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Trail Running calendar near Chicago 2025-2026

We have found 44 Trailruns within 80 miles of Chicago. See below where and when you can find the races.

Timely Nonsense - Chicago, IL

Chicago

Timely Nonsense is a playful timed ultrarun in Chicago offering 3, 6, and 12 hour options on a roughly one mile paved loop inside a scenic 58 acre park. Hourly challenges, team relays, and a lively aid and vendor area keep the day fun for r..

October 2026

Tryon Farm 50k

Michigan City - 40 mi from Chicago

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Run scenic trails at Tryon Farm in Michigan City with distances from a 2 mile fun run to a 50k ultra. Enjoy grassy fields, single track and friendly aid stations while supporting the Tryon Farm Institute and the Crazy Legs Race Series.

Saw Wee Kee - Fall Trail Run

Yorkville - 45 mi from Chicago

Enjoy a scenic fall trail run at Saw Wee Kee Park with twisting soft paths, ups and downs and seasonal mud or wildflowers. Chip timed wave starts, unique series medal piece and seasonal swag for early registrants.

St. Pats 24 Hour Race

South Bend - 72 mi from Chicago

Take on the St Pats timed trail races at St Patrick's County Park in South Bend with 24 hour and 12 hour formats on scenic dirt and grass loops. Proceeds benefit the ALS community.