Cool Destinations
Top Chicago activities
Top Chicago landmarks
Beyond Chicago
Chicago trip ideas
  • Tours by category
  • Tours by accessibility
  • Tours by feature
  • Tours by the numbers
  • Top Chicago landmark tours
  • Tours in nearby places
  • Explore USA tours
  • Chicago travel guides
  • Chicago travel calendar
Language $Currency
Login / Sign up
Bookings
Bookings
Cool Rewards Rewards
$0.00
Cool Rewards Rewards
$0.00
Wishlists
Wishlists
Profile
Help Center
Language
Log out
Start your search
Change your search
Place or activity
Select Dates

Top Chicago Architecture Tours

56 Results
Sort by:
Featured
Filter
Languages Clear
Time of Day Clear
52
47
16
Duration Clear
2
52
5
0
0
Price Clear
$0 $500+
Rating Clear
45
56
56
Specials Clear
52
7
0
11
0
Features Clear
5
30
52
0
56
0
Accessibility Clear
20
39
46
Families Clear
26
38
10

Chicago Tours

Attractions

Guides

Calendar

Chicago Lake and River Architecture Tour
Likely to Sell Out
Likely to Sell Out
4.8 (2,373)

Chicago Lake and River Architecture Tour

An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years...

1 hour 30 minutes • Free Cancellation
4.8 (2,373)
from
$45
Chicago River 45-Minute Architecture Tour from Magnificent Mile
Likely to Sell Out
Likely to Sell Out
4.8 (3,403)

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich...

45 minutes • Free Cancellation
4.8 (3,403)
from
$28
Chicago Architecture River Cruise
4.9 (16,465)

Chicago Architecture River Cruise

Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of...

60 to 90 minutes • Free Cancellation
4.9 (16,465)
from
$39
Chicago Architecture Center River Cruise aboard First Lady
4.9 (7,078)

Chicago Architecture Center River Cruise aboard First Lady

The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only...

1 hour 30 minutes
4.9 (7,078)
from
$57
Chicago Hop-on Hop-off Sightseeing Tour by Open-top Bus
4.1 (2,149)

Chicago Hop-on Hop-off Sightseeing Tour by Open-top Bus

Discover Chicago at your own pace with Big Bus. Travel aboard an open-top, double-decker bus and enjoy panoramic views of the city's most famous landmarks,...

2 hours • Free Cancellation
4.1 (2,149)
from
$49
Chicago City Tour with Architecture River Cruise Option
Likely to Sell Out
Likely to Sell Out
4.8 (715)

Chicago City Tour with Architecture River Cruise Option

Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. On this tour, you will travel through Chicago with...

2 to 4 hours • Free Cancellation
4.8 (715)
from
$50
Chicago River 90-Minute Architecture Boat Tour
4.9 (1,856)

Chicago River 90-Minute Architecture Boat Tour

Marvel at the magnificent architecture on the Chicago River with expert tour guides! All ages welcome. Each architecture river tour is narrated by a professional...

1 hour 30 minutes • Free Cancellation
4.9 (1,856)
from
$37
Chicago Architectural River Cruise
4.7 (826)

Chicago Architectural River Cruise

Take in the views on this award-winning 90-minute Architectural Tour, a jaw-dropping excursion through a city that defies all expectations!...

1 hour 30 minutes • Free Cancellation
4.7 (826)
from
$50
Chicago Architecture and True Crime: Spooky Edition
5.0 (634)

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 (634)
from
$35
Chicago Architecture Tour: Underground Pedway and the Loop
4.9 (557)

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 (557)
from
$35
Historical and Architectural Chicago Fireboat River & Lake Cruise
4.9 (462)

Historical and Architectural Chicago Fireboat River & Lake Cruise

Travel on a piece of history, learning Chicago fire history as well as Architecture! We travel on Lake Michigan and through the Chicago River seeing...

2 hours • Free Cancellation
4.9 (462)
from
$47
Chicago in a Day Walking Tour: Food, History & Architecture
4.9 (1,352)

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 (1,352)
from
$101
Original Chicago Architecture Interiors Tour: Dazzling Interiors
5.0 (1,785)

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 (1,785)
from
$35
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 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 Walking Tour: Must-See Chicago
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 Tour South Side
4.7 (46)

Chicago Tour South Side

The Blue-Collar side of Chicago many call it! This tour will show The Ford Factory, home of the steel mills, the blue-collar neighborhoods and many...

4 hours • Free Cancellation
4.7 (46)
from
$125
Chicago Seadog River & Lake Architectural Tour
4.6 (287)

Chicago Seadog River & Lake Architectural Tour

Soak in unobstructed views of Chicago’s world-famous architecture from the water with an exciting ride on our Seadog River and Lake Architectural Tour! Sail through...

1 hour 15 minutes • Free Cancellation
4.6 (287)
from
$42
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

Frequently Asked Questions

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

Recent tour reviews
Hidden architectural Chicago gems
New York City
Original Chicago Architecture Interiors Tour: Dazzling Interiors
carolrL2166XY, Sep 2026
Hidden architectural Chicago gems
Tour was absolutely fascinating and beautiful. Guide was so knowledgeable and comprehensive on the architecture. Would recommend!!!!
Read more
Totally worth it!
New York City
Chicago Lake and River Architecture Tour
LauraVTR, Sep 2026
Totally worth it!
The tour is totally worth it!! They take you to the river and back. Then after leveling the water between the river and lake they take you into the lake. I would recommend to sit up front.
Read more
Enjoyable and informative
New York City
Chicago Architecture Tour: Underground Pedway and the Loop
joshvM9988HZ, Sep 2026
Enjoyable and informative
Spencer was a wonderful guide, and I was grateful for the knowledge he shared.
Read more
Tour
New York City
Chicago Architecture and True Crime: Spooky Edition
244stefanya, Sep 2026
Tour
Grant was an amazing tour guide and had amazing facts about everything!
Read more
Best activity to do in Chicago
New York City
Chicago Architecture Center River Cruise aboard First Lady
Susan_R, Sep 2026
Best activity to do in Chicago
Anthony was OUTSTANDING! The tour was very informative and fun and we would go on it again with friends and family! Chicago is the cleanest city we have ever been to!
Read more
Amazing and Entertaining Interior Architecture Tour!
New York City
Original Chicago Architecture Interiors Tour: Dazzling Interiors
Beth_L, Sep 2026
Amazing and Entertaining Interior Architecture Tour!
Heath was an amazing tour guide! He shared a wealth of information with us about the architecture of the buildings we visited, and he did it in a very entertaining way. I’m so glad my husband and I booked this tour, and I highly recommend it! It was a great value too!
Read more
Great tour!
New York City
Chicago Architecture Center River Cruise aboard First Lady
355daisyv, Sep 2026
Great tour!
Tamara is amazing and very knowledgeable of the Chicago’s architecture!!!
Read more
Fun Tour
New York City
Chicago River 90-Minute Architecture Boat Tour
D8138FZvirginias, Sep 2026
Fun Tour
Great way to see the city and our guide combined educating us about architecture, architects, and history with some fun anecdotal stories.
Read more
Well worth it!
New York City
Chicago River 90-Minute Architecture Boat Tour
johnnya450, Sep 2026
Well worth it!
our tour guide was amazing! She was very informative and had a great personality!! We actually not thinking of doing a tour since w had walked around looking at all the buildings and felt like we didn’t need to go on this tour. But it is well worth the money and we really enjoyed it!
Read more
The Best Boat Tour inf FOG or Rain
New York City
Chicago Architecture River Cruise
Michelle_A, Sep 2026
The Best Boat Tour inf FOG or Rain
Eric was a great tour guide. He sang and gave us a great Chicago experience. The day waa foggy and had rained all day and still the city was beautiful. Extremely knowledgeable and the jokes were actually really funny. Thanks for a great memorable experience. He also acknowledged someone birthday. Very kind person.
Read more
The cruise was...
New York City
Chicago Architecture River Cruise
Tamara_J, Sep 2026
The cruise was...
The cruise was informative and chock-full of diverse architecture and interesting history. Our guide Richard was knowledgeable, hilarious and attentive! The crew was extremely helpful, helped with my mobility issues (they should find away to add a ramp to the docking area.
Read more
The docent was excellent...
New York City
Chicago Lake and River Architecture Tour
Evalee_D, Sep 2026
The docent was excellent...
The docent was excellent - knowledgeable, funny, and engaging. It was my first time on Lake Michigan, but not my first tour of the River. It was definitely worth the extra time and money!
Read more
Amazing tour
New York City
Chicago in a Day Walking Tour: Food, History & Architecture
Midnightfjord, Sep 2026
Amazing tour
Excellent tour. Chad was very informative. Would highly recommend!
Read more
Worth your time and money...
New York City
Chicago River 45-Minute Architecture Tour from Magnificent Mile
Alexa_D, Sep 2026
Worth your time and money...
Worth your time and money for an amazing experience! Our guide was informative and funny. Great photos taken.
Read more
So much fun/informative! Views were amazing
New York City
Chicago Seadog River & Lake Architectural Tour
LuAna_M, Sep 2026
So much fun/informative! Views were amazing
Did this tour with my mom and tía while they were visiting and we had so much fun! I’ve done a handful of architecture toursbut this was by far my favorite. The smaller boat made it feel more intimate and Darren was such a great guide. You can really tell how passionate he is about Chicago’s history!The best part was the end when the boat picked up speed, the music was amazing, and we got to take in the Chicago skyline. Such a fun experience! ☺️
Read more
Good way to get some...
New York City
Chicago Hop-on Hop-off Sightseeing Tour by Open-top Bus
Wanda_W, Sep 2026
Good way to get some...
Good way to get some history as you view the city. Travelers should know all the busi stops and time schedules.
Read more
Chicago Tours
Attractions
Guides
Calendar
View more
View more