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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 746 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 1150 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 288 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 153 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 4.6 out of 5 from 22 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 4.5 out of 5 from 10 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 56 ratings.From $139.42
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 4.9 out of 5 from 15 ratings.From $32.50
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 2 ratings.From $47.60
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 409 ratings.From $28
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 4.8 out of 5 from 221 ratings.From $32.50
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
Free cancellation
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
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
Downtown Chicago skyline at night with illuminated skyscrapers and a boat on the river.
Chicago Architecture Fireworks Cruises
Sightseeing Cruises
$65
Chicago Architecture Fireworks Cruises. Rated 0 out of 5 from 0 ratings.From $65

What our guests say

Naomi W

United States
Couple
2 weeks ago
Our guide, Claudia, was FABULOUS! She shared details, insights and history with incredible enthusiam. The 1.5 hours was a highlight of our weekend in Chicago.

Official Chicago Architecture Cruise by First Lady

Caroline H

United States
Couple
May 2026
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
May 2026
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
May 2026
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
May 2026

+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

Kevin S

United States
Family
2 days ago
Josh was super energetic and informative and kid-friendly! Really was genuine. Loved the fast ride at the end of course too.

Chicago Sea Dog Architecture Cruise

Diamond C

United States
Solo
2 days ago
Alex was phenomenal and 6:30 was the perfect time! I thoroughly enjoyed knowing the history behind some of the buildings. They looked even more beautiful on the water.

Chicago River Architecture Cruise

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