How queer nightlife shaped Chicago — and America

In Chicago, Boystown — with its mix of cocktail lounges, gay bars, nightclubs, parades and drag brunches — has become a well-oiled machine for queer culture in the city.

Long before Mayor Richard M. Daley anointed the area bounded by Briar Place to the south, Halsted Street to the west, and North Broadway to the east as the nation’s first official gay village in 1997, the community had already made that roughly triangular patch in Lakeview East its home decades before. That’s because Chicago is, and always has been, a very queer town. It’s where the seat of our community’s culture exists in the city today, but it is certainly not the first place in Chicago where identity, politics and partying for the community collided.

It was actually three and a half miles directly south that Chicago's queer community found its first semi-permanent home in the city. Today, it’s hard to imagine the Magnificent Mile and its surrounding blocks, with its mix of luxury new-build construction and brick pre-war walk-ups, as anything but an upper-class repository on Chicago’s North Side. This wasn't the case a century ago, though. The area that surrounded the historic water tower was a known bohemian enclave. Chicagoans referred to the neighborhood as “Towertown,” and it was where writers, artists, communist revolutionaries and queer folks often lived and even more frequently partied during Chicago’s rowdy Jazz Age.

While Towertown was buzzing with progressivism, Bronzeville was beginning to shape a different, yet equally important, queer landscape — a cultural revolution that would come to define Chicago's queer community in the years after World War II. It wasn’t until after increased racial segregation of quietly accommodated queer bars on the city’s North Side, however, that Bronzeville’s queer community would dramatically reshape nightlife and culture for queer Chicagoans.

During the 1920s, though, Towertown became a crucial physical space for the rapidly growing city’s progressive and left-wing citizens. Although the streets are all still there, the only physical landmark of note that remains in the defunct neighborhood is the historic water tower itself. Few Chicagoans would even know what area you were referring to if you mentioned a place called “Towertown.” There is a lineage, though, that should not be forgotten. 

We (queer people in Chicago especially) should make a point to know it and hold onto it.

Under the cover of night, our queer forebears squeezed through a narrow passage down Tooker Alley in Towertown between Dearborn and State Streets. Eventually, those who made the venture came face-to-face with an orange door illuminated by a green light, with the words “STEP HIGH STOOP LOW LEAVE YOUR DIGNITY OUTSIDE” scrawled across the mysterious door. They had reached the entrance to the odd, outlandish, and legendary Dill Pickle Club (sometimes spelled “Dil Pickle Club”). The club itself is remembered for being, basically, a hollowed-out barn in less-than-amazing shape. 

It was, after all, an illegal dram shop during Prohibition and the need for secrecy was essential, especially since the queer patrons themselves were breaking the law by openly existing in public. Once there, clubbers — known as “Picklers” — drank outlawed liquor and listened to leftist activists speak of a better world for working people, dance to jazz, and kiss each other under the discretion of the dark. A few blocks south, in the candlelit dark of the Seven Arts Club, queer people of all stripes, conservative novelty seekers from other areas of the city, and additional alternative crowds of the Jazz Age gathered to debate nudism, communism and to watch the club’s master of ceremonies and known homosexual of the time, Edward Clasby, preside over a drag review while wearing full drag.

Nothing remains of the Dill Pickle Club today beyond memories and a few stray photos on the internet. To date, I’ve never been able to find a picture of the club’s interior, though a few scant sources tell us what it was like inside: there was a, “tearoom, art exhibitions, stage, standing capacity for a reported 700, and without fail, the eccentric [owner John “Jack”] Jones, met visitors with the greeting, ‘Are you a nut about anything? Then you have to talk to the Picklers!’” 

Now all that stands at 10 Tooker Alley, or on today’s map “10 West Tooker Place,” is the backside of a parking garage. The Seven Arts Club that was housed at 59 E Grand Ave, at least for a moment in 1926, has since been demolished and paved over for Nordstrom Michigan Avenue. Our history was not preserved beyond oral tradition and written memory. There aren’t even historical markers to denote the significance of those city lots. Now, the area is instead home to the amenities that supplanted Chicago’s first socially complex, intentionally provocative, and culturally essential queer-accomodating neighborhood.

But queer nightlife in Chicago didn’t begin with Towertown, and it obviously didn’t end there either. A confluence of gentrification and changing social attitudes towards queer people in post-war society fractured the city’s physical queer community north across neighborhoods like Old Town and Lincoln Park. In the 1980’s, though, we finally established a firm foothold in Lakeview East, known then, and still socially for now at least, as Boystown.

Dancing in the dark

Last fall, I interviewed several queer culture experts and entertainers on why drinks in gay bars are stronger than in not-queer bars. There wasn’t a definitive, single answer. Instead, all the perspectives my sources provided me coalesced around the idea that nightlife has been, for at least a century, a safe haven for queer people and that our drinks are poured heavy with the cultural context that more alcohol in the glass signifies a hearty gesture of welcoming. The summation of my sources’ answers didn’t surprise me, but it did leave me asking more. Since then, I’ve been wondering about queer nightlife, the clubs I go to and the history we as a community of queer Chicagoans don’t have easy access to.

I’ve been thinking about all the queer people who partied in this city before me and all the queer people who will take up the mantle after me. I’ve been thinking about the nightclubs our community used to frequent and the ones we patronize now. I wonder how many Saturday-nights-into-Sunday-mornings my queer forebears shared that I’ll never know about, before Boystown existed as it does now. I want to know what they drank through the ages. I wonder about all the streets they wandered down in the night with their friends as part of their partying routine. I’ve been straddling between living in the moment and documenting our culture as we create it and wondering about the history we dance on top of without realizing it. I think of all this with my thoughts punctuated by the grim onslaught of transphobic — and broadly queerphobic — legislation promised to be delivered from Congress and the cultural vitriol espoused by our nation’s sitting president.

These are the thoughts running through my mind at 3:30 a.m. in a dank basement on a dance floor my friends and I love to live on.

On January 4, The Atlantic published an op-ed titled “Americans Need to Party More.” The piece guides readers through the data-backed evidence that as a society, Americans aren’t partying as much as they used to. Americans have fewer friends. Americans are experiencing an epidemic of loneliness. Americans need to throw more parties and be social again in order to save themselves. It was an interesting, quick read.

I don’t like to make assumptions, but I will give the author the benefit of the doubt and believe, even if for my own peace of mind, that she did not intend to oversee the crucial importance of queer partying and nightlife in the scope of her premise that Americans aren’t partying anymore. I finished the piece with the impression that the author’s concept of her imagined community of Americans was too monolithic, too broad and too assuming. As someone who spends a solid chunk of his time in bars, at nightclubs, at gay house parties and at drag shows tipping queens for their community service, I truly felt like she wasn’t talking to me. She couldn’t have been talking to me. She also could not have seriously been talking to any other queer person with a proclivity for our community in Chicago.

This isn’t to say that all queer Chicagoans like to party, at least in the traditional sense. But I’d argue that a lot of us do, and those of us who prefer not to party, per se, still often seek out socialization with our queer peers as a restorative act of self-care — which seemed to be the author’s main motivation for urging Americans to party. The party was simply a means to an end for Americans to be less lonely. I walked away from the brief plea, and rudimentary roadmap, for a renaissance of house parties that the queer experience was not part of her understanding of American social life.

The party is the purpose

At the end of January, I was walking south on North Halsted Street in Boystown. Outside of Progress, a gay man’s sweatshirt caught my eye. He was waiting at the cross walk with his back facing me wearing an off-white mohair sweater. Across his back in bold, black lettering was the phrase “JOY IS AN ACT OF RESISTANCE” (after some digging, I now believe it was this sweater designed by Sherifa Gayle’s brand Black N Ugly Clothing). 

In my relentless pursuit to understand why queer people party and what the function and purpose of our parties is, I have been inching ever closer to an unsurprising realization for someone who pays attention. The vitality so many of us queer folks experience in our culture of dimly lit dance floors, exceptionally strong drinks and unbridled joy in the face of a brutal world is heavily informed by Black culture.

Joy in the face of adversity, or perhaps remaining joyous because of adversity, has a long and storied history in the Black community. A recent, exemplary testament to this feature of Black culture and the significant influence Black culture has had on queer culture is Beyonce’s dance album “Renaissance.” Initially planned to be the second installment of a trilogy of albums, which now includes the 2025 Grammy Album of the Year “Cowboy Carter,” “Renaissance” was instead released as the series’ frontrunner. In a press release reported on by Variety, the lauded singer-songwriter decided to release her testament to the contributions of queer, Black musicians who pioneered dance music on the heels of the COVID-19 pandemic because, as she put it, “there was too much heaviness in the world. We wanted to dance. We deserved to dance.”

And queer Chicagoans aren’t strangers to dancing. Long after the Dill Pickle Club closed, pioneering queer DJ and record producer Frankie Knuckles was instrumental in establishing and fostering house music in Chicago, which has since been popularized across the entire world where anyone loves to dance. Furthermore, the Midwest broadly has a history of engineering new music to dance to, as queer Black men in Detroit are often uncredited as the progenitors of techno as we understand it today.

In Chicago, queer people have been partying for over a century and nightlife has always been a home for us. And yes, at times, it can take a toll. But I never hear people who choose to go to our parties regret the toll it takes on them. For everything getting dolled up and showing out takes, I constantly hear, instead, everyone say they had so much fun that night. They feel better being around our people. Being in a space we have made for ourselves allows us to let our guard down. We realize that even though all of our experiences are individual, our collective experience as queer people across all sorts of demographic lines, like class and race, is singular. I always feel spiritually renewed after being in a queer space, whether it's a dance floor or a queer bookstore.

In the wake of Donald Trump’s inauguration, writer and LGBT activist Dan Savage rallied queer people with this same idea: that we need to remain joyful and energized in order to effectively fight back. “We should spend as much time as we possibly can over the next four years,” he wrote on his Instagram story, “with friends and lovers doing things that bring us joy.” Savage went on to empower our community to admonish naysayers of queer party-going, community enrichment, and quality time — however we choose to define those terms. 

Because the truth is that although a lot of us, myself included, love our nightlife, a lot of us don’t. That’s perfectly fine. There are endless ways to connect with the community outside of a literal party. Partying itself, though, has an unshakably important role in the way we connect with our peers, organize, and fight back against the world beyond the walls of our dance floors. Savage added that this joy in the face of institutional indifference to our suffering, our dancing into the small hours of the night, was indispensable for establishing political force and pushback during the AIDs crisis. “The dance kept us in the fight,” Savage continued, “because it was the dance we were fighting for.”

One of the best feelings in the world is being as joyous and gay as possible in a space our community has fostered for itself without fear of violent retaliation. There’s almost no better feeling than being as free and gay and loud and funny as you want knowing that it just pisses off some nobody who sits at home far, far away. Our political dissidents imagine us to be too flamboyant, too outrageous, too inappropriate, too obscene, too freaky and altogether too much to bear. We remember them as they actually are because we grew up among them: bitter, mean, and self-righteous. So we dance anyway. In fact, for me, it makes the dance even more freeing to know that I’ve chosen to inherit the tradition of being a queer person in a nightclub in a city that loves to dance.

Just as queer Chicagoans throughout the ages before me risked their lives to squeeze down an alley and party at the Dill Pickle Club and drink illegal liquor, today we are still at the clubs. The elements that underpin queer partying are the basic necessities we are fighting for. We deserve to see and be seen; we deserve to celebrate the one life we’ve got; and we deserve to gather with our community and to enjoy openly living our lives. If there is a partying problem in America as The Atlantic says, it’s not among queer people. For us, the party has always been the way we fight and the fight’s purpose.

Queer people never stopped partying. Maybe it’s time the rest of you found a good reason to party, too.