Charlie’s Chicago

Charlie's is Chicago's country-and-western gay bar, a Boystown late-night institution since 1993 that brings a little taste of South Texas to the North Side, complete with cowboy paraphernalia, a cowboy-boot disco ball, and a crowd in hats, buckles, and boots. It's a genuine two-in-one: line dancing and two-stepping to country favorites earlier in the evening, then a switch to high-energy Top-40 and dance after midnight, running later than almost anything else on the scene. Add drag bingo, underwear parties, shirtless go-go cowboys dancing on the bar, and a friendly, "there's always a party" spirit, and you get a night out that's refreshingly different from the Halsted video bars and worth the short walk east to Broadway. Just plan on a Lyft home, since it goes till the small hours.