Part of the Gay Chicago Guide — bars, events & things to do.
Monday, August 24, 2026
Get ready for an open stage talent showcase hosted by Reggay Boots, where you can strut your stuff and compete for a $50 cash prize as Entertainer of the Week! Whether you're performing or cheering on the queens and kings taking the stage, the energy is electric as Charlie's transforms into a spotlight-stealing extravaganza. Grab a drink special—Apple Pie & Jell-O shots, half-off Hennessy & Patron, $5 domestic beer pitchers, and $6 well drinks—and settle in for a night of pure talent and sass under those neon lights. This event was imported by Out x Out. Please visit the venue link to verify details.
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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.
WeeklyFri, 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.
WeeklyFri, 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.
MonthlySat, Aug 15
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.
WeeklySat, Aug 15
11 PM - 4 AM
Charlie's, Chicago
Weekly Saturday drag show at Charlie's Chicago featuring Bella DeBalle, Pixel, and Persephone Brooklyn with DJ Lightning LuLu. Late-night dance party.
WeeklyLet people know you're going, see who else is attending, and share the event with friends.
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