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Are You Smarter Than a Drag Queen?

Are You Smarter Than a Drag Queen?

2Bears Tavern Uptown

1140 West Wilson Avenue, Chicago, IL 60640

Friday, July 24th, 2026

7:00 PM

About This Event

Trivia night with a drag twist at 2Bears Tavern Uptown. Test your knowledge against rotating drag performers hosting the show, with the kind of irreverent humor and competitive energy that makes Friday nights at this neighborhood bar worth showing up for. Free to play, drinks flowing, and the questions get progressively more ridiculous as the night goes on.

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Phone: (773) 672-4900

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More Events at 2Bears Tavern Uptown

Showing 6 upcoming events

Squabble Trivia
Squabble Trivia
Monday, July 20th, 2026
7:30 PM

Monday nights at 2Bears belong to the regulars who show up for free trivia, cheap drinks, and the kind of banter that keeps people coming back. It's unpretentious, reliably fun, and exactly what a neighborhood bar should do well — no pressure, just a good time with people who get it.

Serve! Vocal Edition Karaoke
Serve! Vocal Edition Karaoke
Monday, July 20th, 2026
11:59 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 to attend—just show up and claim your moment.

Beer Belly Open Mic
Beer Belly Open Mic
Thursday, July 23rd, 2026
10:00 PM

Thursday night open mic at 2Bears where regulars and newcomers alike take the stage—comedy, songs, stories, whatever you've got. It's the kind of low-pressure, genuinely welcoming room where people actually listen and cheer each other on. Show up to perform or just to see what happens; either way, you're in for a good time.

Squabble Trivia
Squabble Trivia
Monday, July 27th, 2026
7:30 PM

Monday night trivia at 2Bears Tavern Uptown is the kind of low-key, reliably fun thing that keeps regulars coming back — good questions, cheap drinks, and a room full of people who actually know how to have a good time. Show up solo or bring a team; either way, you'll fit right in.

Serve! Vocal Edition Karaoke
Serve! Vocal Edition Karaoke
Monday, July 27th, 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 3:30 AM at 2Bears Tavern Uptown, hosted by Tyler Hall, Tyler Meyer, and Andrew. Free entry—just show up and claim your moment.

Beer Belly Open Mic
Beer Belly Open Mic
Thursday, July 30th, 2026
10:00 PM

Thursday nights at 2Bears belong to anyone with something to say—step up to the mic and do your thing in front of a crowd that actually listens. Whether you're testing new material, sharing a story, or just feeling brave, this is the kind of low-pressure open mic where the vibe is supportive and the drinks are cheap. Show up early, grab a seat, and see who's got something worth hearing.

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Saturday, July 18th, 2026
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