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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Fri, Aug 21
7 PM - 11 PM
Charlie's, Chicago
Weekly B2B DJ night every Friday at Charlie's, Chicago's queer country bar. Guest DJs spin live—dance, connect, and celebrate with the community.
WeeklyFri, Aug 21
10 PM - 4 AM
Charlie's, Chicago
Weekly Friday night drag party at Charlie's in Chicago. High-energy performances, dancing, and cosmic-themed nights that shift weekly. Join the house queens.
WeeklyFri, Aug 21
11 PM - 4 AM
Charlie's, Chicago
Monthly blackout dance party at Charlie's Chicago. High-energy nights with DJ Foster, hosted by Persephone Brooklyn and Pixel. Every Friday.
MonthlySat, Aug 22
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.
WeeklySat, Aug 22
11 PM - 4 AM
Charlie's, Chicago
Weekly Saturday drag show at Charlie's Chicago featuring Bella DeBalle, Pixel, and Persephone Brooklyn with DJ Lightning LuLu. Late-night dance party.
WeeklySun, Aug 23
5 PM - 7 PM
Charlie's, Chicago
Monthly drag showcase every Sunday at Charlie's Chicago. Hosted by PB, featuring live performances and queer nightlife in a rodeo-themed venue.
MonthlyLet people know you're going, see who else is attending, and share the event with friends.
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