There’s something special about fall running in the Midwest—cooler temps, vibrant foliage, and a calendar packed with races that feel like celebrations. Illinois delivers on all fronts, offering courses that weave through forest preserves, historic towns, and the Chicago skyline. Whether you’re chasing a personal best or just looking for a fun weekend adventure, the Land of Lincoln has a half marathon waiting for you.
Here are four standout Illinois half marathons coming up this September and October.
Naperville Trails Half Marathon & 10K
Date: Saturday, September 5, 2026
Location: Wheaton, Illinois
Quality Score: 81/100
Kick off Labor Day weekend on the trails. The Naperville Trails Half Marathon takes runners through the scenic paths of the DuPage River Trail system, mixing crushed limestone and paved sections. It’s a Runner Favorite for good reason: well-organized aid stations, a welcoming vibe, and a course that’s fast enough for a PR but pretty enough to make you forget you’re racing. Arrive early to enjoy post-race refreshments and the small-town energy of Wheaton.
Hidden Gem Half Marathon
Date: Saturday, September 12, 2026
Location: Flossmoor, Illinois
Quality Score: 80/100
This race lives up to its name. Set in the south suburbs of Chicago, the Hidden Gem Half Marathon offers a rolling, shaded course through quiet residential neighborhoods and parks. The community support is strong, with volunteers and spectators lining the route. It’s an excellent choice for first-timers or anyone who prefers a low-key atmosphere with plenty of heart. Plus, the post-race food is legendary.
2026 Life Time Chicago Half Marathon + 5K
Date: Sunday, September 27, 2026
Location: Chicago, Illinois
Quality Score: 73/100
If the skyline is your motivation, this is the one. The Life Time Chicago Half Marathon starts and finishes in Jackson Park, taking runners along the lakefront with views of the city, the Museum of Science and Industry, and Lake Michigan. It’s a flat, fast course perfect for a late-season PR. The event is well-supported with pacers, entertainment, and a festive finish area. Expect big crowds and big energy.
Long Grove's Oktoberfest Half Marathon, 10K & 5K
Date: Saturday, October 3, 2026
Location: Long Grove, Illinois
Quality Score: 78/100
Celebrate Oktoberfest with a run through one of Illinois’ most charming historic villages. Long Grove’s Oktoberfest Half Marathon winds through covered bridges, past apple orchards, and into downtown Long Grove, where post-race festivities include brats, beer, and live music. The course has gentle hills and plenty of fall color. It’s a perfect capstone to your fall racing season.
Find Your Next Illinois Half Marathon
These four races are just the beginning. Illinois has seven upcoming half marathons in this window, so there’s a perfect fit for every runner—whether you favor trails, city streets, or small-town charm.
Check out the full Half marathons in Illinois directory to see all upcoming events, compare dates, and register early.