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Top Chicago Day Cruises

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Chicago 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
4.8 (10,806)

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 (10,806)
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
4.8 (2,383)

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 (2,383)
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
4.8 (3,452)

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 (3,452)
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

4.9 (16,509)

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 (16,509)
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

4.9 (7,217)

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 (7,217)
from
$57
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

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
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 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

4.9 (1,874)

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 (1,874)
from
$33
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

4.8 (700)

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 (700)
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

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

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
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

Likely to Sell Out
Likely to Sell Out
4.9 (469)

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 (469)
from
$47
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

4.6 (83)

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 (83)
from
$85
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

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
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

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
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 …More

4.6 (290)

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 (290)
from
$42
City Cruises Chicago: River Architectural Lunch Cruise

Fine dining and unrivaled skyline views await from the moment you step aboard our Premier Plus Chicago Lunch Cruise. A selection of delectable plated lunch …More

4.7 (40)

City Cruises Chicago: River Architectural Lunch Cruise

Fine dining and unrivaled skyline views await from the moment you step aboard our Premier Plus Chicago Lunch Cruise. A selection of delectable plated lunch...

2 hours • Free Cancellation
4.7 (40)
from
$85
Small-Group Sightseeing Boat Tour in Chicago

The ultimate custom sightseeing experience in Chicago! Enjoy the City from great vantage points and photograph the world-famous skyline. We zip you to many sights …More

5.0 (121)

Small-Group Sightseeing Boat Tour in Chicago

The ultimate custom sightseeing experience in Chicago! Enjoy the City from great vantage points and photograph the world-famous skyline. We zip you to many sights...

2 hours • Free Cancellation
5.0 (121)
from
$89
Private Chicago City Minibus Tour

Don’t miss Chicago’s famous sights and fabulous views on this award-winning private sightseeing tour of the city. Travel through Chicago with an expert guide on …More

Likely to Sell Out
Likely to Sell Out
5.0 (1)

Private Chicago City Minibus Tour

Don’t miss Chicago’s famous sights and fabulous views on this award-winning private sightseeing tour of the city. Travel through Chicago with an expert guide on...

2 hours • Hotel pickup offered • Free Cancellation
5.0 (1)
from
$999
City Cruises Chicago: Premier Lake Michigan Brunch Cruise

Enjoy a picturesque day dining on Lake Michigan with our Premier Chicago Brunch Cruise. You’ll indulge in a chef-prepared buffet meal featuring savory and sweet …More

4.3 (28)

City Cruises Chicago: Premier Lake Michigan Brunch Cruise

Enjoy a picturesque day dining on Lake Michigan with our Premier Chicago Brunch Cruise. You’ll indulge in a chef-prepared buffet meal featuring savory and sweet...

2 hours • Free Cancellation
4.3 (28)
from
$105

Frequently Asked Questions

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

Recent tour reviews
Great Tour Guide
New York City
Chicago River 90-Minute Architecture Boat Tour
Adam_Y, Sep 2026
Great Tour Guide
The tour guide, Adam was personable, knowledgeable, funny, patient and engaging. I highly recommend this tour!
Read more
River Architecture Tour
New York City
Chicago Architecture River Cruise
rbarnes4, Sep 2026
River Architecture Tour
We took this tour on a recommendation and it did not disappoint! Sam đid a great job teaching us about the architecture of the buildings along the Chicago river! We would recommend this tour!
Read more
This was an awesome tour!...
New York City
Chicago River 90-Minute Architecture Tour
Jenae_D, Sep 2026
This was an awesome tour!...
This was an awesome tour! They were on time, kind and had in board drinks and bathroom. Would def recommend!
Read more
Touring Chicago
New York City
Chicago River 90-Minute Architecture Tour
Howell_B, Sep 2026
Touring Chicago
This tour was excellent. The guide was knowledgeable. The experience was great. This was the easiest and quickest way to see the city.
Read more
Fantastic tour
New York City
Chicago Architecture Center River Cruise aboard First Lady
716dianed, Sep 2026
Fantastic tour
Wow! What a fabulous thing to do in beautiful Chicago. We loved every minute of it. Our tour guide was docent Mark and boy was he ever fantastic. He was sharp, knowledgeable, kind, passionate, professional, and witty. It was the highlight of our 3 day visit and we will be back.
Read more
Architecture in Chicago is worthy.
New York City
Chicago River 90-Minute Architecture Boat Tour
Joanne_J, Sep 2026
Architecture in Chicago is worthy.
The Architecture tours on the Chicago River are wonderful. Hillary our guide was knowledgeable and funny and good at her job.
Read more
Enjoy a relaxing ride to watch the night skyline unfold.
New York City
Chicago Sightseeing River and Lake Cruise
Leslie_O, Sep 2026
Enjoy a relaxing ride to watch the night skyline unfold.
Just a very nice and informative tour and boat ride out on the lake and back. Trip length was very good. Everything advertised about the tour was fulfilled. Tour guide was well informed and courteous. Staff on board were also very attentive.
Read more
Exceeded my expectations!!
New York City
Chicago Architecture Center River Cruise aboard First Lady
paulquinng, Sep 2026
Exceeded my expectations!!
Having grown up in the Chicago area over 50yrs ago, I finally decided to take this well known architectural river cruise with First Lady. It did not disappoint, and surpassed any expectations I may have had.Our docent (guide), Bob P was a wealth of knowledge, and I was truly amazed as to how he remembered so many dates, architectural firms, addresses, and history about each building!! AND he’s a volunteer!!I highly recommend this tour for anyone, and we had a beautiful fall day with perfect sunny weather to enjoy it!
Read more
Chicago Architectural Tour (so original)
New York City
Chicago Architecture River Cruise
Elizabeth_J, Sep 2026
Chicago Architectural Tour (so original)
Boat trip was great, totally lucked out with the weather, crew was wonderful. Tour guide was a bit much.
Read more
Nice short cruise with great views
New York City
Lake Michigan Skyline Cruise in Chicago
William_M, Sep 2026
Nice short cruise with great views
Very nice cruise. Not too long. Beautiful views and friendly staff. Dress warm as it gets chilly out there.
Read more
Beautiful night in downtown Chicago
New York City
Chicago River 45-Minute Architecture Tour from Magnificent Mile
Robert_C, Sep 2026
Beautiful night in downtown Chicago
My girlfriend and I spent a day in Chicago on her birthday! One of the excursions that I booked for us was this cruise. It was totally awesome!
Read more
Don’t miss it
New York City
Chicago River 45-Minute Architecture Tour from Magnificent Mile
749allanl, Sep 2026
Don’t miss it
Don’t miss it, exceptional tour with a very knowledgable and engaging tour guide. Great experience and a must do.
Read more
RIDE THIS TOUR!!!
New York City
Historical and Architectural Chicago Fireboat River & Lake Cruise
Curiosity62712847810, Sep 2026
RIDE THIS TOUR!!!
Wow!! Cliff was INCREDIBLE. Don’t book with a bigger vessel. This one is special. Worth the money
Read more
A great way to see downtown Chicago from the river and the skyline from Lake Michigan
New York City
Chicago Sightseeing River and Lake Cruise
Michele_B, Sep 2026
A great way to see downtown Chicago from the river and the skyline from Lake Michigan
Informative guide and a great small trip with plenty to see. Good facilities on board and good weather was a bonus!
Read more
A good 2 hours spent!
New York City
Historical and Architectural Chicago Fireboat River & Lake Cruise
518brandyj, Sep 2026
A good 2 hours spent!
Very good choice to see both Lake Michigan and the river. The guide is fantastic.If I have anything to recommend improvement, I'd say that the returning half is a bit boring, comparing to the first part when everything is so new. Also it does not match very far to the river, I was expecting to see more of the river.A good 2 hours spent!
Read more
Joyful Cruise
New York City
City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River
515taraa, Sep 2026
Joyful Cruise
This experience was magnificent! Next time Im doing the dinner cruise.
Read more
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