Best time to go to Chicago

Cupid's Undie Run 2019

Chicago loves running wearing hardly anything. Of course, for the good cause

Cupid's Undie Run in Chicago 2019 - Best Time
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Imagine a crowd of cupids wearing only underwear and running somewhere? Join the Cupid's Undie Run and help those awesome and cool people to raise some more money for the Children's Tumor Foundation!

Cupid's Undie Run in Chicago - Best Season 2019

The fastest participants will earn prizes, like shirts, underwear and engraved flasks. There will also be an afterparty at John Barleycorn where you can relax after the run and check out some of the funniest costumes that your fellow runners wore.