Part of the Gay Chicago Guide — bars, events & things to do.
Monday, October 26, 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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Mon, Oct 19
7 PM - 11 PM
Charlie's, Chicago
Monthly gay bingo night at Charlie's with birthday specials, half-off Hennessy & Patron, and prizes. Every Monday in Chicago.
MonthlyMon, Oct 19
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.
MonthlyTue, Oct 20
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.
MonthlyTue, Oct 20
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.
MonthlyWed, Oct 21
7 PM - 11 PM
Charlie's, Chicago
Weekly Wednesday line dancing at Chicago's country-western gay bar. All levels welcome. $5 drafts, $6 wells, $1 from Jack Daniel's supports SCCDA.
MonthlyWed, Oct 21
11 PM - 4 AM
Charlie's, Chicago
Weekly Wednesday male revue and go-go show at Charlie's gay bar in Chicago. High-energy performances hosted by Sapphire Feliciano with DJ Lightning LBW.
MonthlyLet people know you're going, see who else is attending, and share the event with friends.
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