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

Fulton Market "Loop Da Loop" 5k Run + Street Festival

 Sun, 26 Jul at 08:00 am 954 W Fulton Market, Chicago, IL 60607-1323, United States

Chicago Triathlon

 Sat, 22 Aug at 07:00 am Monroe Harbor

4th ANNUAL FREEDOM (BIKE) RIDE ON MAJOR TAYLOR TRAIL

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

Wicker Park Pride Ride

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

Open Water Swim (OWS) Chicago - Supertri Chicago Triathlon Swim Clinic Series

 Tue, 07 Jul at 04:00 pm Ohio Street Beach

Eli's Cheesecake x Rudy's Cycle and Fitness Father's Day Bike Ride

 Sun, 21 Jun at 08:00 am Eli's Cheesecake Company Free

CyclingxSolidarity 5 Year Anniversary Party

 Sat, 15 Aug at 04:00 pm Burnham Park Promontory Point Free

Running Tour of LGNSQ with Ben Tanzer

 Sat, 13 Jun at 09:00 am City Lit Books

RAGBRAI Transportation: End to Chicago powered by Bicycle Illinois

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

Pilsen Canalport Cleanup with Bike Buses & Afterparty!

 Sat, 06 Jun at 10:00 am 1966 S Canalport Ave USD 0 to 13

Southside Critical Mass Chicago Bicycle Ride

 Fri, 03 Apr 1300 E 55th St, Chicago, IL 60615-5302, United States

Southside Critical Mass Chicago (Wear Orange) Bicycle Ride

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

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

League of American Bicyclists - League Cycling Advocate Workshop - Chicago

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

Everyone Belongs in History: 1880s Black Founders of Pullman’s North End

 Sat, 20 Jun at 10:45 am 610 E 111th St Free

Roscoe Village Kidical Mass 2026

 Sun, 07 Jun at 10:00 am 3500 N Hoyne Ave, Chicago, IL 60618-6112, United States

July 4th Old School Ride

 Sat, 04 Jul at 07:45 am 3031 W Armitage Ave, Chicago, IL, United States, Illinois 60647

Bike Vessel ride St. Louis to Chicago 2026

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

Simon Elijah with Kim Schaefer

 Wed, 19 Aug at 07:00 pm UncommonGround - Lakeview USD 13

Southside Critical Mass Chicago Bicycle Ride (1st Fridays)

 Fri, 11 Apr at 05:45 pm Nichols Park Plaza (South End by Fountain) Free

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