Sidetrack, Chicago

About Sidetrack

Sidetrack opened in 1982 as Chicago's first gay video bar — one projector, one screen, and co-founders Art Johnston and José "Pepe" Peña playing the music they loved over old film clips. Four decades later it sprawls across nearly half a city block of Northalsted, with seven connected rooms and bars — the Glass Bar, Main Bar, Cherry Bar and more — wired with dozens of screens that still run music videos all day and all night. It's grown into the largest gay bar in the Midwest without ever losing that video-bar DNA. The frozen cocktails are what people cross town for: grape, black cherry, rosé, and a frozen margarita, a slushie tradition the crew brought back from a Key West Rum Runner in 1986. The other institution is Show Tunes — singalongs that started on Mondays and now fill Friday and Sunday afternoons, packing the rooms with a crowd belting Broadway at full volume. Dance floors run Wednesday through Sunday, the rooftop deck opens on warm evenings, and the rest of the week rotates through trivia, drag, themed pop nights (Beyoncé, Gaga, Taylor, K-pop) and a monthly Sapphic Saturday. There's real substance under the party. Johnston co-founded Equality Illinois, the state's oldest LGBTQ+ rights organization, and helped pass Chicago's 1988 Human Rights Ordinance — the bar and its owners are woven into the city's queer history, and their love story is the documentary Art and Pep. It's 21+ with no cover, right on the Halsted strip, and works equally well as a low-key afternoon slushie stop or the anchor for a full night out in Northalsted.