Part of the Gay Chicago Guide — bars, events & things to do.
Monday, September 14, 2026
Charlie's Chicago Live with Reggay Boots is an open stage talent showcase where you can catch live entertainment and maybe even see yourself on stage—the entertainer of the week takes home a $50 cash prize. Hosted by Reggay Boots, this late-night show brings high-energy performances to Charlie's iconic country-western dance floor, with drink specials including Apple Pie & Jell-O shots, half-off Hennessy & Patron, $5 domestic beer pitchers, and $6 well cocktails. Whether you're performing, cheering on friends, or just soaking in the talent and the crowd's electric energy, it's a fun way to experience what makes this Broadway institution special. This event was imported by Out x Out. Please visit the venue link to verify details.
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Sat, Sep 5
11 PM - 4 AM
Charlie's, Chicago
Weekly Saturday drag and dance party at Charlie's Chicago. DJ Lightning LuLu, performers Bella DeBalle, Pixel, and Persephone Brooklyn. 21+.
WeeklySun, Sep 6
5 PM - 7 PM
Charlie's, Chicago
Monthly open-stage drag show at Charlie's in Chicago. All-levels performers welcome in a non-competitive, supportive space hosted by Luc Ami & Julez Osco.
MonthlySun, Sep 6
7 PM - 11 PM
Charlie's, Chicago
Weekly Sunday karaoke at Charlie's gay bar in Chicago. Hosted by Sutton Fister with country, pop, and more. Sing, cheer, and have fun.
WeeklySun, Sep 6
11 PM - 4 AM
Charlie's, Chicago
Weekly Latin dance party at Charlie's Chicago. DJ X-tasy, hosted by Persephone Brooklyn LaRue and Luna LaCatrina. High-energy vibes every Sunday.
WeeklyMon, Sep 7
7 PM - 11 PM
Charlie's, Chicago
Free drag bingo every Monday at Charlie's Chicago. Cheap drinks, live performances, and community vibes. 21+.
WeeklyMon, Sep 7
11 PM - 2 AM
Charlie's, Chicago
Weekly Monday open stage showcase at Charlie's Chicago. Live entertainment, drink specials, and $50 prize for entertainer of the week. Sign up to perform.
WeeklyLet people know you're going, see who else is attending, and share the event with friends.
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