Chicago, 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

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Family enjoying the view from 360 Chicago observation deck.

360 Chicagofrom $27

Couple lying on glass ledge at SkyDeck, Willis Tower, overlooking Chicago skyline.

Willis Tower Skydeck Ticketsfrom $42.33

Roller coaster loop at Six Flags: Great America with riders in orange seats.

Six Flags: Great Americafrom $46.80

Chicago Riverwalk with 'Chicago's First Lady' tour boat passing by Marina City.

First Lady Cruises Chicagofrom $28

Top experiences in Chicago

What our guests say

Raul R

Mexico

Group

Aug 2026

Excellent service from the staff, punctuality, and a great way to see the city from the highest point in Chicago

Skydeck Chicago Tickets

Javeah T

United States

Couple

Jul 2026

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

Tahamar N

United States

Group

Jul 2026

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

Kristal W

United States

Couple

6 days ago

More selection for the drinks and appetizers added ,could have been better alone with the experience. When booking read throughly bc I was under the impression that I purchase "Tilt and Sip" instead it was "Sip and view"

360 Chicago Sip & View

William L

United States

Group

3 weeks ago

I found it very easy to use and very reliable. I received my tickets very quickly without any issues, and we really enjoyed our time together as a family 💯 highly recommended.

Six Flags Great America Good Any Day Tickets

Randell M

Couple

Sep 2026

My wife and I did this cruise for our anniversary. It was romantic to see the city lit up from the river. To top it off we got alot of really cool spooky history that brought the whole experience together. The tour guide was knowledgeable and friendly. Ended the night by seeing the fireworks going off at navy piere. Sound system was clear. We 100 percent woukd do this again just for the breathtaking sites of the city at night.

Chicago Haunted River "Creepy Cruise" by First Lady

Dianna G

United States

Group

Jul 2026

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