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Top Illinois Tours & Sightseeing

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Illinois Tours

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Chicago River 90-Minute Architecture Tour

Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
4.8 (10,758)

Chicago River 90-Minute Architecture Tour

Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to...

1 hour 30 minutes • Free Cancellation
4.8 (10,758)
from
$45
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 …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
4.8 (2,378)

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 (2,378)
from
$45
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 …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
4.8 (3,419)

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 (3,419)
from
$28
Chicago Crime and Mob Bus Tour

Escape into Chicago's underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus. Explore historic crime scenes with great photo opportunities. …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
4.6 (3,485)

Chicago Crime and Mob Bus Tour

Escape into Chicago's underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus. Explore historic crime scenes with great photo opportunities....

90 to 120 minutes • Free Cancellation
4.6 (3,485)
from
$49
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 …More

Chicago, USA
4.9 (16,486)

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 (16,486)
from
$39
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 …More

Chicago, USA
4.9 (7,136)

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 (7,136)
from
$57
Lake Michigan Sunset Cruise in Chicago

The Lake Michigan Sunset Cruise departs near the DuSable (Michigan Avenue) Bridge on Wendella's world class tour boats. The Cruise will navigate from the Chicago …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
4.7 (1,576)

Lake Michigan Sunset Cruise in Chicago

The Lake Michigan Sunset Cruise departs near the DuSable (Michigan Avenue) Bridge on Wendella's world class tour boats. The Cruise will navigate from the Chicago...

1 hour 30 minutes • Free Cancellation
4.7 (1,576)
from
$45
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, …More

Chicago, USA
4.1 (2,151)

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 (2,151)
from
$49
Lake Michigan Skyline Cruise in Chicago

Embark on an unforgettable journey along Lake Michigan and marvel at Chicago's iconic lakefront sights and attractions. Cruise along Lake Michigan and enjoy stunning views …More

Chicago, USA
4.6 (892)

Lake Michigan Skyline Cruise in Chicago

Embark on an unforgettable journey along Lake Michigan and marvel at Chicago's iconic lakefront sights and attractions. Cruise along Lake Michigan and enjoy stunning views...

30 to 45 minutes • Free Cancellation
4.6 (892)
from
$34
Chicago Sightseeing River and Lake Cruise

Our popular 90-minute daytime river and lake sightseeing tour delights family members of all ages with incredible views of Chicago's world-renowned buildings and stunning skyline. …More

Chicago, USA
4.8 (691)

Chicago Sightseeing River and Lake Cruise

Our popular 90-minute daytime river and lake sightseeing tour delights family members of all ages with incredible views of Chicago's world-renowned buildings and stunning skyline....

1 hour 30 minutes • Free Cancellation
4.8 (691)
from
$46
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 …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
4.8 (716)

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 (716)
from
$50
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
Chicago, USA
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
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 …More

Chicago, USA
4.9 (1,863)

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 (1,863)
from
$37
Chicago City Minibus Tour

Uncover the best of Chicago on an unforgettable highlights tour designed for travelers, sightseers, and history lovers alike! Step off the bus to admire Frank …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
4.9 (648)

Chicago City Minibus Tour

Uncover the best of Chicago on an unforgettable highlights tour designed for travelers, sightseers, and history lovers alike! Step off the bus to admire Frank...

2 hours • Free Cancellation
4.9 (648)
from
$50
Chicago Night Crimes Tour by Bus

Join us for a fun night of exploring Chicago's crime history on this 2-2.5-hour bus tour that includes: * World famous crime scenes like the …More

Chicago, USA
4.8 (510)

Chicago Night Crimes Tour by Bus

Join us for a fun night of exploring Chicago's crime history on this 2-2.5-hour bus tour that includes: * World famous crime scenes like the...

120 to 150 minutes • Free Cancellation
4.8 (510)
from
$55
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

Chicago, USA
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's Original Gangster Tour by Bus

Our guides present an accurate account of the activities in Chicago during the 1920's and 1930's (Prohibition Era). You will hear about the exploits of …More

Chicago, USA
4.7 (173)

Chicago's Original Gangster Tour by Bus

Our guides present an accurate account of the activities in Chicago during the 1920's and 1930's (Prohibition Era). You will hear about the exploits of...

1 hour 45 minutes • Free Cancellation
4.7 (173)
from
$48
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

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

Taste all of Chicago’s classic eats on this 4 1/2 hr Adults-only guided food & bicycle tour! Join the expert guides of Bobby’s Bike Hike, …More

Chicago, USA
5.0 (756)

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

Taste all of Chicago’s classic eats on this 4 1/2 hr Adults-only guided food & bicycle tour! Join the expert guides of Bobby’s Bike Hike,...

4 hours 30 minutes • Free Cancellation
5.0 (756)
from
$89
African American Heritage Tour of Chicago

This tour visits the homes of Louis Farrakhan, the former home of Elijah Muhammad and the former home of Muhammad Ali. We will pass by …More

Chicago, USA
4.6 (141)

African American Heritage Tour of Chicago

This tour visits the homes of Louis Farrakhan, the former home of Elijah Muhammad and the former home of Muhammad Ali. We will pass by...

4 to 7 hours • Free Cancellation
4.6 (141)
from
$125

Frequently Asked Questions

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

Recent tour reviews
Chicago Architectual tour
New York City
Chicago River 90-Minute Architecture Tour
Jackie_B, Sep 2026
Chicago Architectual tour
Beautiful ways to learn about Chicago history and architecture of many amazing buildings in the downtown area!
Read more
Awesome trip with family and friends!
New York City
Chicago Architecture River Cruise
Trail635413, Sep 2026
Awesome trip with family and friends!
Amazing tour with family from the UK. Sam S was the best! Great energy and knowledge of the city and it’s architecture.
Read more
Fabulous Chicago Experience
New York City
Chicago Architecture Center River Cruise aboard First Lady
SandyParrothead, Sep 2026
Fabulous Chicago Experience
Excellent experience on The First Lady. The docent was fascinating and kept everyone’s attention with his knowledge of Chicago and its architecture. I highly recommend this tour.
Read more
Loved it
New York City
Chicago Architecture Center River Cruise aboard First Lady
Culture369260, Sep 2026
Loved it
The docent was great, very interesting and informative.
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
Architecture Boat Tour so worth the voyage
New York City
Chicago Architecture River Cruise
hmbernaldo, Sep 2026
Architecture Boat Tour so worth the voyage
Took the Architecture Boat Tour and thoroughly enjoyed it. Nathan was informative and humorous! I had no idea the history of Chicago and its beautiful buildings.
Read more
Exelent
New York City
Chicago Lake and River Architecture Tour
330elliottg, Sep 2026
Exelent
Amazing loved it the tour goes was very good and frendly
Read more
This Crime/Mob tour is great!
New York City
Chicago Crime and Mob Bus Tour
N7490JLjennyd, Sep 2026
This Crime/Mob tour is great!
This tour was so much fun! Great for crime junkies!
Read more
Must do
New York City
Chicago River 45-Minute Architecture Tour from Magnificent Mile
Bobbi_M, Sep 2026
Must do
Do the twilight trip! It was amazing. Get there early for a seat on the top deck. We were in the back on the benches and it was *chefs kiss*
Read more
Excellent River Cruise
New York City
Chicago River 45-Minute Architecture Tour from Magnificent Mile
David_L, Sep 2026
Excellent River Cruise
I found it informative and our tour guide; Kenny, did an amazing job of explaining the history of the architecture and making it fun while interacting with customers.
Read more
River boat fun
New York City
Chicago River 90-Minute Architecture Tour
Margaret_D, Sep 2026
River boat fun
You learn a lot about the city of Chicago. Great ride with Alex doing the commentary. He was very knowledgable
Read more
Fun & informative!
New York City
Chicago Lake and River Architecture Tour
JennaKJ, Sep 2026
Fun & informative!
Our guide Sarah was great. Very knowledgeable about Chicago and its rich history. We really enjoyed our time and highly recommend this tour.
Read more
Great evening
New York City
Chicago Night Crimes Tour by Bus
renatehH2941WT, Sep 2026
Great evening
Maddie, our tour guide, did a great job - she was very knowledgeable and brought history to life in an informative and entertaining way, so we enjoyed every minute. Thank you so much!
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
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