Endurance Events in Chicago, IL
The Chicago, IL race calendar is stacked with 118+ events. Local favorites span running, cycling, triathlon, drawing athletes from across Illinois and beyond. Browse the full schedule below, filter by sport, and lock in your next start line.
Browse by Sport
Upcoming Events in Chicago
Cycling
RAGBRAI Transportation: Chicago to the Start of RAGBRAI powered by Bicycle Illinois
July 18, 2026
Chicago, IL
Running
Stan's Donut 10K, 5K, and Kids Dash
Chicago, IL
Running
Stan's Donut 10K, 5K, and Kids Dash
July 19, 2026
Chicago, IL
Triathlon
SuperTri Chicago Triathlon
Chicago, IL
Triathlon
SuperTri Chicago Triathlon
August 15, 2026
Chicago, IL
Cycling
Prostate Cancer Awareness 5K Walk/Run/Bike-Most Worshipful Prince Hall Grand Lodge of IL (one race four locations simulantaneously)
August 15, 2026
Chicago, IL
Running
Run to Breast Cancer 5K/10K/13.1 CHICAGO/EVANSTON
Chicago, IL
Running
Run to Breast Cancer 5K/10K/13.1 CHICAGO/EVANSTON
August 29, 2026
Chicago, IL
