Sleigh Belles Bottomless Drag Brunch

Supreme Divas Bottomless Drag Brunch

Oops We Did It Again is a Y2K-themed drag dinner at Kit Kat Club, Chicago's original drag show lounge in Lakeview on Halsted Street. Pull out your frosted tips and butterfly clips, settle in for an elevated dinner by Chef Chelsea Poe, and watch the Kit Kat Divas take the velvet stage. It kicks off Friday, November 13 at 7pm, so you'll want to book a table early.

Drag Brunch

Saturday, November 14th, 2026

Tuesday, November 17th, 2026

Supreme Divas Bottomless Drag Brunch at Kit Kat Club in Chicago's Lakeview neighborhood is the weekend brunch you'll want on your calendar. Expect the Kit Kat Divas serving up drag, bottomless mimosas and a full brunch spread in a velvet-draped Art Deco room that's made for a big Saturday. Grab a seat early, because this one fills up fast.

Cabaret

Wednesday, November 18th, 2026

Kit Kat Club's Cabaret night in Lakeview is a showstopper of Chicago drag, with Art Deco glamour, velvet-draped stages and the Kit Kat Divas working the room. Grab a seat, order a signature craft cocktail, and settle in for a night of sequins and sass. The show kicks off at 7pm on Tuesday, November 17th, 2026, on Halsted Street.

Cabaret

House of Couture Thursdays

Kit Kat Club's Cabaret nights bring the Chicago drag and showtune energy you came for, on the Halsted Street stage in Lakeview. Settle into the velvet-draped room, order a craft cocktail, and let the Kit Kat Divas take it from there. The show starts at 7pm on Wednesday, November 18th, 2026, so you've got time to grab dinner first.

Drag Shows

Thursday, November 19th, 2026

6:00 PM

Every Thursday at Kit Kat Club, step into an evening of glamour and pageant-level drag artistry with Jacky Couture & Friends. From 6 to 9 PM, expect breathtaking looks, high-energy performances, and a rotating cast of talented entertainers who bring sophistication and flair to the stage. The prix fixe menu includes appetizers, your choice of entrée, two martinis, and a two-hour seating—all paired with the kind of polished production that's made Kit Kat one of Chicago's best venues for drag.

Cabaret

Thursday, November 19th, 2026

6:00 PM

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.

More LGBTQ+ Events in Chicago

Discover more events happening around Chicago

Late Night

Sativa's Hot Boxxx

Thursday, November 12th, 2026

11:00 PM

Hydrate Nightclub

Sativa's Hot Boxxx is a late-night drag show at Hydrate in Chicago's Boystown, where Sativa Diamond hosts Kara Mel D'Ville, Howdy Rowan and Judith Priest for an hour-and-change of camp and high-energy fun. It's on Thursday, November 12, from 11 PM to 1 AM, and there's no cover, so you can roll in without the door math. Grab the $12 TT Baby drink special and get settled in for a night you won't see coming.

rooftop

T.g.i.f. Show Tunes

Queer Happy Hour @ Nightshade & Dark

4:00 PM

Sidetrack

Kick off your weekend at Sidetrack's legendary Friday show tunes sing-along! Every other Friday, the rooftop and video bar come alive with a crowd that knows every word to their favorite Broadway classics and pop standards. Grab a drink, catch the sunset, and get ready to belt out the hits with fellow show tune lovers in the kind of communal, joyful singing that makes this Chicago tradition legendary.

Happy Hour

Dusky Waters: The Mother Magnolia Tour Live

LGBTQ+ Center Lake County

A Friday night gathering for queer folks to eat, drink, and connect in a genuinely welcoming space. No pretense, no pressure — just good company and a chance to be yourself. 21+.

Live Music

Are You Smarter Than a Drag Queen?

Dorothy

New Orleans singer-songwriter Dusky Waters brings her ancestral Americana to Chicago for an intimate trio night at Dorothy, the 70s-inspired lesbian speakeasy in West Town. Expect close-up storytelling and rich harmonies in a room built for listening. Doors open at 7pm and the set runs till 8:30pm, so you'll have time for a nightcap after.

Trivia

Artemis Singers Karaoke Fundraiser Party

2Bears Tavern Uptown

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.

Karaoke