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

Content Bosses: Bike & Bites

 Sat, 23 May at 11:00 am 31st Street Beach Free

FREEDOM (BIKE) RIDE ON MAJOR TAYLOR TRAIL

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

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

Bikes and Bonfires: S'more Networking

 Fri, 15 May at 06:00 pm Kathy Osterman Beach Free

Wicker Park Pride Ride

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

CyclingxSolidarity 5 Year Anniversary Party

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

RAGBRAI Transportation: End to Chicago powered by Bicycle Illinois

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

Southside Critical Mass Chicago Bicycle Ride

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

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 (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

Bike Vessel ride St. Louis to Chicago 2026

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

Southside Critical Mass Chicago Bicycle Ride (1st Fridays)

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