Neighborhood Bar · Chicago

Queers Gambit Chess Night

Name: Queers Gambit Chess Night
Start: 2026-12-09T19:00:00-06:00
Location: 2Bears Tavern Uptown

2Bears Tavern Uptown

1140 West Wilson Avenue, Chicago, IL 60640

directions(773) 672-4900website

Coming up

Wed, Dec 9 · 7:00 PM

Wednesday, December 9, 2026

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About

Queers Gambit Chess Night is a relaxed Wednesday evening of chess at 2Bears Tavern Uptown, the late-night LGBTQIA+ neighborhood bar near the Wilson CTA station in Chicago's Uptown. Pull up a board, challenge a friend or just watch the pieces move with a drink in hand, from 7:00 to 8:30 PM on December 9th. Grab a classic cocktail or a cold brew, and bring your best opening moves.

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More Events at 2Bears Tavern Uptown

Showing 6 upcoming events

Trivia

Are You Smarter Than a Drag Queen?

Friday, November 13th, 2026

7:00 PM

High-energy drag trivia night hosted by Tia Pet at 2Bears Tavern Uptown. The questions are tricky, the host is shady, and the room is completely out of control—in the best way. Gather your team and test your wits over three hours of comedy, competition, and chaos. Free to play, no cover, drinks flowing, and the perfect way to kick off a Friday night at this neighborhood bar. Every Friday from 7pm to 10pm.

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Serve! Vocal Edition Karaoke

Monday, November 16th, 2026

11:00 PM

Late-night karaoke for pop stars, divas, and anyone ready to take the stage and make it theirs. Every Monday from midnight to 3:30am at 2Bears Tavern Uptown, hosted by Tyler Hall, Tyler Meyer, and Andrew. Free, 21+, and packed with people who actually know how to have a good time on the mic—just show up and claim your moment.

Free

Poker in the Rear

Tuesday, November 17th, 2026

7:30 PM

Free Texas Hold'em every Tuesday night at 2Bears Tavern Uptown. Beginner-friendly and no experience needed—just show up, learn the game, and vie for prizes with a welcoming crowd of regulars and newcomers. Hosted by Taylor Grimes, it's a low-key weekly game night that keeps people coming back. First come, first served, so grab a seat, play some cards, and stick around for drinks.

Neighborhood Bar

Neighborhood Night

Thursday, November 19th, 2026

5:00 PM

Neighborhood Night at 2Bears Tavern Uptown is a late-night LGBTQIA+ night in Chicago's Uptown, steps from the Wilson CTA station. Expect the usual neighborhood-bar ease: pinball, darts, Nintendo Switch and a crowd that's happy to pull up a stool. Doors open at 5pm, so come early for a relaxed start.

Trivia

Are You Smarter Than a Drag Queen?

Friday, November 20th, 2026

7:00 PM

Karaoke

Serve! Vocal Edition Karaoke

Monday, November 23rd, 2026

11:00 PM

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Friday, November 13th, 2026

4:00 PM

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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 the sunset, and get ready to belt out the hits with fellow show tune lovers in the kind of communal, joyful singing that makes this Chicago tradition legendary.

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Friday, November 13th, 2026

Times on venue site

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