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Chicago Cupid’s Undie Run

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February 22, 2025

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 in about a dozen cities across the country. It 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.

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And let’s be honest, that’s pretty darn gay.
 

Sign up for emails from Fagabond for advice, reviews, and deals to make your vacation as gay as you are.

And let’s be honest, that’s pretty darn gay.
 

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