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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.
Visitor admiring ornate architecture in a historic building with statues and decorative columns.

Top experiences in Chicago

Free cancellation
Chicago River cruise boat passing under a bridge with city skyline.
Sightseeing Cruises
45-min Chicago River Architecture Cruise
4.9(395)
from
$28
45-min Chicago River Architecture Cruise. Rated 4.9 out of 5 from 395 ratings.From $28
Free cancellation
Chicago River cruise boat passing under DuSable Bridge with city buildings in the background.
Sightseeing Cruises
90-min Chicago River Architecture Cruise
4.9(261)
$45
90-min Chicago River Architecture Cruise. Rated 4.9 out of 5 from 261 ratings.From $45
Free cancellation
Odyssey Chicago River boat cruising on the Chicago River with city skyline.
Sightseeing Cruises
Odyssey Chicago River Architecture Dinner Cruise
NEW
from
$176.32
Odyssey Chicago River Architecture Dinner Cruise. Rated 0 out of 5 from 0 ratings.From $176.32
Selling out fast
Guest viewing Chicago skyline from lakefront during Skydeck and Architecture Cruise tour.
Guided Tours
Chicago Skydeck & Architecture Cruise with Small Group Guided Tour
NEW
$129
Chicago Skydeck & Architecture Cruise with Small Group Guided Tour. Rated 5 out of 5 from 1 ratings.From $129
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
4.7(56)
$45
90-min Chicago River and Lake Michigan Architecture Cruise. Rated 4.7 out of 5 from 56 ratings.From $45
Free cancellation
Tourists on Sea Dog Cruise on Lake Michigan with Chicago skyline in background.
Dinner Cruises
Sea Dog Cruise on Lake Michigan
NEW
from
$42.79
Sea Dog Cruise on Lake Michigan. Rated 0 out of 5 from 0 ratings.From $42.79
Selling out fast
View from Willis Tower Skydeck in Chicago at sunset.
Observation Decks
Chicago Night Tour with Skydeck & Architecture Cruise
NEW
$169
Chicago Night Tour with Skydeck & Architecture Cruise. Rated 0 out of 5 from 0 ratings.From $169

Millions love heading out with us

David Naibei
US

David

United States
Oct 2025
5/5

review-image
This was just a lifetime experience. It was like rediscovering the whole history of Chicago in less than a hour. Perfect date with my girlfriend. We learned a lot while having hun.

45-min Chicago River Architecture Cruise

Megan Mitchell
US

Megan

United States
Oct 2025
5/5

review-image
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

Suryanarayana Murthy Majji

Suryanarayana

Oct 2025
5/5
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

Ricardo R. Palo
PH

Ricardo

Philippines
Oct 2025
5/5
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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