Part of the Gay Chicago Guide — bars, events & things to do.
Monday, August 17, 2026
Get ready for an open stage talent showcase hosted by Reggay Boots, where you could win $50 as entertainer of the week—just sign up online! Sip on creative specials like Apple Pie & Jell-O shots, half-off Hennessy & Patron, $5 domestic beer pitchers, and $6 well cocktails while cheering on performers in this high-energy Monday night celebration. Whether you're taking the stage or dancing in the crowd, it's the perfect night to let loose under Charlie's neon lights and embrace the queer rodeo spirit. This event was imported by Out x Out. Please visit the venue link to verify details.
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Sun, Sep 13
7 PM - 11 PM
Charlie's, Chicago
Weekly Sunday karaoke at Charlie's, Chicago's country-western gay bar. Hosted by Sutton Fister with affordable drinks and a welcoming crowd.
WeeklySun, Sep 13
11 PM - 4 AM
Charlie's, Chicago
Latin dance party every Sunday at Charlie's gay bar in Chicago. High-energy dancing hosted by Persephone Brooklyn LaRue and Luna LaCatrina with DJ X-tasy.
WeeklyMon, Sep 14
7 PM - 11 PM
Charlie's, Chicago
Free drag-hosted bingo every Monday at Charlie's Chicago. Play for laughs and prizes with drink specials. Gay bar community night.
WeeklyMon, Sep 14
11 PM - 2 AM
Charlie's, Chicago
Weekly Monday open stage at Charlie's Chicago. Live entertainment, $50 prize, drink specials. High-energy performances on the dance floor.
WeeklyTue, Sep 15
7 PM - 12 AM
Charlie's, Chicago
Weekly Tuesday karaoke at Charlie's, Chicago's country-western gay bar. Hosted by Bella DeBalle and Sutton Fister with surprises and audience participation.
WeeklyTue, Sep 15
11:59 PM - 4 AM
Charlie's, Chicago
Weekly Tuesday late-night dance party at Charlie's Chicago. Reggaeton, R&B, Hip Hop, Bachata, House from midnight. Monthly dance classes for all levels.
WeeklyLet people know you're going, see who else is attending, and share the event with friends.
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