Part of the Gay Chicago Guide — bars, events & things to do.

Wednesday, August 19, 2026
Get ready for a high-energy male revue and go-go show hosted by the fabulous Sapphire Feliciano and DJ Lightning! This weekly Wednesday night at Charlie's is all about celebrating queer joy with killer performances and non-stop dancing energy. Whether you're here to admire the talent, hit the dance floor, or soak up the sass and Southern charm, Boyz and Booze delivers the perfect midweek escape with a side of pure fun. This event was imported by Out x Out. Please visit the venue link to verify details.
Have feedback on this description? Let us knowDrag brunches, circuit nights & every party worth knowing in Chicago — in your inbox every week.

Thu, Aug 13
8 PM - 10 PM
Charlie's, Chicago
Monthly drag showcase at Charlie's gay bar in Chicago. Hosted by Aja Ajani with performances by Umami, Faye Wylde, Klymax, and more. Every Thursday.
Monthly
Thu, Aug 13
11 PM - 4 AM
Charlie's, Chicago
Monthly fashion celebration every Thursday at Charlie's gay bar. Dance floor, styled crowd, design community vibes. Chicago nightlife.
Monthly
Fri, Aug 14
7 PM - 11 PM
Charlie's, Chicago
Weekly B2B DJ night every Friday at Charlie's, Chicago's queer country bar. Guest DJs spin live—dance, connect, and celebrate with the community.
Weekly
Fri, Aug 14
9 PM - 11 PM
Charlie's, Chicago
Cosplay contest with a $500 prize at Charlie's on Broadway, Fri Aug 14, 9-11pm. Hosted by Kimberly Summer.

Fri, Aug 14
10 PM - 4 AM
Charlie's, Chicago
Weekly Friday night drag party at Charlie's in Chicago. High-energy performances, dancing, and cosmic-themed nights that shift weekly. Join the house queens.
Weekly
Fri, Aug 14
11 PM - 4 AM
Charlie's, Chicago
Monthly neon drag party at Charlie's Chicago with go-go dancers, body painting, and DJ Ron Geronimo. Hosted by Sapphire Feliciano and Luna LaCatrina.
MonthlyLet people know you're going, see who else is attending, and share the event with friends.


Your complete guide to LGBTQ+ Chicago — the best gay bars, annual events, neighborhoods, hotels, and things to do in the Windy City.

Everything you need for Chicago's Haunted Halsted Halloween Parade — the route, the costume contest, the Northalsted bars that go all out, and where to stay that's gay.

Parvati Shallow's Survivor brunch, Queen! celebrates Lucy's birthday, and G.E.M. turns five at Jackhammer — plus 92 ways to fill your weekend.

A citywide guide to the best gay bars and clubs in Chicago — Northalsted's neon-lit video bars, Andersonville's laid-back locals, historic South Side spots and everything between.

Laid-back patios, karaoke, and the least pretentious crowd in the city — here's where Chicago's bears, cubs, and otters actually hang out, night by night.

From cruise bars in Rogers Park to the Chicago Eagle, here's every corner of Chicago's leather and kink scene — the birthplace of IML.