Transvestite Bars In Chicago

Transvestite Bars In Chicago



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30s / 40s / Ambient / Bar / Blouses
Party Earth Review Camouflaged behind a colorful plank façade adorned with an ever-changing display of graffiti art, The Violet Hour offers an unexpected touch of upscale luxury to a neighborhood better known for dive bars and hipster hangouts. A series of dark blue floor-to-ceiling curtains part to reveal the various rooms of the venue ... more
1520 North Damen Avenue
Chicago, IL 60622
20s / 30s / 40s / After Work / Casual
Party Earth Review Constructed of old brick and sandwiched against a neighboring restaurant, The Matchbox is a dive bar that looks a lot like its name. All the same, this tiny, tapering corner venue – only three feet wide at its narrowest point – boasts more than thirty varieties of bottled beer, from microbrews to rare French imports, not ... more
770 North Milwaukee Avenue
Chicago, IL 60622
20s / 30s / 40s / After Work / Beer / TVs
Party Earth Review Located at the south end of the city’s famously ritzy Magnificent Mile, Sweetwater Tavern and Grille is a cavernous sports bar and restaurant with an upscale, minimalist vibe. Floor-to-ceiling windows and dozens of plush white booths around the perimeter provide a cozy spot for tourists and local professionals to enjoy ... more
225 North Michigan Avenue
Chicago, IL 60601
30s / 40s / After Work / Bar / Casual
Party Earth Review Despite its proximity to the lavish shops and restaurants of the Magnificent Mile, Pippin’s Tavern has been drawing in one of the most eclectic and diverse crowds in Chicago since 1973 from wealthy shoppers and young businessmen to college students and foreign tourists. The weathered façade, which looks like a gingerbread ... more
806 North Rush Street
Chicago, IL 60611
20s / 30s / 40s / ATM / Balcony / Bar / Club
Party Earth Review Named for its two separate entrances – one for the fans and one for the bands – Double Door is a simple club where music undeniably takes center stage. With its single long bar the only element that takes away from the open wooden dance space and a standing room capacity of only five hundred, it seems incredible that the ... more
1572 North Milwaukee Avenue
Chicago, IL 60622
20s / 30s / ATM / Arcade Games / Dive
Party Earth Review The Empty Bottle has been serving up $5 drink combos and live music seven nights a week since it first opened in 1992, featuring a jam-packed calendar of events ranging from jazz and rock to experimental noise. The venue’s deceptively small exterior hides a spacious three-roomed space decked out in concert posters and packed ... more
1035 North Western Avenue
Chicago, IL 60622
Party Earth Review Popular with an amiable bunch of grad students and young professionals bent on conversation, the modest Hopleaf Bar harbors an intense dedication to beer, and lots of it. Every night, the worn wooden tables and booths on the first floor quickly fill up with easygoing patrons pouring over the selection of more than two hundred ... more
5148 North Clark Street
Chicago, IL 60640
Party Earth Review A Chicago staple since 1936, the Rainbo Club is a cozy one-room venue popular with a creative clientele of artists, musicians, and hipsters. Ambient blues and folk music set the tone in the spare space, whose small stage – which has hosted everything from burlesque performances to dueling pianos – now showcases a rotating ... more
1150 North Damen Avenue
Chicago, IL 60622
Party Earth Review Tucked inside the ultramodern Sofitel Hotel, Le Bar is a stylish and intimate lounge best known for its French fusion snacks, intricate cocktails, and assortment of gourmet cheeses. Early in the evening, upscale hotel guests and fashion-conscious couples sink into warm velvet chairs by a roaring fire to work their way through ... more
Sofitel Chicago Water Tower
20 East Chestnut Street
Chicago, IL 60611
Party Earth Review Even on the most crowded and rowdy evenings, Bull & Bear maintains a level of decorum worlds apart from the often raucous venues that dominate Chicago’s sports bar scene. In true Wall Street style, a forty-foot-long stock market ticker above the main bar reports recent sports updates and scores, while an almost obscene ... more
431 North Wells Street
Chicago, IL 60654
Party Earth Review Marked by a sign with the image of a happy man hugging records and a tagline promising “the most fun you won’t remember,” The Hangge Uppe has been a prime Gold Coast spot for drinking, dancing – and more drinking – since 1973. A few stumbling steps from the wild bar scene of Division Street, the mostly 80s-themed bi-level ... more
14 West Elm Street
Chicago, IL 60611
20s / 30s / ATM / Anything goes / Bar
Party Earth Review With a rich history in the arts and music scene, The Flat Iron, formerly the live music venue The Blue Note, draws a dedicated community of creative patrons. The giant face of a skull immediately greets guests upon entering – usually accompanied by the deafening sounds of Black Sabbath from the jukebox – while murals by ... more
1565 North Milwaukee Avenue
Chicago, IL 60622
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Chicago’s social life invariably revolves around its denizen’s love of sports and beer, but there are still hundreds of bars in Chicago that cater to the highest of the high end and the dingiest of dives to fit into any resident’s social schedule.
There are actually thousands of Chicago bars – and they populate every street and are hidden away in the quaintest residential areas – so if the Cubs, White Sox, Bears, or Bulls are playing, it’s a lock that every bar in town will be playing the game on their TVs. But the biggest spots in town for sports fans are in Wrigleyville where sports bars are dime a dozen.
Meanwhile, many food-heavy bars dot the city and serve perfect beer and food pairings, though it’s just as easy to find the best deep dish pizza and a cold one at other local haunts, or just a wine bar to while away the hours in.
Though neighborhood bars, sports bars, and pubs are the most common nightlife destinations in Chicago, an array of higher-end venues in areas like River North and the Gold Coast draw in the social elite to live, work, and play.
The best part about all the bars in Chicago, whether high-end, sports crazy, or just the hole-in-the-wall variety, is that they stay open really late, with some spots keeping their doors open until 4 or 5am.
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Outside Roscoe’s during Pride
nathanmac87/Flickr
Chicago’s LGBTQ scene is world-renowned
by Grace Perry Oct 25, 2018, 2:00pm CDT
Share All sharing options for: The 14 Essential LGBTQ Bars in Chicago
Outside Roscoe’s during Pride
| nathanmac87/Flickr
by Grace Perry Oct 25, 2018, 2:00pm CDT
Share All sharing options for: The 14 Essential LGBTQ Bars in Chicago
There’s a reason so many young queer people flock to Chicago and never leave: the city’s gay scene is fun as hell. Boystown, of course, is the city’s official gayborhood, with LGBTQ-friendly bars, restaurant, and clubs occupying nearly every storefront on Northalsted. But Chicago’s queer community exists far outside the Lakeview enclave—and so do the great gay bars.
From butch lesbian North Side dives to raucous South Shore dance parties, the spots below are a diverse range of LGBTQ watering holes all over town. Whether they include drag, dancing, or are dives—or a little bit of all three—Chicago’s best gay bars have a little something for everyone.
Note: Restaurants on this map are listed geographically.
A favorite among Rogers Parkers, this male-dominated, multi-level dive features a welcoming vibe and an energetic dance floor on weekends. The basement bar, The Hole, is the city’s foremost leather/fetish bar, so come dressed accordingly. If not, don’t sweat—Leather 64 Ten is a fetish gear shop located next door, for all of patrons’ last-minute jockstrap needs. It was recently close to shuttering but was purchased by new ownership.
Outside Jackhammer
Google Streetview
1137 W Granville Ave
Chicago, IL 60660
Gay Edgewater residents of all ages call themselves regulars at this friendly, casual dive bar. The jukebox is perhaps the Anvil’s greatest accessory, featuring plenty of ‘60s and ‘70s hits people magically know all the words to when they’re buzzed. And with strong, inexpensive pours, the Anvil makes it easy to get to that place.
The Granville Anvil’s sign
Phoenix J./Foursquare
1511 W Balmoral Ave
Chicago, IL 60640
This charming, tiny cocktail joint is the perfect antidote for exhaustion from the Boystown scene. Home to vested bartenders, Toulouse-Lautrec posters and a handsome wooden bar, Marty’s old school ambiance pairs perfectly with its classic cocktail list. Its martinis, of course, are must-trys, but watch out—those Marty’s pours are hefty.
A Marty’s martini
Christopher R./Yelp
Andersonville regulars love to both grab patties from Hamburger Mary’s downstairs and climb the nearly-vertical stairs to the restaurant’s beloved second-floor venue, Mary’s Attic. The intimate upstairs joint throws all kinds of events, from retro dance parties to stand-up comedy to drag shows. Thursdays and Sundays are karaoke nights (dubbed “MaryOke”), so don’t forget to do vocal warm-ups.
Mary’s Attic draws crowds
Mary’s Attic/Facebook
1744 W Balmoral Ave
Chicago, IL 60640
This lesbian-owned Andersonville spot is primarily a wine bar, as the name suggests. But Joe de Vine’s cocktail menu is equally impressive. Well, actually, there’s no cocktail menu. Instead, patrons can simply tell their bartender what kinds of liquor and flavors they like, and voila: a delicious craft cocktail.
Joie De Vine is cozy and fun
Denyce M./Yelp
5024 N Sheridan Rd
Chicago, IL 60640
Every night, the popular brunch spot Tweet transforms into Big Chicks: a funky, divey cocktail lounge in one room, and a dance floor in the room adjacent. This Uptown spot features a relatively mixed-gender clientele (in the scheme of gay bars). The second Friday of each month, Big Chicks hosts FKA (Formerly Known As), a long-running dance party dedicated to welcoming folks of all genders.
The bar at Big Chicks
Big Chicks/Facebook
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4623 N Western Ave
Chicago, IL 60625
If barhoppers are looking to get drunk for less than $10 and to meet some lady-loving-ladies while they’re at it, Spyners Pub is the place to go. The gritty Lincoln Square dive features karaoke on weekends and damn cheap drink specials every night. With no distinguishing signage outside, this unmarked dive is much more discreet than its very gay clientele is.
Spyners Pub is a neighborhood bar and more
Corrine R./Yelp
As far as Boystown bars go, Roscoe’s has it all: a casual bar in the front and a dance club in the back, with drag, karaoke and dueling pianos on weeknights. The pub’s RuPaul’s Drag Race viewing parties on Thursdays are some of the rowdiest parties in Boystown.
Roscoe’s is party central in Boystown
nathanmac87/Flickr
Sidetrack is generally heralded as the king of Chicago gay bars, and not for no reason: the sprawling complex features five different bars year-round. Add another two in the summertime, when the upstairs patio—one of Chicago’s best, gay or straight—is open for business. While it’s a largely male space, Sidetrack attracts a slightly older crowd than most Boystown spots do, with patrons ranging from their early ‘20s into their ‘50s and ‘60s.
Sidetrack has sleek bars and patios
Sidetrack [Official Photo]
Amidst the strobe lights and the thumping baselines of Boystown lies this unpretentious dive bar. With a killer jukebox, a friendly and nonjudgmental atmosphere, and local beers on tap, Town Hall is perfect for a low-key night out. The bar’s sticky floors are probably due to its many Jell-O shots served.
Town Hall is a divey neighborhood spot with great drink specials
Daniel I./Yelp
Berlin is one of the best nightclubs citywide, regardless of who patrons like to get down with. The 35-year old dance club is home to different DJs and curated parties nearly every night of the week, ranging from glittery ragers hosted by drag queens to experimental installations hosted by art students. As a 4 a.m. bar, Berlin becomes a late-night hot spot once most Boystown bars close at 2 a.m.
Berlin hosts some of the most unique nightlife in Chicago
Berlin Nightclub/Facebook
Streeterville isn’t exactly a happening ‘hood, but this dive off the Mag Mile is an absolute gem. Climb a flight of carpeted stairs to find Second Story Bar: a dingy, charming tavern with TVs typically screening ‘80s movies and TV shows. The drinks are cheap (and strong) but it’s cash-only.
Second Story Bar is low-lit hidden gem downtown
Mark K./Yelp
7041 S Jeffery Ave
Chicago, IL 60649
Not only is the Jeffrey Pub one of the oldest gay bars in the country, it’s also the only black-owned LGBTQ bar in Chicago. The South Shore pub has incubated some of Chicago’s premier African-American drag queens, and regularly hosts amateur drag shows several nights a week. The music ranges from hip-hop to disco to house, and the drinks stay cheap and strong.
Jeffrey Pub gets jammed
The Jeffrey Pub/Facebook
Friendly staff, down-to-earth attitudes and cheap drinks make this no-frills dive a go-to for LGBTQ south siders. On Saturdays, drag queen Miss Ruff ‘N Stuff, who has been entertaining Chicago since the ‘90s, hosts her weekly showcase.
A packed house at Club Escape
Club Escape/Facebook
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Outside Jackhammer
Google Streetview
A favorite among Rogers Parkers, this male-dominated, multi-level dive features a welcoming vibe and an energetic dance floor on weekends. The basement bar, The Hole, is the city’s foremost leather/fetish bar, so come dressed accordingly. If not, don’t sweat—Leather 64 Ten is a fetish gear shop located next door, for all of patrons’ last-minute jockstrap needs. It was recently close to shuttering but was purchased by new ownership.
1137 W Granville Ave, Chicago, IL 60660
The Granville Anvil’s sign
Phoenix J./Foursquare
Gay Edgewater residents of all ages call themselves regulars at this friendly, casual dive bar. The jukebox is perhaps the Anvil’s greatest accessory, featuring plenty of ‘60s and ‘70s hits people magically know all the words to when they’re buzzed. And with strong, inexpensive pours, the Anvil makes it easy to get to that place.
1137 W Granville Ave
Chicago, IL 60660
1511 W Balmoral Ave, Chicago, IL 60640
A Marty’s martini
Christopher R./Yelp
This charming, tiny cocktail joint is the perfect antidote for exhaustion from the Boystown scene. Home to vested bartenders, Toulouse-Lautrec posters and a handsome wooden bar, Marty’s old school ambiance pairs perfectly with its classic cocktail list. Its martinis, of course, are must-trys, but watch out—those Marty’s pours are hefty.
1511 W Balmoral Ave
Chicago, IL 60640
Mary’s Attic draws crowds
Mary’s Attic/Facebook
Andersonville regulars love to both grab patties from Hamburger Mary’s downstairs and climb the nearly-vertical stairs to the restaurant’s beloved second-floor venue, Mary’s Attic. The intimate upstairs joint throws all kinds of events, from retro dance parties to stand-up comedy to drag shows. Thursdays and Sundays are karaoke nights (dubbed “MaryOke”), so don’t forget to do vocal warm-ups.
1744 W Balmoral Ave, Chicago, IL 60640
Joie De Vine is cozy and fun
Denyce M./Yelp
This lesbian-owned Andersonville spot is primarily a wine bar, as the name suggests. But Joe de Vine’s cocktail menu is equally impressive. Well, actually, there’s no cocktail menu. Instead, patrons can simply tell their bartender what kinds of liquor and flavors they like, and voila: a delicious craft cocktail.
1744 W Balmoral Ave
Chicago, IL 60640
5024 N Sheridan Rd, Chicago, IL 60640
The bar at Big Chicks
Big Chicks/Facebook
Every night, the popular brunch spot Tweet transforms into Big Chicks: a funky, divey cocktail lounge in one room, and a dance floor in the room adjacent. This Uptown spot features a relatively mixed-gender clientele (in the scheme of gay bars). The second Friday of each month, Big Chicks hosts FKA (Formerly Known As), a long-running dance party dedicated to welcoming folks of all genders.
5024 N Sheridan Rd
Chicago, IL 60640
4623 N Western Ave, Chicago, IL 60625
Spyners Pub is a neighborhood bar and more
Corrine R./Yelp
If barhoppers are looking to get drunk for less than $10 and to meet some lady-loving-ladies while they’re at it, Spyners Pub is the place to go. The gritty Lincoln Square dive features karaoke on weekends and damn cheap drink specials every night. With no distinguishing signage outside, this unmarked dive is much more discreet than its very gay clientele is.
4623 N Western Ave
Chicago, IL 60625
3356 N Halsted St, Chicago, IL 60657
Roscoe’s is party central in Boystown
nathanmac87/Flickr
As far as Boystown bars go, Roscoe’s has it all: a casual bar in the front and a dance club in the back, with drag, karaoke and dueling pianos on weeknights. The pub’s RuPaul’s Drag Race viewing parties on Thursdays are some of the rowdiest parties in Boystown.
3349 N Halsted St, Chicago, IL 60657
Sidetrack has sleek bars and patios
Sidetrack [Official Photo]
Sidetrack is generally heralded as the king of Chicago gay bars, and not for no reason: the sprawling complex features five different bars year-round. Add another two in the summertime, when the upstairs patio—one of Chicago’s best, gay or straight—is open for business. While it’s a largely male space, Sidetrack attracts a slightly older crowd than most Boystown spots do, with patrons ranging from their early ‘20s into their ‘50s and ‘60s.
3340 N Halsted St, Chicago, IL 60657
Town Hall is a divey neighborhood spot with great drink specials
Daniel I./Yelp
Amidst the strobe lights and the thumping baselines of Boystown lies this unpretentious dive bar. With a killer jukebox, a friendly and nonjudgmental atmosphere, and local beers on tap, Town Hall is perfect for a low-key night out. The bar’s sticky floors are probably due to its many Jell-O shots served.
954 W Belmont Ave, Chicago, IL 60657
Berlin hosts some of the most unique nightlife in Chicago
Berlin Nightclub/Facebook
Berlin is one of the best nightclubs citywide, regardless of who patrons like to get down with. The 35-year old dance club is home to different DJs and curated parties nearly every night of the week, ranging from glittery ragers hosted by drag queens to experimental installations hosted by art students. As a 4 a.m. bar, Berlin becomes a late-night hot spot once most Boystown bars close at 2 a.m.
157 E Ohio St #2, Chicago, IL 60611
Second Story Bar is low-lit hidden gem downtown
Mark K./Yelp
Streeterville isn’t exactly a happening ‘hood, but this dive off the Mag Mile is an absolute gem. Climb a flight of carpeted stairs to find Second Story Bar: a dingy, charming tavern with TVs typically scr
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