Trail Run races in Chicago, IL

Looking for trail races near you in Chicago, IL? There are 22 upcoming trail races listed here. The next one is StRides Against Suicide & Overdose on Sat, Aug 1, 2026 at Rogers-Lakewood Park — see the full list below for dates, venues, and registration links, and browse trail races in other cities.

All 5K (257) 10K (67) Half Marathon (53) Marathon (13) Trail Run (22)

★ Featured Sat, Sep 5, 2026 Naperville Trails Half Marathon & 10K 3S580 Naperville Rd · Wheaton, IL · From $50 5K10KHalf MarathonTrail Run Trail Register →
Sat, Aug 1, 2026 StRides Against Suicide & Overdose Rogers-Lakewood Park · Valparaiso, IN · From $40 5KTrail Run Trail
Sat, Aug 8, 2026 The Next Loop Endurance Series | Deer Grove East 1599 Pepper Tree Dr · Palatine, IL · From $90 5K10KMarathonTrail Run Trail
Sat, Aug 15, 2026 The Next Loop Endurance Series - Busse Woods E Higgins Rd & Arlington Heights Rd · Elk Grove Village, IL · From $90 5K10KMarathonTrail Run Trail
Sat, Aug 29, 2026 The Next Loop 40M/50M Challenge | Half Day Forest Preserve 24255 N Highway 21 · Vernon Hills, IL · From $200 Half MarathonTrail Run Trail
Sat, Aug 29, 2026 The Next Loop Endurance Series | Half Day Forest Preserve 24225 N HWY 21 · Vernon Hills, IL · From $90 5K10KHalf MarathonMarathonTrail Run Trail
Sat, Aug 29, 2026 Tails on the Trail 5K & 1-Mile Wag & Walk 21800 Central Ave · Matteson, IL · From $30 5KTrail Run Trail
Sat, Sep 12, 2026 CHICAGO TRAIL RUNNING FESTIVAL 27064 Dutton Rd · Beecher, IL · From $35 5K10KTrail Run Trail
Sat, Sep 26, 2026 Bloomingdale Trail 5K 1834 N LAWNDALE AVE · Chicago, IL · From $5 5KTrail Run Trail
Sat, Oct 3, 2026 Creekside Trails Race 5k & Team 30k Hosted by Valparaiso Firefighters Local 1124 2551 Clifford Rd. · Valparaiso, IN · From $40 5KTrail Run Trail
Sat, Oct 3, 2026 Chicago Vocational Alumni Association, Inc. 5K Torch Trail 2100 E 87th Street · Chicago, IL · From $45 5KTrail Run Trail
Fri, Oct 23, 2026 Haunted Highlander Assault Trail Run 42w813 Reinking Rd. · Pingree Grove, IL · From $50 5KTrail Run Trail
Sat, Oct 24, 2026 Run for Your Life Race at Robinson Lake - 5K and Haunted Fun Walk/Run 5240 S Liverpool Rd · Hobart, IN · From $15 5KTrail Run Trail
Sat, Nov 14, 2026 The Forge Trail Run Festival 227 Heritage Quarries Dr. · Lemont, IL · From $45 5K10KHalf MarathonTrail Run Trail
Sat, Nov 28, 2026 Turkey Trails - Greater Chicago Route 59 Access · Shorewood, IL · From $17 5K10KHalf MarathonTrail Run Trail
Sat, Jan 23, 2027 Fox Valley Winter Challenge Trail Series 5K 39W115 Main St · Batavia, IL · From $60 5KTrail Run Trail
Sat, Jan 23, 2027 Fox Valley Winter Challenge Trail Series 5k/8k/10k 39W115 Main St. · Batavia, IL · From $40 5K10KTrail Run Trail
Sat, Feb 20, 2027 Fox Valley Winter Challenge Trail Series 8K 1680 5th Ave · Aurora, IL · From $65 Trail Run Trail
Sat, Mar 13, 2027 Muddy Shamrock @ The Forge 227 Heritage Quarries Dr. · Lemont, IL · From $40 5KHalf MarathonMarathonTrail Run Trail
Sun, Mar 14, 2027 Fox Valley Winter Challenge Trail Series 10K 3795 Campton Hills Dr. · St. Charles, IL · From $70 10KTrail Run Trail
Sat, May 8, 2027 F^3 Cap Sauers Trail Marathon & 10 Mile 11200 S Willow Springs Rd · Palos Hills, IL · From $60 10KMarathonTrail Run Trail
Sat, Jun 12, 2027 Waubonsee Foundation Trail Run Tennis & Pickleball Court Complex · Sugar Grove, IL · From $30 5K10KTrail Run Trail

New to the distance? Read trail vs. road racing, or set your target with the pace chart.

Quick answers

When is the next trail race in Chicago?

The next Trail Run in Chicago, IL is StRides Against Suicide & Overdose on Sat, Aug 1, 2026 at Rogers-Lakewood Park.

How many trail races are coming up near me in Chicago?

There are currently 22 upcoming trail races listed in Chicago, IL, each with a date, venue, and direct registration link.

What's the cheapest Trail Run in Chicago?

The lowest listed entry right now is Bloomingdale Trail 5K at from $5. Registration prices usually rise as race day nears, so early entry is cheapest.