Illinois Obstacle Race Calendar 2025-2026

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Explore the best obstacle runs in Illinois for 2025-2026! Our updated list features 258 exciting races across the region. Find your next race in Illinois below and join the running community at these great events!

October 2025
Oct
4
Saturday

Scarecrow Scramble

5 km
Oct
4
Saturday

Mattoon Last Chance Triathlon

Triathlon
Oct
4
Saturday

Long Grove's Prairie State Half Marathon

5 km 10 km 13 mi
Oct
4
Saturday

Your Ways 5K

5 km
Oct
4
Saturday

Stone & Steel Spooky 5k

5 km
Oct
5
Sunday

Cheesy Pretzel 5K

5 km
Oct
5
Sunday

Bronzeville 5K

5 km
Oct
5
Sunday

Chicago 5k

5 km
Oct
5
Sunday

Shoreline Classic

5 km 15 km
Oct
11-12
Sa - Su

Arrowhead Endurance Run

Backyard Ultra 3 hr 6 hr 12 hr 24 hr
Oct
11
Saturday

Des Plaines River Trail Races

Trail Run 13 mi 26 mi 50 km 50 mi
Oct
11-12
Sa - Su

Farmdale Trail Run

Trail Run 10 km 13 mi ... 50 mi 100 mi
Oct
12
Sunday

Chicago Marathon

Oct
18
Saturday

Spooky Sprint - Chicago

5 km 10 km 13 mi
Oct
18
Saturday

Run Stephenson County

5 km 10 km 13 mi
Oct
18
Saturday

Shake Your Trail Feather Trail Run

Trail Run 5 km 10 km 13 mi 50 km
Oct
18
Saturday

Rosehill Cemetery 'Crypt' 5K

5 km
Oct
18
Saturday

Country Sole Half Marathon

5 km 10 km 13 mi
Oct
19
Sunday

Run with the Nuns

5 km
Oct
19
Sunday

Naperville Half Marathon

5 km 10 km 13 mi
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