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Chicago

Sports groups in downtown Chicago

18 groups in Goose Island, Streeterville, West Loop, Loop, South Loop, Burnham Park Harbor and nearby. The most listed sports are running (8), swimming (3) and walking (1). 11 are free, 16 welcome beginners and 3 play indoors. The busiest days are Saturday and Friday.
Running8 Swimming3 Walking1 Climbing1 Pickleball1 Fitness1 Kayaking1 Dragon boat1 Sailing1 Skating1

Upcoming races & events

Groups

18 groups

Chicago Backpackers

Hiking · Goose Island (monthly social), Chicago

Monthly social on a Wednesday evening (Nov 18 and Dec 16, 6:30-9:30 pm). Overnight trips need an RSVP on Meetup and a signed release, and attendees must be 18+. The Dec 11-13 Point Beach State Forest cabin trip ($25) is for members with prior camping experience.

Beginner-friendly

Chicago Typhoon Dragonboat Team

Dragon boat · Goose Island / Near North, Chicago

Seasonal: the 2026 season ran May-September with practices every Sunday at a fixed time starting May 17, 2026. The start time is not published; sign up for each practice in advance (20 seats). Team chat is on WhatsApp; email the team for an invite.

Beginner-friendly

Grit Endurance

Running · Streeterville / various, Chicago

Mon & Wed 6pm · Tue, Wed & Thu 6:30am · +3 more

Beginner-friendly

South Loop Runners

Running · South Loop, Chicago

Sun & Sat 9am · Thu 6:15pm

FreeBeginner-friendly

Urban Rivers – Wild Mile kayak river cleanup

Kayaking · Goose Island, Chicago

Two-hour shifts are released one month at a time on Urban Rivers' volunteer page (October 2026 had Sun, Tue and Thu shifts between 9am and 5pm); no November shifts were posted as of Nov 1. Ages 18+ only, and you must finish a kayak safety training before signing up. Weekday daytime shifts are the easiest to get.

FreeBeginner-friendly