Cycling Race Calendar in Illinois, United States

Sweet Ride | Bike • Run • Walk

Willow Springs, Illinois, United States

03 Oct, 2026 (Sat)

$30.00 - $50.00

Running, Cycling

5K 40K Ultra

Site M: Redacted

Chandlerville, Illinois, United States

03 Oct, 2026 (Sat)

Free - $50.00

Cycling

Ultra 48.3K +1

Everybody Rides 2026

St. Charles, Illinois, United States

31 May, 2026 (Sun)

Cycling

2.4K 16.1K 46.7K Ultra +1

2026 10th Annual Gold Star 500

Springfield, Illinois, United States

30 May, 2026 (Sat) – 26 Sep, 2026

Free - $500.00

Running, Cycling

Ultra +7

2026 Walk & Roll Chicago

Chicago, Illinois, United States

30 May, 2026 (Sat)

Walking, Running, Nordic ice skating, Cycling

5K 10K 15K +8

Tour de Tunnel Bike Ride Hosted by Revive Vienna

Vienna, Illinois, United States

23 May, 2026 (Sat)

Cycling

16.1K 32.2K Ultra

White Squirrel Roubaix

Olney, Illinois, United States

16 May, 2026 (Sat)

Cycling

49.9K 20K

Ride to Blue Sky

Carterville, Illinois, United States

02 May, 2026 (Sat)

Cycling

Ultra 48.3K 19.3K

Rock River Madness 2026: Dixon, Illinois

Dixon, Illinois, United States

02 May, 2026 (Sat)

Cycling

Ultra 16K Half-Marathon 16.1K +5

Tour de Stooges

Lebanon, Illinois, United States

02 May, 2026 (Sat)

Cycling

24.1K 48.3K Ultra