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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

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 …More

Likely to Sell Out
Likely to Sell Out
4.9 (2,304)

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 (2,304)
from
$85
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 …More

5.0 (1,793)

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 (1,793)
from
$35
Chicago Architecture and True Crime: Halloween 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 …More

5.0 (642)

Chicago Architecture and True Crime: Halloween 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 (642)
from
$35
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 …More

4.9 (558)

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 (558)
from
$35
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, …More

5.0 (1,522)

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 (1,522)
from
$70
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, …More

4.9 (69)

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 (69)
from
$35
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 …More

4.9 (1,363)

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 (1,363)
from
$101
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 …More

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 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 …More

Likely to Sell Out
Likely to Sell Out
4.9 (1,011)

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 (1,011)
from
$85
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. …More

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
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 …More

4.9 (330)

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 (330)
from
$36
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 …More

5.0 (764)

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 (764)
from
$35
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 …More

4.9 (207)

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 (207)
from
$40
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 …More

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

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 …More

4.9 (128)

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 (128)
from
$81
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 …More

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

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 …More

5.0 (165)

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 (165)
from
$35
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 …More

Likely to Sell Out
Likely to Sell Out
4.9 (802)

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 (802)
from
$80
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 …More

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
Haunted Chicago: Lincoln Park Ghost Escape Game

A dating app. A stranger with arctic blue eyes. A meeting in Lincoln Park on Halloween. This self-guided ghost escape game drops you into Chicago's …More

4.0 (6)

Haunted Chicago: Lincoln Park Ghost Escape Game

A dating app. A stranger with arctic blue eyes. A meeting in Lincoln Park on Halloween. This self-guided ghost escape game drops you into Chicago's...

2 hours • Free Cancellation
4.0 (6)
from
$7

Frequently Asked Questions

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

Recent tour reviews
Great experience
New York City
Chicago Architecture and True Crime: Halloween Edition
jamesfR9739KC, Sep 2026
Great experience
A lot of great locations to take pictures filled with interesting history and the guide Joseph was knowledgable and fun. Definitely recommend this tour
Read more
Great tour!
New York City
Chicago Architecture Tour: Underground Pedway and the Loop
James_F, Sep 2026
Great tour!
My daughter and I took the Chicago Architecture Tour: Underground Pedway & Secrets of the Loop this Tuesday while we were downtown for the day. We’re from the suburbs but had never heard about the pedway, so we figured it might be interesting.Our tour guide, Heath, was an outstanding! He was able to weave Chicago history, people, architecture, and artwork into a captivating tour about the pedway. Without him, we would have gotten lost in the pedway and had no idea about why it is so special and unique. We have walked away with a new understanding of what makes Chicago “Chicago”, and received some cool dining, drink, and shopping recommendations along the way.We highly recommend this tour if you have the time.
Read more
Interesting Tour
New York City
Original Chicago Architecture Interiors Tour: Dazzling Interiors
William_T, Sep 2026
Interesting Tour
Interesting tour with lively guide, good review of history & architecture. Plus a nice walk through the city.
Read more
Wonderful way to learn about Chicago!
New York City
Chicago Favorites Ultimate Food and Walking Tour
danielbX4333MU, Sep 2026
Wonderful way to learn about Chicago!
Cassie was awesome! The food was only so-so, but that wasn’t the tour’s fault - New York Pizza is simply the best (and Colorado Rocky Mountain pizza is second). The Chicago dawg was very good, but the Palmer House brownie was my favorite. But the highlight of the tour was Cassie’s leadership and commentary. You can tell she really loves Chicago! And the city itself is a gem, of course. Whether you end up liking the food or not, a food tour is the best way to learn about a city.
Read more
Great Chicago Architecture Tour
New York City
Chicago in a Day Walking Tour: Food, History & Architecture
I3658GI_, Sep 2026
Great Chicago Architecture Tour
We had a great time on the Chicago architecture tour. Our guide Chad was very patient, knowledgeable, and took the time to explain the history and details behind the buildings. He was also happy to answer questions, which made the experience feel relaxed and informative. The food was really good as well and was a nice addition to the tour. Overall, it was a fun and enjoyable experience, and I would definitely recommend it.
Read more
Really great tour
New York City
Chicago in a Day Walking Tour: Food, History & Architecture
H8691CBryank, Sep 2026
Really great tour
I took a few coworkers on a tour today with Chad and it was an excellent experience. I’ve visited Chicago many times before but didn’t know some of the history until today. Visiting the Chicago Cultural Center and having a Chicago dog were the highlights of the tour. Would highly recommend.
Read more
Worth your time
New York City
Original Chicago Architecture Interiors Tour: Dazzling Interiors
FranchescaG24, Sep 2026
Worth your time
Excellent tour! It was great becoming familiar with Chicago’s history and architecture.
Read more
DONUTS!!!!!!
New York City
Chicago’s Delicious Downtown Donut Tour with 8 Amazing Tastings
GlobeTrotting71372, Sep 2026
DONUTS!!!!!!
Lauren was amazing! She had some wonderful stories to tell about all the donut places and about Chicago itself! It was all so interesting and exciting! She was so friendly and and so bubbly and had a wonderful personality! We enjoyed ourselves extremely!!!
Read more
Tasty food with an excellent tour guide!!
New York City
Chicago’s Chinatown Food and Walking Tour
Sara_M, Sep 2026
Tasty food with an excellent tour guide!!
The Chinatown food tour was the highlight of our trip! Hands down! York was a delight! His combination of city history and personal experiences was exactly what a tour like this needs. It could have been very bland. But York gave it heart. Also DELICIOUS!! Fantastic selection of area restaurants. I learned so much over that 3 hours. And had a full belly! Do yourself a favor and ask for York!!
Read more
A thrilling mix of stunning architecture and dark history!
New York City
Chicago Architecture and True Crime: Halloween Edition
jacobmE8054UH, Sep 2026
A thrilling mix of stunning architecture and dark history!
This was such a unique and engaging tour! Combining Chicago's iconic architecture with real true crime stories and spooky history made for an unforgettable evening. Our guide was fantastic super knowledgeable, dramatic in the best way possible, and kept everyone hooked from start to finish. If you love true crime or want a fresh perspective on the city, don't miss this one!
Read more
Good Chicago history and delicious foood!
New York City
Chicago Favorites Ultimate Food and Walking Tour
Rodrigo_A, Sep 2026
Good Chicago history and delicious foood!
If you are interested in knowing some of the history of Chicago and enjoying some of Chicago’s best and classic food this is the tour to take. Plus our tour guys made the experience 10 times more worth it.
Read more
The best walking tour
New York City
Chicago Loop Food Tour: Taste the Most Iconic Local Eats
W4533GT, Sep 2026
The best walking tour
Brilliant tour Chad was great Lots of stops and food amazing
Read more
So much food and so...
New York City
Chicago’s Chinatown Food and Walking Tour
Hutch_Y, Sep 2026
So much food and so...
So much food and so little walking. We enjoyed this one immensely. Valerie was a wonderful tour guide.
Read more
Lauren was awesome!
New York City
Chicago’s Delicious Downtown Donut Tour with 8 Amazing Tastings
Meander23146309253, Sep 2026
Lauren was awesome!
Lauren was an awesome, super friendly and energetic tour guide. She has awesome Chicago architecture stories and there was never a dull moment. Lauren kept a great attitude even when it started to rain! Would recommend this tour to all, be prepared for a sugar rush tho!
Read more
Great storytelling
New York City
Haunted Chicago Booze and Boos Ghost Walking Tour
belindasH5380SX, Sep 2026
Great storytelling
Mallory was an incredible guide!!! Super fun and a great story teller 👻
Read more
Excellent Chicago food tour
New York City
Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich
Trail789249, Sep 2026
Excellent Chicago food tour
We went on a 3 hour food your which, not only allowed us to taste the foods Chicago is known for, but Sue Gould our tour guide, also showed an interesting architecture and provided a bit of Chicago history. The amount of food was right on and the pacing was excellent as well. The delivery of the tiur matched its description. Seeing the Rookery Building and hearing of its history gave us a deeper appreciation of the city.
Read more
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