Chicago for architecture enthusiasts
Discover Chicago's unique architecture and heritage. Explore centuries of design evolution - from historic to modern - with our curated experiences and guided tours.

Top things to do
Slide 1 of 6
Top experiences in Chicago
Free cancellation
Slide 1 of 1, Chicago River cruise boat passing under DuSable Bridge with city buildings in the background.

Slide 1 of 1, Cruise boat on Chicago River passing under Clark Street Bridge.

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Slide 1 of 1, Chicago River cruise boat passing under a bridge with city skyline.

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Slide 1 of 1, Chicago River architecture cruise boat passing under a lift bridge with city skyscrapers in the background.

4.8(198)
Sightseeing Cruises
$45
Free cancellation
Slide 1 of 1, Chicago River with tour boats and bridges in downtown Chicago.

Slide 1 of 1, Chicago River cruise boat with city skyline in the background.

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Slide 1 of 1, Odyssey Chicago River boat cruising on the Chicago River with city skyline.

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Slide 1 of 1, Tour boat on Chicago River with city skyline in background.

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Slide 1 of 1, Cruise boat on Lake Michigan with Chicago skyline in the background.

Free cancellation
Slide 1 of 1, Sea Dog Cruise boat on Lake Michigan with Chicago skyline in the background.

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Slide 1 of 1, Guests exploring architectural models at the Chicago Architectural Center.

Slide 1 of 1, Chicago River cruise with tourists viewing downtown skyscrapers.

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Slide 1 of 1, Tour boat on Chicago River with city skyscrapers in the background.

Free cancellation
Slide 1 of 1, Guided group walking under Calder's Flamingo sculpture in Chicago.

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Slide 1 of 1, Guest viewing Chicago skyline from lakefront during Skydeck and Architecture Cruise tour.

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Slide 1 of 1, View from Willis Tower Skydeck in Chicago at sunset.

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Slide 1 of 1, Skyscrapers at 111 E. Wacker Dr. in Chicago with clear blue sky.

Slide 1 of 1, Downtown Chicago skyline at night with illuminated skyscrapers and a boat on the river.

What our guests say
V
Valerie K
United StatesGroup
5/5
Tess was our guide and she was wonderful! Very informative and you can tell she loves what she does. The crew was professional and we had a wonderful smooth ride!
90-min Chicago River Architecture Cruise by Wendella
J
Jacinda H
United StatesCouple
5/5
The Chicago Architecture Cruise by First Lady was fascinating. Our docent was so knowledgeable about the history, engineering feats, and even some political reasons why and how these amazing skyscrapers were built. The "fun facts" were so intriguing. It is definitely worth your time. P.S. if you go on a sunny day, don't forget your sunscreen.....however if you do forget, they have some on-board to purchase!😉
Official Chicago Architecture Cruise by First Lady
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Cristina K
United StatesCouple
5/5
+1 more
It was a great easy ride around the city thanks to the captain. We liked how you timed the cruise so people could see the sunset just in time. Boarding was easy. The guide was informative but not intrusive in letting people enjoy the view to the nice music. It was a very pleasant experience and I will recommend to anyone I know who is visiting Chicago. It was truly the highlight of my visit.
Lake Michigan Cruise
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Lydia U
United StatesCouple
5/5
This tour covered a lot more buildings than I though it would, it felt as though the guide had something to say about nearly every building we passed. For 45 minutes, the guide, who did speak pretty quickly, was able to fit in so much information! I also appreciate the sense of humor with which the tour was given; this and other factors made it so that you didn't at any point feel like you were being lectured at and want to zone out. I was engaged the whole time. One of the best parts was heading closer to the mouth of the river and being shown such a scenic view of the city, this was beautiful! Though I would consider doing a longer cruise because I would have loved to learn more, this is very worthwhile in and of itself and especially if you only have (exactly) 45 minutes.
45-min Chicago River Architecture Cruise by Wendella
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Barbara F
United StatesSolo
5/5
The crew was great and the ride was fantastic! The captain timed the tricks with the music and it could not have fit more perfectly!
Sea Dog Cruise on Lake Michigan
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Jill C
Couple
5/5
The views of the city from the water, learning about the architecture, fun facts, the tour guide very good. hot but interesting day!
90-min Chicago River and Lake Michigan Architecture Cruise by Wendella
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Louise H
United StatesSolo
5/5
+2 more
Our evening on the Odyssey Chicago River Architecture Dinner Cruise was unforgettable. The views of Chicago’s iconic skyline and historic buildings were breathtaking, and the narration made the city’s architecture come alive. The staff was genuinely warm and attentive, the meal was delicious, and the atmosphere on board felt both elegant and relaxed. Watching the city lights reflect on the river while enjoying dinner with friends was a perfect experience. I would gladly recommend this cruise to anyone looking for a memorable way to experience Chicago.
Odyssey Chicago River Architecture Dinner Cruise
J
Jeannie M
Couple
5/5
Evening cruise was wonderful. Sunset and no wind. We were able to go on the lake with no choppy waves. Professional crew. Matthew gave an informative narrative.
Chicago River & Lake Sightseeing Cruise by First Lady
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