best walking tours in chicago

• North America
• The Best Walking Tours In...

The 10 Best Walking Tours in Chicago

Even native Chicagoans have trouble exploring the city’s 77 neighborhoods, each community its own odd microcosm. Whether you’ve lived here your whole life or are visiting for a few days, there’s a walking tour that will wear out your soles and teach you something new. Below, you’ll find tours covering a range of subjects, from architecture and pizza to ghosts and street art.

Offbeat street art.

Historical Landmark, Architectural Landmark

In recent years, Chicago neighborhoods have expanded their identity through bold street art adorning brick walls. Don’t make the same mistake as the average passerby by overlooking some of the best murals and paintings in Logan Square and Wicker Park – both of which have many restaurants, coffee shops, bars and book stores worth exploring before or after your tour. Offbeat Street Art Tour – Urban Graffiti, Art, and Mural Tour costs only $25 and takes place on Saturdays and Sundays.

An architectural primer

Chicago’s eclectic architecture could consume an entire trip to Chicago. A good primer is Chicago Architecture Center’s Historic Treasures of Chicago tour, which unravels the mystery of Chicago’s ‘urban safari.’ Through the city’s early architectural achievements, you’ll get an idea of how Chicago has influenced the world. Set off for Michigan Avenue to get an art-deco thrill for around $25. Admission to the Chicago Architecture Center is included.

The dazzling interiors of the Loop

Inside Chicago prides itself on its ability to uncover the hidden secrets inside some of downtown Chicago ’s most famous skyscrapers. The World Within: Inside the Dazzling Interiors of the Loop highlights the concrete structures reaching for the sky along with their intricate insides: Art Deco lobbies from the ’20s, glass mosaics and more. The price of the tour is $30 and takes place every day of the week but Tuesday and Wednesday.

Secret gardens, live music and fireworks

Chinatown adventure for foodies.

This Chinatown Culinary walking tour paints a picture of Chicago’s Chinese culture through the exploration off the beaten path. Gorge on authentic cuisine from the Canton, Mandarin and Szechuan regions of China with a traditional lunch included and explore the history of Chinese culture and food in Chicago. End your tour at an authentic tea house and try the special blends.

Become a Culture Tripper!

Sign up to our newsletter to save up to $1,058 on our unique trips..

See privacy policy .

Chicago for Chicagoans Walking Tours

Walk among unmarked graves

Architectural Landmark

Get your spook on with Chicago Hauntings, a tour company that’s been in the ghost business for 15 years. Thousands of unmarked graves compose the landscape of their Lincoln Park Ghost Walk – can you think of a better locale? See if you can spot ghosts from the Great Chicago Fire and learn about mob history by exploring the scene of the St. Valentine’s Day Massacre . Tours take place Monday through Thursday, along with Sunday. Tickets cost $28 for adults.

A modern walking tour

The Chicago Architecture Center is devoted to both the old and the new. Learn how to parse the differences between Chicago’s many architectural styles through the Chicago Icons: Connecting the Past and Present tour, or focus on the architecture that helped define design aesthetics around the world on the Chicago Modern tour.

Chicago Pizza Tour

Pizzeria, American

From swamp to skyscrapers

Park, Architectural Landmark

The Riverwalk is a recent addition that struck ground in the early 2000s and wasn’t finished until 2017, meaning it may be new to Chicago veterans and first-timers alike. Though you could easily entertain yourself with the restaurants, bars, and boats lining the walk, this tour will help explain how the Riverwalk is one piece of a larger, metropolitan puzzle. It’s among the few tours that concisely explains how a swamp is now a skyscraper-filled metropolis.

This article is an updated version of a story created by Katie Mastropieri.

Where to Find Stunning Fall Foliage in the Pacific Northwest

San Francisco's 6 Most Haunting Ghost Tours

This is Everything Donald Trump Eats in a Day

16 Things You’ll Only Find in America

15 Stylish Cocktails Made With Only Three Ingredients

10 Traditional American Dishes You Need to Try

Words That Have Completely Different Meanings in England and America

The Best Books by Charles Bukowski You Should Read

The 5 Best Day Trips From Chicago for a Local Experience

The Most Luxurious Nature Getaways in the US

13 Reasons to Visit New England This Fall

The Sunniest Cities in the World

Culture Trip Fall Sale

Save up to $1,058 on our unique small-group trips! Limited spots.

This website uses cookies to improve your browsing experience and analyze the use of the website. Learn More

Reserve Your Spot with Confidence! Full Refunds with 24 Hrs Notice. Reschedule at any point, even after tour, if space allows!

Chicago Walking Tours

See our Calendar Below for All Tours, as well as Things to Do & Travel Tips

Featured tours.

Loop and Millennium Park

Loop and millennium park highlights.

• Marshall Fields
• The Picasso/Daley Plaza
• Millennium Park
• Crown Fountain
• The Great Fire
• The L (elevated trains)
• Start of Route 66
• The Art Institute of Chicago
• Cloud Gate (a.k.a. the Bean)

Haunted History

Haunted history highlights.

Highlights of our Chicago ghost tours:

• The Congress Hotel : Begin your eerie adventure at the Congress Hotel, known for its unsettling ambiance and ghostly legends. Discover why this historic landmark is often called the most haunted hotel in Chicago.
• Murderous Tales of H. H. Holmes and John Wayne Gacy:  Dive into the chilling stories of two of America's most infamous serial killers. Learn about the sinister acts of H. H. Holmes, who constructed a "Murder Castle" during the 1893 World's Fair, and John Wayne Gacy, the "Killer Clown" who terrorized Chicago in the 1970s.
• Death Alley and the Iroquois Theatre Fire : Walk through Death Alley, the site of the tragic Iroquois Theatre Fire of 1903. Feel the lingering sorrow as you hear the harrowing stories of the 600 lives lost in one of the deadliest theater fires in U.S. history.
• S.S. Eastland Disaster Hauntings : See the haunting grounds of the S.S. Eastland Disaster. Learn about the catastrophic

Riverwalk & History Tour

Riverwalk & history tour highlights.

• Jean Baptise Dusable: Uncover the tale of Chicago's earliest settler and how his legacy shaped the city.
• The Great Chicago Fire: Learn about the catastrophic fire that transformed Chicago's landscape forever.
• Ludwig Mies van der Rohe's Masterpiece: Marvel at the last building designed by the "Father of Modernism" himself.
• The Aqua Building & The Wrigley Building: Delight in the stunning and diverse architectural styles.
• Fort Dearborn: Walk the grounds of the original Chicago settlement.
• The Jeweler’s Building: Witness this iconic piece of Chicago history.
• Marina City Towers: Explore these unique structures along the river
• Chicago Flag History: Discover the symbolism behind the city's iconic flag.
• Apple Store & Centennial Fountain: End your tour near the modern Apple Store and the Centennial Fountain, celebrating Chicago’s engineering triumphs.

Welcome to Tours by Foot, offering small-group Chicago walking tours, including food tours.

Our tours are led by experienced and real Chicagoans who are the most highly rated in the city.

Our expert guides offer local knowledge of the Loop, Millenium Mile, the Chicago Pedway, Lincoln Park, and more.

• Guided Walking Tours
• Free Self Guided Tours (researched and written by our professional guides)
• Audio Tours (researched AND recorded by the same guides!)

These exciting and informative sightseeing city tours will take you through many of the Windy City's most famous neighborhoods.

Searching Availability...

We are so well-reviewed.   Read the reviews  for yourself.  

• Walking Tours
• Architecture Tours
• Tourist Discount Passes
• Chicago Travel Tips

CHICAGO WALKING TOURS

We provide a platform for local, freelance tour guides to lead walking tours as well as ghost and architecture tours so that you may enjoy a worry-free quality sightseeing experience.

Walking tours are our forte, and we offer several daily and weekly small-group tours as well as pay-what-you-like walking tours of Chicago and completely free self-guided options.

You can browse our tours by clicking the links below, scrolling through our public calendar (also below), or going directly to our  booking page . 

Our premiere Chicago walking tours are great day or night and serve as introductions to the city, Chicago history and cover the many of the main tourist attractions. 

Our Regularly Scheduled Tours

• The Birth of the Skyscraper:  Architecture Tour is a great way to discover and appreciate the incredible landscape of buildings in Chicago and it ends in Grant Park near the famed Buckingham Fountain.
• The  Riverwalk and Chicago History Tour follows the path of the Chicago River and focuses on the history of Chicago, the Chicago Flag, and the beautiful buildings that line the river.
• North Loop and Millennium Park Tour , which covers a great portion of Chicago’s downtown Loop neighborhood, public art, and ends in Millennium Park.
• Our  Chicago Ghost Tour -Haunting History is for folks who love haunting history and creepy tales of the dark side of the White City.
• On The Magnificent Mile Tour , you will discover fun Chicago facts like the history of deep dish pizza while exploring our most popular downtown area.

Weekly Tours

• Our  Gold Coast Tour  meanders through the history of high society where you will be introduced to the glamorous residential neighborhood built around Lakeshore Drive.
• Explore Lincoln Park on our Lincoln Park and Gangster Tour to appreciate a unique neighborhood scattered with hidden history including tales of Chicago Gangsters.
• We also offer a West Loop tour which combines great storytelling for history buffs with great photo ops for those more in the “sightseeing” mood! 
• Get out of downtown and check out the Chicago Street Art on our Wicker Park Culture & Street Art tour.

Winter Tours

We offer tours year-round, even in Chicago's winter, but we take into account the need to be seasonably appropriate for walking tours. Check out our special Winter offers:

• In the winter, we offer a Pedway Tour that explores the indoor tunnels and paths to discover Chicago architecture and arts in a warmer way.
• There is also a Winter Loop option where we will spend about half of the time outdoors looking up at the skyscrapers and the other half will be spent inside exquisite public buildings and lobbies.
• Our Winter Architecture Tour explores the unique landscape of buildings in the downtown area while also popping into many lovely lobbies for warmth!  This tour is abbreviated and adjusted for our Chicago winters.

OTHER TOURS

In addition to walking tours, Chicago has bus, bike & boat tours. Read all about them...

• What is the Best Chicago Architecture Tour?
• Chicago Boat Tours Compared
• Hop on Hop off Chicago Bus Map and Routes
• Chicago Ghost Tour
• Chicago Segway Tours
• Chicago Bike Rentals and Tours

AUDIO TOURS

Can't make one of our guided tours?

That is no problem; we have recorded some of our best tour guides who give their tours and made them available to you anytime.  

Here is how it works:

• Purchase an Audio Tour
• Receive a confirmation email with details.
• Enjoy the tour(s).

Available Tours:

• Downtown Chicago ($2.99)

PRIVATE TOURS

We also offer our guiding services for private groups, families, or school groups where we can guide you in the Loop, the South Side and anywhere else in Chicago.

Find out more about private tours .

And much, much more

North america, united kingdom & ireland, middle east & india, asia & oceania.

Best Walking Tours in Chicago

From the iconic landmarks of Millennium Park to the charming neighborhoods of Lincoln Park, every corner of Chicago has a story to tell. The best way to truly grasp the essence of this dynamic city is by embarking on a walking tour that will lead you off the beaten path and into the heart of Chicago’s hidden gems. If you’ve got three days in Chicago (or more) I highly suggest putting on walking shoes and heading out on a walking tour of Chicago.

I’ve personally done a few of these tours but didn’t have enough time to do them all, so I’ve done the research for you – here are the best walking tours in Chicago – whether you prefer ghost stories or food tastings! Please be sure to bring a tip for your guide 15 to 20% of the tour is fine.

This post contains affiliate links. This means if you purchase something from a link, I may make a small commission, at no cost to you. This helps me keep the site running and free.

If you like this post, be sure to sign up for my e-mail list for travel inspiration (and get your FREE budget printable), or connect with me on Facebook , Instagram , Twitter , or Pinterest .

General Walking Tours of Chicago

These walking tours are perfect for first-time visits to Chicago. There’s a little bit of everything on these tours and many show you some icons, like the Art Institute of Chicago .

Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

One of my favorite things to do in any city is find street art. I find the personality of the city comes alive with locally created art. With a knowledgeable guide leading the way, you’ll explore urban graffiti, murals, and art installations while learning about the street art community, the artists, and the stories behind their work. This walking tour offers a unique way to experience the city, showcasing areas that many tourists miss and providing engaging commentary on the creative expressions that color Chicago’s streets.

Key information:

5 stars with over 170 reviews

• Not wheelchair accessible

You’ll walk about 2 miles in 2 hours

Operated by Offbeat Street Art Tour

Chicago in a Day: Food, History & Architecture Walking Tour

Ideal for first-time visitors, this three-in-one tour offers a comprehensive introduction to Chicago’s top landmarks, rich history, and culinary highlights. In a small group, you’ll explore the city’s architectural icons on foot, visiting spots like the Chicago Riverwalk and Millennium Park. Along the way, enjoy generous tastings of classic Chicago dishes, from deep-dish pizza to Italian beef sandwiches. Perfect for those short on time, this half-day tour combines the best of the city with enough bites to make up a hearty lunch, all while your guide brings Chicago’s vibrant history to life.

Key Information:

• 5 stars with over 800 reviews
• 4 food stops with four tastings including hot dogs, pizza, popcorn, and chocolate!
• Walk the Chicago Riverwalk, Millenium Park, and see the Chicago Theatre

Chicago: Prohibition Speakeasies Bus Tour or Walking Tour

On this walking tour, you’ll discover how alcohol flowed through the streets of Chicago during Prohibition. You’ll hear stories about gangster hangouts and the upscale venues for high society. Your guide will take you to three iconic speakeasies in the Loop and River North. You’ll learn about the notorious figures and gangsters who frequented these places and see how things have changed over the years.

4.9 stars with over 50 reviews

Not suitable for anyone under 21

Bring ID card or passport with you

Drinks are not included at the speakeasies, so bring cash/card if you want one.

Chicago Walking Tour: Historic Treasures of Chicago

You’ll get to immerse yourself in Chicago’s architectural wonders on this walking tour of Michigan Avenue, State Street, and the vibrant Loop area. You’ll explore celebrated buildings, revisiting the heyday of the skyscraper while marveling at stunning art deco interiors, including the Palmer House Hotel and the Chicago Cultural Center. With admission to the Chicago Architecture Center and an introduction by a knowledgeable docent, this small-group tour offers a personal and enriching way to see the city’s most iconic landmarks, uncovering architectural highlights often overlooked by other visitors.

• 5 stars with almost 300 reviews
• Includes admission to the galleries of the Chicago Architecture Center
• Wheelchair and stroller accessible
• Hosted by the Chicago Architecture Foundation

Walkin’ with Colin: Chicago History-Mystery-Comedy-Tragedy Tour

Set off on an immersive downtown walking tour to uncover the fascinating stories and hidden secrets of the city in this must-do street-level adventure! As we loop through “Da Loop,” we’ll peel back the layers of this vibrant “Big Onion” town, stepping in and out of remarkable buildings and admiring stunning art and architecture. Along the way, you’ll discover how it all came to be in an engaging, entertaining, and eye-opening exploration of Colin’s beloved Chicago.

• 5 stars with 75 reviews
• Wheelchair accessible
• Not recommended for travelers with back problems or heart problems
• The tour is 2 hours, 2 miles, upstairs & downstairs, inside & outside.

Ghosts & Gangs Walking Tours of Chicago

These walking tours feature the stories of some infamous Chicago-ians. You could learn about Al Capone and other gangsters and how they ran the city. You may learn about the SS Eastland tragedy in the Chicago River and Death Alley.

Chicago: Discover the Gangsters & Ghosts of the City’s Past

Spencer and I took this tour during our three days in Chicago and were impressed. Our guide was knowledgeable and passionate about the topic and made the tour.

The tour primarily takes place in Chicago’s South Loop, but we also explored Death Alley, the Riverwalk, Palmer House, and the Chicago Theater. We learned about Al Capone and the history of Chicago’s gangster past. You’ll also listen to heartbreaking stories of the ghosts that are said to lurk around historic landmarks.

We took this tour at night to add to the ambiance of the tour.

• 4.7 star rating, over 1,000 reviews!
• 1.5 miles of walking, with a 20-minute break at a famous gangster hangout
• Children 6 and under join for free, but it is not recommended for people with infants

Windy City Ghosts: Hauntings of Chicago Walking Tour

Delve into Chicago’s spookiest ghost stories and step back in time to the era of gangsters, bootleggers, and jazz on this small-group walking tour. Starting in Lincoln Park after dark, you’ll explore haunted former burial grounds, pubs, theaters, and more, all while hearing eerie legends and tales of unexplained happenings. This tour offers a unique way to experience the city’s haunted history, with an option to upgrade for even more frights and ghostly encounters at Lincoln Park’s most notorious sites.

• 4.5 starts with 80 reviews
• This tour starts at 8:00 pm
• Travelers should have a moderate physical fitness level

Haunted Chicago Booze and Boos Ghost Walking Tour

Experience a unique side of Chicago on this haunted pub tour, where a costumed guide—dressed as a Flapper or 1920s Gangster—will lead you on a mile-long journey filled with spooky tales of forgotten cemeteries and lingering spirits. As you explore the city’s hidden corners, you’ll stop at three different bars for drinks (at your own expense) while uncovering the eerie secrets behind Chicago’s haunted past. This tour offers a memorable way to dive into the city’s history and enjoy a night out with a ghostly twist.

• 4.5 stars with 49 reviews
• Tour is about 1 mile long with 3-4 stops in pubs
• Travelers should have a moderate physical fitness level, it is not wheelchair accessible
• Tour operates in all weather conditions, dress appropriately
• Minimum age of 21, bring ID with you

Chicago Gangsters & Food Tour

This unique tour pairs Chicago’s Prohibition-era history with its most famous foods, offering a rare combination of flavors and stories. Explore the trendy River North neighborhood as you visit historic “gangster” hideouts, such as a steakhouse with a secret tunnel and a mansion serving deep-dish pizza. With a small group, you’ll enjoy personalized attention from your guide while learning about the city’s notorious past, making stops at iconic spots that bring Chicago’s gangster history to life.

• 5 stars with almost 400 reviews!
• You’ll enjoy Prime Cut Steak, a Chicago Hot Dog, and Deep Dish Pizza
• Walk the River North neighborhood and learn about one of Al Capone’s hideouts
• Try an iconic hot dog at one of the oldest serving establishments in the city

Food Walking Tours of Chicago

For my fellow foodie travelers, here are the best walking tours that feature Chicago’s distinct culinary scene. See the city and tantalize your taste buds with these tours.

Chicago: Ultimate Food Walking Tour with Tastings

Get ready for a delicious Chicago food tour in the River North neighborhood. This area is known as the original foodie destination in the city. You’ll get to sample some iconic dishes, local favorites, and even some sweet treats! From the famous Chicago-style hot dog, to deep dish pizza – this is the ultimate foodie Chicago walking tour.

• 4.5 stars, about 50 reviews
• The company is a Carbon-Neutral Company!
• It’s a kid-friendly tour, children under 6 can join for free
• Suitable for all ages and fitness, but it does cover about 1.5 miles (2.4 kilometers) of walking.
• It happens in rain, shine, or snow. Dress appropriately.

Chicago: Classic Food Walking Tour with Bike or Kayak Rental

Take a delightful 3-hour guided walk around downtown Chicago. You’ll get to see some of the city’s most famous sites while tasting its best foods. Enjoy the iconic deep-dish pizza and the original recipe brownie. Don’t miss the classic Chicago-style hot dog and a tasty Italian beef sandwich. If you’re interested, you can opt for a VIP craft beer sample for an extra $19.99 per person. This includes three craft beer pairings offered when you arrive.

As you stroll, you’ll pass by notable spots like the Magnificent Mile, the Wrigley Building, and the Chicago Theatre. Make sure to check out Millennium Park, the Chicago Riverwalk, the Art Institute, and the world-famous Bean.

After your walking tour, you can enjoy a free 2-hour bike or kayak rental. Bike rentals are at Bobby’s Bike Hike, 540 N Lake Shore Drive, and Kayak rentals are at Bobby’s Kayak on Ohio Street Beach. This has to be used within 3 days of your tour booking.

• 4.8 starts with over 100 reviews
• Kayak or bike rental has to be used within 3 days of tour booking
• There is a mid-day and evening tour available
• Tours run in rain, shine, or snow. Dress accordingly.
• Drinks are available for purchase.

Chicago: Taste of Chinatown Food Walking Tour

Chinese culture is rich and has greatly influenced both Chicago and the world. One of the best ways to experience this culture is through food. This Chicago walking tour will help you navigate any confusion and overcome language barriers.

Your tour starts at Phoenix Restaurant. Here, you can enjoy yummy dim sum dumplings and participate in a traditional Chinese tea tasting. Afterward, it’s time for a sweet treat: buttery custard tarts from Chinatown’s oldest bakery.

Next, you’ll try a unique spicy meat sandwich from the Xi’an region. Following that, take a stroll through the charming Chinatown Square, where you can explore ethnic grocery stores and souvenir shops.

To wrap up your tour, you’ll sample succulent dry chili chicken and the famous spicy Szechuan hot pot. On this delicious journey, you’ll experience a taste of different regions in China while only walking a few blocks in one of Chicago’s most interesting (and often overlooked) neighborhoods.

• 4.8 starts with 60 reviews
• You can upgrade for $19.99 per person, payable on site, which includes 3 adult drink pairings.
• Bring your passport or ID card
• Vegetarian options are available, please let your guide know in advance.
• 3 people are required to for this tour to take place, if less, then it’ll be canceled with a full refund or rescheduled.

Chicago Favorites Ultimate Food & Walking Tour

Enjoy all the icons of the city with this Chicago walking tour. Enjoy deep-dish pizza, Chicago-style hot dogs, and Italian beef sandwiches. You’ll also get a nice tour of the city – strolling down the Magnificent Mile, seeing the Wrigley Building and Chicago Theatre, and of course Millenium Park with the Chicago Bean (or its more formal name, the Cloud Gate).

This tour also comes with a free 2-hour bike or kayak rental to be used within 3 days of the walking tour booking. You can rent a bike at Bobby’s Bike Hike World on Lake Shore Drive or the kayak at Bobby’s Kayak at Ohio Street Beach.

Key Information :

• 5 stars with over 1,000 reviews!
• Suitable for all ages & fitness levels, but it does cover 1.5 miles (2.4 kilometers)
• Vegetarians can be accommodated, just let the tour guide know in advance. Also allows for those that don’t eat beef or pork. It cannot accommodate gluten-free or vegan.
• You can upgrade for $19.99 per person, payable on-site, which includes 3 adult drink pairings.
• TripAdvisor rated this tour its highest-level Traveler’s Choice Award each year since 2002.

Chicago’s Delicious Donut Adventure with Underground Donut Tour

Dessert lovers rejoice! Indulge in the Windy City’s sweetest treats on the Underground Donut Tour, where you’ll sample some of Chicago’s best donuts. This unique excursion takes donut lovers on a journey through the city’s top donut shops in the Chicago Loop, offering a chance to savor a variety of delicious styles, from glazed to cream-filled. With all tastings included and options for vegan, gluten-free, and nut-free diets, this tour is perfect for anyone looking to celebrate the magic of donuts.

• 5 stars with over 1,000 reviews
• Stop at 4 donut shops and try a few donuts at each place
• Donuts are included in the cost of the tour. You can purchase additional donuts if you want
• Vegan, Gluten-free, and nut-free options are available

Downtown Chicago Walking Pizza Tour

Dive into Chicago’s pizza culture on this small-group walking tour, where you’ll savor a variety of styles, from deep-dish and Neapolitan to Roman and artisanal. As you indulge in these delicious slices, you’ll also learn about the city’s rich culinary history and spot key landmarks along the way. With enough samples to make a generous meal, this tour offers a personalized experience as you explore vibrant neighborhoods like the Loop and River North, all while discovering the dish that Chicago is famous for.

• 5 stars with 82 reviews
• Tour happens in all weather conditions, dress appropriately
• Children under 6 are free, but let the tour operator know. Infants must sit on laps.
• Wheelchair & stroller accessible

Architecture Walking Tours of Chicago

Chicago architecture walking tour: dazzling interiors of the loop.

Discover the hidden gems of Chicago’s Loop district on a walking tour that showcases the neighborhood’s most impressive interior spaces. Step beyond the façades to explore beautifully designed interiors along a carefully curated route, led by an expert guide. As you delve into the city’s architecture, art, and history, you’ll uncover a side of Chicago that’s often missed by tourists, gaining a fresh, local perspective on the Windy City.

This tour takes you through various spots of The Loop

• 5 stars with over 900 reviews!
• Max of 15 travelers
• Operated by Inside Chicago Walking Tours

Chicago Architecture Tour: Underground Pedway and the Loop

Discover the hidden side of Downtown Chicago on a small-group walking tour that takes you through the Pedway, an underground network of tunnels connecting the city’s buildings, and the vibrant Loop. If you’ve ever wondered how Chicago-ians handle the winter, this is the walking tour for you! Perfect for architecture enthusiasts, this tour reveals insider stories and landmarks often missed by locals, offering a chance to see iconic sights like the Picasso Statue and Millennium Park. With a small group, you’ll enjoy a personal sightseeing experience, uncovering Chicago gems that are frequently overlooked on other tours.

• 5 stars with almost 200 reviews

Final Thoughts

Chicago’s walking tours offer an incredible way to experience the city’s rich history, diverse neighborhoods, and iconic architecture up close. Whether you’re a foodie eager to taste local specialties, a history buff intrigued by the tales of Prohibition-era gangsters, or an architecture enthusiast fascinated by the evolution of skyscrapers, there’s a tour tailored to your interests. Each step through Chicago’s streets reveals a new story, making these walking tours an unforgettable way to connect with the Windy City’s vibrant culture and charm. So, lace up your walking shoes and get ready to explore the best of Chicago, one step at a time.

Read More about Chicago

An In-Depth, Honest Review of StayPineapple Hotel in Chicago

How to Spend 3 Days in Chicago

Ultimate Guide to Public Transportation in Chicago

Chicago CityPass: Is it worth it?

Save “Best Walking Tours in Chicago” for Later

About The Author

9 thoughts on “Best Walking Tours in Chicago”

Love all the great tours that you recommended espescially the food tours! Next time we are in Chicago will check out some of your recommendations! Thanks!

The architectural tour looks like it would be our choice. Thanks for highlighting these top tours, as there are so many to choose from.

Chicago is a great city to take a walking tour in. The architecture is exciting and plentiful.

Blooming ‘eck, that is a lot of tour options! I do love exploring cities on food – but I think it’s the food tours (and the ghost tour) that are the most appealing. 🙂

I’d go for the underground pedway in the wintertime!

Perfect timing – my son is going to Chicago next weekend – I have shared this article with him!!!

I love Chicago, but I’ve never really thought of it as being a “foodie” city, but the amount of food tour options is telling me I’m wrong about that! Maybe I should check one out next time I’m visiting (:

Oh boy, those deep dish pizza pictures made me hungry! I’ll definitely be booking one of those tours when i visit Chicago!

Hadn’t wanted to visit Chicago until recently but this really affirms I need to go, so much to do!

I didn’t think there would be so many tours. How fun! I would love to do the walking pizza tour. Thank you for sharing!

Leave a Comment Cancel Reply

Your email address will not be published. Required fields are marked *

Rated as the best tours in Chicago. Our expert docents will guide you by boat, bus, train or on foot and share the stories behind the buildings.

Voted #1 Boat Tour in the US

6 best tours and walks in Chicago

#1 Chicago Boat Tour for 10+ years

This Saturday, October 19, the upstairs galleries of the center will close at 6 PM.

CAC River Cruise aboard Chicago's First Lady

Voted #1 boat tour in the United States by USA Today readers in 2024,...

Chicago's First Skyscrapers

Chicago is home to some of the world’s first skyscrapers. Get an up-close look...

Chicago Architecture: A Walk Through Time

Journey through Chicago’s architectural evolution, from the Great Fire’s aftermath to towering modern marvels,...

Explore Chinatown

Navigate through Chicago’s Chinatown, where cultural heritage meets urban design, revealing a neighborhood rich...

Modernism: Reviving the Loop

Formerly known as "Mid-Century Modern Skyscrapers," this tour delves into Chicago’s Mid-Century Modern architecture...

Art Deco Skyscrapers: The Riverfront

Explore Chicago's roaring '20s optimism through opulent Art Deco skyscrapers along the vibrant riverfront....

Historic Treasures of Chicago’s Golden Age

Learn about the great architectural landmarks of Michigan Avenue and State Street.

Architecture of the Magnificent Mile

Explore Chicago’s evolution from a dirt road called Pine Street to the iconic Magnificent...

Elevated Architecture: Downtown 'L' Train

Gain insight into Chicago’s elevated 'L' train, exploring its history and impact on urban...

Chicago Icons: Connecting Past and Present

Explore downtown Chicago's diverse architecture on a tour featuring 19th-Century, Beaux-Arts, Modern, and Postmodern...

Fulton-Randolph Market

Visit Chicago’s fastest developing neighborhood. Discover its transformation from a meatpacking hub to a...

What's New

Discover Chicago’s architectural innovation with the “What’s New” tour, highlighting recent landmarks and urban...

Must-See Chicago

This fast-paced introductory tour features some of Chicago's most famous buildings.

CAC River Cruise aboard Chicago's First Lady

Chicago's first skyscrapers, elevated architecture: downtown 'l' train.

boat tours FAQ

walking & bus tour faq

discounted tour pricing for members

Free essential walking tours, 66% off premier walking tours, invitations to exclusive members-only events, and more.

accessibility & safety

The Chicago Architecture Center welcomes all visitors and is committed to making its offerings feel safe and accessible to everyone.

Looking for more to do?

Group Tours

Private Groups

Custom Tours

Field Trips

• Book Online
• Walking Tours
• Private Tours
• Become a Guide

Riverwalk & North Loop Walking Tour

Searching availability... new checkfront.widget ({host: 'freechicagowalkingto.checkfront.com',pipe: '/wp-content/plugins/checkfront-wp-booking/pipe.html',target: 'checkfront_widget_1',item_id: '57,133,115,25,113,24,61,78,124',category_id: '3',tid: 'river landing page',options: 'tabs',provider: 'wordpress'}).render(); continue to secure booking system », don't see a date that works for you check out our full tour calendar here.

Guests on our Riverwalk & North Loop Walking Tour will enjoy the perfect mix of Chicago history, architecture and beautiful views along the Chicago Riverwalk. This Chicago Walking tour has something for everyone making this one of our most popular tours.

The Riverwalk

This Riverwalk & North Loop Walking Tour begins at the Du Sable Bridge - where it all began for Chicago back in the 1670s. After a brief Chicago history lesson, we'll head west along the Chicago River.

Of course, we're going to stop and chat a bit about Trump International Hotel & Tower, Marina City Towers & The Jewelers Building. We'll also stop by Heald Square Monument where we share a story on the financiers of the American Revolutionary War. And there is no such thing as a Chicago Riverwalk Tour without a stop and story about America's worse maritime disaster in its history - The Eastland Disaster which happened right on the shores of the Chicago River.

Just past the halfway point of the tour, the group will head south into Chicago's Loop for a few stops. Poking our heads into one of Chicago's most unique buildings, The State of Illinois Building, you will see why this entire city block-covering building is an absolute nightmare to heat in cool.

Our route will take us past a couple of Chicago's most famous public art pieces - Monument with a Standing Beast and the Picasso in Chicago. We'll conclude our tour in the often over-looked but rather stunning Chicago Cultural Center which is home to the world's largest Tiffany Glass-domed roof.

Tour Details

Meeting Point: Meeting Point: Outside the The Wrigley Building (400-410 N Michigan Ave, Chicago, IL 60611) under the American Flag Google Maps

Distance: 1.7 miles walking distance

Time: 2 hours from start to finish

Cost: FREE! Our guides work off the generosity of our guests. If you felt your guide has done a good job you can show your appreciation at the end of the tour by leaving a tip.

What you will see:

• Gorgeous Chicago River
• Jewelers Building
• Heald Square Monument
• Trump Tower
• Marina City Towers
• State of Illinois Building
• Daley Plaza
• Picasso in Chicago
• Chicago Cultural Center

Stories you will be told:

• The beginning of Chicago
• Trump International Hotel & Tower
• The Financiers of the American Revolutionary War
• The Jewelers Building
• Eastland Disaster
• Cadillac Palace: Surprise!
• State of IL Building: Truly One-of-a-Kind

More Free Chicago Walking Tours

• Tour Schedule
• Free Chicago Walking Tour Experience
• Friends & Partners