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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Tue, Jul 7
7 PM - 12 AM
Charlie's, Chicago
Weekly Tuesday karaoke at Charlie's in Chicago with hosted chaos, song sabotage, and comedy. Hosted by Bella DeBalle and Sutton Fister.
WeeklyTue, Jul 7
11:59 PM - 3:59 AM
Charlie's, Chicago
Weekly Tuesday dance party at Charlie's featuring Reggaeton, R&B, Hip Hop, Bachata, and House. Hosted by Sapphire Feliciano and Persephone Brooklyn.
WeeklyWed, Jul 8
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.
WeeklyWed, Jul 8
11 PM - 4 AM
Charlie's, Chicago
Weekly Wednesday gay male revue and go-go show at Charlie's Chicago. Hosted by Sapphire Feliciano with DJ Lightning. Country-queer nightlife and dancing.
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