Head to the Windy City for some Chicago-style pizza, Chicago-style hot dogs, and Chicago-style gay bars! West Lakeview’s “Boystown” continues to be a thriving gayborhood riddled with LGBTQ businesses, nightlife, and residents, but Andersonville offers a less tourist-y selection of queer watering holes. If you're looking to watch the game at a gay sports bar, dance among a sea of twinks, get your leather on, be woofy with the bears, sing karaoke with the sisters, or watch drag queens lip sync your favorite songs, Chicago has it all covered (and uncovered, certainly when it comes to beguiling go-go-boys)!
You’ll need a Lake Michigan-sized reservoir of stamina to attempt a bar crawl of our 15 top LGBTQ bar picks, so spread them out over at least a few nights’ stay, mm-kay?
While it looks like an upscale, classic, European speakeasy hotel bar, no secret phrase or check-in is required for entrance to this Andersonville gay professional set favorite. A menu of tasty (and strong AF!) martinis rule, plus a selection of wines and altruism—multiple Sundays every month, sales benefit local organizations and charities.
Wilkommen to Berlin, where dancing, drag queens, and diversity reign. Opened in Boystown during 1983 with an accepting, eclectic, all-types attitude (a la 1930s Weimar-era Berlin and the film “Cabaret,” sans German nationalists, of course), today’s Berlin is as diversity-friendly as it comes, for people of all genders, sexualities, and ethnicities. Weekdays see viewing parties for shows like Pose, queer variety performances, music from goth to 1980s to alternative, indie, and electronica, and the weekly Saturday night drag show (“Drag Matinee”) and dance party (“Twisted”), which runs until 5 a.m.
Queer chain restaurant serving hamburgers and comfort food, Hamburger Mary’s also serves up a whole lot of drag, DJ, and dancing action in its Andersonville location’s upper level club/theater, Mary’s Attic. Every first Sunday, the Attic hosts Chicago’s longest-running, traditional East Coast-style (think Fire Island and Provincetown, Massachusetts) T-dance, “Tea In A’Ville,” with no cover! Be sure to check the calendar for a juicy line-up of edgy, out-there local drag talent (e.g. Lexi Pro and Aubrey Del Mar), off-kilter cabaret, and comedy.
“Drink, dance, repeat” is the slogan at this 11-year-old Boystown favorite, which draws a bouncy mix of millennials, 30-somethings, and dance-happy people of all ages. Work the dance floor and laser lights to a musical blend of pop with a dash of R&B, hip-hop, and Latin music, with select nights designated as themed “takeovers,” featuring the likes of Ariana Grande, Miley Cyrus, Lady Gaga, and Selena. Sunday afternoons are popular for the “liquid brunch” of bargain-priced drinks and champagne starting at 2 p.m., plus drag kings and queens for your entertainment.
A 22-year-old fixture on the Boystown circuit, situated on the corner of North Halstead and West Roscoe Streets and split into both bar and dance club spaces, Roscoe’s ticks a whole lot of boxes. American comfort food! Raucous RuPaul’s Drag Raceviewing parties! Performances and meet and greets with visiting Drag Racequeens! Britney, K-pop, and other themed music nights! A Roscoe’s Drag Race competition! Karaoke! And, of course, dancing!
Pool tables, dartboards, giant TV screens, and paraphernalia from Chicago’s Cubs, Bulls, and Bears adorn this enduring neighborhood gay sports bar. Now in its 36th year, The North End is all about watching the games, engaging in some friendly pool and dart competitions, and throwing back some beer, cider, and whatever drink specials the bar is offering.
Lately, The Jeffery Pub’s claim to fame is Chicago native drag queen, and RuPaul’s Drag Race: Season 10 finalist, The Vixen, who made her first professional public performance here in 2013. Expect industrial, disco-chic interiors, a mix of R&B, house, hip-hop, and neo-soul tunes, drag, go-go boys, and even nights dedicated to a “chill mature crowd.”
Pride Weekend 2003 marked the opening of this aptly named nightclub, which allows guests to sweat and dance until 5 a.m. Saturday nights, and 4 a.m. during the rest of the week. A prolific line-up of resident and international guest DJs—the list has featured Chris Cox, Ralphi Rosario, and Alyson Calagna—keep the sounds pumping, and Wednesday’s weekly Honeys On Halstead Drag Show is reason enough to visit this bar.
In 2018, Bon Appetit fleshed out the history of this Uptown Chicago institution and its “Big Chick” owner, Michelle Fyre. Dating back to 1944, and bought by Fyre in 1986, today’s Big Chicks serves as a great equalizer and de facto community center, with everyone from the non-binary to bears savoring food and drinks within art-filled walls. Don't miss its monthly FKA (a.k.a. "Formerly Known As") dance party, on second Fridays.
Is the name a cheeky acknowledgement of this LGBTQ dive bar’s far-flung suburban location, just near the Chicago Midway International Airport? Expect a down-to-earth crowd—including airport staff—plus weekly karaoke, Top 40 and Latin tunes (and folks), a go-go dancer or two, and videos playing on a large screen. If you’ve got a layover or connection, find yourself InnExile!
The striking, snaking cloud-like installation—comprised of 19,000 light bulbs that change color—that hovers over the illuminated bar of this six-year-old Boystown venue may as well come with a rainbow, given its beautiful, multicolored mix of visitors. Expect equal emphasis on cocktails and craft brews, attentive bartenders, and, by midnight, frenzied dancing to pop, dance, and hip-hop tunes.
In 2018, the owners of Andersonville’s SoFo Tap and Meeting House Tavern bought and brought a new life to Rogers Park’s nearly two-decade old Jackhammer complex—but retained its 4 a.m. liquor license. Broken into a handful of distinct spaces, they include basement-level leather and fetish bar, The Hole, a dance floor, and an outdoor patio while an eclectic weekly calendar boasts the Monday “Chicago’s Best Worst Drag Show,” naked bear play parties, and late night karaoke.
Opened in 1982 as a single 1,000-square-foot space, Sidetrack is the kudzu of Chicago gay bars, having expanded to a multi-level, eight-space complex that draws a largely male crowd. Take advantage of the expansive open-air rooftop during good weather (open weekends from 1 p.m.) where there’s no shortage of events, happy hours, frozen drinks, poppy dance tunes, and even show tune sing-alongs.
Billed as the city’s “largest Black gay alternative club,” this South Side hole-in-the-wall, disco bar got a video system upgrade in spring 2018 and keeps its crowd energized with hot go-go boys on Saturday nights, a blend of music, and beloved Chicago drag queen Mz. Ruff N’ Stuff, who's been working it for over 20 years. Her weekly Ruffy’s Thursdays are not to be missed!
Serving Chicago since 1978, Boystown’s unpretentious neighborhood “staple video bar” has been around since before video bars became a thing. Lesbians and gay men mingle well here over games of darts, and there’s a monthly “Spectrum” drag queen and king show. This closet is open, girl!