Top Chicago Walking Tours

Chicago Favorites Ultimate Food and Walking Tour

(1,993)

Free Cancellation
3 hours

from $85

Discover the hidden gems of Chicago’s Loop area on a walking tour that showcases the best of the neighborhood’s stunning interiors and architectural must-sees. Step behind the facades to explore beautifully designed interiors—from art deco spaces to stained glass mosaics—as you follow a carefully curated route led by a guide. Along the way, learn about the city’s architecture, art, and history, and experience a side of Chicago often missed by travelers, all from a local’s perspective.

Original Chicago Architecture Interiors Tour: Dazzling Interiors

(1,540)

Free Cancellation
2 hours

from $35

A picture of Chicago Chinatown’s landscape shows vibrant streets, iconic arches, and rich culture—everything guests explore on our Chinatown Food Tours. Food Tours in Chinatown bring it all to life.

Immerse yourself in one of Chicago's most vibrant neighborhoods—and head off the tourist trail to discover sights and bites many visitors miss—on this small-group Chinatown food and walking tour. With your guide in the lead, learn about the cuisine of different regions of China, and discover the history of Chicago's Chinatown. Along the way, enjoy a generous array of tastings, from dim sum to Sichuan cuisine and beyond.

Chicago's Chinatown Food and Walking Tour

(613)

Free Cancellation
3 hours

from $80

Total Chicago: From Architecture to Food

Experience Chicago like a true insider on this top-rated walking tour that blends the city’s most iconic food, awe-inspiring architecture, and rich history — all in one unforgettable day. From deep-dish pizza to legendary skyscrapers, you’ll taste, see, and learn what makes the Windy City a world-class destination. Led by expert local guides and limited to just 12 guests, this immersive, small-group tour is the perfect way to discover the real Chicago — not just the tourist spots.

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

(1,174)

Free Cancellation
4 hours 30 minutes

from $101

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

(76)

Free Cancellation
1 hour 30 minutes

from $35

Immerse yourself in the taste and culture of pizza on this small-group walking tour that focuses on the food Chicago does best. You'll have the chance to sink your teeth into different pizza styles—including deep-dish, Neapolitan, Roman, and artisanal—then decide which one you like best. As you go, you'll learn more about Chicago's culinary history and culture, and can spot key city landmarks en route.

Downtown Chicago Walking Pizza Tour

(107)

Free Cancellation
2 to 3 hours

from $69

Skip the guesswork and discover the real haunts of Capone, Dillinger, and The Outfit on a walking tour that then also you shows how those same streets become movie stars. Walk the city corners seen in *The Untouchables* and *Public Enemies,* and hear how Chicago wrote the script for American gangster history. This isn’t just another sightseeing tour—it’s a front-row seat to crime, cinema, and the city that made them both.

Chicago Crime and Movies Tour

(46)

Free Cancellation
1 hour 30 minutes

from $35

Explore Chicago's buzzing food scene—and see some of its best-known landmarks on the way—on this two-in-one walking tour. The small group size offers are more intimate experience as you stroll around the vibrant Loop area, spotting highlights from the Willis Tower to the Rookery building. Indulge in a variety of famous Chicago foods, from deep-dish pizza to the world-famous dipped Italian beef sandwiches.

Chicago Loop District Food Tour with Deep Dish & Beef Sandwich

(883)

Free Cancellation
3 hours

from $85

Chicago Walking Tour: Must-See Chicago

(139)

Free Cancellation
1 hour 30 minutes

from $35

Likely to Sell Out

What do the artists Picasso, Chagall, Miro, and Kapoor all have in common? Incredible public art hiding in plain sight amidst world famous architecture. This 2.5 hour small group (12 Guest Maximum) guided walking tour is perfect for busy sidewalks and getting up close to monumental art! Highlights Include: Edward Kemeys’s “Lions” Juame Plensa’s “Crown Fountain” Anish Kapoor’s “Cloud Gate” (The Bean) Eduardo Kobra’s “Muddy Waters” Pablo Picasso’s “Untitled” Joan Miro’s “Chicago” Alexander Calder’s “Flamingo” Marc Chagall’s “Four Seasons” Louis Comfort Tiffany Art Glass Creation Augustus St. Gaudens “Abraham Lincoln” Marcel Francois Loyau “Clarence Buckingham Fountain”

Downtown Chicago Guided Walking Tour Semi-Private 12ppl Max

(1)

Free Cancellation
2 hours 30 minutes

from $52

Get to know the “must eats” in Chicago's buzzing Loop District on this small-group or private walking tour. As you explore, listen to in-depth commentary from your guide about the culinary history of Chicago, and get a taste of the city's most iconic foods, from hot dogs to deep-dish pizza. You'll enjoy personalized attention and the chance to chat about your favorite tastings, all while admiring Chicago landmarks along the way.

Chicago Food Tour: Taste the City’s Most Iconic Eats

4.8

(111)

Free Cancellation
2 hours

from $87

The Art Institute of Chicago houses one of the finest American and Impressionist painting collections in the world, but it can be overwhelming to explore on your own. Remove the guesswork and maximize your time inside the museum on a private tour that covers major highlights by Picasso, Chagall, Warhol, Hopper, and others. Plus, there's no waiting to get inside, as the tour includes a skip-the-line ticket.

Private Art Institute of Chicago Skip-the-Line Guided Tour

(282)

Free Cancellation
2 hours 30 minutes

from $90

4.6

(18)

Chicago City Tours

Free Cancellation
2 to 8 hours

from $199

Per group

Guide discussing A Sunday on La Grande Jatte

Skip-the-line: Art Institute of Chicago Guided Tour

(448)

Free Cancellation
2 hours 30 minutes

from $84

Get an insider's introduction to Chicago's most celebrated buildings during this architecture-focused walking tour of Michigan Avenue, State Street, and the vibrant Loop area. Revisit the heyday of the skyscraper and visit stunning, art deco-era interiors, from the Palmer House Hotel to the Chicago Cultural Center. Admission to the Chicago Architecture Center is included, with an introduction by the docent.

Chicago Walking Tour: Historic Treasures of Chicago

(416)

Free Cancellation
2 hours

from $35

Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this pet-friendly Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you cover multiple branches of the Chicago River and learn insider facts and stories you'd otherwise miss.

Chicago Architecture River Cruise

4.8

(15,842)

Free Cancellation
1 hour to 1 hour 30 minutes

from $39

Chicago Architecture and True Crime Tour

(334)

Free Cancellation
1 hour 30 minutes to 1 hour 45 minutes

from $35

Chicago's Dark Side: Ghosts, Gangsters, and True Crime Tour

(32)

Free Cancellation
2 hours

from $35

Take a deep dive into Chicago's food scene on a small-group walking tour. Head for several of the city's most-notable eateries, including Billy Goat Tavern, known for its "cheezborger," Pizzeria Uno, birthplace of Chicago’s legendary deep-dish pies; and Al’s Beef, a favorite since 1938. Along the way, hear about the friendly rivalry with New York's pizza scene, Chicago's meatpacking roots, 1920s speakeasies, gangsters, and more.

Chicago Food and Culture Walking Tour

4.6

(16)

Free Cancellation
2 hours

from $39

Special Offer

Tourgoers in front of the Marshall Field Mansion

Considered Chicago’s original “Millionaire’s Row,” Prairie Avenue in the Near South Side is renowned for its Gilded Age mansions—and this tour makes exploring easy (and delightfully spooky). In the evening, meet your guide in front of the Glessner House, and set off with ghost-hunting gear to accompany you. In between spotting highlights including the Marshall Field Jr. Mansion and the Henry B. Clarke House, you’ll hunt for specters and hear ghost stories.

Prairie Avenue Haunted History Tour and Ghost Hunt

(12)

2 hours 20 minutes

from

$32

$37

Admire the ornamental facades and intricate interiors of the Windy City's art deco buildings during this in-depth walking tour of the vibrant Loop. This small-group tour will introduce you to some of the city's highlight architectural landmarks and its rich history, all in a single excursion. As you go, get an up-close look at landmarks that many other tours overlook—and learn insider stories from your architecture-expert guide.

Chicago Walking Tour: Art Deco Skyscrapers Loop

4.8

(177)

Free Cancellation
1 hour 30 minutes

from $35

Learn all about the history beyond one of Chicago’s best-known thoroughfares—and spot numerous architectural icons as you go—on this small-group walking tour of the Magnificent Mile. Meet your guide at the Chicago Architecture Center and set off to soak up the street’s ambiance, and discover highlights like the Wrigley Building, John Hancock Center, and more. Entry to the Chicago Architecture Center is also included, so you can extend the experience.

Chicago Walking Tour: The Magnificent Mile

(45)

Free Cancellation
1 hour 30 minutes

from $35

Likely to Sell Out

Join us in the daytime or evening for City lights and breathtaking views

Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.

Chicago River 45-Minute Architecture Tour from Magnificent Mile

4.7

(3,024)

Free Cancellation
45 minutes

from $28

The Chicago Loop is the city's epicenter of culture, commerce, and design.

Discover the vibrant essence of Chicago with a self-guided tour through the Loop, the city’s historic downtown. This journey unveils a blend of striking skyscrapers and hidden architectural gems, allowing you to explore at your own pace. Uncover the rich history from the Great Fire of 1871 to the architectural masterpieces that define the skyline. Stroll past renowned theaters, museums, and captivating public art pieces that contribute to the city’s creative spirit. The Loop offers a unique perspective on Chicago's past and present, whether it's your first visit or a familiar stroll. — Self-guided exploration of Chicago’s historic Loop area — Learn about the city’s architectural innovations and history — Visit iconic landmarks like the Art Institute and Millennium Park — Perfect for first-time visitors or seasoned Chicagoans alike

Self-Guided Chicago Loop Tour Explore the City at Your Own Pace

(3)

Free Cancellation
2 hours to 2 hours 30 minutes

from $10

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Chicago Architecture Tour: Underground Pedway and the Loop

Julienne_T, Mar 2026

Pedway Tour

Heath was our tour guide and he was terrific! His face seemed very familiar and probably have met him as one of the various other tours that we have done. He was very knowledgeable about the history of the pedway and he did it with great enthusiasm, very funny and sarcastic (in a good way). What a way to learn about Chicago than traveling the city through the pedway! Awesome tour, bring a water bottle and have comfy sneakers for the tour! Thanks!

Chicago Mobs and Haunts Walking Tour

Sven_Z, Mar 2026

Great experience - not only for visitors.

Bryson is a great guide who enthusiastically engaged in riveting stories about Chicago. Living in Chicagoland for 20+ years, this experience is not only for tourists and visitors - you learn about the hidden sides of Chicago. I am somewhat glad that I didn't live in the 1920's Chicago.

Chicago City Minibus Tour

Molly_C, Jan 2026

Amazing Tour!

Alan was wonderful!! He contacted us early to keep us updated. His narration was fun and informative. He even allowed us to make an additional stop that we wanted pictures at! I will definitely be taking the tour again for all our out of town friends and will be requesting Alan again for our next tour!

Haunted Chicago Booze and Boos Ghost Walking Tour

Marissa_B, Dec 2025

SO worth it!

Our tour guide was amazing! She felt like a friend just hanging out telling stories with us. She was an amazing storyteller and had a wonderful personality. Highly recommend! I felt like I learned so much. It was one of those hidden gem things to do that didnt feel touristy. The tour made me feel connected in a way to chicago. Very cool experience.

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

Amy_F, Nov 2025

Even Stevie Wonder Would Give 5 Stars

We have done several tours in Chicago over the years, including one that was architectural-specific. Collin was by far the most knowledgeable. He took us to several hidden gems that other tours didn't even hint at. On top of his witticism, we are still discussing some of the historical stories he shared. Best time investment of our visit! Now we just need Collin to do a Chicago foodie tour.

Chicago Loop District Food Tour with Deep Dish & Beef Sandwich

Sabrina_C, Oct 2025

Excellent

Michael was our tour guide and he was excellent. He even helped us find parking on the street .The tour starts with a short visit inside the library which was the meeting spot. He had lots of stories to tell, and he was very entertaining. He was also very knowledgeable about Chicago. I expected sample servings of all the food, but we actually had an entire slice of pizza, a half of a beef sandwich, an entire hotdog, an entire churro, an entire brownie, and a small sample bag of popcorn. The tour took exactly 3 hours as advertised. I recommend this tour and hopefully you have Michael as your tour guide.

Delicious Donuts & City Sights: Chicago's Original Donut Tour

DJ_O, Oct 2025

Great tour every time

This is my favorite tour! I’ve booked it 3 times in the past year and brought new people. It’s always a hit and everyone’s favorite. Aside from the amazing Chicago doughnuts, you get a history of the shops and some of the local building’s you pass on the way. I particularly like that history is more personal and includes nuanced stories that you don’t hear on other tours. I’ve had the same guide all 3 times, Nick, and he is GREAT. He’s funny, personable and makes a point to talk with everyone in the group as we walk around. I highly recommend this tour.

Chicago Sightseeing River and Lake Cruise

Erica_S, Sep 2025

Great experience but hard to find

The tour was great with a very knowledgeable narrator. I enjoyed it. However, we missed out scheduled tour because. Of the difficulty in finding the location. We had to call and a wonderful agent stayed on the phone with us gave us directions and told us where to park. Patrons should be given more information on the location.

Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults

Alison_P, Sep 2025

Bike tour around Chicago

I had an afternoon to myself and live the outdoors so I booked the 4 hr bike, bites, and brews tour. I had a great time and was completely comfortable doing this tour by self as the guide was great and others in the group very friendly. Not overly strenuous at all, just a decent ride with plenty of stops to learn about Chicago.