Outdoor activities in West Side

Top 10 Outdoor Activities in West Side (Chicago)

Outdoor Activities in West Side

  • 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.
Outdoor Activities
Traveller rating
Neighbourhoods
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13 places sorted by traveller favourites
Things to do ranked using Tripadvisor data including reviews, ratings, photos, and popularity.

What travellers are saying

  • MadMike96
    Madison, WI46 contributions
    Great urban trail to walk, run, or bike. No cross traffic. Was not too busy on a weekday. Well maintained and lots of access points. 2.7 miles long.
    Written 21 June 2021
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • Joseph B
    Chicago, IL101 contributions
    I nice, clean, modern way to cut across neighborhoods. This is a multiuse trail, with walkers, joggers, bikers, skaters, strollers, etc, so be prepared.
    Written 11 January 2021
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • Tara K
    2 contributions
    Very fun and slightly challenging! The lady and guy in the office (forgot their names) were so nice and easy going. The guy also came down to the beach and helped us get started. We had a wonderful time !
    Written 4 July 2022
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • Paige N
    2 contributions
    This walking tour was great! I had family visit from out of town and Leeuw customized our tour to what my family’s interests are . She not only took us to great spots and knew all the history behind them but also lead us to different shops/ bakery’s that we had time
    To explore ! It was a great activity for my family and I and I definitely recommend !
    Written 18 May 2021
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • Mark B
    Indian Rocks Beach, FL75 contributions
    Two roomettes (spouse and I, second for adult daughter). Adequate and good enough privacy. Included meals in the dining car, shower and toilets private room our car. Upper bunk was a bit tight and only barely “sleepable”. Lower bunk was better (we swapped and my wife is a bit smaller and sleeps more soundly). Food was adequate or slightly above. The desserts were better in most cases. Good variety for two days.

    Staff was mostly good and friendly. Helpful. The cabin steward was off and on. He did NOT like it when I put our own beds down and said (only half joking), “Hey, you’re getting into my pocket there.” Which I wasn’t, as is tipping anyway—but, I understood, others might do their own and then NOT tip.

    I always wanted to take a cross country train and would never do it sleeping even in the first class seating. So this worked. I have traveled by train in Europe and Japan and AmTrak could learn something from them.

    Over all it was “good enough” and I got exactly what I paid for. But in my book that is a Three. I do educational presentation for a living and even tell my audience to give me a “3” if I met their expectations. Four and Fives are for exceeding expectations. Didn’t happen here.
    Written 4 June 2022
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • danotwenty
    Trumbull, CT48 contributions
    Amazing way to see Chicago, great experience for a family with kids!!! Thank you to the staff, so awesome! Take a few minutes to check out the view by the locks, it is amazing.
    Written 26 June 2022
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • Colin Knight
    5 contributions
    I spent an amazing 4.5 hours touring Chicago neighborhoods with Steve. He knows an amazing amount about the art, architecture, and history along the ride. He totally customizes the tour based on your interests. After the trip he provided me with a detailed map of the route with photos of some of the stops and with informational links. A+ experience.
    Written 17 August 2021
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • Tour733807
    Chicago, IL3 contributions
    I rented the g63 and it was honestly a fantastic experience. The car was so pristine and my husband LOVED IT! I surprised him with the booking for date night for four hours ($400) we picked the car up off of their location and went to dinner to Tao which they also helped to reserve a table for us.
    Written 8 March 2019
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • GuatemalaCiclista
    Chicago, IL357 contributions
    The north branch of the Chicago River has a celebrated history when it comes to natives and settlers alike. The woods have produced evidence of indigenous settlement and even the likes of Kinzie put roots down in these parts on the river. I grew up in these woods so for me nostalgia plays a part in its magnetism. The begining of a bike path starts right on Foster and continues north to the Chicago Botanical Gardens. I would only hope that future visitors be more litter conscious and respect the well trodden dirt paths along the river bank. Read up on the history before visiting and the place will come alive.
    Written 24 December 2020
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.