Here is a list of bike races in the Chicago area, plus things to do on a bike for May of 2025. Events are divided into races for competitive cycling, and rides for social outings or non-competitive endurance events (like brevets).
If you’re looking for a regular group ride, check out Half Acre Cycling’s group ride finder.
Races:
May 3: 1904 Gravel Race – Illinois City, IL
May 4: Harvard 33.3k Time Trial – Harvard, IL
May 6: Labagh Woods Ladies’ Night Crits – Chicago, IL
May 13: Labagh Woods Practice Crits – Chicago, IL
May 15: Thursday Night Track Racing – Northbrook, IL
May 18: Kankakee 20k Time Trial – Kankakee, IL
May 24: ABD Memorial Day Weekend Omnium #1 – Wood Dale, IL
May 25: ABD MDW Omnium #3 – Wood Dale, IL
May 25: Kane County Ten Mile Time Trial – Maple Park, IL
Rides
May 3: The Chicago Tweed Ride – Oak Park, IL
May 3: Barrington Boomerang 200k – Barrington, IL
May 4: Pastry-Bike-Pastry – North Aurora, IL
May 17: Pedalpalooza – Crystal Lake, IL
May 17: Chicago-Milwaukee-Chicago300k – Chicago, IL
May 18: Everybody Rides – St. Charles, IL
May 24: Blackhawk Country Roads – Rockford, IL
May 25: McHenry County Century – Lake in the Hills, IL
May 30: Chicago Critical Mass – Chicago, IL
May 31: Aurora City of Lights 400k – Aurora, IL
Pic from The Garden, Chicago’s north side bike jumping park.