Part of the Gay Chicago Guide — bars, events & things to do.
Monday, August 31, 2026
Get ready for an open stage talent showcase hosted by Reggay Boots, where you could win $50 as Entertainer of the Week! This is your chance to strut your stuff on Charlie's stage or cheer on fellow performers in an anything-goes atmosphere. Grab a drink special—Apple Pie & Jell-O shots half off, discounted Hennessy & Patron, $5 domestic beer pitchers, and $6 well cocktails—and settle in for a night of pure, unfiltered talent and sass under the neon lights. 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.
Tue, Aug 18
7 PM - 12 AM
Charlie's, Chicago
Weekly Tuesday karaoke at Charlie's in Chicago with hosted chaos, song sabotage, and comedy. Hosted by Bella DeBalle and Sutton Fister.
WeeklyTue, Aug 18
11:59 PM - 3:59 AM
Charlie's, Chicago
Weekly Tuesday dance party at Charlie's featuring Reggaeton, R&B, Hip Hop, Bachata, and House. Hosted by Sapphire Feliciano and Persephone Brooklyn.
WeeklyWed, Aug 19
7 PM - 11 PM
Charlie's, Chicago
Weekly Wednesday line dancing at Charlie's for Chicago's queer country community. Two-step, drink specials, and $1 Jack Daniel's support for SCCDA.
WeeklyWed, Aug 19
11 PM - 4 AM
Charlie's, Chicago
Weekly Wednesday gay male revue and go-go show at Charlie's Chicago. Hosted by Sapphire Feliciano with DJ Lightning. Country-queer nightlife and dancing.
WeeklyThu, Aug 20
8 PM - 10 PM
Charlie's, Chicago
Monthly Thursday male revue at Charlie's featuring Ivan Tequila and Andy Santos with DJ Frister. Gay nightlife entertainment in Chicago.
MonthlyThu, Aug 20
9 PM - 11 PM
Charlie's, Chicago
Monthly Thursday Paint & Sip at Charlie's in Chicago. All supplies included, $4 drinks, no experience needed. Hosted by Kimberly Summer.
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.
Robbie S.
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.
Robbie S.
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.
Robbie S.
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.
Robbie S.
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.
Robbie S.
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.
Robbie S.