Part of the Gay Chicago Guide — bars, events & things to do.
Wednesday, September 2, 2026
Get your boots ready for the Second City Country Dance Association's weekly line dancing night! Learn new moves, master classic two-steps, and join the queer country community for an evening of boot-scootin' fun. Enjoy drink specials including $5 domestic draft pitchers and $6 well cocktails, plus support a great cause—$1 from every Jack Daniel's cocktail goes directly to SCCDA during line dancing hours. This event was imported by Out x Out. Please visit the venue link to verify details.
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Thu, Aug 27
8 PM - 10 PM
Charlie's, Chicago
Monthly Thursday drag show at Charlie's featuring Aja Ajani, Persephone Brooklyn, Apollo Xenom, and rotating performers. High-energy gay nightlife in Chicago.
MonthlyFri, Aug 28
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 28
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.
WeeklySat, Aug 29
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 30
7 PM - 11 PM
Charlie's, Chicago
Weekly gay karaoke every Sunday at Charlie's in Chicago. Hosted by Sutton Fister. Sing, celebrate, and connect with the LGBTQ+ community.
WeeklySun, Aug 30
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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