Headout logo. Link to home.
Help

Top experiences in Chicago

See all
Free cancellation
Double-decker bus on Chicago Hop-On-Hop-Off Tour passing by the iconic Chicago skyline.
Hop-on Hop-off Tours Chicago
Big Bus: Chicago Hop-On Hop-Off Bus Tour
Instant confirmation
4.7
Rated 4.7 out of 5.0 from 249 ratings.
from
$52.20
Free cancellation
Global eSIM card with unlimited 5G/4G data for use in 120 countries.
Wifi & SIM Cards
Global eSIM with Unlimited 5G/4G Data: Access to 120 Countries
3.5
Rated 3.5 out of 5.0 from 73 ratings.
from $9.90
$8.91
10% off
Free cancellation
Chicago River cruise showcasing iconic architecture along the riverbank.
Sightseeing Cruises
90-min Chicago River Architecture Cruise
Instant confirmation
New
$45
Chicago River cruise boat passing iconic skyscrapers on 45min architecture tour.
Sightseeing Cruises
45-min Chicago River Architecture Cruise
Instant confirmation
New
from
$28
Free cancellation
Chicago River cruise boat passing under a raised lift bridge with city skyline in the background.
Sightseeing Cruises
90-min Chicago River and Lake Michigan Architecture Cruise
Instant confirmation
New
$45
Free cancellation
Chicago River cruise boat with tourists viewing Lake Michigan skyline.
Sightseeing Cruises
30-min Lake Michigan Skyline Cruise
Instant confirmation
New
$28.44
Sunset view from a 90-Min Scenic Sunset Lake Michigan Cruise with Chicago skyline in the background.
Sightseeing Cruises
90-min Scenic Sunset Lake Michigan Cruise
Instant confirmation
New
$45
Free cancellation
Tourists watching Chicago skyline from 360 Chicago Observation Deck\Tourists enjoying Chicago Hop On and Hop Off Tour
Combo
Combo (Save 10%): Chicago Hop-On-Hop-Off Bus Tour + 360 Chicago Observation Deck Skip-the-Line Tickets
Instant confirmation
4.5
Rated 4.5 out of 5.0 from 352 ratings.
from $82.20
$73.98
10% off
Exterior view of the Chicago River Architecture Cruise
Sightseeing Cruises
75-min Chicago River Architecture Cruise
Instant confirmation
4.1
Rated 4.1 out of 5.0 from 70 ratings.
from
$48.77
Free cancellation
Couple taking a selfie on Chicago's 360 Observation Deck
360 Chicago
360 Chicago Observation Deck Skip-the-Line Tickets
Instant confirmation
4.2
Rated 4.2 out of 5.0 from 102 ratings.
from
$30
Free cancellation
Family exploring the Chicago 360 Observation Deck
360 Chicago
360 Chicago Sip & View
Instant confirmation
New
from
$44
Free cancellation
Go City Chicago All-Inclusive Pass
City Cards
Go City Chicago All-Inclusive Pass: 25+ Attractions
Instant confirmation
4.4
Rated 4.4 out of 5.0 from 2130 ratings.
from
$139

Browse by themes

Chicago City Cards
Landmarks in Chicago
Observation Decks in Chicago
View all Chicago Attractions
Guided Tours in Chicago
Hop-on Hop-off Tours Chicago
View all Chicago Tours
Airport Transfers in Chicago
Public Transport Tickets in Chicago
Shared Airport Transfers
View all Transportation in Chicago
Wifi & SIM Cards in Chicago
View all Travel Services in Chicago
Sightseeing Cruises in Chicago
View all Cruises in Chicago
Combos Tickets in Chicago
View all Chicago Specials

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 32 million+ guests and we are here for you

32 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