Pink Pony Club

Real stories from real people — the kind of intimate, unfiltered storytelling that only happens when a room full of queer folks decides to get honest. OUTspoken brings the community together to share what matters, laugh, and listen to each other. Tuesday nights at Sidetrack become a space where your story belongs.

Stew hosts Sidetrack's weekly trivia night—test your pop culture knowledge against the crowd, then stick around for Pop Favorite Videos spinning until 2am. It's the kind of reliably fun Tuesday that builds a crowd of regulars who actually know their stuff (and aren't afraid to shout the answers).

A Taylor Swift-themed dance party that takes over Sidetrack's dance floor for five hours of pure pop euphoria. Expect singalongs, themed cocktails, and a room full of Swifties ready to celebrate every era from Fearless to Midnights. Wednesday nights just got a whole lot more fun.

Pop music videos all night long in the Glass Bar at Sidetrack, running from open until 2am. A Thursday tradition for anyone who wants to sing along, dance, and soak up the energy of a room full of people who know every word.

Sidetrack's weekly Thursday night party takes over the Main, Cherry, and North Bars with high-energy Latin beats, DJ-driven dance floors, and a crowd that knows how to move. Expect a packed dance floor, strong drinks, and great vibes — the go-to Thursday escape for anyone who wants to dance to Latin rhythms without the pretense. Occasional themed editions swap in pop music videos and special guest hosts.

Kick off your weekend at Sidetrack's legendary Friday show tunes sing-along! Every other Friday, the rooftop and video bar come alive with a crowd that knows every word to their favorite Broadway classics and pop standards. Grab a drink, catch the sunset, and get ready to belt out the hits with fellow show tune lovers in the kind of communal, joyful singing that makes this Chicago tradition legendary.