21 Plus in Chicago

Locktober comes to Jackhammer with Chicago Chastity Club hosting an all-levels gathering for everyone from seasoned cage players to curious key holders just starting out. Nine hours to connect with people who get it, in a space that's genuinely welcoming...

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...

Fridays at the SoFo Tap belong to GRRR — Chicago's longest-running weekly bear night for the big, the hairy, and the ones who love them. No cover, no attitude, just a packed room of regulars and newcomers who show up...

Two DJs making their Dorothy debut spin back-to-back for a cover-free night in the subterranean lounge. DJ th3m opens with early 2000s nostalgia and bass-heavy rap (9-11pm), then Naughty G takes over with house, reggaeton, electronic, and hip hop until...

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...

Northalsted's official after-brunch party at Hydrate Nightclub. Every Sunday afternoon starting at 2pm, DJ Laura B keeps the dance floor packed with go-go dancers, cheap drink specials ($3 Bud Lights, $4 wells until 4pm), and free pizza to fuel the...

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....

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...

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...

Chicago's kinkiest karaoke night happens every Wednesday at Jackhammer, hosted by Tim Bell. Step up to the mic and let it out, or settle in and watch the beautiful chaos unfold — this is a midweek release where bold performances,...

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...

A seven-hour muscle worship party built for big men and their admirers. Built go-go dancers perform muscle worship scenes on stage while classic bodybuilder motivation plays on the screens. The night peaks at midnight with a bicep contest and prizes,...

Fridays at the SoFo Tap belong to GRRR — Chicago's longest-running weekly bear night for the big, the hairy, and the ones who love them. No cover, no attitude, just a packed room of regulars and newcomers who show up...

Dorothy's resident DJ Ca$h Era brings her open-format mastery to the underground speakeasy every month. With over a decade of experience and a title as Chicago's Best Hip-Hop DJ since 2021, she'll be spinning from 10pm to last call at...

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...

Northalsted's official after-brunch party at Hydrate Nightclub. Every Sunday afternoon starting at 2pm, DJ Laura B keeps the dance floor packed with go-go dancers, cheap drink specials ($3 Bud Lights, $4 wells until 4pm), and free pizza to fuel the...

A monthly gathering for readers who want the joy of books without the pressure of assignments or discussion requirements. Show up, settle in, and read in quiet camaraderie with fellow book lovers at Dorothy. It's free, no prep needed, and...

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....

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...

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...

A private, members-only gathering for LGBTQ+ men inside Cell Block's backroom — consensual, undressed connection in a judgment-free space. Doors open at 6:30 for check-in; action runs 7:30–9:00. Two drinks, lube, towels, and condoms provided. $25 entry, 21+ with valid...

Chicago's kinkiest karaoke night happens every Wednesday at Jackhammer, hosted by Tim Bell. Step up to the mic and let it out, or settle in and watch the beautiful chaos unfold — this is a midweek release where bold performances,...

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...

Fridays at the SoFo Tap belong to GRRR — Chicago's longest-running weekly bear night for the big, the hairy, and the ones who love them. No cover, no attitude, just a packed room of regulars and newcomers who show up...

Dorothy's monthly queer karaoke night runs the third Friday from 10pm to 2am, hosted by bartender E. Doors open at 6pm, sign-ups start at 9pm, and the singing goes all night — cover free, 21+, and exactly the kind of...

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...

Northalsted's official after-brunch party at Hydrate Nightclub. Every Sunday afternoon starting at 2pm, DJ Laura B keeps the dance floor packed with go-go dancers, cheap drink specials ($3 Bud Lights, $4 wells until 4pm), and free pizza to fuel the...

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...

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....

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...

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...

Chicago's kinkiest karaoke night happens every Wednesday at Jackhammer, hosted by Tim Bell. Step up to the mic and let it out, or settle in and watch the beautiful chaos unfold — this is a midweek release where bold performances,...

The Velvet Vixens and a killer lineup of Chicago burlesque performers are bringing Halloween heat to Dorothy—think fierce femmes, spooky seduction, and a certain Rocky Horror tradition creeping out of the shadows. Doors at 6pm, show at 7pm. $20 general...

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...

Fridays at the SoFo Tap belong to GRRR — Chicago's longest-running weekly bear night for the big, the hairy, and the ones who love them. No cover, no attitude, just a packed room of regulars and newcomers who show up...

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...

Northalsted's official after-brunch party at Hydrate Nightclub. Every Sunday afternoon starting at 2pm, DJ Laura B keeps the dance floor packed with go-go dancers, cheap drink specials ($3 Bud Lights, $4 wells until 4pm), and free pizza to fuel the...

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....

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...

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...

A private, members-only gathering for LGBTQ+ men seeking consensual, undressed connection in Cell Block's backroom. Doors open at 6:30 for check-in and clothes storage; action runs 7:30–9:00. Two drinks, lube, towels, and condoms provided. $25 entry, 21+ with valid ID...

Chicago's kinkiest karaoke night happens every Wednesday at Jackhammer, hosted by Tim Bell. Step up to the mic and let it out, or settle in and watch the beautiful chaos unfold — this is a midweek release where bold performances,...

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...

Fridays at the SoFo Tap belong to GRRR — Chicago's longest-running weekly bear night for the big, the hairy, and the ones who love them. No cover, no attitude, just a packed room of regulars and newcomers who show up...

Northalsted's official after-brunch party at Hydrate Nightclub. Every Sunday afternoon starting at 2pm, DJ Laura B keeps the dance floor packed with go-go dancers, cheap drink specials ($3 Bud Lights, $4 wells until 4pm), and free pizza to fuel the...

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....

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...

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...

Chicago's kinkiest karaoke night happens every Wednesday at Jackhammer, hosted by Tim Bell. Step up to the mic and let it out, or settle in and watch the beautiful chaos unfold — this is a midweek release where bold performances,...

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...

Fridays at the SoFo Tap belong to GRRR — Chicago's longest-running weekly bear night for the big, the hairy, and the ones who love them. No cover, no attitude, just a packed room of regulars and newcomers who show up...

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+.

Friday nights at Nightshade & Dark are for the people who want to unwind with other queer folks in a space that actually gets it. Good drinks, good company, and the kind of relaxed vibe where you can be exactly...