Cycling Events in Chicago

Check out happening cycling events all around Chicago, IL

World Naked Bike Ride Chicago 2026 20th Anniversary

 Sat, 11 Jul at 05:00 pm TBD Free

Chicago Worldwide Bicycle Day Ride!

 Sun, 19 Apr at 12:00 pm Palmer Square Park

FREEDOM (BIKE) RIDE ON MAJOR TAYLOR TRAIL

 Fri, 19 Jun at 06:00 pm Dan Ryan Woods Pavilion Free

Southside Critical Mass Chicago Bicycle Ride

 Fri, 03 Apr at 05:45 pm 1300 E 55th St, Chicago, IL 60615-5302, United States

Wicker Park Pride Ride

 Sun, 14 Jun at 10:00 am Trek Bicycle Chicago Wicker Park Free

Self Care Sunday-Networking Event for Therapists

 Sun, 03 May at 01:00 pm SALT Fitness Chicago USD 50

2026 Chicago A.B.AT.E. AWARNESS RUN

 Sun, 26 Apr at 08:30 am TBD

Free Wellness Day: Seasons of Change

 Sat, 25 Apr at 10:00 am In Touch & Motion Free

Pink With A Purpose-2nd Annual Suicide Prevention Ride

 Sat, 12 Sep at 09:00 am TBD

RAGBRAI Transportation: End to Chicago powered by Bicycle Illinois

 Sat, 25 Jul at 03:30 pm Crowne Plaza Chicago West Loop by IHG Free

League of American Bicyclists - League Cycling Advocate Workshop - Chicago

 Thu, 17 Sep at 08:30 am Illinois Medical District USD 55 to 109

Bike Vessel ride St. Louis to Chicago 2026

 Wed, 26 Aug at 06:00 am St. Louis, MO

RAGBRAI Transportation: Chicago to the Start powered by Bicycle Illinois

 Sat, 18 Jul at 07:00 am Crowne Plaza Chicago West Loop by IHG Free

BEGINNER FRIENDLY Tuesday Night Ride 369 Sponsored By Electric Movement & Ryamer

 Tue, 07 Apr at 07:00 pm Electric Movement

Indoor Triathlon at Midtown Athletic Club Chicago

 Sun, 12 Apr at 08:00 am Midtown Athletic Club

HumboldtTown Safe Streets Bike Ride!

 Sun, 12 Apr at 11:00 am The Center of Order and Experimentation Free

DPS Cycle

 Sat, 23 May at 10:00 am 2134 W 18th St USD 189 to 349

Burrito Brigade Chicago

 Sun, 24 Aug at 11:30 am Morgan Park Presbyterian Church Free

Burrito Brigade Chicago Bike Distribution

 Sun, 13 Jul at 02:30 pm Plaza Tenochtitlán Free

Bike Repair Skill Share

 Thu, 09 Apr at 07:00 pm Kozy's Cyclery Megastore Free