Chicago, United StatesChicago 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.
Top things to do
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Top experiences in Chicago
Slide 1 of 1, View from the Skydeck at Willis Tower, Chicago, overlooking the cityscape.
Slide 1 of 1, Riders upside down on Maxx Force roller coaster at Six Flags Great America.
Free cancellation
Slide 1 of 1, Sea Dog boat cruising on Lake Michigan with Chicago skyline and Ferris wheel at dusk.
Free cancellation
Slide 1 of 1, Family enjoying view from Chicago 360 Observation Deck with city skyline.
Slide 1 of 1, Crowd on Chicago Haunted River "Creepy Cruise" by First Lady under moonlit skyline.
Free cancellation
Slide 1 of 1, Sea Dog Cruise boat on Lake Michigan with Chicago skyline in the background.
Slide 1 of 1, Riders upside down on Maxx Force roller coaster at Six Flags Great America.
What our guests say
J
Javeah T
United StatesCouple
5/5
such a great time, the tour guide was great the driver was great, the music was on point and went along with the excursions going on i loved it would visit again
Chicago Sea Dog Fireworks Cruise on Lake Michigan
T
Tahamar N
United StatesGroup
4/5
I had a great experience booking with Headout. The tickets were delivered instantly, the entry process at Six Flags Great America was fast, and everything worked exactly as expected. The park had incredible rides, friendly staff, and a fun atmosphere. Overall, it was a smooth experience from booking to the end of the day, and I would definitely book through Headout again.
Six Flags Great America One Day Tickets
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Anggie C
EcuadorCouple
5/5
It's so easy to shop online, and the app is very user-friendly. I really liked that it shows you photos of all the available tour options, so you know exactly what you'll be doing! Highly recommended
Skydeck Chicago Tickets
D
Dianna G
United StatesGroup
5/5
Great mix of architecture and go fast boating! Josh did an excellent job with the tour and everyone was sooo nice. Definitely will do again when we return to Chicago.
Chicago Sea Dog Architecture Cruise
E
Elicia N
United StatesSolo
5/5
Andy was amazing! Went on the creepy nighttime boat tour focused on Chicago crimes. His stories and personality are perfect and loved the cheesy bits he added in! Would highly recommend this tour to others! Still talking about his stories the next day. Also appreciated him addressing the people loudly talking and laughing right in front of him while he was story telling.
Chicago Haunted River "Creepy Cruise" by First Lady
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Henry L
United StatesCouple
5/5
The. Views were incredible and the atmosphere delightful. Our bartender was very attentive and helpful. We never felt rushed only relaxing vibes.
360 Chicago Sip & View
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How Headout makes choosing experiences effortless
Slide 1 of 4, We curate the best ways to experience
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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