Part of the Gay Chicago Guide — bars, events & things to do.
Monday, August 3, 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 28
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.
MonthlyTue, Jul 28
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 28
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 29
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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