Part of the Gay Chicago Guide — bars, events & things to do.
Monday, September 7, 2026
Charlie's Chicago Live with Reggay Boots is an open stage talent showcase where you can catch live entertainment and maybe even take home a $50 cash prize as entertainer of the week. The night features drink specials including half-off Hennessy & Patron, $5 domestic beer pitchers, and $6 well cocktails, plus Apple Pie & Jell-O shots. Sign up online if you want to perform, or come ready to cheer on fellow performers in this welcoming, high-energy showcase hosted by Reggay Boots. This event was imported by Out x Out. Please visit the venue link to verify details.
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Tue, Sep 1
11:59 PM - 4 AM
Charlie's, Chicago
Weekly Tuesday night dance party at Charlie's Chicago. Reggaeton, R&B, hip hop, bachata & house. Monthly dance classes. High-energy late-night venue.
WeeklyWed, Sep 2
7 PM - 11 PM
Charlie's, Chicago
Weekly queer country line dancing at Charlie's in Chicago. Learn two-steps, enjoy drink specials, and support SCCDA. Every Wednesday.
WeeklyWed, Sep 2
11 PM - 4 AM
Charlie's, Chicago
Weekly Wednesday male revue and go-go show at Charlie's Chicago. DJ Lightning LDW, hosted by Sapphire Feliciano. High-energy gay nightlife.
WeeklyThu, Sep 3
8 PM - 10 PM
Charlie's, Chicago
Monthly Thursday male revue at Charlie's Chicago featuring Ivan Tequila, Andy Santos, and DJ Fister. Gay bar with drinks, dancing, and queer rodeo vibes.
MonthlyThu, Sep 3
10 PM - 4 AM
Charlie's, Chicago
Monthly cosplay and video game tournaments at Charlie's gay bar in Chicago. Compete Thursdays 11pm, sign up 10–11pm. Prizes up to $75.
MonthlyFri, 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.
WeeklyLet people know you're going, see who else is attending, and share the event with friends.
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