Part of the Gay Chicago Guide — bars, events & things to do.
Sunday, September 13, 2026
Bring your best vocals to Charlie's weekly Sunday karaoke night, hosted by Sutton Fister. It's the perfect way to kick off your week at Chicago's only country-western gay bar—whether you're belting out your favorite songs or cheering on friends from the crowd. The vibe is fun and low-pressure, with an affordable drinks menu and a welcoming mix of regulars and newcomers ready to have a good time. This event was imported by Out x Out. Please visit the venue link to verify details.
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Mon, Sep 7
7 PM - 11 PM
Charlie's, Chicago
Free drag bingo every Monday at Charlie's Chicago. Cheap drinks, live performances, and community vibes. 21+.
WeeklyMon, Sep 7
11 PM - 2 AM
Charlie's, Chicago
Weekly Monday open stage showcase at Charlie's Chicago. Live entertainment, drink specials, and $50 prize for entertainer of the week. Sign up to perform.
WeeklyTue, Sep 8
5:30 PM - 6:30 PM
Charlie's, Chicago
Free Bachata, Salsa & Cumbia lessons every Tuesday at Charlie's gay bar in Chicago. All levels welcome. $4 drinks 4PM–8PM, charity shots.
MonthlyTue, Sep 8
7 PM - 12 AM
Charlie's, Chicago
Weekly Tuesday karaoke at Charlie's with unpredictable twists. Hosted by Bella DeBalle and Sutton Fister—high-energy, welcoming gay nightlife in Chicago.
WeeklyTue, Sep 8
11:59 PM - 4 AM
Charlie's, Chicago
Weekly Tuesday night dance party at Charlie's Chicago. Reggaeton, R&B, hip hop, bachata & house with hosts Sapphire Feliciano & Persephone Brooklyn. Monthly.
WeeklyWed, Sep 9
7 PM - 11 PM
Charlie's, Chicago
Weekly Wednesday line dancing at Chicago's country-western gay bar. Cheap drinks, two-stepping, and a welcoming community vibe for all skill levels.
WeeklyLet people know you're going, see who else is attending, and share the event with friends.
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