Cupid's Undie Run - Chicago

Dare to bare for a fantastic cause at Cupid's Undie Run - Chicago, set for Saturday, February 28, 2026, in the vibrant Wrigleyville neighborhood. This unique 1-mile fun run isn't just a race; it's a spirited charity event where participants brave the Chicago winter in their skivvies or fun costumes to raise awareness and funds for Neurofibromatosis (NF) research.

The day kicks off and concludes with a lively party at Slugger's Sports Bar, providing both a pre-run celebration and an epic after-party with dancing and drinks. The "mile-ish" course takes runners through the streets of Wrigleyville, often including a jog down Clark Street or around Wrigley Field, promising an unforgettable urban backdrop for this unconventional dash. With typical race day conditions in late February seeing highs around 40°F and lows near 26°F, and only an 8% chance of precipitation, the chilly weather adds to the exhilarating and slightly audacious atmosphere that runners embrace.

Cupid's Undie Run is renowned for its vibrant, fun-loving community and its profound impact, having raised millions for the Children's Tumor Foundation (CTF) to fight NF, a genetic disorder causing tumors to grow on nerves throughout the body. Runners frequently highlight the event's "pure fun with so much heart," making it a memorable experience where participants show up boldly to support those affected by NF. Whether you're running solo or with a team, prepare for an energetic, impactful, and hilariously heartwarming adventure in the heart of Chicago.