Series · Every Tuesday at 19:30

Poker in the Rear

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

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Tue, Sep 15 · 7:30 PM

In 3 weeks · Tuesday, September 15, 2026

Other dates

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.

Ran 2 times since August — see past dates

Tue, Aug 18
Tue, Aug 11

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

More Events at 2Bears Tavern Uptown

Showing 6 upcoming events

Squabble Trivia

Monday, August 24th, 2026

7:30 PM

Monday nights at 2Bears belong to Squabble—a fast-paced, feud-style game night where teams compete, laugh, and maybe argue a little along the way. Hosted by Pup Figaro, it's the kind of free, unpretentious fun that keeps people coming back. Show up, grab a team, and settle in for two hours of the kind of chaos that only works in a room full of people who get it.

Serve! Vocal Edition Karaoke

Monday, August 24th, 2026

11:00 PM

Late-night karaoke where pop stars and divas take over the stage—hosted by Tyler Hall, Tyler Meyer, and Andrew every Monday from midnight to 3:30am. Free, no cover, just show up ready to sing and own it.

Beer Belly Open Mic

Thursday, August 27th, 2026

10:30 PM

Late-night comedy and chaos hosted by Paul Miller and Jason Melton every Thursday at 2Bears Tavern Uptown. First-timers, seasoned comics, and unexpected moments all collide on one stage—free, no filter, and running until late. Show up, sign up, or just watch the beautiful mess unfold.

Are You Smarter Than a Drag Queen?

Friday, August 28th, 2026

7:00 PM

High-energy trivia hosted by Tia Pet where the questions are tricky, the host is shady, and the room is completely out of control. It's the kind of Friday night that starts with confidence and ends with everyone laughing at how wrong they were. Free, every week at 2Bears Tavern Uptown.

Squabble Trivia

Monday, August 31st, 2026

7:30 PM

Monday nights at 2Bears belong to Squabble—a fast-paced, feud-style game night where teams compete, laugh, and maybe argue a little along the way. Hosted by Pup Figaro, it's the kind of free, unpretentious fun that keeps people coming back. Bring your team, your wit, and your willingness to get a little rowdy in the best way possible.

Serve! Vocal Edition Karaoke

Monday, August 31st, 2026

11:00 PM

Late-night karaoke where pop stars and divas take the stage and make it theirs. Hosted by Tyler Hall, Tyler Meyer, and Andrew, this Monday night ritual runs midnight to 3:30am—the kind of no-judgment zone where you can belt out your favorite anthem and actually have fun doing it. Free, always.

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Bearaoke

Sunday, August 23rd, 2026

9:00 PM

Sunday nights at SoFo Tap belong to anyone with a mic and the guts to use it. Hosted by Rhett Butlah, Bearaoke is a night of big vocals, bold energy, and a crowd that's genuinely here for it—whether you're belting out country favorites, power ballads, or whatever else you've got in you. Bring the confidence; the bear community will bring the cheers. Free, 9pm to 1am.

Sunday Funday After Dark

Sunday, August 23rd, 2026

9:00 PM

The party doesn't stop when the sun goes down — Sidetrack's late-night Sunday keeps the dance floor packed with high-energy music and a crowd that's ready to keep going. It's the perfect way to stretch out the weekend before Monday shows up.

Sunday After Dark

Sunday, August 23rd, 2026

10:00 PM

Every Sunday night after 10pm, Hydrate shifts into high gear with a rotating mix of throwbacks, hip hop, and today's hottest hits. VJ George G keeps the visuals sharp while the dance floor fills up with people who know how to make a Sunday night count. No cover, cheap Bud Lights, and a room that gets better as the night goes on.

Chicago House TransSafe Drop In

Monday, August 24th, 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, August 24th, 2026

5:00 PM

Monday nights at SoFo Tap are built for people who need to shake off the work week—$5 You Call It drinks, 90s and 2000s music videos on rotation, and a room full of folks who get it. Free entry, open till 2am. Comfort, nostalgia, and easy vibes, every single week.

Your Friend Rachel x The God Awful Small Affairs

Monday, August 24th, 2026

7:00 PM

Two queer musicians, one intimate night underground. Brooklyn's Your Friend Rachel brings her distinctive sound to Dorothy's subterranean stage, sharing the bill with Chicago's The God Awful Small Affairs. Live music for people who actually listen — expect the kind of performance that reminds you why you showed up in the first place.

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