Live Entertainment in Chicago

Jacky Couture & Friends bring glamour and pageant-level artistry to Kit Kat Club every Thursday. From 6 to 9 PM, expect stunning drag performances, high-energy sets, and a rotating cast of talented entertainers. Elevated dining by Chef Chelsea Poe pairs...

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...

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...

A themed drag dinner spectacular featuring the world-famous Kit Kat Divas in full Addams Family costume and choreography. Your evening includes a prix fixe menu with starter and entree, two martinis (or non-alcoholic substitutes), and a 2-hour seating with pumping...

Freshman 15 is Hydrate's weekly showcase for Chicago's up-and-coming drag artists—a rotating lineup of fresh talent, hosted by Headmistress Bambi Banks with Faculty Starr Banks and Neutral Gena. DJ Geo Diamond and VJ George G keep the energy moving. $5...

Choreographed themed drag shows with the world-famous Kit Kat Divas, a two-course brunch menu, and two hours of free-flowing bottomless drinks—mimosas, bellinis, sangria, bloody marys, margaritas, and more. High-energy performances, personal interaction with the divas, and pumping music make this...

An evening that does good while having a great time—live music, fierce drag performances, and a silent auction that benefits both E3 Radio and other meaningful organizations across Chicago. It's the kind of fundraiser where the energy matches the cause.

Roz Hernandez brings her chart-topping queer paranormal comedy podcast to life for one night only—and she's turning it into a ghost story competition. Bring your best real paranormal tale (3 minutes or less) for a shot at winning merch, or...

Draglicious is Hydrate's signature Saturday night drag show—a rotating lineup of top-tier performers bringing glitz, glamour, and the greatest hits to the stage every week. Whether you're celebrating a birthday, an anniversary, or just a night out with friends, this...

Roz Hernandez brings her chart-topping queer paranormal comedy podcast to the stage for a second sold-out show — and this time, the audience gets to compete. Bring your best real ghost story (3 minutes or less) for a chance to...

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,...

Every Monday, Sidetrack turns into Chicago's ultimate show tunes sing-along. Broadway classics and movie musicals play on the big video screens while a room full of people who know every word belts along together. It's a beloved weekly tradition blending...

Chicago's favorite way to survive Mondays. Every week at Hydrate Nightclub, host Mz Ruff 'N Stuff brings a rotating lineup of fabulous queens for a lively drag showcase, backed by beats from DJ MARTIN keeping the packed dance floor moving...

Real stories from real people — OUTspoken is where LGBTQ+ folks gather to share the moments that shaped them. Whether it's coming out, finding community, or just the weird and wonderful stuff that happens in between, these are the kinds...

Jacky Couture & Friends bring glamour and pageant royalty to Kit Kat Club every Thursday. Expect breathtaking drag performances, high-energy entertainment, and a rotating cast of talented performers from 6 to 9 PM. The package includes appetizers, your choice of...

Fast-paced stand-up meets interactive chaos — Mary Kelly and Sharron Palm host a night that feels like a pride parade exploded into a comedy show. Expect drag, popstar trivia, audience games, and a rotating lineup of LGBTQ+ comics who actually...

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...

Themed drag dinner theater at Chicago's award-winning Kit Kat Club, featuring the world-famous Kit Kat Divas in full costume spectacle. Your ticket includes a prix fixe menu with starter, entrée choice, and two martinis, plus two hours of pumping music,...

Freshman 15 is Hydrate's weekly drag competition that keeps things fresh with inventive challenges and rotating talent every Friday night. Hosted by Bambi Banks with faculty judges Starr Banks and Neutral Gena, plus DJ Geo Diamond on the wheels and...

The Kit Kat Divas bring the heat to this themed drag brunch spectacular — choreographed performances in killer costumes, bottomless mimosas and Bloody Marys, and a room that's ready to dance and sing along. Two-course brunch, two-hour seating, and the...

Draglicious is Hydrate's signature Saturday night drag showcase — top-tier queens performing every week from 9pm to 11pm, delivering glitz, glamour, and the greatest hits. Whether you're celebrating a birthday, an anniversary, or just a night out, this is the...

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,...

Every Monday, Sidetrack turns into Chicago's ultimate show tunes sing-along. Broadway classics and movie musicals play on the big video screens while a room full of people who know every word belts along together. It's a beloved weekly tradition blending...

Chicago's favorite way to survive Mondays. Every week at Hydrate Nightclub, host Mz Ruff 'N Stuff brings a rotating lineup of fabulous queens for a lively drag showcase, backed by beats from DJ MARTIN keeping the packed dance floor moving...

Jacky Couture & Friends bring pageant royalty energy to Kit Kat Club every Thursday night. Expect dazzling drag performances, stunning fashion, and rotating guest entertainers who each bring their own flair to the stage. The evening runs 6–9 PM with...

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...

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...

A themed drag dinner show at Kit Kat Club where the world-famous Kit Kat Divas bring cinematic glamour to the stage. Expect elevated dining, signature craft cocktails, and the kind of theatrical performance that makes this Chicago institution unmissable. Dinner...

A weekly drag competition where performers battle for supremacy on Hydrate's stage. Hosted by Bambi Banks with faculty judges Starr Banks and Neutral Gena, Freshman 15 showcases the creativity, talent, and stage presence that define Chicago's drag scene. DJ Geo...

The Kit Kat Divas bring the horror-themed heat to this legendary drag brunch — think choreographed shows, fabulous costumes, and two hours of bottomless mimosas, Bellinis, sangria, and margaritas with your two-course prix fixe brunch. It's the kind of high-energy,...

Boystown's Saturday night institution — top-tier drag queens performing back-to-back sets of the greatest hits, the kind of show that's equally perfect for a birthday celebration, an anniversary, or just a night out with people who know how to have...

Six local drag artists performing two numbers each that bring them genuine joy — whether it's a long-time favorite or a debut they can't wait to share. Produced by Ryder Knight, Chicago's sluttiest glam rockstar and trans drag king, this...

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,...

Every Monday, Sidetrack turns into Chicago's ultimate show tunes sing-along. Broadway classics and movie musicals play on the big video screens while a room full of people who know every word belts along together. It's a beloved weekly tradition blending...

Chicago's favorite way to survive Mondays. Every week at Hydrate Nightclub, host Mz Ruff 'N Stuff brings a rotating lineup of fabulous queens for a lively drag showcase, backed by beats from DJ MARTIN keeping the packed dance floor moving...

Amy Armstrong and Honey West bring the heat to Kit Kat Club for a special one-night performance. Dinner and two martinis included with your $64.95 ticket — settle in for an evening of top-tier drag in one of Chicago's most...

Jacky Couture & Friends bring pageant royalty energy to Kit Kat Club every Thursday. From 6 to 9 PM, expect breathtaking drag performances, stunning fashion, and rotating guest entertainers who know how to command a stage. The whole evening pairs...

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...

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...

Freshman 15 is a weekly drag competition that turns up the heat every Friday night at Hydrate. With the finale approaching, the pressure's on for a thrilling showcase of local talent under the direction of Headmistress Bambi Banks and faculty...

The Kit Kat Divas bring the heat to this legendary bottomless brunch — choreographed themed drag shows, incredible costumes, and two hours of free-flowing mimosas, bellinis, sangria, and signature cocktails. Two-course prix fixe brunch included. Book your table or walk...

Hydrate's signature Saturday night drag show brings top-tier entertainers performing the greatest hits for two hours of glitz and glamour. Whether you're celebrating a birthday, anniversary, or just looking for a reliably stellar night out, Draglicious delivers the kind of...

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,...

Every Monday, Sidetrack turns into Chicago's ultimate show tunes sing-along. Broadway classics and movie musicals play on the big video screens while a room full of people who know every word belts along together. It's a beloved weekly tradition blending...

Chicago's favorite way to survive Mondays. Every week at Hydrate Nightclub, host Mz Ruff 'N Stuff brings a rotating lineup of fabulous queens for a lively drag showcase, backed by beats from DJ MARTIN keeping the packed dance floor moving...

Glamour and pageant royalty take over Kit Kat Club every Thursday with House of Couture, led by the incomparable Jacky Couture and a rotating cast of talented performers. From 6 PM to 9 PM, expect breathtaking looks, high-energy drag performances,...

The crypt is back for its one-year anniversary, and this sapphic celebration is pulling out all the haunts. Expect a night of 90s horror-inspired cabaret performances, a dress code that demands drama (think Scream Queen meets Hoochie nostalgia), and an...

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...

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...

Two nights of Halloween drag spectacle at Chicago's best-in-class drag venue. October 30th brings Devils Night with the world-famous Kit Kat Divas in full costume glory, two seatings with a prix fixe dinner and two martinis. October 31st adds a...

The Kit Kat Divas transform Halloween into pure theatrical chaos with this themed drag brunch spectacular. Expect world-class choreography, fabulous villain costumes, bottomless mimosas and Bloody Marys, and two hours of high-energy performances that'll have you dancing in your seat....

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,...

Every Monday, Sidetrack turns into Chicago's ultimate show tunes sing-along. Broadway classics and movie musicals play on the big video screens while a room full of people who know every word belts along together. It's a beloved weekly tradition blending...

Chicago's favorite way to survive Mondays. Every week at Hydrate Nightclub, host Mz Ruff 'N Stuff brings a rotating lineup of fabulous queens for a lively drag showcase, backed by beats from DJ MARTIN keeping the packed dance floor moving...

Wednesday night bingo with a drag twist — local performers call the numbers, the energy's high, and the prizes are worth sticking around for. It's the kind of midweek gathering that reminds you why this community knows how to have...

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...

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...

Jacky Couture & Friends bring pageant royalty energy to Kit Kat Club every Thursday. Expect dazzling drag performances, stunning fashion, and high-energy entertainment from 6 to 9 PM. Enjoy all martinis for just $10, elevated dining by Chef Chelsea Poe,...

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...

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...

Jacky Couture & Friends bring pageant royalty glamour to Kit Kat Club every Thursday. Three hours of dazzling drag performances, stunning fashion, and high-energy entertainment paired with elevated dining and $10 martinis. Book your table for the full experience —...

Jacky Couture & Friends take over Kit Kat Club every Thursday with three hours of pageant-level drag, stunning fashion, and rotating guest performers. The setup is dinner-and-show done right: elevated food, a three-course prix fixe, and $10 martinis all night....

Thursday nights at Kit Kat Club belong to Jacky Couture and friends — a weekly celebration of drag artistry, pageant elegance, and high-energy performances. From 6 to 9 PM, expect breathtaking looks and rotating talent that brings real sophistication to...

Jacky Couture & Friends bring pageant royalty energy to Kit Kat Club every Thursday — think dazzling drag performances, stunning fashion, and the kind of stage presence that only comes from true artistry. From 6 PM to 9 PM, you...