Worldwide icon-chevron-right North America icon-chevron-right United States icon-chevron-right Illinois icon-chevron-right Chicago icon-chevron-right The best things to do on Valentine’s Day

The best things to do on Valentine’s Day

Shake things up on Valentine's Day with a music festival, an ice skating outing or a nearly-nude run

Runners streaked through Wrigleyville in their undergarments during Cupid's Undie Run, February 7, 2015.
Photograph: Max Herman

Whether you’re single, locked down or questioning your life choices, there are plenty of things to do in Chicago for Valentine's Day. And though the most romantic restaurants in Chicago have plenty to offer, we're challenging you to think outside of the box this year. Sprint around town in your skivvies at Cupid's Undie Run, stuff your face at Chicago Pizza Party, catch award magnet Dear Evan Hansen or dance the day away at Pitchfork's winter music festival. These events make for unique date ideas and awesome solo outings. No matter your relationship status, get out there and do something different for Valentine's Day this year.

RECOMMENDED: Our complete guide to Valentine's Day in Chicago