December 6
Forget ugly sweaters—Chicago’s LGBTQ+ community knows how to heat up the holidays with the Chicago Santa Speedo Run. Hosted by the legendary Sidetrack bar in Boystown, this annual event is equal parts festive fun, outrageous spectacle, and meaningful fundraising for local nonprofits.
Each December, brave (and barely dressed) runners don their most festive red Speedos, Santa hats, and holiday accessories before dashing through the chilly streets of Chicago. Despite the frigid temperatures, the atmosphere is anything but cold. The sight of hundreds of ho-ho-homosexual Santas jogging past is enough to warm even the iciest winter day. And yes—there are plenty of packages on display, and not just under the Christmas tree!
But the Chicago Santa Speedo Run isn’t just a cheeky excuse to hang out your holiday decorations—it’s also a celebration with purpose. Proceeds from the event benefit nonprofits serving the city’s LGBTQ+ community, making it an opportunity to give back while showing off. Runners and spectators alike get to enjoy the mix of philanthropy, pageantry, and playful holiday mischief.
The run itself may be short, but the party lasts all day. Sidetrack hosts post-run festivities with DJs, themed cocktails, holiday drag shows, and plenty of opportunities to mix, mingle, and snap photos of the festive athletes. The event has become a holiday tradition in Boystown, drawing crowds of participants, spectators, and supporters from across Chicago and beyond.
Bottom line: the Chicago Santa Speedo Run proves that the best way to spread holiday cheer is to strip down, speed up, and give back. Whether you’re running in your skivvies, cheering from the sidelines, or joining the afterparty, this is one Chicago holiday tradition you won’t want to miss.