Flights
Hotels & Homes
Trains
Car Services
Car Rentals
Airport Transfers
Attractions & Tours
Attractions & Tours
eSIM & SIM
Flight + Hotel
Travel Inspiration
Travel Guides
Top Picks
Trip.Planner
Map
Gift cards
Trip.com Rewards
Deals
App
Customer Support
SGD
Find bookings
Top Picks for Chicago
Search attractions or local attractions & tours
Trip.com
Chicago
Attractions & Tours category
Top Picks
Book now for today
Book now for tomorrow
55042 Results for Chicago
Sort by
Recommended
The Art Institute of Chicago
No.1 of Best Things to Do in Chicago
Immediate access
Book now for today
Museums
Themed exhibition halls
4.7
/5
· 457 reviews
From
SGD 51.30
360 CHICAGO
No.2 of Best Things to Do in Chicago
Immediate access
Book now for today
Night view
4.8
/5
· 35 reviews
10% off
From
SGD 35.78
SGD 39.76
Field Museum
2025 Americas 50 – Best Things to Do
Book now for tomorrow
Museums
4.7
/5
· 313 reviews
Save SGD 1.86
From
SGD 35.43
SGD 37.29
Willis Tower
No.3 of Night Attractions in Chicago
Immediate access
Book now for today
Night view
4.5
/5
· 504 reviews
From
SGD 54.33
Museum Of Contemporary Art Chicago
No.11 of Best Things to Do in Chicago
Immediate access
Book now for today
Museums
Themed exhibition halls
4.3
/5
· 82 reviews
9% off
From
SGD 25.44
SGD 28.26
875 North Michigan Avenue
No.1 of Night Attractions in Chicago
Immediate access
Book now for today
Night view
4.6
/5
· 243 reviews
5% off
From
SGD 37.88
SGD 39.87
Skydeck Chicago
2025 Americas 50 – Night Attractions
Immediate access
Book now for today
Night view
4.8
/5
· 69 reviews
From
SGD 54.33
Navy Pier
No.7 of Best Things to Do in Chicago
Night view
4.5
/5
· 339 reviews
Free
Lake Michigan Skyline Cruise in Chicago
Book now for today
Conditional cancellation
From
SGD 41.68
Shoreline Sightseeing
No.12 of Best Things to Do in Chicago
Book now for tomorrow
Boat tour
Sightseeing bus
4.5
/5
· 16 reviews
From
SGD 62.82
Millennium Park
2025 Americas 50 – Night Attractions
Night view
4.6
/5
· 595 reviews
Free
Explore Chicago’s Hidden Past: Prohibition Culture & Architecture
Book now for tomorrow
Conditional cancellation
From
SGD 64.07
Cloud Gate
No.17 of Best Things to Do in Chicago
4.6
/5
· 299 reviews
Free
Explore Chicago’s Hidden Past: Prohibition Culture & Architecture
Book now for tomorrow
Conditional cancellation
From
SGD 64.07
Magnificent Mile
No.5 of Night Attractions in Chicago
Night view
4.6
/5
· 172 reviews
Free
Chicago River 45-Minute Architecture Tour from Magnificent Mile
Conditional cancellation
100+ booked
From
SGD 35.91
Shedd Aquarium
2025 Global 100 – Family-Friendly Attractions
Museums
4.4
/5
· 244 reviews
Chinatown
No.16 of Best Things to Do in Chicago
4.3
/5
· 141 reviews
Grant Park
No.5 of Best Things to Do in Chicago
Natural scenery
Night view
4.3
/5
· 117 reviews
The Chicago Theatre
Historic buildings
Performances
4.6
/5
· 26 reviews
Bite into Chicago: Discover the City’s Most Iconic Food
Book now for tomorrow
Conditional cancellation
From
SGD 98.08
Griffin Museum of Science and Industry
No.19 of Best Things to Do in Chicago
Museums
4.6
/5
· 118 reviews
Historic Route 66 Begin Sign
No.15 of Best Things to Do in Chicago
Historic buildings
4.4
/5
· 71 reviews
Riverwalk
Natural scenery
4.7
/5
· 43 reviews
Free
Chicago River 90-Minute Architecture Tour
Book now for tomorrow
Conditional cancellation
100+ booked
From
SGD 57.71
Lincoln Park
No.18 of Best Things to Do in Chicago
4.7
/5
· 79 reviews
Free
Chicago City Tour with Architecture River Cruise Option
Book now for tomorrow
Conditional cancellation
From
SGD 62.78
1
2
3
4
5
6
2753
Contact Us
Customer Support
Service Guarantee
More Service Info
About
About Trip.com
News
Careers
Terms & Conditions
Privacy Statement
Accessibility statement
About Trip.com Group
Other Services
Investor Relations
Trip.com Rewards
Affiliate Program
List Your Property
Become a Supplier
Security
Payment methods
Our partners
Europe’s Best Online Travel Agency 2023
Contact Center
of the year 2024
Trip.com is part of Trip.com Group Limited, one of the world's leading providers of travel services.
Copyright © 2025 Trip.com Travel Singapore Pte. Ltd. All rights reserved
Site Operator: Trip.com Travel Singapore Pte. Ltd.