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Top Chicago Walking Tours

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Chicago Tours

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Chicago Favorites Ultimate Food and Walking Tour
Likely to Sell Out
Likely to Sell Out
4.9 (2,287)

Chicago Favorites Ultimate Food and Walking Tour

The perfect Food Tour of Chicago for first timers or anyone eager to explore Chicago's famous foods & top attractions—all in one tour. Stroll the...

3 hours • Free Cancellation
4.9 (2,287)
from
$85
Chicago Architecture and True Crime: Spooky Edition
5.0 (626)

Chicago Architecture and True Crime: Spooky Edition

Get the best of both worlds: explore Chicago’s stunning architecture while uncovering its dark past. Inspired by Devil in the White City, this expert-led walking...

90 to 105 minutes • Free Cancellation
5.0 (626)
from
$35
Chicago Architecture Tour: Underground Pedway and the Loop
4.9 (555)

Chicago Architecture Tour: Underground Pedway and the Loop

This tour explores some of the best hidden details, secret buildings and spaces, and untold stories that add wonderful bits of color and texture to...

2 hours • Free Cancellation
4.9 (555)
from
$35
Chicago's Delicious Downtown Donut Tour with 8 Amazing Tastings
5.0 (1,514)

Chicago's Delicious Downtown Donut Tour with 8 Amazing Tastings

Recently voted one of Cool Destinations's top food tours in the US. Discover the sweet side of the Windy City on the Underground Donut Tour,...

2 hours • Free Cancellation
5.0 (1,514)
from
$70
Chicago in a Day Walking Tour: Food, History & Architecture
4.9 (1,350)

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

Immerse yourself in Chicago's rich history and vibrant culinary scene on this captivating walking tour. Discover the city's iconic architecture and Prohibition-era charm while indulging...

4 hours 30 minutes • Free Cancellation
4.9 (1,350)
from
$101
Original Chicago Architecture Interiors Tour: Dazzling Interiors
5.0 (1,778)

Original Chicago Architecture Interiors Tour: Dazzling Interiors

UPDATE 2024: Don't be fooled by the copycats out there offering shady copies of our award-winning tours for $1 cheaper! There's only one company that's...

2 hours • Free Cancellation
5.0 (1,778)
from
$35
Embers of the Windy City: Chilling Chicago Ghost Tours
4.5 (123)

Embers of the Windy City: Chilling Chicago Ghost Tours

Come on our chilling ghost tour presented by US Ghost Adventures! Windy City Ghosts walking Ghost Tour provides a look into the darkness that lurks...

1 hour • Free Cancellation
4.5 (123)
from
$26
Chicago's Dark Side: Ghosts, Gangsters, and True Crime Tour
4.9 (68)

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

Discover Chicago’s dark side on a chilling 2-hour walking tour. Strolling just under 2 miles at an easy pace, we reveal stories of gangsters, tragedies,...

2 hours • Free Cancellation
4.9 (68)
from
$35
Frank Lloyd Wright Robie House Admission
4.4 (143)

Frank Lloyd Wright Robie House Admission

The Frederick C. Robie House on the University of Chicago campus is considered one of the most important buildings in the history of American architecture....

1 hour • Free Cancellation
4.4 (143)
from
$27
Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich
Likely to Sell Out
Likely to Sell Out
4.9 (1,003)

Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich

On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city. You'll experience all...

3 hours • Free Cancellation
4.9 (1,003)
from
$85
Chicago Murder Mystery Tour
5.0 (761)

Chicago Murder Mystery Tour

You will solve a murder as you learn real Chicago history! Play detective as you unravel a murder mystery, and learn about Chicago's true crime...

2 hours • Free Cancellation
5.0 (761)
from
$35
Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals
4.9 (206)

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

The Offbeat Street Art Tour is the first tour in Chicago that truly celebrates Chicago's street art scene. No other tour takes guests out into...

2 hours • Free Cancellation
4.9 (206)
from
$40
Haunted Chicago Booze and Boos Ghost Walking Tour
4.9 (329)

Haunted Chicago Booze and Boos Ghost Walking Tour

Join this Chicago haunted pub tour which is a combination ghost tour and pub crawl that will take you on a walking tour to explore...

2 hours 30 minutes • Free Cancellation
4.9 (329)
from
$36
Chicago Walking Tour: Art Deco Skyscrapers Loop
4.9 (190)

Chicago Walking Tour: Art Deco Skyscrapers Loop

View Art Deco masterpieces built in the heart of Chicago’s financial district during the Roaring '20s. Learn how Art Deco reflected the era’s fun-loving optimism...

1 hour 30 minutes • Free Cancellation
4.9 (190)
from
$35
Chicago Loop Food Tour: Taste the Most Iconic Local Eats
4.9 (127)

Chicago Loop Food Tour: Taste the Most Iconic Local Eats

Join a local guide for the ultimate foodie adventure in Chicago’s historic Loop, tasting classics like deep‑dish pizza and Chicago‑style hot dogs while discovering insider...

2 hours • Free Cancellation
4.9 (127)
from
$81
Chicago Crime, Mobsters & Ghosts Walking Tour
4.8 (452)

Chicago Crime, Mobsters & Ghosts Walking Tour

Join us along the historic streets and alleys of Chicago as we walk among the spirits of mobsters and ghosts of the condemned. This tour...

90 to 120 minutes • Free Cancellation
4.8 (452)
from
$34
Chicago Walking Tour: Must-See Chicago
5.0 (163)

Chicago Walking Tour: Must-See Chicago

Must-See Chicago is a fast-paced, 90-minute introductory tour to Chicago featuring some of its most famous buildings, including the Wrigley Building, Tribune Tower, the Art...

1 hour 30 minutes • Free Cancellation
5.0 (163)
from
$35
Chicago Architecture Walking Tour: What's New
5.0 (90)

Chicago Architecture Walking Tour: What's New

Over the course of 90 minutes, explore some of the newest buildings around the Chicago Architecture Center, focusing on construction elements and their impact on...

1 hour 30 minutes • Free Cancellation
5.0 (90)
from
$35
Chicago's Chinatown Food and Walking Tour
4.9 (794)

Chicago's Chinatown Food and Walking Tour

Chicago's Chinatown: Few neighborhoods in America combine such delicious cuisine with fascinating history. Join Bobby’s Bike Hike & Food Tours, whose food tours have ranked...

3 hours • Free Cancellation
4.9 (794)
from
$80
Skip-the-line: Art Institute of Chicago Guided Tour
5.0 (622)

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

Beat the crowds with an expert art historian guide on this exclusive early morning tour. Immerse yourself among the masterpieces housed within the acclaimed museum...

2 hours 30 minutes • Free Cancellation
5.0 (622)
from
$71

Frequently Asked Questions

These answers are based on answers previously given to Cool Destinations customers' questions.

Recent tour reviews
Fascinating!!
New York City
Original Chicago Architecture Interiors Tour: Dazzling Interiors
CallMeKate73, Sep 2026
Fascinating!!
Leaned a lot - well-done and nicely paced
Read more
Chicago Bob was great & Bring back the Palmer House Brownie!
New York City
Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich
GeoMomNE, Sep 2026
Chicago Bob was great & Bring back the Palmer House Brownie!
Chicago Bob was excellent. A great balance of food knowledge, Chicago culture & history, with a few dad jokes thrown in the mix. Easy walking tour with a great variety of foods to sample. We asked why the brownie was not officially from the Palmer House. He told us because that was generally the thing people complained about the most in reviews We bought our own just to try it and I enjoyed it. Yes it's a bit different than your standard brownie - but isn't that why you go on a food tour - to try things you normally wouldn't? I say go back to the Palmer House brownie and ignore the Karens.
Read more
Walk into the past
New York City
Chicago Crime, Mobsters & Ghosts Walking Tour
peterthetraveler98, Sep 2026
Walk into the past
Really interesting tour made even better by Ben who made two hours both interesting and informative. Who knew what lurked in Chicago’s history.
Read more
Enriching experience thanks to our tour guide Bernie
New York City
Skip-the-line: Art Institute of Chicago Guided Tour
mermaidd2019, Sep 2026
Enriching experience thanks to our tour guide Bernie
Our visit to the Art Institute of Chicago was a beautiful Sunday experience, largely thanks to our tour guide, Bernie. From the very beginning, it was clear that his depth of knowledge was vast and impressive. We greatly appreciated the early start of the tour, scheduled before the regular opening hours, as it allowed us to immerse ourselves in the museum’s serene atmosphere before the galleries filled with other art enthusiasts. There was something almost surreal about being surrounded by masterpieces in quiet solitude.The two-hour tour covered beautiful highlights of the second largest art museum in the United States. Bernie had a remarkable talent for selecting intriguing pieces and shared "behind-the-scenes" knowledge while offering insights into the artists' creative processes and the historical contexts of the works.This insider perspective added layers of meaning that typical visitors might miss, enriching our overall experience. I genuinely hope to return to uncover more of the museum's treasures. Bernie's passion and expertise and engaging demeanor truly enhanced our visit, eager to experience more of what the museum has to offer.
Read more
Do it!
New York City
Chicago Favorites Ultimate Food and Walking Tour
Marie_N, Sep 2026
Do it!
Awesome experience. Perfect blend of good and iconic Chicago food, history, and sights. Our tour guide Lillian did a fantastic job!
Read more
Great tour
New York City
Chicago Architecture and True Crime: Spooky Edition
annaaR3736CZ, Sep 2026
Great tour
Wonderful tour! Grant was very knowlegeable and personable. We had a great time and learned a lot!
Read more
Great Experience!
New York City
Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich
veronicamG9830VE, Sep 2026
Great Experience!
I loved this experience. Elliot was so knowledgeable and fun! Definitely recommend!
Read more
Superb
New York City
Original Chicago Architecture Interiors Tour: Dazzling Interiors
Shawie_M380, Sep 2026
Superb
Adam gave us a superb tour of Chicago’s interior architecture! He was knowledgeable, engaging, and passionate, bringing the city’s remarkable buildings and design details to life. We learned so much while enjoying every moment. I highly recommend this tour—and especially Adam—to anyone visiting Chicago!
Read more
Great donut experience
New York City
Chicago’s Delicious Downtown Donut Tour with 8 Amazing Tastings
stanw875, Sep 2026
Great donut experience
The guide Nivk was very knowledgeable and fun! We love him!!
Read more
Fantastic tour!
New York City
Chicago Architecture and True Crime: Spooky Edition
L4498UQabbyw, Sep 2026
Fantastic tour!
Grant was such a great guide! I’ve visited Chicago many times and heard new stories and got to see the inside of some of the stunning buildings the city has to offer. Highly recommend for anyone looking for a different type of architecture tour.
Read more
Awesome Tour
New York City
Chicago’s Dark Side: Ghosts, Gangsters, and True Crime Tour
elizabethgW4983FB, Sep 2026
Awesome Tour
Scott was so kind and knowledge. We learned a lot!
Read more
Scott was great!
New York City
Chicago’s Dark Side: Ghosts, Gangsters, and True Crime Tour
Flyer64544362312, Sep 2026
Scott was great!
Scott was a fantastic tour guide. He truly loves what he does and it showed throughout our tour. This tour is a great way to see the city and learn the untold history of the city.
Read more
A whole new Chicago experience
New York City
Chicago Architecture Tour: Underground Pedway and the Loop
davebork, Sep 2026
A whole new Chicago experience
Talk about the unknown. The Pedway experience opened a whole new world that was so uniquely Chicago. I’ve always heard about the underground and my grandmother using it to stay out of the elements on the way to work. Our guide, Spencer, is as knowledgeable and energetic. Well done
Read more
Architectural walking tour
New York City
Chicago Architecture Tour: Underground Pedway and the Loop
663kaydeeb, Sep 2026
Architectural walking tour
Great tour, excellent guide (Spencer) . Lots of hidden nooks and crannies of the city!
Read more
Sweet side of Chicago
New York City
Chicago’s Delicious Downtown Donut Tour with 8 Amazing Tastings
Relax49046444854, Sep 2026
Sweet side of Chicago
Lauren was super fun and very informative! We thoroughly enjoyed the entire tour and the donuts were exceptional!
Read more
Great way to experience Chicago
New York City
Chicago Favorites Ultimate Food and Walking Tour
oindrilam2022, Sep 2026
Great way to experience Chicago
Great way to experience Chicago if you are there for the first time. The tour is a great mix of food, walking and historical tour. Our guide was very accommodating and energetic. We enjoyed our tour.
Read more
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