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Top experiences in Chicago

20 experiences

Free cancellation
Chicago River cruise boat passing under DuSable Bridge with city buildings in the background.
90-min Chicago River Architecture Cruise by Wendella
Cruises
$45
90-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 605 ratings.From $45
Cruise boat on Chicago River passing under Clark Street Bridge.
Official Chicago Architecture Cruise by First Lady
Cruises
$57
Official Chicago Architecture Cruise by First Lady. Rated 4.8 out of 5 from 217 ratings.From $57
Free cancellation
Chicago River cruise boat passing under a bridge with city skyline.
45-min Chicago River Architecture Cruise by Wendella
Cruises
from
$28
45-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 953 ratings.From $28
Tour boat on Chicago River with city skyline and bridge in background.
75-Minute Chicago River Architecture Cruise by Shoreline
Cruises
from
$39
75-Minute Chicago River Architecture Cruise by Shoreline. Rated 4.5 out of 5 from 130 ratings.From $39
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
Cruises
$45
90-min Chicago River and Lake Michigan Architecture Cruise by Wendella. Rated 4.8 out of 5 from 119 ratings.From $45
Free cancellation
Fireworks over Chicago River with boats during dinner cruise.
Chicago Fireworks Dinner Cruises
Cruises
from
$112.10
Chicago Fireworks Dinner Cruises. Rated 4 out of 5 from 4 ratings.From $112.10
Free cancellation
Fireworks over Chicago River with boats during dinner cruise.
Chicago Fireworks Cruise
Cruises
from
$54.76
Chicago Fireworks Cruise. Rated 4.5 out of 5 from 8 ratings.From $54.76
Free cancellation
Odyssey Chicago River boat cruising on the Chicago River with city skyline.
Odyssey Chicago River Architecture Dinner Cruise
Cruises
from
$139.42
Odyssey Chicago River Architecture Dinner Cruise. Rated 4.6 out of 5 from 47 ratings.From $139.42
Free cancellation
Cruise boat on Lake Michigan with Chicago skyline at sunset.
90-min Scenic Sunset Lake Michigan Cruise by Wendella
Cruises
$45
90-min Scenic Sunset Lake Michigan Cruise by Wendella. Rated 4.9 out of 5 from 40 ratings.From $45
Free cancellation
Moored tour boats on the Chicago River at sunrise with city skyline.
Chicago Architecture Evening Cruise by Shoreline
Cruises
from
$46
Chicago Architecture Evening Cruise by Shoreline. Rated 4.9 out of 5 from 38 ratings.From $46
Free cancellation
Tour boat on Chicago River with city skyline in background.
Chicago River Architecture Cruise
Cruises
from
$28
Chicago River Architecture Cruise. Rated 4.8 out of 5 from 352 ratings.From $28
Chicago River cruise boat with city skyline in the background.
Chicago River & Lake Sightseeing Cruise by First Lady
Cruises
from
$46
Chicago River & Lake Sightseeing Cruise by First Lady. Rated 4.7 out of 5 from 3 ratings.From $46
Chicago River cruise boat at night with city skyline in the background.
Chicago at Night: River & Lake Sightseeing Cruise by First Lady
Cruises
from
$50
Chicago at Night: River & Lake Sightseeing Cruise by First Lady. Rated 0 out of 5 from 0 ratings.From $50
Free cancellation
Cruise boat on Lake Michigan with Chicago skyline in the background.
45-Min Lake Michigan Tour by Shoreline
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
Sea Dog Cruise boat on Lake Michigan with Chicago skyline in the background.
Chicago Sea Dog Architecture Cruise
Cruises
from
$47.60
Chicago Sea Dog Architecture Cruise. Rated 5 out of 5 from 1 ratings.From $47.60
Free cancellation
Tour boat on Chicago River with city skyscrapers in the background.
Lake Michigan Cruise
Cruises
from
$32.50
Lake Michigan Cruise. Rated 4.8 out of 5 from 171 ratings.From $32.50
Free cancellation
Sea Dog boat cruising on Lake Michigan with Chicago skyline and Ferris wheel at dusk.
Chicago Sea Dog Fireworks Cruise on Lake Michigan
Cruises
from
$54.76
Chicago Sea Dog Fireworks Cruise on Lake Michigan. Rated 5 out of 5 from 1 ratings.From $54.76
Crowd on Chicago Haunted River "Creepy Cruise" by First Lady under moonlit skyline.
Chicago Haunted River "Creepy Cruise" by First Lady
Cruises
from
$46
Chicago Haunted River "Creepy Cruise" by First Lady. Rated 0 out of 5 from 0 ratings.From $46
Chicago River cruise with tourists viewing downtown skyscrapers.
Chicago River Architecture Cruise
Cruises
$37
Chicago River Architecture Cruise. Rated 0 out of 5 from 0 ratings.From $37
Free cancellation
Tour boat near Chicago's Navy Pier on a sunny day during the Chicago Skyline Lake Tour.
Chicago Skyline Lake Tour
Cruises
from
$32.50
Chicago Skyline Lake Tour. Rated 4.5 out of 5 from 35 ratings.From $32.50

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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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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

Asha M

United States
Solo
3 weeks ago

+3 more

Explanation was excellent. I loved the way he interacted with people. Lot of laughing! We waved people besides the river and it was fun. And the view was incredible!! A beautiful city!

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!

90-min Scenic Sunset Lake Michigan Cruise by Wendella

Justin B

Solo
May 2026
Honestly the cruise was great but the guide Scotty D was incredible. He was fun, knowledgeable, and engaging. The cruise was a good mix of architecture and lake views, timely, and comfortable.

90-min Scenic Sunset Lake Michigan Cruise by Wendella

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