Poker in the Rear

Serve! Vocal Edition Karaoke

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.

Thursday, November 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.

Neighborhood Night

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.

Are You Smarter Than a Drag Queen?

Friday, November 20th, 2026

Serve! Vocal Edition Karaoke

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.

Monday, November 23rd, 2026

11:00 PM

Queers Gambit Chess Night

Wednesday, November 25th, 2026

Queers Gambit Chess Night is a low-key Wednesday game night at 2Bears Tavern Uptown in Chicago, where queer players sit down for a few rounds of chess over drinks. Bring your best opening or just your sharpest bluff, and pull up a stool at the pinball machine when you need a break. It runs 7:00 to 8:30 PM on November 25, 2026, and entry is free.

More LGBTQ+ Events in Chicago

Discover more events happening around Chicago

Poker in the Bottom

Free Texas Hold'em every Sunday night at Meeting House Tavern — no gambling, no stress, just a damn good game night. Whether you're a beginner learning the ropes or a competitive card shark, you'll find a welcoming table full of regulars and new faces alike. Play for prizes, bring a friend for bonus chips, and settle in for cards with people who know how to have a good time. Low-key, social, and exactly the kind of thing that keeps regulars coming back.

Bearaoke

9:00 PM

Sunday nights at SoFo Tap belong to anyone brave enough to grab the mic. Hosted by Rhett Butlah, Bearaoke is a karaoke night where the energy is high, the crowd is genuinely supportive, and nothing's off limits—country, power ballads, showtunes, whatever you've got. Free entry, 9pm to 1am, in the heart of Chicago's bear bar scene. Just bring confidence and a song in your heart.

Sunday After Dark

Chicago House TransSafe Drop In

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.

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

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