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, Dec 4 · 7:00 PM

In 3 weeks · Friday, December 4, 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 17 times since July — see past dates

Fri, Nov 13
Fri, Nov 6
Fri, Oct 30
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

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More Events at 2Bears Tavern Uptown

Showing 6 upcoming events

Soul Sundays

Sunday, November 15th, 2026

6:00 PM

Soul Sundays at 2Bears Tavern Uptown is a Sunday evening soul night in Chicago's Uptown neighborhood, running 6:00 PM to 10:00 PM, just steps from the Wilson CTA station. Put on your best groove, grab a cocktail from the bar, and let the music carry you through the evening. Dog-friendly and easy to reach, it's a low-key way to end your weekend with good company.

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.

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 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.

Serve! Vocal Edition Karaoke

Monday, November 23rd, 2026

11:00 PM

Poker in the Rear

Tuesday, November 24th, 2026

7:30 PM

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Bearaoke

Sunday, November 15th, 2026

9:00 PM

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Sunday After Dark

Sunday, November 15th, 2026

10:00 PM

Every Sunday night at Hydrate, the party shifts into high gear after 10pm with a rotating mix of throwbacks, hip hop, and today's hottest hits. VJ George G keeps the energy moving and the dance floor packed all night long. No cover charge and $6 Bud Lights make it an easy reason to show up—this is the neighborhood's reliable late-night reset for those who want to keep the weekend going.

Chicago House TransSafe Drop In

Monday, November 16th, 2026

2:00 PM

A free, judgment-free weekly drop-in for trans and non-binary folks at Center on Halsted. No appointment needed — just show up and connect with real, practical support including housing navigation, employment services, legal help with name changes and discrimination cases, medical referrals, and more. As the Midwest's first comprehensive one-stop resource designed specifically for the trans community, TransSafe connects you with people and resources that actually understand what you're navigating.

Make Mondays Suck Less

Monday, November 16th, 2026

5:00 PM

The SoFo Tap's weekly Monday reset — log off, shake off the work week, and settle into $5 You Call It drinks while 90s and 00s music videos play all night long. Free entry, low-key neighborhood-bar energy, and open from 5pm to 2am, every Monday.

Floq Adult Support Group

Monday, November 16th, 2026

7:00 PM

This peer-led support group is a safe space for LGBTQ+ adults (18+) to support each other, share resources, and offer encouragement. Coffee, tea, water and fellowship are provided. Contact the Center with questions. email: info@lgbtqlc.com or call: 847-975-3561

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