A lot of history has unfolded in Chicago, one of America’s most iconic cities whose residents have always been proud of who they are. This is true of no one more than the Chicago LGBTQ community, who were amongst some of the first in the country to organize and openly advocate for their rights. By 1920, a gay village had been developed in Chicago’s Old Town, where one can still visit the house of gay rights pioneer Henry Gerber.

After his Society for Human Rights, one of the most influential LGBTQ organizations in Chicago, was granted a charter by the state of Illinois in 1924, many of its members were arrested on obscenity charges that ended up only solidifying the organization’s legacy as a progenitor of later sexual freedom movements. While the depression and wartime periods momentarily slowed further progress, Illinois still became the first state to abolish its sodomy law in 1961. 

LGBTQ History in Chicago

As many groups in America fought for their rights and openly opposed the government in the 60s, LGBTQ culture made a comeback in Chicago (and in Old Town) with the opening of a string of gay and lesbian bars, which ultimately paved the way for the modern gay village of Boystown. By the 70s, annual marches with attendance in the thousands were being held in memory of the violence at Stonewall. The rest, as they say, is history, as local and state politicians began to recognize LGBTQ rights as a salient issue and the first community centers opened to support LGBTQ individuals. In 1988, Harold Washington, who was also the first black mayor of Chicago, made strides for the LGBTQ community by signing into law an anti-discrimination ordinance for the city.

Today and things to do

These days, it is believed that Chicago has the third-highest LGBTQ population in the U.S., with more than 100,000 residents who identify as such. A community of that size is always going to make its mark on a city, and LGBTQ Chicagoans support one another and shine a light on issues of gender and sexuality on a broader scale. If Boystown is the heart of LGBTQ Chicago, then Center on Halsted is the heartbeat itself. The organization has since moved and changed its name, but this was the first LGBTQ community center to open in Chicago, in 1973. They have specific programming to support seniors, youth, women, and other groups within the overall community, as well as special events like art gallery openings and scavenger hunts organized in partnership with groups and authorities in greater Chicago. These are open to all, and there are volunteering opportunities.

If you want to support LGBTQ artwork, then Reeling Film Festival and About Face Theatre are two institutions worth your time. The former is approaching the 37th year in its mission to recognize LGBTQ contributions, educate the public on them, and push back against stereotypes by showcasing films from around the world. The latter performs in the Chicago area and beyond to advance the national conversation on sexual and gender identity, having made many world premieres since its inception in 1995.

Be sure to make time for the Chicago LGBTQ Hall of Fame for exhibitions dedicated to some of the city’s most impactful members of the LGBTQ community throughout history. 

Eat and drink

Chances are that between your comedy shows, museum trips, and sports outings you’ll want to settle down—or turn up—for a drink and a bite to eat. If you are preparing for a night out in Boystown (and they do go all night), you’ll need a good meal first, and there’s nothing better than the combination of healthy-ish and satisfying available at Chicago Diner. The comfort food here has been vegetarian and vegan since 1983, perfect for lining the stomach or helping you get over the inevitable local hangover. After all, there are plenty of places to get one: in the summer months, maybe that’s on the rooftop patio at Sidetrack. This huge club has plenty of room for dancing, but is probably best known for its show-tune sing-alongs: three times a week, you can find crowds gathered to belt out Broadway hits together. What could be more Chicago than that?

lgbtq guide to chicago
Photo by Tim Trad.

After singing your heart out at Sidetrack, you can stick around to hit the lounge or dance areas or move on to another of Boystown’s popular institutions. The best thing about this string of bars and clubs is that they let you ball on a budget (think $12 USD pitches of long island iced tea at Roscoe’s) and each specialize in their own kind of party. At Berlin, the after-midnight tunes and drag shows match the bohemian energy of its namesake city. You’ll be dancing into the early hours of the morning, making it the perfect club to end a bar crawl that ought to include visits to Scarlet and Little Jim’s. The former is an energetic hole-in-the-wall with some of the friendliest staff in the city, daily drink specials to accompany DJ sets, and themed music nights. Arrive early for happy hour, or later on for the lounge scene. The latter was the very first LGBTQ bar to open in Boystown, in 1975. It’s more of a dive, but the drinks are cheap, strong, and the conversation is always good (and most importantly, audible). 

The activities neither start nor end in Boystown, though, with other friendly and lively spots all over the city that are creating new spaces for the Chicago LGBTQ community and honoring some of Chicago’s legacies. Over at Smartbar by Wrigley Field, the Sunday basement club Queen! is Chicago’s house music mecca, where legends of the genre that developed in this city still come to spin discs late into the night (think the women of LCD Soundsystem, Nancy Wong, and Rayna Russom). There are also pop-up parties that take up residence around the city, such as Slo ‘Mo, “providing slow jams for queer fam,” in their own words. Since 2012, they’ve had a residency every third Thursday of the month at The Whistler on

Logan Square (with no cover), performing in between at venues like The Promontory and Museum of Contemporary Art. Another great strip of queer venues is in the Andersonville neighborhood, where Hamburger Mary’s serves up some of the best American bar fare in town while providing happening entertainment like cabaret and comedy upstairs at Mary’s Attic. There are also great drag shows up the street at The Call, cover-free clubbing opportunities galore at Atmosphere, and expertly-crafted cocktails at Marty’s

Whether or not it’s your first time in Chicago, there are also some essential day-out experiences that will make you want to keep coming back to the Windy City. Navy Pier is packed with attractions and restaurants for all tastes and travelers, from beer gardens and deep-dish pizza to a Shakespeare stage, dining cruises on the Lake, and outdoor Monday movie nights in the summertime. Sweeping views of the city, the ferris wheel, glass-roofed shopping complex, and regular fireworks also make it an incredibly Instagrammable spot—a great way to announce your arrival in Chicago. Once there, you’re not far from the city’s Magnificent Mile, with some of the very best shopping in the world at North Bridge, Water Tower Place, and 900 North Michigan. Finally, a trip to Chicago is incomplete without a visit to the Art Institute, an international center of art and culture with an unmatched collection spanning “centuries and the globe.”

Check out our LGBTQ guide to Chiang Mai for more tips on LGBTQ travel!

Photo by Brandi Ibrao.