Every Monday at 7:30 PM

Squabble Trivia

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

Next up

Mon, Oct 26 · 7:30 PM

In 3 days · Monday, October 26, 2026

Upcoming dates

MonNov 27:30 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.

Ran 14 times since July — see past dates

Mon, Oct 19
Mon, Oct 12
Mon, Oct 5
Mon, Sep 28
Mon, Sep 21
Mon, Sep 14
Mon, Sep 7
Mon, Aug 31
Mon, Aug 24
Mon, Aug 17
Mon, Aug 10
Mon, Aug 3

+2 more

More Events at 2Bears Tavern Uptown

Showing 6 upcoming events

Are You Smarter Than a Drag Queen?

Friday, October 23rd, 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.

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.

Are You Smarter Than a Drag Queen?

Friday, October 30th, 2026

7:00 PM

Serve! Vocal Edition Karaoke

Monday, November 2nd, 2026

11:00 PM

More LGBTQ+ Events in Chicago

Discover more events happening around Chicago

Senior Tai Chi: 4 Week Course

Friday, October 23rd, 2026

9:00 AM

A four-class beginner Tai Chi series for adults 45 and up, held in the third-floor gymnasium at Center on Halsted in Chicago. You can take part standing or seated, so it's easy to join at whatever mobility you have. Registration covers all four sessions, and each class runs from 9 to 10 a.m.

Care Navigator Services

Friday, October 23rd, 2026

9:00 AM

Connect with a Care Navigator at Center on Halsted in Chicago for resource navigation, referrals, and case management support. Services are open to everyone, regardless of HIV status, with specialized support for people living with HIV.

Gender Affirming Clothing Closet

Friday, October 23rd, 2026

11:00 AM

Gender-affirming clothing, accessories, and pantry items, free for the taking at Center on Halsted's Gender-Affirming Closet in Chicago. Stop by during open hours, no appointment needed. Pick up what you need, no questions asked, and take what fits your life right now.

Tgif: Friday Afternoon Show Tunes

Friday, October 23rd, 2026

4:00 PM

Kick off your weekend at Sidetrack in Chicago's Lakeview neighborhood with Friday Afternoon Show Tunes, where the whole room sings along to the classics from 4-9pm. Doors open at 3pm, and when the sing-along wraps up, you can stick around for the Friday Night Dance Party.

The Rocky Horror Drag Dinner

Friday, October 23rd, 2026

6:00 PM

Rocky Horror meets drag at Kit Kat Club's themed dinner show featuring the world-famous Kit Kat Divas in full costume spectacle. Your ticket includes a prix fixe menu with starter, choice of entree, and two martinis, plus two hours of pumping music, personal interaction with the divas, and high-energy performances. This is the kind of night that lives in your memory.

Chaotic Singles: Sapphic Halloween Party

Friday, October 23rd, 2026

6:00 PM

Halloween is for the sapphic singles — and this party proves it. Costumes are mandatory, the DJ is spinning, and there's a costume contest with a real prize waiting. Spooky icebreaker games, a confessional booth for making out, and drink specials for singles only round out the night. The vibe is pure chaos in the best way: show up solo, invite your dating app matches if you're feeling it, and spend the evening flirting and being the most chaotic version of yourself. Tickets start at $15 for general admission, with group and match pass discounts available.

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