YA Support Group (Ages 16-39)

Neighborhood Night at 2Bears Tavern Uptown is a late-night LGBTQIA+ bar night in Chicago's Uptown, steps from the Wilson CTA station. Pull up a stool, grab a classic cocktail or a cold brew, and bring your pup along, since this tavern is dog-friendly. Starts at 5:00 PM and runs until 4:00 AM the next morning, so you can settle in for the long haul.

Thursday nights at Kit Kat Club belong to Jacky Couture and a rotating cast of pageant royalty. Expect three hours of dazzling drag performances, stunning fashion, and the kind of stage presence that only true entertainers can deliver. All martinis are just $10, and your ticket includes appetizers, an entree, two cocktails, and a two-hour seating. This is elevated drag dining done right.

Showtunes, but make it Tuesday (and Wednesday, and Thursday) - a weekly live cabaret at Kit Kat Club, with drag shows, live performances and a piano bar soundtrack of showtunes. Your midweek finally has a plot twist. Cocktails and food are on hand, there's a dress code, so bring your best, and the nightclub energy means a dance party is never far off.

You Are Here is a vibey, nostalgic, multidimensional show at Dorothy in Chicago's West Town, where colorful characters wrestle with everyday challenges. It's a night built on character and mood, so settle in, get lost in the story, and let it pull you along. It starts at 7:00 PM on Thursday, November 5th.

The first Thursday of every month belongs to the Pop Brats at Sidetrack's Pink Pony Club. Dance and sing-along to Chappell Roan, Charli XCX, Sabrina Carpenter, and Kesha with a crowd that knows every word. It's the kind of night that reminds you why video bars do community better than anyone.

Grab the mic and own the room every Thursday night at Meeting House Tavern's Karaoke Cabaret. Hosted by Bradley K8 Olsen with music powered by Creaoke Karaoke, this high-energy late-night singalong welcomes everyone — seasoned divas and first-timers alike. Expect big vocals, crowd favorites, cocktails, and a genuinely supportive room full of unapologetic queer nightlife energy. It's the kind of low-pressure, high-fun night that keeps people coming back week after week.