Few cities play as hard as Chicago — that toddlin’ town, where cops and inspectors were once so easily bribed. And, of course, hardly anybody parties better than gay people, paragons of taste and hedonism. Chicago’s lesbian, gay, bisexual and transgender community may not make up so high a percentage of the population as that in Minneapolis or San Francisco, but, in a city so cheap and diverse, there is a space for everyone. Chicago is perfect for those not smart enough for New York or pretty enough for Los Angeles.
Visit the city that gave the world house music, where many clubs stay open until 5 a.m. on Sunday — where gay villages not only exist, but thrive. Come to the city of big-shouldered daddies, where, 49 years after Chicago held one of the nation’s first four pride parades, its newly elected lesbian mayor, Lori Lightfoot, will be this year’s parade grand marshal on June 30.
Chicago is infamously segregated, and there is no small controversy in the fact that LGBT-oriented services are centralized on the North Side — home to the Boystown neighborhood just east of Wrigley Field, as well as Andersonville, Chicago’s lesbian hub. But queer people live in each of the city’s 50 wards.
Soon after a drunken mob famously rioted on Disco Demolition Night at Comiskey Park in 1979 — an event often associated with racism and homophobia — a new musical style emerged from 4/4 beats, synthy bass lines and soul. House music was birthed out of the black, queer Chicago underground, unwelcome in the city’s discothèques.
At the Stony Island Arts Bank in the South Shore neighborhood (1-312-857-5561), records from house godfather Frankie Knuckles’ decadeslong career are played and digitized from noon every Friday, followed at 4 by an open bar with a live DJ. “That record collection essentially is what first brought the LGBT community together,” said music historian Duane Powell. “It was the music that united them, and it was also the music that brought the outside world in and made spaces more comfortable for all.”
In Rogers Park is the Leather Archives and Museum (1-773-761-9200, leatherarchives.org). Director Gary Wasdin explains that the leather subculture grew out of a hypermasculine riff on postwar motorcycle culture. “A big part was defying an image and stereotype of what it meant to be gay and taking back that power and authority,” he said. Full Kit Gear (1-773-657-8000, fullkit.com) is Chicago’s foremost kink and fetishwear retailer.
Women and Children First in Andersonville (1-773-769-9299, womenandchildrenfirst.com) is one of the nation’s surviving feminist bookstores. “We have not just books on our shelves that are curated with an inclusive and queer-minded lens,” said lead bookseller H. Melt, but “a lot of the authors whom we host every month are queer and building queer communities.” The Unabridged Bookstore in Boystown (1-773-883-9119, unabridgedbookstore.com) has a number of carefully curated LGBT titles less likely to surface on Amazon.
Along Halsted Street, Boystown’s main drag, the cavernous Sidetrack (1-773-477-9189, sidetrackchicago.com) is a good place to start the night, especially with a frozen cocktail from one of its six bars. With a high-definition video system throughout the facility constantly streaming music videos, it’s a prime spot for diva worshiping.
The city’s best drag is at Berlin (1-773-348-4975, berlinchicago.com), where Drag Matinee is held every Saturday at 10:30 p.m. Some queens come out in big wigs and sequined gowns, others in punk or metal attire. “We close the curtains at the bar, so we can’t see outside,” said T Rex, who emcees. “You come here, and you forget about your day. We don’t talk politics. We don’t talk much about the outside world. You just come see some of the most fierce performers currently working.”
The best venue for house music is Smartbar (1-773-549-4140, smartbarchicago.com). “It always seesaws on the fulcrum of a good party,” said Joe Shanahan, who opened the club, which is not itself a gay bar, in 1982. Attendees as well as musicians make the atmosphere: “The people who support Smartbar are the ones who somewhat dictate that style. We know what works by the reception we receive.” Queen! — a party held every Sunday night while the 9-to-5 gays sleep — is a playground for artists and service workers.
Chicago is best when you’re at the lakefront, especially on hot days. The LGBT beach is Hollywood Beach, aka Osterman Beach, at the northern terminus of Lakeshore Drive. Between the Speedos, sunscreen and eventually-warm-enough-to-swim-in Lake Michigan, it’s a small slice of heaven.
Paradise also manifests at cash-only Big Chicks (1-773-728-5511, bigchicks.com), where guests are served free hamburgers and hot dogs (puns abound) on Sundays. Before 3 p.m. daily, the storefront hosts Tweet (1-773-728-5576, tweet.biz), serving classic American brunch. Complimentary coffee cake awaits at your table; the jumbo bloody Marys don’t (immediately) hurt.
Big Chicks’ art collection is museum-quality: images of women on the bar side, landscapes in the restaurant. “It’s a unique vision that isn’t homogenized, franchised or dumbed down in any way,” said owner Michelle Fire. Walk through the terra cotta art deco facade and into her space. “It makes you feel like you’re stepping into a jewel box.”
Pride is held over the last weekend in June. Over a million have attended the Chicago Pride Parade in recent years — and this year, coinciding with a worldwide backlash against hard-won LGBT rights on the 50th anniversary of Stonewall, it feels as necessary as ever (chicagopridecalendar.org).
On a lighter note, the highly recommended Pride Parade After-Party at the Annoyance Theatre in the Lakeview neighborhood (1-773-697-9693, theannoyance.com) is a deeply odd yet chill affair with amazing installation art and drag performers in high-concept looks. It’s best if you come wearing something self-expressive.
Pride is not limited to the north lakefront. This year’s Dyke March will be in the predominantly Latino Little Village, beginning at 1:30 p.m. Saturday. TRQPITECA Queer Pride, free with a lineup of amazing DJs, is scheduled for June 30 at Chinatown’s riverside Ping Tom Memorial Park from 3 p.m., preceded by a family barbecue at 11. And the inaugural South Side Pride Festival has music, film screenings and a beach picnic planned.
International Mr. Leather is held every Memorial Day weekend in the Loop, offering unrestrained bacchanalia.
Boystown’s Northalsted Market Days (northalsted.com/marketdays) is scheduled for the weekend of Aug. 10. It functions like a second Pride, but with fewer straight people.
Aaron Gettinger lives and works on the South Side of Chicago.