Unsanctioned races in Chicago
Illinois, USA
Upcoming
- Sat 11/07/26CyclingSign up
Cranksgiving Chicago
- Sun 11/15/26RunningOn ALLEYKAT →
Star of David 5K 2026
The scene
Chicago’s courier alleycats often run through the Loop, because checkpoints are places messengers visit for work. The Chicago Courier Classic carries on the Cutting Crew Classic, which ran from the mid-2000s until the pandemic, and Cosmic Bikes runs a Northwest Side Cranksgiving each November, set for November 7 in 2026.
Notable races
- CyclingWebsite ↗
Chicago Courier Classic
A three-day courier event built around alleycats, including one whose checkpoints were five Loop post offices and a roughly 40-mile citywide race.
Recently run on ALLEYKAT
Running[00]
No running race in Chicago has run on ALLEYKAT yet.
Cycling[00]
No cycling race in Chicago has run on ALLEYKAT yet.
How races get in here
The directory is curated by ALLEYKAT. Races timed on the app appear in their city on their own once they have a date or have been run, and everything else is added by hand after we have checked it against the organiser’s own page. There is no form and no fee.