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Home/Venues/Chicago/2Bears Tavern Uptown

Part of the Gay Chicago Guide — bars, events & things to do.

2Bears Tavern Uptown, Chicago

2Bears Tavern Uptown, Chicago

Chicago, Illinois

Out's Take

A bear-friendly Uptown neighborhood bar with games and free karaoke.

Uptown·$$
1140 W Wilson Ave, Chicago, IL 60640, United States
Neighborhood BarLaid BackLate NightKaraokeDog FriendlyBearsMostly MenLocalsMixed Crowd
WebsiteInstagramFacebook(773) 672-4900Email

About 2Bears Tavern Uptown

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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Events at 2Bears Tavern Uptown

Fri, Jul 31 — Thu, Aug 6

Friday, July 31

Are You Smarter Than A Drag Queen?

Are You Smarter Than A Drag Queen?

7 PM - 10 PM

2Bears Tavern Uptown, Chicago

Weekly drag trivia game show hosted by Tia Pet at 2Bears Tavern Uptown. Compete for prizes, enjoy performances, and connect with the queer community every Friday.

Weekly

Monday, August 3

Squabble: A Game of Queeries

Squabble: A Game of Queeries

7:30 PM - 9:30 PM

2Bears Tavern Uptown, Chicago

2Bears Tavern Uptown's free feud-style game night every Monday at 7:30pm, hosted by Pup Figaro — teams compete on LGBTQ+ poll questions for prizes.

Weekly
SERVE! Vocal Edition - Karaoke

SERVE! Vocal Edition - Karaoke

11:59 PM - 3:30 AM

2Bears Tavern Uptown, Chicago

Weekly Monday karaoke at 2Bears Tavern Uptown. Hosted by Tyler Meyer, Andrew, and Tyler Hall. Late-night singing in a welcoming gay space.

Weekly

Tuesday, August 4

Poker In The Rear

Poker In The Rear

7:30 PM - 9:30 PM

2Bears Tavern Uptown, Chicago

Weekly Tuesday poker night at 2Bears Tavern Uptown. All skill levels welcome. No gambling—just cards, friends, and prizes in a laid-back gay bar vibe.

Weekly

Thursday, August 6

Beer Belly Open Mic

Beer Belly Open Mic

10 PM - 1 AM

2Bears Tavern Uptown, Chicago

Weekly Thursday open mic at 2Bears Tavern Uptown. Sign up at 10PM, show starts 10:30PM. Live performances, community vibes, gay bar atmosphere.

Weekly
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