Cycling & running events in Chicago, 2026

Chicago-Naperville-Elgin Training Notes

Running: The Lakefront Trail runs 5 miles from Ardmore Avenue in Edgewater to 71st Street in South Shore. The trail covers 25 miles and connects back to the lake when you want easy miles. The Columbia Basin and Wooded Island Loop gives you 9 miles. Lincoln Park Run Club has Sunday Group Runs at 9:00 AM CDT, and Riverside Running Club meets Saturdays at 9:30 AM CDT. The Chicago Marathon is the anchor event, with Shamrock Shuffle, Soldier Field 10, Mag Mile, and Naperville Women's Half Marathon & 5K filling the calendar.

Cycling: Naperville riders stack base miles on the Illinois Prairie Path and Great Western Trail because the paths stay easygoing and useful. The East Branch DuPage River Trail and Salt Creek Greenway give a bigger effort when Z2 turns into intervals. The route covers 1 km and gains 399 m. Palos Trail System brings the gravel, and Swallow Cliff might break you with the climbs. Naperville Bicycle Club, Downers Grove Bicycle Club, Major Taylor Cycling Club Chicago, and Chicago Randonneurs keep the rides moving. Bike the Drive, Arlington 500, North Shore Century, and Bike MS: Tour de Farms are anchor rides.

Season: March through October works for both running and riding, and September and October are the best months. June through August can get pretty warm, so locals move long runs, group rides, and tempo work earlier. Chicago runners still train at all times of the year for local races, because the running community is super friendly and always down to cheer you on. McHenry County Bicycle Club changes Tuesday night rides to hiking starting in November, and cyclists also shift toward winter hikes, snowshoeing, and cross-country skiing. The Lakefront Trail stays central, while gravel and limestone routes can feel different after prolonged rain or winter weather.