Game Night · Chicago

Queers Gambit Chess Night

Name: Queers Gambit Chess Night
Start: 2026-11-25T19:00:00-06:00
Location: 2Bears Tavern Uptown

2Bears Tavern Uptown

1140 West Wilson Avenue, Chicago, IL 60640

directions(773) 672-4900website

Coming up

Wed, Nov 25 · 7:00 PM

Wednesday, November 25, 2026

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About

Queers Gambit Chess Night is a low-key Wednesday game night at 2Bears Tavern Uptown in Chicago, where queer players sit down for a few rounds of chess over drinks. Bring your best opening or just your sharpest bluff, and pull up a stool at the pinball machine when you need a break. It runs 7:00 to 8:30 PM on November 25, 2026, and entry is free.

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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.

Karaoke

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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Oops We Did It Again: Y2K Drag Dinner

Friday, November 13th, 2026

Times on venue site

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Friday, November 13th, 2026

7:00 PM

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Live Music

Dusky Waters: The Mother Magnolia Tour Live

Friday, November 13th, 2026

7:00 PM

Dorothy

New Orleans singer-songwriter Dusky Waters brings her ancestral Americana to Chicago for an intimate trio night at Dorothy, the 70s-inspired lesbian speakeasy in West Town. Expect close-up storytelling and rich harmonies in a room built for listening. Doors open at 7pm and the set runs till 8:30pm, so you'll have time for a nightcap after.

Karaoke

Artemis Singers Karaoke Fundraiser Party

Friday, November 13th, 2026

7:00 PM

Whiskey Girl Tavern, 6318 N Clark St, Chicago, IL, 60660

Artemis Singers, Chicago's all-volunteer lesbian feminist chorus, is throwing a karaoke party at Whiskey Girl Tavern on Clark Street in Chicago's Edgewater neighborhood. Grab the mic, grab a drink, and support 46 years of community singing: 100% of net proceeds go straight to the chorus. All ages until 9 PM, 21+ after. Food and drinks are for purchase, and there are pay-what-you-wish baked goods.