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Are You Smarter Than a Drag Queen?
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 20 · 7:00 PM

In 5 weeks · Friday, November 20, 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 13 times since July — see past dates
  • 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
  • Fri, Jul 31

Every date in this series runs the same way. Back to the series

Trivia
Neighborhood Bar
Drag Shows
Game Night
Interactive
Entertainment
+3 more
Drag Culture
Game Nights

More Events at 2Bears Tavern Uptown

Showing 6 upcoming events

Squabble Trivia
Squabble Trivia
Monday, October 19th, 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
Serve! Vocal Edition Karaoke
Monday, October 19th, 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
Poker in the Rear
Tuesday, October 20th, 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
Beer Belly Open Mic
Thursday, October 22nd, 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
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
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.

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Post Brunch Fun
Post Brunch Fun
Saturday, October 17th, 2026
1:00 PM

The Saturday afternoon shift at Sidetrack — when brunch hangs on and the dance floor starts calling. Grab a drink, catch up with friends, and ease into the weekend vibe before things really heat up. It's that sweet spot between lazy brunch energy and full-on nightlife, with good music, good people, and a rooftop if you need air.

Pokémon Raid Social
Pokémon Raid Social
Saturday, October 17th, 2026
2:00 PM

Free monthly Pokémon GO hangout at Meeting House Tavern where trainers team up for raids, trade Pokémon, and meet fellow players. Hosted by Flops, this laid-back Saturday afternoon combines gaming, drinks, and community energy — perfect for longtime players, competitive trainers, and newcomers alike.

BearUnion Play Party
Saturday, October 17th, 2026
3:00 PM

BearUnion Play Party is a Saturday afternoon play party in the back bar at Cell Block Chicago, the kinky side of Boystown. Tickets are required for the backroom and can be bought online or at the door. Everyone entering must be 21+ with valid ID, and it runs 3:00 to 7:30 p.m.

Daddy Disco Party
Daddy Disco Party
Saturday, October 17th, 2026
4:00 PM

Daddy Disco is back for a Saturday afternoon tea dance at Sidetrack — dance hits from the 80s, 90s, and 2000s with hosts Michael and Jeremy keeping the energy up. It's the kind of daytime dance party that hits different, with a crowd that knows how to have a good time and a sound system that makes you remember why you love these songs.

National Coming Out Day Sk8 The Rainbow
Saturday, October 17th, 2026
8:30 PM

Lace up and celebrate National Coming Out Day at the roller rink — a free, all-ages event where skating, community, and self-expression come together. Whether you're hitting the floor or cheering from the sidelines, there's something for everyone. Registration is recommended to secure your spot.

KoK Halloween
KoK Halloween
Saturday, October 17th, 2026
9:00 PM

A nostalgic throwback party for anyone looking to relive their college days. High energy frat party atmosphere soundtracked by iconic 90s and 2000s hits, with a Halloween twist. Costumes encouraged but not required. Music by DJ Bearbie.

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