RaceReady 5KRace-Backwards C25K
Home/5K Races/IL/Chicago
Chicago, Illinois Local Race Hub

Best 5K Races in Chicago, IL

Fast, pancake-flat skyline courses along Lake Michigan and historic parks.

2 upcoming 5K races found in Chicago.Next local event kicks off in 42 days. Ready to start training?
Start Countdown Plan →

Upcoming Chicago 5K Races

Select a race to reverse-engineer your day-by-day training countdown

In 42 Days Flat & Fast PR

Chicago Lakefront Skyline 5K

Wed, Oct 21, 2026
Grant Park - Butler Field, Chicago, IL

Pancake-flat course hugging Lake Michigan with unobstructed views of Willis Tower and Museum Campus. The definitive Chicago running experience.

#Flat & Fast#Waterfront#Scenic Park $45
In 72 Days Flat & Fast PR

Chicago Lincoln Park Turkey Trot 5K

Fri, Nov 20, 2026
Lincoln Park South Field, Chicago, IL

A beloved Thanksgiving tradition! Stroll or sprint through Lincoln Park’s tree-lined avenues with thousands of fellow runners.

#Turkey Trot#Family Friendly#Charity $38 - $42
Local Runner Knowledge Base

Running in Chicago: Trails, Weather & Tips

With its iconic 18-mile paved Lakefront Trail, Chicago is famous for having some of the flattest, fastest PR-friendly 5Ks in the country. Grant Park and Lincoln Park frequently host charity runs, holiday turkey trots, and beer garden 5Ks.

Top Training Trails in Chicago
  • Chicago Lakefront Trail (18.5 miles)
  • The 606 (Bloomingdale Trail)
  • Humboldt Park Loop
Weather & Race Day Advice

Watch for lake breeze resistance in early spring and late fall. Flat courses make pacing easy for first-time runners.

Picked your Chicago 5K race?

Generate an audio-guided interval schedule built backwards from your starting gun.

Build Countdown Plan Free