Part of the Gay Chicago Guide — bars, events & things to do.
Monday, July 27, 2026
Get ready for an open stage talent showcase hosted by Reggay Boots, where you could snag a $50 cash prize as Entertainer of the Week! This high-energy Monday night brings the perfect mix of live performances and killer drink specials including Apple Pie & Jell-O shots, half off Hennessy & Patron, $5 domestic beer pitchers, and $6 well drinks. Whether you're hitting the stage or cheering from the crowd, it's your chance to experience Charlie's signature sass and energy in full swing. This event was imported by Out x Out. Please visit the venue link to verify details.
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Thu, Jul 23
8 PM - 10 PM
Charlie's, Chicago
Monthly Thursday drag show at Charlie's featuring Aja Ajani, Persephone Brooklyn, Apollo Xenom, and rotating performers. High-energy gay nightlife in Chicago.
MonthlyFri, Jul 24
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, Jul 24
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.
WeeklySat, Jul 25
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.
WeeklyLet people know you're going, see who else is attending, and share the event with friends.
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