Adventurous Things to Do in Chicago

Top Adventurous Things to Do in Chicago, IL

Best Adventurous Things to Do in Chicago

  • Traveller favourites
    Things to do ranked using Tripadvisor data including reviews, ratings, photos, and popularity.
  • Traveller ranking
    Highest rated attractions on Tripadvisor, based on traveller reviews.
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40 places sorted by traveller favourites
Things to do ranked using Tripadvisor data including reviews, ratings, photos, and popularity.
Showing results 1-30 of 40

What travellers are saying

  • Heather B
    2 contributions
    We 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 2022
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • gemmap81
    Liverpool, UK129 contributions
    Been 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 2019
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • ss101529
    Chicago, IL1 contribution
    We 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 2021
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • Katarina L
    1 contribution
    The hardest escape room that I have done! Very fun, very challenging, definitely would recommend. Joanna was the best hostess!
    Written 1 May 2022
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • familiadeicaza
    Panama Province, Panama40 contributions
    Jeremy 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 2021
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • Megan F
    1 contribution
    I 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 2021
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • Sarah Horn
    Chicago, IL15 contributions
    Went 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 2020
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • Mazzy M
    1 contribution
    John was a great instructor and axe throwing was super fun with him! By the end, my friend and I were pros!
    Written 6 August 2020
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • James Meador
    1 contribution
    Magic 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 2021
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • Abdul R
    1 contribution
    this 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 every
    Written 4 January 2021
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • Mitchell W
    Chicago, IL2 contributions
    My 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 2022
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • Paula R
    8 contributions
    Fun and interesting part of the city! I never knew about! Margaret was very entertaining and knowledgeable!
    Written 1 February 2020
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • Aliandkan
    Nashville, TN1 contribution
    It was our first time, we made it out with a bit of help. Definitely will return. Staff was very friendly.
    Written 13 November 2020
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • Mitch T
    Saint Louis, MO1 contribution
    Amazing 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 2022
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • Cara H
    Flushing, MI17 contributions
    One 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 2022
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.