Part of the Gay Chicago Guide — bars, events & things to do.
Thursday, September 17, 2026
Get creative with brushes and canvas while sipping on $4 you-call-it drinks at Charlie's monthly Paint & Sip, hosted by Kimberly Summer. All supplies are provided and participation is free—just show up ready to make some art and have fun with the community. It's the perfect low-key night out that lets you tap into your creative side without the pressure, all set to the welcoming vibe of Chicago's favorite country-western gay bar. This event was imported by Out x Out. Please visit the venue link to verify details.
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Tue, Sep 15
11:59 PM - 4 AM
Charlie's, Chicago
Weekly Tuesday late-night dance party at Charlie's Chicago. Reggaeton, R&B, Hip Hop, Bachata, House from midnight. Monthly dance classes for all levels.
WeeklyWed, Sep 16
7 PM - 11 PM
Charlie's, Chicago
Weekly Wednesday line dancing at Chicago's country-western gay bar. All levels welcome. $5 drafts, $6 wells, $1 from Jack Daniel's supports SCCDA.
WeeklyWed, Sep 16
11 PM - 4 AM
Charlie's, Chicago
Weekly Wednesday male revue and go-go show at Charlie's gay bar in Chicago. High-energy performances hosted by Sapphire Feliciano with DJ Lightning LBW.
WeeklyFri, Sep 18
7 PM - 11 PM
Charlie's, Chicago
Open Decks B2B every Friday at Charlie's Chicago. Two guest DJs and Reggay Boots host high-energy dancing with country-western charm. Gay bar nightlife.
WeeklyFri, Sep 18
10 PM - 4 AM
Charlie's, Chicago
Weekly Friday night dance party at Charlie's in Chicago. New themed galaxy each month with high-energy performances by House Queens.
WeeklyFri, Sep 18
11 PM - 4 AM
Charlie's, Chicago
Monthly blackout dance party at Charlie's Chicago. DJs Persephone Brooklyn, Pixel & Foster spin high-energy club vibes every Friday.
MonthlyLet people know you're going, see who else is attending, and share the event with friends.
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