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Top experiences in Chicago

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Chicago River cruise boat passing under DuSable Bridge with city buildings in the background.
Sightseeing Cruises
90-min Chicago River Architecture Cruise
$45
90-min Chicago River Architecture Cruise. Rated 4.9 out of 5 from 293 ratings.From $45
Free cancellation
Chicago River cruise boat passing under a bridge with city skyline.
Sightseeing Cruises
45-min Chicago River Architecture Cruise
from
$28
45-min Chicago River Architecture Cruise. Rated 4.8 out of 5 from 461 ratings.From $28
Free cancellation
Cruise boat on Lake Michigan with Chicago skyline at sunset.
Sightseeing Cruises
90-min Scenic Sunset Lake Michigan Cruise
$45
90-min Scenic Sunset Lake Michigan Cruise. Rated 4.9 out of 5 from 17 ratings.From $45
Free cancellation
Chicago River architecture cruise boat passing under a lift bridge with city skyscrapers in the background.
Sightseeing Cruises
90-min Chicago River and Lake Michigan Architecture Cruise
$45
90-min Chicago River and Lake Michigan Architecture Cruise. Rated 4.7 out of 5 from 56 ratings.From $45
Free cancellation
Tour boat on Chicago River with city skyline and bridge in background.
Sightseeing Cruises
60-Minute Chicago River Architecture Cruise
from
$44.43
60-Minute Chicago River Architecture Cruise. Rated 4.4 out of 5 from 98 ratings.From $44.43
Free cancellation
Tourists on Sea Dog Cruise on Lake Michigan with Chicago skyline in background.
Dinner Cruises
Sea Dog Cruise on Lake Michigan
from
$42.79
Sea Dog Cruise on Lake Michigan. Rated 0 out of 5 from 0 ratings.From $42.79
Free cancellation
Odyssey Chicago River boat cruising on the Chicago River with city skyline.
Sightseeing Cruises
Odyssey Chicago River Architecture Dinner Cruise
from
$135.31
Odyssey Chicago River Architecture Dinner Cruise. Rated 5 out of 5 from 2 ratings.From $135.31
Free cancellation
Guests dining on Odyssey Lake Michigan Dinner Cruise at sunset.
Dinner Cruises
Odyssey Lake Michigan Dinner Cruise
from
$135.31
Odyssey Lake Michigan Dinner Cruise. Rated 0 out of 5 from 0 ratings.From $135.31
Free cancellation
Guests enjoying drinks on a Lake Michigan dinner cruise with Chicago skyline in the background.
Dinner Cruises
Lake Michigan Dinner Cruise
from
$121.65
Lake Michigan Dinner Cruise. Rated 0 out of 5 from 0 ratings.From $121.65
Selling out fast
View from Willis Tower Skydeck in Chicago at sunset.
Willis Tower Skydeck Tickets
Chicago Night Tour with Skydeck & Architecture Cruise
$169
Chicago Night Tour with Skydeck & Architecture Cruise. Rated 0 out of 5 from 0 ratings.From $169
Selling out fast
Guest viewing Chicago skyline from lakefront during Skydeck and Architecture Cruise tour.
Willis Tower Skydeck Tickets
Chicago Skydeck & Architecture Cruise with Small Group Guided Tour
$129
Chicago Skydeck & Architecture Cruise with Small Group Guided Tour. Rated 5 out of 5 from 1 ratings.From $129
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Millions love heading out with us

Sweta Joshi
US

Sweta

United States
Jan 2026

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My mom is visiting Chicago for first time and taking her to the cruise and showing her the city was one of thing on my bucket list.

45-min Chicago River Architecture Cruise

Yera Suleiman
US

Yera

United States
Dec 2025

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I enjoyed this so much that I did it twice during my trip, once at night and one during the day! The architecture around is so beautiful and the tour guides did an amazing job sharing its history.

45-min Chicago River Architecture Cruise

Chetna Dhembla
US

Chetna

United States
Dec 2025

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+1 more

I absolutely loved this tour! The JBL speakers were fantastic and made it so easy to hear the guide clearly, even in a busy and noisy environment. The tour guide was incredibly knowledgeable and shared information in such a fun, engaging, and effortless way that it really stayed with me. I still remember interesting facts like the Chicago River being 22 feet wide and how it turns green on St. Patrick’s Day. The clear sound from the JBL speakers and the amazing guide together made this tour truly memorable and enjoyable.

90-min Chicago River Architecture Cruise

Megan Mitchell
US

Megan

United States
Oct 2025

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I had the best time with my grandfather on the cruise. He is older and struggles with mobility. This was the best way for him to see the city. Very relaxing. Our tour guide was extremely informative. #1 tourist attraction in Chicago

90-min Chicago River Architecture Cruise

Bebs Catherine Mediana
US

Bebs

United States
Sep 2025

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The tour gave us an amazing experience and a picturesque view of the Chicago architecture which is really awesome. Natalie the tour guide was the best! 😊

60-Minute Chicago River Architecture Cruise

Barbara Stender

Barbara

Aug 2025

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+1 more

I thought the tour was perfectly guided, educational and beautiful! The seats were nice, the tour guide was very witty and hilarious! I learned so much on our guide today.

60-Minute Chicago River Architecture Cruise

Janet Stache

Janet

Aug 2025

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We are very happy that we did this cruise! I would say the best cruise I've ever made. Our guide Charlie was a major part in this though. Without him that would only have been half as good.

Chicago Architecture Evening Cruise

Ricardo R. Palo
PH

Ricardo

Philippines
Oct 2025
The architectural tour offered a truly enlightening perspective on Chicago, its majestic skyline, historical evolution, and the vibrant energy that seems to pulse through every street and waterway. Beyond admiring the city’s striking skyscrapers and timeless facades, I was fascinated by the narrative interwoven through each structure. The Chicago River, once the city’s industrial lifeline, tells a remarkable story of transformation. From enabling trade and transport to inspiring architectural innovation, it stands as a symbol of resilience and renewal. Our guide, Cynthia, made the experience even more memorable. Her passion for Chicago was contagious, as she skillfully blended historical insights with personal anecdotes about the city’s iconic landmarks. Her storytelling brought depth and warmth to the experience, making it feel less like a tour and more like a journey through time. For a first-time visitor, this tour is a perfect introduction to Chicago’s soul—its beauty, creativity, and strength reflected not only in glass and steel but also in the stories behind them.

First Lady's Chicago Architecture Boat Tour

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