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United StatesChicago, United States

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 things to do

Chicago River Architecture Cruises
Chicago River Architecture Cruises
from $32.50
First Lady Cruises Chicago
First Lady Cruises Chicago
from $28
Wendella Cruises Chicago
Wendella Cruises Chicago
from $28
Shoreline Cruises Chicago
Shoreline Cruises Chicago
from $32.50
Chicago Architecture Center
Chicago Architecture Center
from $7

Top experiences in Chicago

Free cancellation
Chicago River cruise boat passing under DuSable Bridge with city buildings in the background.
Sightseeing Cruises
90-min Chicago River Architecture Cruise by Wendella
$45
90-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 409 ratings.From $45
Free cancellation
Chicago River cruise boat passing under a bridge with city skyline.
Sightseeing Cruises
45-min Chicago River Architecture Cruise by Wendella
from
$28
45-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 648 ratings.From $28
Cruise boat on Chicago River passing under Clark Street Bridge.
Sightseeing Cruises
Official Chicago Architecture Cruise by First Lady
$57
Official Chicago Architecture Cruise by First Lady. Rated 4.9 out of 5 from 92 ratings.From $57
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 by Wendella
$45
90-min Chicago River and Lake Michigan Architecture Cruise by Wendella. Rated 4.7 out of 5 from 63 ratings.From $45
Free cancellation
Tour boat on Chicago River with city skyline in background.
Sightseeing Cruises
Chicago River Architecture Cruise
from
$28
Chicago River Architecture Cruise. Rated 4.9 out of 5 from 648 ratings.From $28
Free cancellation
Odyssey Chicago River boat cruising on the Chicago River with city skyline.
Sightseeing Cruises
Odyssey Chicago River Architecture Dinner Cruise
from
$153.08
Odyssey Chicago River Architecture Dinner Cruise. Rated 4.7 out of 5 from 29 ratings.From $153.08
Free cancellation
Tour boat on Chicago River with city skyscrapers in the background.
Sightseeing Cruises
Lake Michigan Cruise
from
$32.50
Lake Michigan Cruise. Rated 4.7 out of 5 from 94 ratings.From $32.50
Free cancellation
Tourists on Sea Dog Cruise on Lake Michigan with Chicago skyline in background.
Dinner Cruises
Sea Dog Cruise on Lake Michigan
from
$30.94
Sea Dog Cruise on Lake Michigan. Rated 5 out of 5 from 1 ratings.From $30.94
Free cancellation
Cruise boat on Lake Michigan with Chicago skyline in the background.
Sightseeing Cruises
30-Min Lake Michigan Tour by Shoreline
from
$32.50
30-Min Lake Michigan Tour by Shoreline. Rated 4.2 out of 5 from 11 ratings.From $32.50
Free cancellation
Guests exploring architectural models at the Chicago Architectural Center.
Museums
Chicago Architecture Center Exhibit Admission
from
$7
Chicago Architecture Center Exhibit Admission. Rated 0 out of 5 from 0 ratings.From $7
Free cancellation
Guided group walking under Calder's Flamingo sculpture in Chicago.
Museums
Architecture Center Admission with Must-See Chicago Walking Tour
$35
Architecture Center Admission with Must-See Chicago Walking Tour. Rated 0 out of 5 from 0 ratings.From $35
Free cancellation
Skyscrapers at 111 E. Wacker Dr. in Chicago with clear blue sky.
Museums
Chicago Architecture Center Admission With Walk Through Time Tour
$35
Chicago Architecture Center Admission With Walk Through Time Tour. Rated 0 out of 5 from 0 ratings.From $35

What our guests say

Ariana V

United States
Solo
Last week
Funny and engaging tour guide. Lovely views, especially on the cruise at sunset. I learned so many cool facts and have shared them with my friends and family. Money well spent!

45-min Chicago River Architecture Cruise by Wendella

Martina G

Group
2 weeks ago
Our guide was very informative and it was great to see the city from the river which gives a completely different perspective to the buildings and the layout. Would highly recommend First Lady architecture tours

Official Chicago Architecture Cruise by First Lady

Destiny M

United States
Couple
Mar 2026
Views were incredible, food was good , vibes were there , wasn't a rocky ride would highly recommend for date night & quality time spent with your significant other

Odyssey Chicago River Architecture Dinner Cruise

Chetna D

United States
Couple
Dec 2025

+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 by Wendella

Tara V

United States
Couple
Yesterday
Kenny the tour guide was very knowledgeable and kept us entertained! The history of the architecture was fascinating to learn about.

Chicago River Architecture Cruise

Suryanarayana M

Group
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 by Wendella

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How Headout makes choosing experiences effortless

We curate the best ways to experience

We research and organise all unique experiences - from tickets to tours to special combos - so you get all the choices without the clutter.

We partner with the best

Every supplier is vetted for quality, reliability, and value so you only get top rated experiences. No surprises, no disappointments.

All the best options, in one place

Each experience is thoughtfully organised to give you maximum availability, great value and an easy way to choose.

Book with complete peace of mind

Free cancellations, Flexible payments, and 24/7 support - thoughtfully designed for flexibility, assurance, and total peace of mind.

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We curate the best ways to experience
We partner with the best
All the best options, in one place
Book with complete peace of mind

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