Cupid's Undie Run - Chicago
Chicago, Illinois, United States
Feb, 2027 (TBD)
Fun Run, Fundraiser
Race Information
This February be a part of something great. There are fewer things in this world that feel better than getting half naked for charity. Cupid's Undie Run lets you live that dream in the winter, in Chicago.
The run itself happens around Valentine's weekend each year and is a “brief” fun run that takes place in the middle of a BIG party. That’s right: party, run (a mile-ish, at your own pace), party – all to find a cure for neurofibromatosis (NF), a genetic disorder that causes tumors to grow on nerves throughout the body and affects 1 in every 3,000 births.
Be a part of something great. Last year Cupid’s raised over $3.5 Million to #EndNF and they’re relying on YOU to join and make this year’s fundraising the biggest and best yet. Start a team, join a team, or just run solo and make some new friends!
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👍 Run Pick of the Month: Milwaukee Lakefront Marathon
📍Milwaukee - October 3-4, 2026
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😄 Why We Like This Run
✅PR-friendly terrain
✅ Incredible community and high-fives at every hydration station
✅ Post-race celebration with local brews, great food, and a lakefront festival that only Milwaukee can throw
Ready to experience one of the most scenic courses in the Midwest? Enjoy a fast, flat, and famously beautiful run along the stunning shores of Lake Michigan. Whether you are aiming for a Boston qualifying time or crossing your first finish line, this race offers the perfect backdrop for your next big achievement.
With options from the 5K through to the Marathon, every mile is designed to keep you moving and inspired.
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Race Facts
Race Size: 500 - 1,000
Course Type: Road
Boston Qualifier: No
Kids Run: No
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