3501 N. Halsted St. (3500N, 800W) Chicago, IL 60657
(773) 871-6116

Little Jim's Chicago For those of you history buffs, Little Jim’s Tavern at the northeast corner of Halsted & Cornelia, was Chicago’s first LGBTQ+ friendly bar to open in Boystown back in 1975. Don’t blink or you’ll miss it—it’s a tiny late-night hook-up joint disguised as a neighborhood bar. Little Jim’s is meant for getting together with friends, having a few drinks, chatting and, to be blunt, an easy place to meet easy older guys and “bears.”

I can honestly say that the only times I have ever stepped foot in Little Jim’s were after a night of carousing at other Boystown bars like Hydrate. And it’s only because one of my lonely—I mean lovely—gay male friends wanted to go there. Before making my fist trip about a year ago, I had heard some less-than-pleasant things about it, such as the bar’s nickname “pig farm” (named after the men or “pigs” that want to use other men for sex) and its notoriety as the sleaziest bar in Boystown, which kept me from high-tailing it over for a drink previously. Even though the bar is meant for men, actually reminding me of your grandpa’s rec room, the occasional woman can be seen at Little Jim’s, most likely dragged there by friends just like me.

Little Jim's Bar RoomIf sex is the furthest thing from you mind, you’re likely part of the minority at Jim’s but there’s plenty to keep you distracted. The bar offers two pinball machines, a jukebox and two televisions playing various TV shows. A few years ago the bar used to play videos of men going at it but, for unknown reasons, the videos mysteriously disappeared. I personally never witnessed this but have over heard friends reminiscing about it over Little Jim’s cheap drinks.

Speaking of which, the daily specials at Little Jim’s can’t be beat, especially with well drinks and domestic beer for $2.25 on Mondays and $6 Miller Lite pitchers on Fridays. Some advice that I have been given by Little Jim’s regulars is to make friends with the bartenders who’ll hook you up with drinks; make enemies with them and they’ll talk about you behind your back to everyone in the bar. Little Jim’s is cash only, doesn’t serve food, and has a late-night license so is open until 4am during the week, 5am on Saturdays, and opening noon daily.

Little Jim's Bar
The downside to Little Jim’s, aside from gossiping bartenders, is its small size. The place tends to make you feel a little claustrophobic at peak hours, especially when loud drunk men get in your face or back you into a corner to share their life stories. Of course, I speak from personal experience having to listen to an intoxicated 40-year-old man tell me how lonely he was. I think he was so hard up, that he would’ve gone home with me that night if I had so graciously offered. Needless to say, if you’re a gay man looking for a hookup, Little Jim’s is for you. I can’t promise you that you will go home with the man of your dreams but there’s a good possibility you will go home with someone, keeping in mind that the average Little Jim’s bar goer is about 30 years old or older. If a hook up isn’t what you are looking for, check out Little Jim’s during daylight hours when there’s a few guys sitting at the bar enjoying cheap drinks and good conversation. If you like Little Jim’s, you might also like Cell Block a few blocks north on Halsted. For more information, check out the Little Jim’s website . Go Bears!