Sidetrack

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...

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...

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...

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...

Thursday nights at Sidetrack belong to Pink Pony Club — a themed dance party that draws a reliably fun crowd ready to move. The kind of weekly reset that keeps people coming back.

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...

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...

Saturday afternoons at Sidetrack belong to the dogs and their people — bring your pup (or just yourself) for drinks, treats, and zero pressure to be anywhere else. No cover charge, no judgment, just a laid-back crowd and a rooftop...

The Saturday afternoon shift at Sidetrack — when brunch hangs on and the dance floor starts calling. Grab a drink, catch up with friends, and ease into the weekend vibe before things really heat up. It's that sweet spot between...

Sidetrack's legendary Sunday afternoon tradition — the whole room singing along to Broadway classics and pop standards across the Main, Cherry, and North Bars. It's the kind of joyful, communal sing-along that makes strangers harmonize together, with rooftop and video...

Every Monday, Sidetrack turns into Chicago's ultimate show tunes sing-along. Broadway classics and movie musicals play on the big video screens while a room full of people who know every word belts along together. It's a beloved weekly tradition blending...

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...