Heartbreak Run Chicago offers running training, practice, and speed sessions in Lincoln Park.

Heartbreak Run Chicago is a running community located in Lincoln Park at 2148 N Halsted St. The group provides daily running opportunities with sessions open from Monday through Sunday. Specific training offerings include Tuesday and Thursday heartbreaker practice led by a coach, which features warm-ups, active stretching, drills, and cooldowns along the Lakefront covering 4 to 9 miles. A signature speed session is held on Saturdays from June through October, offering 3 to 6 mile workouts designed to help runners of all fitness levels get faster while having fun. Additionally, the group organizes long runs on Saturdays during the same period, where pace groups are formed based on attendance and water stops are provided. All runs begin and end at the store in Lincoln Park, which also provides bins for gear storage. The organization has been operating since 2009 with a consistent mission to make runners faster and make running fun. Training for the Chicago 2026 marathon begins on June 1st, and the community encourages members to follow them on Instagram at heartbreak.chi for updates on weekly free sessions, upcoming events, and RSVPs.