with another code you must enter to continue making an appointment.
• Complete the process of scheduling your appointment. 
• Check your email for a message confirming the details of your appointment. The system will hold your appointment for 15 minutes. If you do not confirm your appointment within 15 minutes, you will need to start over.
• If you need to cancel or change the appointment, click the link in the confirmation email to get information about your appointment. 

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• Call  1-877-487-2778  from 8:00 a.m. to 10:00 p.m. Eastern Time on Mondays through Fridays, or on Saturdays and Sundays from 10:00 a.m. to 3:00 p.m. Se habla español. 

If you are deaf or hard of hearing, call  1-888-874-7793  for TDD/TTY teletype services. 

• We will provide you unique information that we will check on the day of your appointment to confirm your appointment is legitimate. If you are not the appointment holder, the passport agency or center will not be able to see you.
• If you need to cancel or change your appointment, please call us. We will give your appointment to a new customer calling to make an appointment. You cannot transfer your appointment.

Frequently Asked Questions

How do i know which location is processing my application and has my documents.

The first two digits of your nine-digit passport application locator number allow you to know which agency or center is working on your application. You can find your application locator number by checking our Online Passport Status System . 

How and when should I contact a passport agency or center by mail?

You can find an agency or center's mailing address on each agency or center webpage. You can contact our locations by mail if:

We sent you a letter : If we need more information to process your application , we will send you a letter in the mail. Send the information to the full mailing address in Sterling, VA listed on your letter. Do not send information to the agency’s physical address.

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We have two types of appointments: Life-or-Death Emergency Service and Urgent Travel Service . You cannot walk-in. 

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