Cupid's Undie Run - Chicago
Chicago, Illinois, United States
Feb 27, 2027 - Saturday
Fun Run
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: SKECHERS Hot Chocolate Run – Chicago
📍Chicago - Sunday November 1, 2026
💸 Get a free tumbler. Use Code RGCHI
😄 Why We Like This Run
✅ Exclusive SKECHERS Hot Chocolate Run Fleece
✅ Chocolate Fondue Finisher’s Mug
✅ Free Race Photos
Ready for "America’s Sweetest Race"? Join thousands of runners in the heart of Chicago for the iconic SKECHERS Hot Chocolate Run! Whether you’re tackling the 5K, 10K, or the signature 15K, every mile is fueled by fun and every finish line is paved with chocolate.
Bring your friends, bring your family, and get ready to earn that cocoa - because there’s truly no finish line sweeter than this one. Sign up now and prepare to indulge!
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Race Facts
Race Size: 500 - 1,000
Course Type: Road
Boston Qualifier: No
Kids Run: No
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