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Charlie's Chicago Live with Reggay Boots | Chicago (click for info!)
Monday, July 27, 2026
11 PM - 2 AM
Charlie's, Chicago3726 North Broadway, Chicago, IL 60613, United States
About Charlie's Chicago Live with Reggay Boots
Get ready for an open stage talent showcase hosted by Reggay Boots, where you could snag a $50 cash prize as Entertainer of the Week! This high-energy Monday night brings the perfect mix of live performances and killer drink specials including Apple Pie & Jell-O shots, half off Hennessy & Patron, $5 domestic beer pitchers, and $6 well drinks. Whether you're hitting the stage or cheering from the crowd, it's your chance to experience Charlie's signature sass and energy in full swing.