Ari Bendersky is a journalist and video producer based in Chicago. He grew up in Chicago’s northern suburbs and eventually landed a gig at Rolling Stone, where he says he “finally” came out at age 26. He lives with his husband in Chicago’s Uptown neighborhood, and his favorite thing about queer life in Chicago right now is that “many more people seem to have a larger presence in queer life in Chicago—people of color, femmes, trans men and women, genderqueer and more.” Here, he details his guide to queer-friendly Chicago, from the best neighborhoods to hang out in, to the ultimate nightlife must-visits.
One thing I love about queer life in Chicago is how so many faces and voices are being recognized. In the past, you’d go to Boystown and it seemed like it was mostly just a place for gay white guys. Today so many more people seem to have a larger presence in queer life in Chicago—people of color, femmes, trans men and women, genderqueer and more. And what’s beautiful to me is everywhere you go in Chicago, queers are there. Even though many of us still live in gay-heavy ‘hoods, we’re not ghettoized anymore and live everywhere — and the city, for the most part, is open and accepting.
Despite the name, Boystown is Chicago’s largest inclusive LGBTQ+ neighborhood with bars, shops, restaurants, gyms, theaters, a historical legacy walk with rainbow-clad demarcations along Halsted Street and the Center on Halsted, the city’s large LGBTQ+ center. The annual Pride parade and festival take place here each June as does Market Days, one of the country’s largest street fairs. Gays started moving here in the 1960s and ‘70s and it officially became a gay village in 1997, the first in country.
Set on the Far North Side centered along Clark Street between Winnemac and Irving Park, this former Swedish enclave started attracting more gays and lesbians in the late 1980s, especially with the opening of Women & Children First Bookstore. Today, Andersonville is a lively, colorfully-mixed neighborhood with fantastic restaurants and bars like Anteprima, Little Bad Wolf, Replay and Marty’s Martini Bar. There are beautiful homes and easy access to Hollywood Beach, a.k.a. the gay beach, just a few blocks to the east.
While not really considered an official LGBTQ+ neighborhood, Wicker Park (and Bucktown and Logan Square for that matter) is very gay friendly, as evidenced by the large number of queer folk who live in that part of the city. This area is a hub of creativity, excellent nightlife, live music bars, galleries, theaters, and so much more.
In this day and age, you’d be hard pressed to find a hotel in Chicago that isn’t gay friendly (not to mention gay welcoming), whether the high-end spots around Michigan Avenue, hip hotels in Fulton Market like the Ace, Hoxton, and Soho House, uber-cool Robey in Wicker Park, or the design-forward Hotel Zachary across the street from Wrigley Field and just blocks from Boystown. But if you want to stay close to the action, check out the Hawthorne Terrace or Villa Toscana guesthouse right in Boystown, or the Guesthouse Hotel, just south of the heart of Andersonville on Clark Street.
Chef/owner Paul Fehribach beautifully prepares Southern-heritage fare like shrimp and grits, Ponchartrain blue crab cakes, fried chicken, and sweet potato barley jambalaya while offering one of the deepest bourbon selections in Chicago.
Andersonville lacked a quality men’s shop until this opened. Now you can pick up fashion-forward wares, candles, grooming products, hats, wallets and pretty much everything a guy might need — maybe even a future date browsing the table next to you.
This wonderful flower shop that also sells artisan jewelry has been a Wicker Park mainstay since 1999. In 2018, it increased its presence by opening a much-larger second outpost attached to the Ace Hotel in Fulton Market where you can get a flower arrangement, new set of candles, esoteric magazines, taxidermy, pottery, and an array of gorgeous things you didn’t even know you needed.
This men’s boutique in Boystown offers hip fashion from denim to shirts to outerwear on one side while the other allows you to pick up all your party-party go-go boy attire from tank tops to skimpy swim trunks to an array of undies.
When you need a cheese plate, a great bottle of wine for a party, or just some snacks for home, there are few places better than Pastoral. With its original location in East Lakeview and two others in the Loop and the French Market, your next foodie fix is not far.
You want ephemera? You’ve come to the right place. At first a frame shop, Foursided has one of the best collections of greeting cards in Chicago along with lovely candles, giftable books, and a broad Chicago-focused product selection.
While Amazon has dominated the larger book world, Unabridged continues to be your loyal, trusted local bookseller with a huge LGBTQ section—and an unparalleled travel section so you can plan your next great world adventure.
Wood offers a seasonal, farm-to-table approach to dining in Boystown where you can get a well-made cocktail or settle in for brunch on the sidewalk patio to watch all the boys and girls stroll by.
Arts & Culture
How do you pick in a city built around culture and art? You’ve got Millennium Park, the Cultural Center, Art Institute, MCA, and Chicago History Museum, which are all obvious must-sees. And just look around the Loop—the architectural marvels are worth a walking tour or boat tour. With so much culture to soak up in Chicago, it’s hard to narrow it down when you only have a few days while visiting, but these are a few that everyone could get into.
What started as a short-term pop-up has turned into a permanent space at the intersection of art, science, and a little whimsy. Located between Near West Side and Greektown, walk through installations intended to make you think while also squealing with a little glee. Music, color, poetry, luminescent trickery, and more—and don’t leave without laughing your way down the rainbow slide, naturally.
Taking in so much culture around Chicago can be a tad exhausting. So pause in the Drawing Room at the Chicago Athletic Association Hotel across from Millennium Park. This institution dates back to 1893 and was restored to its vintage glory. Enjoy a cocktail while you relax in the library next to carved stone fireplaces soaking up the history seeping through iron work, marble, wood carvings, stained glass, and more beautiful aspects of this chic space.
If you’re into leather, kink, BDSM and any fetishes—or merely curious about it all—head north to Rogers Park to take in an extensive history of leather in the LGBT community. Visit the leather bar, the dungeon, and a Room of Her Own, an exhibit by the Women’s Leather History Project.
Chicago claims one of the most robust LGBTQ+ nightlife scenes in the country, mostly centered around Boystown and Andersonville, but you’ll find fun parties around the city. Whatever you’re looking for, you can find at one of the many bars, including Roscoe’s, North End, The Closet, and so many others. Here are just a few picks.
One of the most fun, hot, and inclusive dance parties takes place every Sunday down at Smart Bar. If you’re into sexy house music and people letting loose with their inhibitions, definitely check this out—especially on holiday weekends when it overflows with all walks of queer life.
Somewhat of an outlier, Big Chicks has cradled the LGBTQ+ community from its Uptown haunt for more than 30 years with a neighborhood bar feel, a small backyard patio to gather for free Sunday barbecues, super-fun energy, and a dance floor that heats up with queers Friday and Saturday nights. Oh, and during the day, it’s a super-cute restaurant called Tweet.
Visiting Sidetrack, the grande dame of Chicago’s LGBTQ+ community, is pretty much a must as you’ll see a vast cross-section of gay life in the city spread out over multiple rooms, a front patio and a sprawling roof deck. Come to this video bar for different themed nights like show tunes and comedy and be warned: drink those slushies cautiously. They will knock you on your ass.