The Essential Gay Bars Chicago Guide


Gay Bars Chicago

Chicago is one of the most up and coming cities for Gay Bars in the United States. While most men prefer to spend their days enjoying a hot dog at Wrigley Stadium watching a White Sox game, we would like to spend our time in Chicago a little differently. The Windy City is excited to show you all the Gay Bars Chicago has to offer with the help of Manplay. Let yourself get carried away and have a blast. If you only get one vacation this year, why not go to the Windy City and get blown away by the culture and nightlife that this city has to offer?

Gay Bars Chicago: History

Let’s take a second to quickly talk about the beautiful Gay Bars Chicago history. The story begins in the Near North neighbourhood of Towertown, where speakeasies were popular with the gay crowd. The Bally Hoo Cafe hosted contests for cross-dressed patrons and by 1930, there were lots of places for men to hang out. The action moved to the south side with the onset of Prohibition with a series of drag balls. After Prohibition was repealed, there was a growth in popular gay bars around the Loop. The best known was Waldman’s on Michigan Avenue.

In the 1950s and 60s, new hot spots formed in Old Town, Hyde Park and Lake View. By the early 1970s a number of notable bars and nightclubs started popping up around town like Stars, Sparrows, etc. These bars didn’t last long, but they paved the way for more clubs to start showing off. In 1976, an article written by Gaylife’s writer Rhonda says "Hearts and fairies ... Valentine's weekend was certainly something else. All the parties were great, but one has to be singled out as spectacular. And that, of course, was the glorious red, white and pink cloud atmosphere created by Donn Abbinanti for Ye Old Mill. The sweet table was loaded with red and white goodies, including some erotic cookies that melted in your mouth." about the Ye Old Mill, a very popular gay bar at the time. However, a year later, it sadly became a straight bar.

In 1982, a small venue opened in Chicago that had a cold buffet called the Spice Tree. They even had a cabaret act featuring some amazing performers in the gay community. A year later the Stardust Ballroom opened its doors, it was listed as being gay, but no one really knew anything about it. Which was a shame because in our research those who knew about it said ti was one of the best times in their lives. So, if you find a gay bar that you like, make it known, otherwise it could go unnoticed and be a lost Chicago treasure.

Now Chicago is a booming city for the gay community. Division Street is packed with bars that are gay friendly and Boystown is the number one Gay Bars Chicago district. So, now that you know a little something about Chicago's nightlife history, it is time for you to make some history yourself.

Gay Bars Chicago: Directory

Welcome the Windy City and its amazing Boyztown/Gay district. We have put together a list of some amazing bars all within walking distance of each other, just in case you wanted to turn your night on the town into a Chicago Gay Bar crawl. Who doesn’t love a good bar crawl?

The Closet

Type: Gay and Lesbian Bar
Space: Tiny but quaint
Crowd: College kids, young to middle aged adults
Address: 3325 N Broadway St
Any Notes: Features Karaoke, billiards, and a dance floor

Brief Description: Opened in 1978, this gay bar has been a staple in the gay and lesbian community and in the Boystown area of Chicago. They boast the best Bloody Marys in town. We gotta say they be on to something with those. They play the newest music videos on the big screen televisions and it’s the perfect place to just kick it and hang out with like minded people who just want to relax and have a good time after a long week. Considering they are open 24 hours a day, every day, we recommend kicking back on a Friday night at 10pm. Come here and meet some very cool people over a cheap beer and a round of pool. This is one CLOSET you will not want to come out of.


Type: Neighborhood style gay and lesbian bar
Space: Mid range sized with a dance floor with outdoor patio
Crowd: College students and young adults
Address: 3356 N Halstead St, Chicago IL 60657
Any Notes: Billiards, outdoor space and dance floor.

Brief Description: Established in 1987, Roscoes has carved out their own little piece of heaven for the gay and lesbian community. With their bar and lounge feel, they make it easy to meet men and women while having a good time. Fridays at 11pm seems to be the night to head out with $15 Absolut pink lemonade pitchers, $15 Absolut Blue Hawaiian pitchers, $5 Skyy vodka bombs and $5 Jack Daniels honey and fire shots. With these prices on such delicious drinks, why would you want to go anywhere else? There’s a lot to be said for a gay bar with such reasonably priced drinks and a dance floor with an adjacent pool table.

Progress Bar Chicago

Type: LGBT bar, nightclub, lounge
Space: Large with flashy lights, large bar with plenty of seating
Crowd: Young to middle aged adults
Address: 3359 N Halsted St, Chicago IL 60605
Any Notes: There is a huge lightbulb sculptureBrief Description: of Progress Chicago Bar

The name of the bar alone speaks volumes about what this bar is all about in the Gay Bars Chicago nightlife. With the venue being more modern style with a gorgeous and large lighting sculpture. As for the best night to get together it’s a straight up toss up between Monday at 9pm with $5 Jameson and DJ Timmy Loop or Thursday nights with $4 Fireball shots and $3 Miller Lite featuring DJ Avi Sic and a few other guest DJs. There is no better way to spend and evening or two then here at Progress Bar Chicago.

Second Story Bar

Type: Gay bar, lounge
Space: Two floors, big stage, two full bars, seating available
Crowd: College to young adults
Address: 157 E Ohio St #2, Chicago IL 60611
Website:Second Story Bar
Any Notes: Cash only, parking available, no coat check, no wheelchair access, close to transit

Brief Description: While it be called Second Story, this place is definitely the number one story you want to tell all your friends. One of the oldest gay bars in Chicago, this place has a lot to live up to. The bartenders make an effort here to remember your name and what you ordered to make you feel welcomed and at home even if you have never been there before in your life. While they got a bad reputation for a while due to an unsavory bartender, that problem has been fixed and they are back on top. Nothing can keep this bar down. Hungry for snacks while you drink? Ask the bartender and he will scoop you up some chips or maybe even some candy hearts if you are lucky. Every night here after 8pm makes you feel like your at home when your away from home. You can not go wrong at all. However, if we were to decide a night to go we would say Wednesday night when the place is crowded but not over flowing, you can still get a seat, the drinks are cheap and the men are hot. That right there is an unbeatable combination if I ever saw one. Make Second Story bar a first story in your tales about Chicago and Boyztown.

Gay Clubs Chicago: Directory

Alright, so bar hopping might not be your thing. Maybe your thing is going out dancing until 3am. Well if that’s the case, than we have the solution for you because we also like going out dancing until 3 in the morning. Let’s put on your best clothes and head out and paint the town rainbow in Gay Clubs Chicago.

Side Track

Type: LGBT nightclub,
Space: Large dance floor with stage, big screen tvs, long tables and fairy large sized bar. Can host up to 1000 people.
Crowd: Young and Middle aged adults
Address: 3349 N Halstead St, Chicago, IL 60657
Any Notes: Can hold up to 1000 people and was the very first version of BackBar

Brief Description: Sidetrack has been around since 1982 but things were different back then. They had no sign and beer cases were used for seating. Now they have a large bar, huge dance floor and a stage for their live performances. Live musical sing a longs, Cocky boy auctions, celebrating everything that is Beyonce, and my personal favorite, dog day Saturday afternoon where you can bring your own dogs for a community play date. While their drink specials vary from event to event, everyone recommends heading out on a Friday or Saturday night at 11pm when the party is in full swing. With 4 different frozen drinks on hand and bumping tunes every night, Sidetrack is a must. We recommend the Caesar, it’s more garnish than drink and comes with half a croissant.


Type: Dance club, gay bar
Space: Large dance floor, stage, and full bar
Crowd: Young to middle age adult
Address: 3458 N Halsted, Chicago IL 60657
Any Notes: Close to transit, paid parking available

Brief Description: Open every night but Tuesday, but they make up for it by staying open until 4 to 5 am every other night of the week. Half naked men dance on the stage, drag queens perform live,and they make incredibly strong drinks. There is also a lot to be said for nice bouncers and hot bartenders. Saturday nights at 10:30pm are the nights to go, packed wall to wall with gorgeous men and live drag queens on stage. It’s one of the hottest spots to be at on Saturday night in Boystown.


Type: Night club, LBGT bar
Space: Large space, full luxury bar, huge dance floor
Crowd: College students
Address: 3341 N Halsted St, Chicago IL 60657
Any Notes: Paid parking available, casual dress code enforced

Brief Description While it may not be open on Mondays and Tuesdays, the rest of the week the club remains open until 2 to 3 am. It’s down the street from Wrigley field, catch a quick game than head out and enjoy some reasonably priced specialty cocktails and a very large dance floor. Saturday night is the night to be there, open until 3 am. This place goes wild with half naked men, girls in bikinis and bumping music all night long. Come out and lose your shirt.

Gay Bars Chicago: Concluding Thought

Chicago is beginning to become one of the hottest Gay Bar spots and people are welcoming it. Especially sports fans, considering Chicago is home to one of the major baseball fields and a staple in American sports teams. Whether you are here for a day, a weekend, a week, a month or you are moving here Manplay knows you will find a community that is open to all new members and makes you feel like you have been there your whole life. Make Chicago and Boyztown your number one spot for anything and everything gay bars. You do not want to miss out on a chance at something amazing.

With all the places to go and things to see, Chicago Gay Bars are going to blow your mind. This city, with its beautiful history, amazing bars, and a prominent gay district you will fit right in. You will party all night, dance with gorgeous men, and enjoy as many cheap drinks as possible. With all these bars and nightclubs being so close to each other, it makes bar hopping a breeze. So let the Windy City carry you away. You never know where you might just end up. If you want to see more of what Chicago has to offer click here.

For any needs or information, check out Also, if you want to read our GAY BARS NYC guide, CLICK HERE!

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