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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 things to do

Chicago River Architecture Cruise Tickets
Chicago River Architecture Cruise Tickets
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 $15

Top experiences in Chicago

Free cancellation
Chicago River cruise boat passing under DuSable Bridge with city buildings in the background.
90-min Chicago River Architecture Cruise by Wendella
Sightseeing Cruises
$45
90-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 600 ratings.From $45
Free cancellation
Chicago River cruise boat passing under a bridge with city skyline.
45-min Chicago River Architecture Cruise by Wendella
Sightseeing Cruises
from
$28
45-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 945 ratings.From $28
Cruise boat on Chicago River passing under Clark Street Bridge.
Official Chicago Architecture Cruise by First Lady
Sightseeing Cruises
$57
Official Chicago Architecture Cruise by First Lady. Rated 4.9 out of 5 from 213 ratings.From $57
Free cancellation
Chicago River architecture cruise boat passing under a lift bridge with city skyscrapers in the background.
90-min Chicago River and Lake Michigan Architecture Cruise by Wendella
Sightseeing Cruises
$45
90-min Chicago River and Lake Michigan Architecture Cruise by Wendella. Rated 4.8 out of 5 from 118 ratings.From $45
Free cancellation
Chicago River with tour boats and bridges in downtown Chicago.
Sea Dog Cruise on Lake Michigan
Dinner Cruises
from
$35.72
Sea Dog Cruise on Lake Michigan. Rated 5 out of 5 from 4 ratings.From $35.72
Chicago River cruise boat with city skyline in the background.
Chicago River & Lake Sightseeing Cruise by First Lady
Sightseeing Cruises
from
$46
Chicago River & Lake Sightseeing Cruise by First Lady. Rated 4.7 out of 5 from 3 ratings.From $46
Free cancellation
Odyssey Chicago River boat cruising on the Chicago River with city skyline.
Odyssey Chicago River Architecture Dinner Cruise
Sightseeing Cruises
from
$139.42
Odyssey Chicago River Architecture Dinner Cruise. Rated 4.6 out of 5 from 47 ratings.From $139.42
Free cancellation
Tour boat on Chicago River with city skyline in background.
Chicago River Architecture Cruise
Sightseeing Cruises
from
$28
Chicago River Architecture Cruise. Rated 4.8 out of 5 from 349 ratings.From $28
Free cancellation
Sea Dog Cruise boat on Lake Michigan with Chicago skyline in the background.
Chicago Sea Dog Architecture Cruise
Sightseeing Cruises
from
$47.60
Chicago Sea Dog Architecture Cruise. Rated 5 out of 5 from 1 ratings.From $47.60
Free cancellation
Cruise boat on Lake Michigan with Chicago skyline in the background.
45-Min Lake Michigan Tour by Shoreline
Sightseeing Cruises
from
$32.50
45-Min Lake Michigan Tour by Shoreline. Rated 4.8 out of 5 from 12 ratings.From $32.50
Free cancellation
Tour boat on Chicago River with city skyscrapers in the background.
Lake Michigan Cruise
Sightseeing Cruises
from
$32.50
Lake Michigan Cruise. Rated 4.9 out of 5 from 170 ratings.From $32.50
Chicago River cruise with tourists viewing downtown skyscrapers.
Chicago River Architecture Cruise
Sightseeing Cruises
$37
Chicago River Architecture Cruise. Rated 0 out of 5 from 0 ratings.From $37
Free cancellation
Guests exploring architectural models at the Chicago Architectural Center.
Chicago Architecture Center Exhibit Admission
Museums
$15
Chicago Architecture Center Exhibit Admission. Rated 0 out of 5 from 0 ratings.From $15
Selling out fast
Skyscrapers at 111 E. Wacker Dr. in Chicago with clear blue sky.
Chicago Architecture Center Admission With Walk Through Time Tour
Museums
$35
Chicago Architecture Center Admission With Walk Through Time Tour. Rated 0 out of 5 from 0 ratings.From $35
Free cancellation
Guided group walking under Calder's Flamingo sculpture in Chicago.
Architecture Center Admission with Must-See Chicago Walking Tour
Museums
$35
Architecture Center Admission with Must-See Chicago Walking Tour. Rated 0 out of 5 from 0 ratings.From $35

What our guests say

Naomi W

United States
Couple
2 weeks ago
Claudia, the docent and guide was FABULOUS! Not only was she knowledgeable, but she shared info and history with lots if enthusiasm. You couldn't help but be excited and impressed by the range and backstreet of the buildings and their designers. A must-see tour!

Official Chicago Architecture Cruise by First Lady

Caroline H

United States
Couple
2 weeks ago
My 1st time to Chicago, everyone I talked to who'd been there mentioned the Architecture Tour was a must. They were not wrong! The guide was a great mix of really intersting information and light humor so the 90 minutes flew by.

90-min Chicago River Architecture Cruise by Wendella

Gomes L

Group
3 weeks ago
Only a cruise like this one lets you take such beautiful photos of Chicago at night. Beyond the cruise itself, there was a great atmosphere on board thanks to the wonderful crew. I highly recommend it!

Lake Michigan Cruise

Nakisha A

United States
Couple
3 weeks ago
I absolutely loved the view, the food, and the drinks...everyone was so friendly and welcoming...I've never had dinner on the water so that was definitely a great experience, I took my fiancé for his bday and he never been there so that was great seeing his face and how much he loved it 🥰

Odyssey Chicago River Architecture Dinner Cruise

Lisa W

United States
Solo
3 weeks ago

+1 more

Very nice overview about the architecture and history of Chicago combined with amazing views from both River and Lake. Tess was an amazing narrator and answered all questions, perfect combination of Information and humor

90-min Chicago River and Lake Michigan Architecture Cruise by Wendella

Nephateria L

United States
Solo
May 2026
The experience was more than amazing. I'm from out of town and learned so much about Chicago and its history. The tour guide was phenomenal. The river, the buildings and architecture was beautiful. I would highly recommend going if you haven't.

45-min Chicago River Architecture Cruise by Wendella

Sally E

United States
Family
Yesterday
It was amazing even with a little rain. The city line at night was absolutely beautiful. Our tour guide gave us so much history and information. She was the bomb!

Chicago River Architecture Cruise

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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

We've served 51 million+ guests and we are here for you

51 million+

Happy customers across 10,000+ experiences

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