The city of Chicago was founded in the heart of Potawatomi traditional territory by the Black trader Jean Baptiste Point du Sable, who established a settlement here in the 1780s. Over the ensuing centuries, the metropolis was built up, burnt down, and built again, coalescing into a series of neighborhoods, each with its own personality and ethnocentric flavor, including Chinatown, Greektown, and Little Lithuania.
A lion greets visitors to Art Institute of Chicago
But far from fragmented, Chicagoans are drawn together, unified particularly in their love of the city’s unique culture. This makes the Art Institute of Chicago, with its wide range of works from ancient to modern, a great place to start a day in the Windy City. From there, walk the few blocks to Cloud Gate, more commonly known as The Bean, the public artwork meant to mimic an enormous drop of mercury. It’s the perfect place to take amazing pictures and enjoy the adjacent Millennium Park.
life underwater in the only German WWII submarine displayed in the U.S.
Continue to the Shedd Aquarium where you can get your hands on a beluga whale. Seriously, you put on a pair of waders, stand on a ledge in chest deep water, touch the whale and say, “Hello!”
A Beluga whale at Shed Aquarium
Take the “El,” the elevated trains are worth a ride simply for the view. Or grab a cab to see the boys, grrlz, and cute queers of all sorts in the city’s two LGBTQ+ neighborhoods. The Lakeview neighborhood Boystown has hosted the annual Pride parade since 1971.
The gayborhood — recently renamed Northalsted to be more inclusive (but locals don’t call it that) — has something for everyone, including the LGBTQ+ resource space, the Center on Halsted.
Indulge your need to express your sexiness and snark in pins, posters, plants, and more at Foursided Card & Gift. Stroll down the Legacy Walk, America’s first outdoor LGBTQ+ museum, and read plaques honoring queer heroes such as Harvey Milk and Frida Kahlo — then stop at Chicago Diner, which boasts an array of vegetarian and vegan options. While famous for their Radical Ruben, their gyros deserve a shout out and the vegan milkshakes are amazing.
Swedish flag colors over the Andersonville neighborhood
Stop, shop, and stroll, in the city’s other queer neighborhood, Andersonville, the “coolest neighborhood in the U.S.,” and second in the world to Copenhagen’s Nørrebro, according to Time Out. Home to the Swedish American Museumand the famous water tower painted with the Swedish flag, Andersonville has everything from fine dining to comic books (Alley Cat Comics, across the street from the famously feminist Women & Children First independent bookstore, and the nearby Graham Cracker Comics). Traveling kinksters will also be pleased to find tons of sexy supplies for consenting adult fun atFull Kit Gear, aka FKG.
Along this strip you’ll find another Foursided store, as well as Kopi Cafe, the evergreen lesbian meeting place with a lounging space that’s made for sitting cross-legged on pillows.
A few blocks south is Urban Vegan, which makes such tasty Thai cuisine you’ll forget that it’s all plant based. Or go a little farther to Budacki’s Drive In in nearby Ravenswood. This classic, cash-only hot dog stand serves fries so good the late Anthony Bourdain was a fan. Eat like a local and ask for your dog “dragged through the garden,” which means smothered in relish, pickles, onions, tomato, celery salt, mustard, and sport peppers. The celery salt is key, and there is no ketchup. Ever.
Walk down the block from Budacki’s to Rock N Roll Vintage & Synth City, where you can explore, indulge, and encourage the rock star in your life. Round off your night with a trip to the truly all-embracing Black and queer-owned bar, Nobody’s Darling.