Points of Interest & Landmarks • Architectural Buildings
Downtown / The Loop
Top Adventurous Things to Do in Chicago, IL
Best Adventurous Things to Do in Chicago
- Traveller favouritesThings to do ranked using Tripadvisor data including reviews, ratings, photos, and popularity.
- Traveller rankingHighest rated attractions on Tripadvisor, based on traveller reviews.
Category types
Traveller rating
Neighbourhoods
Good for
40 places sorted by traveller favourites
Things to do ranked using Tripadvisor data including reviews, ratings, photos, and popularity.
Escape Games • Game & Entertainment Centres
Near North Side
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Open now
Escape Games • Amusement & Theme Parks
Downtown / The Loop
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Segway Tours • Ghost & Vampire Tours
Downtown / The Loop
Theatres • Theatre & Performances
Downtown / The Loop
Game & Entertainment Centres
Northwest Side
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Open now
Game & Entertainment Centres
Downtown / The Loop
Theatre & Performances
Downtown / The Loop
Escape Games • Game & Entertainment Centres
West Town
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Open now
City Tours • Literary, Art & Music Tours
Downtown / The Loop
Escape Games • Game & Entertainment Centres
Bucktown
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Open now
Theatres • Comedy Clubs
Downtown / The Loop
Admission tickets from HK$233.33
Escape Games
Near North Side
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Open now
Game & Entertainment Centres
West Loop
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Open now
Bars & Clubs • Theatre & Performances
Far North Side
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Open now
City Tours • Segway Tours
Downtown / The Loop
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Open now
Kayaking & Canoeing
Downtown / The Loop
Boat Hire • Kayaking & Canoeing
Near North Side
City Tours • Cultural Tours
Near North Side
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Open now
Segway Tours • Bike Tours
Millennium Park
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Open now
Escape Games
Near North Side
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Open now
Game & Entertainment Centres
Downtown / The Loop
Game & Entertainment Centres
North Side
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Open now
Showing results 1-30 of 40
What travellers are saying
- Heather B2 contributionsWe pre-purchased our tickets and were able to walk right onto the elevator with no waiting. The area was clean and the bar was well stocked. The app you could download didn't ever work, but the views of the water and the city were breathtaking.Written 9 May 2022This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
- gemmap81Liverpool, UK129 contributionsBeen up to the top of lots of big famous buildings around the world. First to have one of these so had to have a go. Extra charge on top of entrance fee though which makes it a bit overpriced.Written 30 December 2019This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
- ss101529Chicago, IL1 contributionWe did the Heist Escape Room and had so much fun. There were so many unique puzzles that we were all able to contribute. This is a great team building experience and would highly recommend.Written 28 October 2021This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
- Katarina L1 contributionThe hardest escape room that I have done! Very fun, very challenging, definitely would recommend. Joanna was the best hostess!Written 1 May 2022This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
- familiadeicazaPanama Province, Panama40 contributionsJeremy our guide was very friendly, funny and informative. He took pictures of us as we stopped in each highlight. It is a comfortable way to cover a large area and make the most out of your time in the city. Just hopping on the segway its fun on its own. Im now a segway fan and will take these types of tours whenever possible. The office team was also very helpful. Just a wonderful experience.Written 1 October 2021This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
- Megan F1 contributionI highly recommend this show!! Dennis is a true entertainer! It’s was intimate, classy, amazing and I honestly was in awe of his magic! Loved every minute of it!!Written 7 September 2021This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
- Sarah HornChicago, IL15 contributionsWent for my husband's birthday. Fun competing against each other. We had someone who works there show us the basics and kept score for us. They have league's, my husband will most likely be joining one :).Written 5 March 2020This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
- Mazzy M1 contributionJohn was a great instructor and axe throwing was super fun with him! By the end, my friend and I were pros!Written 6 August 2020This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
- James Meador1 contributionMagic Penthouse really hit the spot after a long workday! I went solo and was immediately introduced to fun, like-minded people. I was transported into a world of multiple live, simultaneous shows. It was a feast for the senses and the hosts treating me like a VIP make me feel like an included part of the overall experience. The venue was a colorful and lively Latin American theme, with top notch drinks and the plentiful food was super on point. The acts combined humor, skill, and world class magic knowledge. I honestly can't say enough about how impressed I was. I would highly recommend this entertainment concept with no reservations. If you haven't visited already, get your tickets now!Written 20 November 2021This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
- Abdul R1 contributionthis is my view ident there with my hoverboard and it said so fun and then you should have called you back downtown to go look at people and the people riding hoverboards thank you for watching myAll 4 without having an account atAll 4 without having account everyWritten 4 January 2021This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
- Mitchell WChicago, IL2 contributionsMy family and I were drawn to Escape Artistry by the creative, Chicago-themed game rooms. We were also pleased to find an affordable, private escape room. We signed up for the Railcar. The journey through the Wicker Park building was very exciting. There was an old elevator and neat paintings. The room itself was very cool and made from recycled materials.
Though I've done a few rooms around Chicago, some of my family were brand new to escape games. This room had puzzle that ranged in difficulty, so everyone had something they could contribute. More advanced gamers might find themselves a little frustrated with some misleading puzzles. Additionally, clues were readily provided, so if you don't want them you may have to say that up front. But for the gamer who is just out to have fun, Escape Artistry is the one for you!Written 18 March 2022This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC. - Paula R8 contributionsFun and interesting part of the city! I never knew about! Margaret was very entertaining and knowledgeable!Written 1 February 2020This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
- AliandkanNashville, TN1 contributionIt was our first time, we made it out with a bit of help. Definitely will return. Staff was very friendly.Written 13 November 2020This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
- Mitch TSaint Louis, MO1 contributionAmazing to of the Chicago architecture with an amazing crew!!! Cpt Matt and Jake the Showman really know how to make this tour of the city fun and memorable!Written 4 May 2022This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
- Cara HFlushing, MI17 contributionsOne of our top experiences in years of coming to Chicago. The group of actors were fun and raunchy, breaking down Macbeth into a side splitting tale that allowed anyone to follow along. If you have a questionable sense of humor, like to drink (or at least don't mind being one of the sober few), you will thoroughly enjoy every minute of this "Whose Line Is It Anyways" meets Shakespeare production.
There wasn't a bad seat in the tiny house. We bid on the King and Queen thrones and won, spending the evening being pampered, part of the production, and on the only seats with cushions. It was worth the $.
Be prepared to spend 90 minutes laughing, being included in the actors scenes, given free drinks here and there, and blushing once or twice.
Do not come here if swearing offends you, you mind sitting cheek to cheek with your neighbor, you frequent AA, or dirty jokes make you uncomfortable.Written 20 February 2022This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
