Headout logo. Link to home.
Help
United StatesChicago, United States

Chicago for thrill seekers

Crank up the adrenaline in Chicago. Dive into the most thrilling activities the city has to offer with our pick of the best adventurous experiences.
Tandem skydiving over clouds, adventure seekers in freefall.

Top things to do

360 Chicago
360 Chicago
from $30
Willis Tower Skydeck Tickets
Willis Tower Skydeck Tickets
from $42.33

Top experiences in Chicago

View from the Skydeck at Willis Tower, Chicago, overlooking the cityscape.
Skydeck Chicago Tickets
Observation Decks
from
$42.33
Skydeck Chicago Tickets. Rated 4.7 out of 5 from 127 ratings.From $42.33
Free cancellation
Family enjoying view from Chicago 360 Observation Deck with city skyline.
360 Chicago Sip & View
Observation Decks
from
$44
360 Chicago Sip & View. Rated 4.2 out of 5 from 17 ratings.From $44
Free cancellation
Sea Dog Cruise boat on Lake Michigan with Chicago skyline in the background.
Chicago Sea Dog Architecture Cruise
Sightseeing Cruises
from
$47.60
Chicago Sea Dog Architecture Cruise. Rated 0 out of 5 from 0 ratings.From $47.60

Browse by themes

Museums in Chicago
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
Dinner Cruises in Chicago
Lunch Cruises in Chicago
View all Cruises in Chicago
Combos Tickets in Chicago
View all Chicago Specials

Nearby cities to explore

See all
Things to do in Nashville
United States
Things to do in Atlanta
United States
Things to do in Washington DC
United States
Things to do in Philadelphia
United States
Things to do in New York
United States
Things to do in Myrtle Beach
United States
Things to do in Charleston
United States
Things to do in Savannah
United States
Things to do in Dallas
United States
Things to do in New Orleans
United States

How Headout makes choosing experiences effortless

We curate the best ways to experience

We research and organise all unique experiences - from tickets to tours to special combos - so you get all the choices without the clutter.

We partner with the best

Every supplier is vetted for quality, reliability, and value so you only get top rated experiences. No surprises, no disappointments.

All the best options, in one place

Each experience is thoughtfully organised to give you maximum availability, great value and an easy way to choose.

Book with complete peace of mind

Free cancellations, Flexible payments, and 24/7 support - thoughtfully designed for flexibility, assurance, and total peace of mind.

1/4

Slide 1 of 4
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

We've served 51 million+ guests and we are here for you

51 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