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 266 ratings.
from
$52.20
View from Skydeck at Willis Tower, Chicago, overlooking city skyline and Lake Michigan.
Willis Tower Skydeck Tickets
Skydeck Chicago Tickets
Instant confirmation
New
from
$42.33
Free cancellation
Chicago River cruise showcasing iconic architecture along the riverbank.
Sightseeing Cruises
90-min Chicago River Architecture Cruise
4.6
Rated 4.6 out of 5.0 from 27 ratings.
$45
Free cancellation
Moored tour boats on the Chicago River at sunrise, showcasing the city's iconic skyline.
Sightseeing Cruises
Chicago Architecture Evening Cruise
Instant confirmation
New
from
$32.50
Exterior view of the Chicago River Architecture Cruise
Sightseeing Cruises
75-min Chicago River Architecture Cruise
Instant confirmation
4.2
Rated 4.2 out of 5.0 from 74 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 106 ratings.
from
$30
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
New
$45
Free cancellation
Family exploring the Chicago 360 Observation Deck
360 Chicago
360 Chicago Sip & View
Instant confirmation
New
from
$44
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 373 ratings.
from $82.20
$73.98
10% off
Chicago River cruise boat passing iconic skyscrapers on 45min architecture tour.
Sightseeing Cruises
45-min Chicago River Architecture Cruise
4.6
Rated 4.6 out of 5.0 from 36 ratings.
from
$28
Free cancellation
Chicago River cruise boat with tourists viewing Lake Michigan skyline.
Sightseeing Cruises
30-min Lake Michigan Skyline Cruise
Instant confirmation
New
$32.50
Free cancellation
Go City Chicago Explorer Pass
City Cards
Go City Chicago Explorer Pass: Choose 2 to 7 Attractions
Instant confirmation
4.5
Rated 4.5 out of 5.0 from 2112 ratings.
from
$84

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
Sightseeing Cruises in Chicago
View all Cruises in Chicago
Combos Tickets in Chicago
View all Chicago Specials
Download app section background

We've served 39 million+ guests and we are here for you

39 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