Charlie's is a little taste of South Texas smacked dab in the middle of North Halsted. With sister bars in Denver and Arizona, this country bar seems to have more of a dual personality than anything else—line dancing to country favorites and hits borrowed directly from the now defunct Nashville Network before 2 AM; mainstream pop and dance in a disco after the switchover.
The actual bar is a decent size square with bars surrounding the dance floor (notice the cowboy boots disco ball) and country paraphernalia lining the walls. Western in its style, wagon barrel trashcans sit next to hay loft stall benches--behind, pictures of men in cowboy hats are hung on the wall.
The crowd is about ninety-eight percent gay men, thirty-something and up cowboys in Wranglers, boots, and Stetsons early in the night; twenty-something boys from Roscoe's and Circuit mixed in with leather daddy types who closed down Cell Block after the switch.
For late night options, Charlie's is one of the few where the men keep their clothes on and the music remains mainstream. Best bets for going are Friday and Saturday nights a little before the change over—grab a beer and a stool and watch ten minutes of line dancing as the slow invasion of the guppie morphs the bar.
I have to say, I have not been to Charlie's when I wasn't completely wasted, however I had an extremely fun time every time. It's the perfect after-hours club (best after 2am). - JimmyBoi
What can you say about Charlies...it's truly a boystown fixture. Hit it at 2:30 on weekends for a kickin dance party! Charlies is a great place to find a late night hook-up! ;-) - TwinkCraig
I'm relatively new to Chicago, but I learned quickly that Charlie's is THE late night spot. The crowd packs in after most of the other Boystown bars close at 2am. - RyanOH
You guys are crazy - NJSkidmore
What can you say about Charlies...it's truly a boystown fixture. With hotties like Eric at the door along with Larry & Ricardo behind the bars....and the fabulous Lauren Jacob's Show on Sundays......if you don't have fun there...it's no bodies fault but your own! Eventhough this has primarily been the "afterhours" spot for more drinking and dancing....It's actually pretty fun coming in alittle early for the C&W dancing before 2am....the cowboys are hot and very friendly. Then around 2:30...HANG ON GURLFRIEND, the dance music begins and it fills up FAST, with a line down the block. Hope you're not shy...cuz you will be touching someone ...and they will be touching you....I'm amazed my heels stay on the ground with how crowded it gets. So...bring your "Bumper Boyz"...set -up you're own little bumper-zone around you...and have fun!!!! "Love you all more than my luggage!!!" xoxox Jessika Sterling & the Bumper Boyz - jessikasterling
There's nothing better than a man in a Stetson hat...and Charlie's is the only place in Boystown you're gonna see that. Even if you don't line dance you're sure to have a great time here. - bdecker