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Running calendar near South Side 2025-2026

Explore the top running races near South Side for 2025-2026! We've gathered 42 exciting races in the area. Check out our detailed list below to find your next local race.

October 2025
Oct
18
Saturday

Rosehill Cemetery 'Crypt' 5K

5 km
Oct
19
Sunday

Run with the Nuns

5 km
Oct
19
Sunday

Naperville Half Marathon

5 km 10 km 13 mi
Oct
25
Saturday

Fancy Nonsense 25K/50K

Trail Run 25 km 50 km
Oct
26
Sunday

Haunted Halloween Half Marathon

5 km 13 mi
Oct
26
Sunday

Endeavor Health Fraidycat 8k

5 km 8 km
November 2025
Nov
8
Saturday

Jail Break 5K

5 km
Nov
15
Saturday

The Forge Trail Run Festival

Trail Run 10 km 20 km 30 km 60 km
Nov
27
Thursday

Thornton Turkey Trot

5 km
Nov
27
Thursday

Flying Turkey 5K

5 km
December 2025
Dec
13
Saturday

Candy Cane Course - Chicago

5 km 12 km
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