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 ideasand awesome solo outings. No matter your relationship status, get out there and do something different for Valentine's Day this year.