Every Friday at 7 PM

Are You Smarter Than a Drag Queen?

2Bears Tavern Uptown1140 West Wilson Avenue, Chicago, IL 60640 Directions(773) 672-4900Website

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Fri, Nov 27 · 7:00 PM

In 5 weeks · Friday, November 27, 2026

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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.

Ran 14 times since July — see past dates

Fri, Oct 23
Fri, Oct 16
Fri, Oct 9
Fri, Oct 2
Fri, Sep 25
Fri, Sep 18
Fri, Sep 11
Fri, Sep 4
Fri, Aug 28
Fri, Aug 21
Fri, Aug 14
Fri, Aug 7

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More Events at 2Bears Tavern Uptown

Showing 6 upcoming events

Squabble Trivia

Monday, October 26th, 2026

7:30 PM

Monday nights belong to Squabble at 2Bears Tavern Uptown — a fast-paced, feud-style trivia game night hosted by Pup Figaro. Teams go head-to-head answering questions, laughing, and maybe arguing a little along the way. It's free, unpretentious fun with cheap drinks and a room full of regulars who know how to have a good time. Bring your team (or fly solo) and settle in for two hours of friendly chaos, every Monday from 7:30–9:30pm.

Serve! Vocal Edition Karaoke

Monday, October 26th, 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.

Poker in the Rear

Tuesday, October 27th, 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.

Beer Belly Open Mic

Thursday, October 29th, 2026

10:30 PM

A weekly Thursday night open mic at 2Bears Tavern Uptown, hosted by Paul Miller and Jason Melton. First-timers and seasoned comics alike take the stage for an anything-goes night of comedy, songs, and stories in a supportive, no-pressure room. Free and 21+—come perform or just soak in the beautiful chaos.

Squabble Trivia

Monday, November 2nd, 2026

7:30 PM

Serve! Vocal Edition Karaoke

Monday, November 2nd, 2026

11:00 PM

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Saturday, October 24th, 2026

11:00 AM

The Kit Kat Divas bring the heat to this legendary bottomless brunch — choreographed themed drag shows, incredible costumes, and two hours of free-flowing mimosas, bellinis, sangria, and signature cocktails. Two-course prix fixe brunch included. Book your table or walk in; expect pumping music, personal interaction with the divas, and the kind of high-energy performance that's made Kit Kat Chicago's best venue for drag.

Doggy Days

Saturday, October 24th, 2026

12:00 PM

A weekly dog-friendly hangout at The SoFo Tap where pups and their people gather for easy vibes, cheap drinks, and free treats for the dogs. From noon to 3pm every Saturday, this neighborhood bar's patio fills up with a relaxed, welcoming crowd that knows the best company comes with fur and a tail. No pretense, just good drinks and genuine community.

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