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Top experiences in Chicago

7 experiences

Free cancellation
Chicago River cruise boat passing under a bridge with city skyline.
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
Chicago River cruise boat passing under DuSable Bridge with city buildings in the background.
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
Guests dining on Odyssey Lake Michigan Dinner Cruise at sunset.
Cruises
Odyssey Lake Michigan Dinner Cruise
from
$139.41
Odyssey Lake Michigan Dinner Cruise. Rated 0 out of 5 from 0 ratings.From $139.41
Free cancellation
Tour boat on Chicago River with city skyline and bridge in background.
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
Cruise boat on Lake Michigan with Chicago skyline at sunset.
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.
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
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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+2 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

Suryanarayana Murthy Majji

Suryanarayana

Oct 2025
I absolutely loved my experience on the Wendella Chicago River Architecture Cruise! The tour was both relaxing and educational, offering an incredible perspective of Chicago’s iconic skyline and its rich architectural history. Cruising through the river gave me a completely different appreciation of the city’s design — from the classic art deco buildings to the stunning modern skyscrapers. What I enjoyed the most was seeing the downtown view open up as we entered Lake Michigan — the panoramic view from the water was breathtaking. The guide was knowledgeable and engaging, making the entire journey both fun and insightful. A truly memorable Chicago experience!

90-min Chicago River and Lake Michigan Architecture Cruise

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