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Top Illinois Boat Tours

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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 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
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 CityPASS — Save 40%

Experience 5 top attractions and save up to 50% with Chicago CityPASS® tickets. One simple purchase removes the stress of planning, so you can relax …More

Special Offer
Special Offer
Chicago, USA
4.6 (475)

Chicago CityPASS — Save 40%

Experience 5 top attractions and save up to 50% with Chicago CityPASS® tickets. One simple purchase removes the stress of planning, so you can relax...

9 days
4.6 (475)
$144
$143
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 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! …More

Chicago, USA
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 River Ghost & Dark History Night Cruise

See Chicago from a different perspective on this evening cruise that explores the city’s darker side. As twilight settles over the skyline, glide along the …More

Chicago, USA
4.3 (213)

Chicago River Ghost & Dark History Night Cruise

See Chicago from a different perspective on this evening cruise that explores the city’s darker side. As twilight settles over the skyline, glide along the...

1 hour 30 minutes • Free Cancellation
4.3 (213)
from
$46
Lake Michigan 30 Minute Speedboat Ride

Enjoy Chicago’s iconic skyline with an exciting speedboat Tour on Lake Michigan. Departing from Navy Pier, the Lakefront Speedboat Tour is the best way to …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
4.5 (317)

Lake Michigan 30 Minute Speedboat Ride

Enjoy Chicago’s iconic skyline with an exciting speedboat Tour on Lake Michigan. Departing from Navy Pier, the Lakefront Speedboat Tour is the best way to...

30 minutes • Free Cancellation
4.5 (317)
from
$39
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 …More

Chicago, USA
4.9 (463)

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 (463)
from
$47
Chicago By Night River and Lake Cruise

Glide along the Chicago River and Lakefront as you're dazzled by the sparkle of the city at night! Enjoy breathtaking views of the dramatic skyscrapers …More

Chicago, USA
4.6 (415)

Chicago By Night River and Lake Cruise

Glide along the Chicago River and Lakefront as you're dazzled by the sparkle of the city at night! Enjoy breathtaking views of the dramatic skyscrapers...

1 hour 30 minutes • Free Cancellation
4.6 (415)
from
$50
City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

Sail along the magnificent skyline on our Premier Plus Chicago Brunch Cruise. A chef-curated menu of plated brunch specials will delight your palate while unparalleled …More

Chicago, USA
4.6 (82)

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

Sail along the magnificent skyline on our Premier Plus Chicago Brunch Cruise. A chef-curated menu of plated brunch specials will delight your palate while unparalleled...

2 hours • Free Cancellation
4.6 (82)
from
$85
Chicago River Tiki Bar Party Cruise from Chicago River Wednesdays

See Chicago the Island Party Way. Our floating Tiki Bar offers you the opportunity to take in all the sights and sounds as you relax …More

Chicago, USA
4.4 (111)

Chicago River Tiki Bar Party Cruise from Chicago River Wednesdays

See Chicago the Island Party Way. Our floating Tiki Bar offers you the opportunity to take in all the sights and sounds as you relax...

1 hour 15 minutes
4.4 (111)
from
$42
Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
5.0 (71)

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed...

2 hours • Free Cancellation
5.0 (71)
from
$508
Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
4.8 (30)

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy,...

1 hour 15 minutes
4.8 (30)
from
$91
City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

Join us for an unforgettable afternoon on Lake Michigan with a Signature Chicago Lunch Cruise. Whether it’s a family outing or a meal with friends, …More

Chicago, USA
4.2 (339)

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

Join us for an unforgettable afternoon on Lake Michigan with a Signature Chicago Lunch Cruise. Whether it’s a family outing or a meal with friends,...

2 hours • Free Cancellation
4.2 (339)
from
$63

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
It was incredible
New York City
Chicago By Night River and Lake Cruise
Samuel_R, Sep 2026
It was incredible
I loved it. I have done this tour before but during the day i thought the one by daytime was the best because you could appreciate the architecture a lot but the night tour is another level is beautiful. that night was rainy, foggy and cold and still worth every penny. Tour guide explaining every detail very informative, loved it.
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
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
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
Nice trip
New York City
Lake Michigan Sunset Cruise in Chicago
Vanessa_S, Sep 2026
Nice trip
Nice trip. Started with a few architectural and city facts, and once we were out on Lake Michigan, music played as my husband and I had a couple drinks and took some pictures. We left at 6pm and returned about 7:30pm. Plenty of time to get a late dinner.
Read more
Great time on Lake Michigan
New York City
Lake Michigan Sunset Cruise in Chicago
D1623BHpatrickc, Sep 2026
Great time on Lake Michigan
A very enjoyable and informative tour. We were lucky enough to have great weather so the views of the chicago skyline was spectacular. We would highly recommend this cruise.
Read more
Great activity for everyone
New York City
Chicago Sightseeing River and Lake Cruise
Kimberly_C, Sep 2026
Great activity for everyone
We had wonderful time on this river and lake cruise. Our guide was great and had plenty of bad puns to go around! Always recommend this activity to anyone visiting Chicago. We do it everytime we visit.
Read more
Best way to see Chicago's highlights!
New York City
Chicago City Tour with Architecture River Cruise Option
jacobmE8054UH, Sep 2026
Best way to see Chicago's highlights!
We booked the city tour with the architecture river cruise option and it was well worth it! The minivan tour covered so much ground that we wouldn't have been able to see on foot, and our guide was extremely knowledgeable and entertaining. The river cruise afterward was the absolute highlight—stunning views of the architecture and a very engaging guide on board. Highly recommended for anyone visiting Chicago for the first time!
Read more
Chicago River Ghost & Dark History Night Cruise
New York City
Chicago River Ghost & Dark History Night Cruise
Brad_C, Sep 2026
Chicago River Ghost & Dark History Night Cruise
The Chicago River Ghost & Dark History Night Cruise was the right pace & timing. Doug the presenter was funny and entertaining - he made the stories clear & to the point. It was more weird & fun rather than fear/horror stories. I think the tone of the stories was good - not too much horror/terror. The staff on the boat watched the attendees - one person spilled their drink all over the floor - the staff immediately cleaned up the spill so there would not be any slip/fall accidents. Giving time for short breaks to use the restroom or get drinks was good - you had time to do things and not disrupt the presentation.
Read more
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