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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
Six Flags: Great America
Six Flags: Great America
from $46.80
First Lady Cruises Chicago
First Lady Cruises Chicago
from $28
Six Flags
Six Flags
from $46.80

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 4.8 out of 5 from 132 ratings.From $42.33
Riders upside down on Maxx Force roller coaster at Six Flags Great America.
Six Flags Great America One Day Tickets
Theme Parks
from
$46.80
Six Flags Great America One Day Tickets. Rated 4.9 out of 5 from 10 ratings.From $46.80
Free cancellation
Sea Dog boat cruising on Lake Michigan with Chicago skyline and Ferris wheel at dusk.
Chicago Sea Dog Fireworks Cruise on Lake Michigan
Sightseeing Cruises
from
$54.76
Chicago Sea Dog Fireworks Cruise on Lake Michigan. Rated 5 out of 5 from 3 ratings.From $54.76
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 5 out of 5 from 3 ratings.From $47.60
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 4.3 out of 5 from 19 ratings.From $44
Crowd on Chicago Haunted River "Creepy Cruise" by First Lady under moonlit skyline.
Chicago Haunted River "Creepy Cruise" by First Lady
Sightseeing Cruises
from
$46
Chicago Haunted River "Creepy Cruise" by First Lady. Rated 4.5 out of 5 from 2 ratings.From $46

Browse by themes

Museums in Chicago
Theme Parks in Chicago
Water Park Tickets 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

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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.

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