Chicago offers so many different gay bars in a variety of different neighborhoods. Gay visitors to the city invariably head first to the area of Chicago’s Lakeview and Wrigleyville neighborhoods known as Boystown.
What makes a Boystown bar-crawl so easy is that 99% of the bars run down about a ½ mile stretch of North Halsted Street. Beginning at the southernmost bar and running north, this is Boystown U.S.A.
Spin, located at the corner of Halsted and Belmont, is a dance bar that attracts mainly a younger crowd. Being 42, I’ve only been inside Spin because it’s the place that participants in the annual Halloween Costume Parade register. This is definitely an under-30 crowd.
Sidetracks, at 3349 N. Halsted, is a multi-room, multi-level video bar. They have theme nights like Show Tunes on Mondays, as well as comedy nights and retro music theme nights. In the summer, there’s a relatively new roof deck. Sidetracks is not for claustrophobes – the bar is usually packed.
Roscoe’s, at 3356 N. Halsted, is what TV’s Cheers bar would be if Norm and Cliff were 28, hot, and gay. At times a stand-and-model video bar, there’s also dancing in the back room at night. Roscoe’s can get as crowded as Sidetracks but never feels as closed-in because the bar’s entire “east wall” is glass window looking onto Halsted.
Cocktail, at 3359 N. Halsted, is directly across the street from Roscoe’s – you can see Cocktail if you look out the front windows of Roscoe’s. Often Cocktail gets the run off of people from Roscoe’s. Cocktail has one unique thing to offer – go-go boys.
Buck’s, at 3349 N. Halsted, gets gays of all sexes, shapes, and sizes. The walls are adorned with the heads of real bucks but if that scares you, in the summer, there’s a surprisingly tranquil and festive back patio with its own bar.
Hydrate, at 3458 N. Halsted, is a late night dance club. They get some of the better known national DJs. During the week, the bar has teamed up with some interesting drag performers. Recently, they started a manicure special on Tuesday nights. Hydrate is open late typically till 4 AM.
Little Jim’s, at 3501 N. Halsted, is the neighborhood seedy bar. It’s where you go after everyplace else is closed and you just want to seal the deal and go home. They’re open nightly till 4 AM and 5 AM on weekends. The bar attracts all kinds – mainly men.
There’s always one TV screen dedicated to gay porn. They recently got a digital jukebox which is a major improvement over the old jukebox’s same-old never changing offerings.
Cellblock, at 3702 N. Halsted, is Boystown’s leather bar. It is not as hard core as the leather venues further north like the Eagle and Touché. But recently, they reopened “the Yard” – which is essentially their backroom, so that’s a good sign for the depraved. To get into the back room – open on weekends only – you need to wear a major item of leather. Don’t worry if you don’t own chaps – a leather vest will do (a leather jacket will not however).
Bobby Loves, at 3729 N. Halsted, is – I’m told – where people go who are serious about drinking and getting a bang for their buck. The bar looks like the type of place a lounge singer named Bobby Love might perform but it is a no-attitude environment. They have fun karaoke nights.
North End, at 3733 N. Halsted, is a gay sports bar. Sure there’s karaoke, but there’s a whole room of pool tables, dart boards, and video games and usually a sporting event of some kind on the tube.
All along the way, you’ll find more interesting gay destinations. Predominantly gay restaurants/bars X/O (owned by Hydrate’s owners), Kit Kat Club and Cornelia’s all combine upscale fare with the gay bar environment. And no trip to Boystown is complete without a sojourn to Steamworks, they Disney World of bathhouses. A block off Halsted and you’ll find country-bar and late-night dance club Charlie’s as well as neighborhood bar The Closet – both on Broadway.