Part of the Gay Chicago Guide — bars, events & things to do.
Monday, July 13, 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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Sat, Aug 8
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.
WeeklySun, Aug 9
7 PM - 11 PM
Charlie's, Chicago
Weekly gay karaoke every Sunday at Charlie's in Chicago. Hosted by Sutton Fister. Sing, celebrate, and connect with the LGBTQ+ community.
WeeklySun, Aug 9
11 PM - 4 AM
Charlie's, Chicago
Weekly Latin dance party at Charlie's Chicago hosted by Persephone Brooklyn LaRue and Luna LaCatrina. DJ X-tasy spins every Sunday night.
WeeklyMon, Aug 10
7 PM - 11 PM
Charlie's, Chicago
Free drag bingo every Monday at Charlie's Chicago with hosts Aurora and Bella. Drink specials, 21+. Gay nightlife in Chicago.
WeeklyMon, Aug 10
11 PM - 2 AM
Charlie's, Chicago
Weekly Monday open stage talent showcase at Charlie's Chicago. Perform or watch for $50 prize, drink specials, and live entertainment.
WeeklyTue, Aug 11
5:30 PM - 6:30 PM
Charlie's, Chicago
Free salsa, bachata & cumbia dance lessons every Tuesday at Charlie's Chicago. All levels welcome. $4 drinks, Jell-O shots for charity.
MonthlyLet people know you're going, see who else is attending, and share the event with friends.
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