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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Fri, Sep 4
7 PM - 11 PM
Charlie's, Chicago
Weekly B2B DJ night at Charlie's in Chicago. Guest DJs and open decks hosted by Reggay Boots every Friday. Dance, spin, and celebrate with the queer community.
WeeklyFri, Sep 4
10 PM - 4 AM
Charlie's, Chicago
Weekly Friday drag and dance night at Charlie's Chicago. High-energy performances, themed destinations, and queer nightlife every week.
WeeklySat, Sep 5
11 PM - 4 AM
Charlie's, Chicago
Weekly Saturday drag and dance party at Charlie's Chicago. DJ Lightning LuLu, performers Bella DeBalle, Pixel, and Persephone Brooklyn. 21+.
WeeklySun, Sep 6
5 PM - 7 PM
Charlie's, Chicago
Monthly open-stage drag show at Charlie's in Chicago. All-levels performers welcome in a non-competitive, supportive space hosted by Luc Ami & Julez Osco.
MonthlySun, Sep 6
7 PM - 11 PM
Charlie's, Chicago
Weekly Sunday karaoke at Charlie's gay bar in Chicago. Hosted by Sutton Fister with country, pop, and more. Sing, cheer, and have fun.
WeeklySun, Sep 6
11 PM - 4 AM
Charlie's, Chicago
Weekly Latin dance party at Charlie's Chicago. DJ X-tasy, hosted by Persephone Brooklyn LaRue and Luna LaCatrina. High-energy vibes every Sunday.
WeeklyLet people know you're going, see who else is attending, and share the event with friends.
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