GoPride Chicago calendar
Browse Chicago LGBTQIA+ events throughout May 2025.
Roscoe’s Presents: Chicago Entertainer of the Year 2025! Featuring National Entertainer of the Year 2024 Genesis • Honoring Chicago Entertainer of the Year 2024 Vanda LaRose • Hosted by…
Come join a group of wrestlers and guys interested in wrestling at Sidetrack for a happy hour event. The bar will have a private area closed off for us until 8PM. Wear your favorite…
Be Our Guest! Dinner and Disney Musical Bingo Every Wednesday at 7pm. Hosted by Kimberly Summer
Live for the Applause and Just Dance as if A Star Is Born when we spin all of your favorite Gaga Music Videos every month at Sidetrack. Don't miss Perfect Illusion Lady Gaga Drag…
Lip Service is Chicago’s kinkiest karaoke night—where lyrics meet leather , rhythm meets rubber , and singing meets spandex . Whether you're belting ballads , screaming metal , or serving…
The most infamous night of the year is BACK! ??Get ready for Skin Trade 26—the official Grabby Weekend Opening Party! Come dance, drink, and get up close with the men of gay adult…
Kick off your IML weekend in classic style with a night of leather, cigars, and connection at Jackhammer. Slip into your harness, vest, or full cow—whatever makes you feel bold—and join…
?? Things are about to get slippery! ??LUBE WRESTLING: IML EDITION is taking over Hydrate for one wild night! Watch as competitors battle it out for cash, prizes, and ultimate bragging…
Start your weekend with Show Tunes! Doors open at 3pm every Friday. Sing along to Sidetrack's Famous Show Tunes from 3-7pm then stay for Chicago's RuPaul's Drag Race All Stars Viewing Party…
It takes Sidetrack's beautiful BIG SCREENS to truly deliver all the Realness that is RuPaul's Drag Race. Join us every Friday starting Friday, May 9, 2025, to WATCH PRDR All Stars Season 10…
Enter the dark. Tighten the restraints. PRIMAL is a BDSM-inspired dance party where instinct rules and inhibition is left shackled at the door. With pounding bass, seductive shadows, and…
Dance under the glow of remixed pop anthems and music video magic from DJ RONS , serving up the icons you love with a twist. Cool off between songs with drink specials , free pool and darts…
GRRRab your denim, leather, rubber or whatever kinks it up for you because Chicago's Best Bear Night is gearing up to give a great BIG bear hug to our IML guests at GRRR: Leather Bear on…
Welcome to MANHOLE. Legendary DJ Deanne takes over Hydrate for a night of deep beats, dark vibes, and non-stop energy. ?? Known for headlining the biggest parties across the…
No one brunches like Chicago. No one does drag like Roscoe’s. Look out baby! You’ve been SERVED! Roscoe’s Drag Brunch hosted by Batty Davis! Seatings at 12PM & 2PM • Roscoe’s is serving you…
Bring the pups to play at Sidetrack for a Special Edition of Dog Day Saturday Memorial Day Weekend. Doggos are invited to join us with their Human Saturday, May 24, from 1-5pm for a fun day…
No one brunches like Chicago. No one does drag like Roscoe’s. Look out baby! You’ve been SERVED! Roscoe’s Drag Brunch hosted by Batty Davis! Seatings at 12PM & 2PM • Roscoe’s is serving you…
Draglicious every Saturday at 9pm. Hosted by Mimi Marks, Mz Ruff N' Stuff, Dida Ritz, Veronica Pop and Gina Belle.
Chicago’s LEADING leather queer party is back and turning up the heat for IML Weekend!
