Name: 2Bears Tavern
Address: 1140 W Wilson Ave, Chicago, IL 60640, USA
Telephone: (773) 672-4900
Rating: 4.1

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2Bears Tavern is a bar in Chicago. Located at 1140 W Wilson Ave, Chicago, IL 60640, USA.

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Sing your heart out every Monday night at 2Bears Tavern Uptown.

2Bears Tavern Uptown

Monday Night Karaoke

Join us every Monday for a fun and challenging trivia night at 2Bears Tavern Uptown.

Weekly Monday Night Trivia

Play poker and enjoy a night of friendly competition every Tuesday at 2Bears Tavern Uptown.

Tuesday Poker Night

Dance the night away with our Thursday DJ sessions at 2Bears Tavern Uptown.

Thursday Night DJ Party

Poker night event hosted by Taylor Grimes, open to all skill levels, no gambling involved, just fun. Win prizes!

Texas Hold'em Poker in The Rear

Taylor Grimes

Uptown's late night singsation featuring Tyler Meyer, Andrew, and Tyler Hall. Every Monday night from 12AM to 3:30AM at 2 Bears Tavern Uptown.

Serve! Voice Edition

Weekly queer trivia game hosted by Pup Figaro at 2 Bears Tavern, every Monday from 7:30 PM to 9:30 PM.

SQUABBLE: A GAME OF QUEERIES

Pup Figaro

Enjoy an entertaining drag performance every Friday starting at 7 PM at 2Bears Tavern Uptown.

Friday Night Drag Show

Join us for game nights featuring hosts Deanie and Ruff. Every 1st and 3rd Friday from 11 PM to 1:30 AM.

Game Night at 2 Bears Tavern

Deanie and Ruff

A beginner-friendly Texas Hold’em poker night held at 2Bears Tavern Uptown in Chicago, featuring prizes and a welcoming environment for all skill levels. Hosted by Taylor Grimes, the event takes place every Tuesday from 7:30 PM to 9:30 PM.

Poker in the Rear - Texas Hold’em Night

Open mic night at 2 Bears Tavern featuring signups at 10pm, starting at 10:30pm. Come enjoy performances and community fun.

Belly Open Mic

Weekly Texas Hold'em poker game at 2Bears Tavern, featuring a friendly environment for poker enthusiasts.

A late-night comedy open mic at 2Bears Tavern Uptown in Chicago, featuring a mix of first-timers, seasoned comedians, and unexpected moments. Hosted by Paul Miller and Jason Melton, the event occurs every Thursday from 10:30 PM until late.

BEER BELLY OPEN MIC

A high-energy trivia night hosted by Tia Pet at 2Bears Tavern Uptown in Chicago, featuring tricky questions, shady hosting, and chaotic fun. The event takes place every Friday from 7:00 PM to 10:00 PM.

Are You Smarter Than a Drag Queen?

A fun and lively event featuring drag performances, hosted by Tia Pet.

Are You Smarter Than a Drag Queen

Tia Pet

A fast-paced, feud-style game night where teams compete, laugh, and maybe argue a little along the way. Hosted by Pup Figaro, this event takes place every Monday from 7:30 PM to 9:30 PM at 2Bears Tavern Uptown in Chicago, IL.

SQUABBLE TRIVIA

A beginner-friendly Texas Hold’em poker night hosted by Taylor Grimes, featuring prizes and a welcoming environment for all skill levels. The event takes place every Tuesday at 2Bears Tavern Uptown in Chicago, IL.

Poker in the Rear

A late-night comedy open mic at 2Bears Tavern Uptown, featuring a mix of first-timers, seasoned comedians, and unexpected moments. Hosted by Paul Miller and Jason Melton, the event takes place every Thursday from 10:30 PM until late.

A high-energy trivia night hosted by Tia Pet, featuring tricky questions, shady hosting, and lively chaos. The event takes place every Friday from 7:00 PM to 10:00 PM at 2Bears Tavern Uptown in Chicago, IL.

2Bears Tavern is a welcoming bar in Chicago that offers a friendly atmosphere and attentive bartenders, with patrons praising the drinks and overall vibe. However, some reviews mention inconsistencies in service, particularly regarding game setups and drink options. While many enjoy the lively environment and community feel, others feel the bar has declined in quality compared to nearby options.

Chicago's LGBTQ+ community is centered around Boystown (now officially called Northalsted), the first officially recognized gay village in the United States. The area features iconic venues like Sidetrack, Roscoe's Tavern, and The Closet. The city also has vibrant queer scenes in Andersonville, Lakeview, and the South Loop. Chicago Pride is one of the largest Pride celebrations globally, and the city hosts numerous LGBTQ+ events including Market Days and the Chicago International Film Festival's LGBTQ+ programming. The city's diverse queer community spans multiple neighborhoods and includes strong representation across all identities.

2Bears Tavern

About

What People Say

Location

Hours

Events at 2Bears Tavern

Upcoming events

May 2026

Are You Smarter Than a Drag Queen?

Past events (last 90 days)

March 2026

Monday Night Karaoke

Weekly Monday Night Trivia

Tuesday Poker Night

Thursday Night DJ Party

Texas Hold'em Poker in The Rear

Serve! Voice Edition

SQUABBLE: A GAME OF QUEERIES

Friday Night Drag Show

April 2026

Game Night at 2 Bears Tavern

May 2026

Poker in the Rear - Texas Hold’em Night

Belly Open Mic

Texas Hold'em Poker in The Rear

BEER BELLY OPEN MIC

Are You Smarter Than a Drag Queen?

Are You Smarter Than a Drag Queen

SQUABBLE TRIVIA

Poker in the Rear

BEER BELLY OPEN MIC

Take Chicago's queer scene with you

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Photos