Headout logo. Link to home.
Help

Top experiences in Chicago

23 experiences
Sort by: Picked for you
Free cancellation
Double-decker bus on Chicago Hop-On-Hop-Off Tour passing by the iconic Chicago skyline.
Hop-on Hop-off Tours Chicago
Instant confirmation
4.5
Rated 4.5 out of 5.0 from 261 ratings.
from
$52.20
Global eSIM card with unlimited 5G/4G data for use in 120 countries.
Wifi & SIM Cards
3.2
Rated 3.2 out of 5.0 from 35 ratings.
from $9.90
$6.93
Save up to 30%
Free cancellation
Couple taking a selfie on Chicago's 360 Observation Deck
Landmarks
Instant confirmation
4.0
Rated 4 out of 5.0 from 109 ratings.
from
$30
Free cancellation
Tourists watching Chicago skyline from 360 Chicago Observation Deck\Tourists enjoying Chicago Hop On and Hop Off Tour
Combo
Instant confirmation
4.3
Rated 4.3 out of 5.0 from 371 ratings.
from $82.20
$73.98
Save up to 10%
Free cancellation
Family exploring the Chicago 360 Observation Deck
Observation Decks
Instant confirmation
New
from
$44
Free cancellation
Go City Chicago Explorer Pass
City Cards
Instant confirmation
4.5
Rated 4.5 out of 5.0 from 2112 ratings.
from
$84
Exterior view of the Chicago River Architecture Cruise
Sightseeing Cruises
Instant confirmation
4.1
Rated 4.1 out of 5.0 from 70 ratings.
from
$45.41
Free cancellation
Go City Chicago All-Inclusive Pass
City Cards
Instant confirmation
4.4
Rated 4.4 out of 5.0 from 2130 ratings.
from
$139
Chicago skyline with red double-decker bus for Hop-On Hop-Off Tour.
Hop-on Hop-off Tours Chicago
New
Unavailable
Tourists enjoying a boat ride on the Chicago Skyline Lake Tour with the city's iconic skyscrapers in the background
Sightseeing Cruises
4.5
Rated 4.5 out of 5.0 from 35 ratings.
Unavailable
Adler Planetarium exterior with Lake Michigan in the background, Chicago.
Landmarks
New
Unavailable

Get the Headout app, save up to 80%

Enjoy exclusive deals, offline access to your tickets & live booking updates.
Download iPhone appDownload Android app
iphone

We've served 36 million+ guests and we are here for you

36 million+

Happy customers across 10,000+ experiences

In the media

Featured and recommended by the best brands

24 x 7 help center

Have a question? Live chat with local experts anywhere, anytime