Under the Boots

Under the Boots | Charlie's Chicago

Part of the Gay Chicago Guide — bars, events & things to do.

Weekly Event

Under the Boots
Saturday, November 7, 2026

Nov7
Saturday, November 7, 2026
11 PM - 4 AM

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Charlie's, Chicago3726 North Broadway, Chicago, IL 60613, United States

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About Under the Boots
Catch drag performers Bella DeBalle, Pixel, and Persephone Brooklyn taking the stage while DJ Lightning LuLu keeps the energy high on the dance floor. This late-night show and dance party is where Charlie's signature two-step energy transforms into a full high-octane celebration—expect glamour, dancing, and the kind of fun that keeps the party going strong. 21+.

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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.

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Latin dance party every Sunday at Charlie's gay bar in Chicago. High-energy dancing hosted by Persephone Brooklyn LaRue and Luna LaCatrina with DJ X-tasy.

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Free drag-hosted bingo every Monday at Charlie's Chicago. Play for laughs and prizes with drink specials. Gay bar community night.

Charlie's Chicago Live with Reggay Boots
Mon, Nov 9
11 PM - 2 AM
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Weekly Monday open stage at Charlie's Chicago. Live entertainment, $50 prize, drink specials. High-energy performances on the dance floor.

Ven Y Baila
Tue, Nov 10
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Free Bachata, Salsa & Cumbia lessons every Tuesday at Charlie's gay bar in Chicago. All levels welcome. $4 drinks 4PM–8PM, charity shots.

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