Part of the Gay Chicago Guide — bars, events & things to do.
Chicago, Illinois
A bear-friendly Uptown neighborhood bar with games and free karaoke.
2Bears Tavern Uptown is a laid-back, bear-friendly gay bar at 1140 W. Wilson Avenue, a few steps from the Wilson Red Line stop in Chicago's Uptown. It opened in 2022 from the 2Bears Tavern Group — the team behind Meeting House Tavern in Andersonville and the reopened Jackhammer — and brings the same unpretentious, no-attitude streak north of the Northalsted bar strip. There's no cover and no dress code; the draw is strong pours, a friendly room, and a steady run of low-key events — drag trivia, karaoke, and bear socials. It's dog-friendly and runs late, which makes it a natural last stop or a neighborhood alternative when you'd rather skip the Halsted crowds. For travelers staying on the North Side, it's an easy, welcoming entry point to Uptown's quieter queer nightlife.
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$89
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