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Top experiences in Chicago

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What our guests say

Samanth P

Canada
Couple
2 weeks ago
I had the best experience at the Skydeck Chicago. It was magical. I highly recommend going there and experiencing it. Also, Headout app made it easy to book tickets right from the comfort of your couch.

Skydeck Chicago Tickets

Israel O

Mexico
Family
Sep 2026
A wonderful place with a beautiful view of the whole city. It was even more fantastic because we went at the end of the day with an orange sky and the entire city lit up, which made the experience even better and truly enchanting.

Skydeck Chicago Tickets

Antonio G

United States
Couple
3 weeks ago
What made the 360 tower experience great was just the feeling of being over Windy City great experience would do again loved it so much I want to use this app again to purchase my tickets

360 Chicago Observation Deck Skip-the-Line Tickets

Audra A

United States
Group
Aug 2026
Well worth it! We actually went twice: once at nite (10pm) & during the day (4pm). Easy to adjust our reservation which was necessary due to airline delays out of New Haven, CT. Digital tix were easy. Very organized/timely arrival & greeting in lobby, elevator up to observation floor. I'm a large scale event planner so have extremely high expectations when it comes to logistics, registration, processes. I have to say, 360 has it down. No complaints from this pretty tough customer. The view is fantastic, a must see. Especially coming from always being in NYC or Boston. That flat Midwest expanse reminds me of Los Angeles at Griffith Park, it's magical. Drinks were decent, too. I wasnt expecting much,cso was pleasantly surprised. We didn't do tilt, just b/c husband doesn't like heights ^ I've done plenty of that type of thing in my time. Although, if I go back, I prob would do it. I have no b fear of heights, etc. Bottom line, you have to do 360 if you're in Chi-town. Thought it was great!

360 Chicago Observation Deck Skip-the-Line Tickets

Antonia V

United States
Family
Jul 2026

+1 more

This experience was amazing it was our first time using it and it is the best option to check out the city of chicago with out the hustle of the traffic my family and I enjoyed every second of it and is easy-to-use once you download the app you can see where the next bus is so you dont wait long time on the bus stop we are most definitely going back.

Combo: Chicago Hop-on Hop-off Bus Tour + 360 Chicago Observation Deck Skip-the-Line Tickets

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

Lonyae C

United States
Couple
2 weeks ago
I booked through Headout and had no problems at all. The place was a bit scary being so high up, my ears popped so make sure to chew some gum.

360 Chicago Sip & View

Kristal W

United States
Couple
Sep 2026
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