Getting The Deep Dish On Chicago: A Queer Girl’s Guide To The City

Featured Image: Photo by Dawid S Swierczek via Getty Images.

What do you think of first when someone mentions Chicago? Deep-dish pizzas and mustard-free hot dogs? Tall buildings? Frigid winters? What about the fact that Chicago has been a pioneer in LGBTQIA+ rights for over a century now? In the early 1920s, the nation’s first gay rights organization, the Society for Human Rights (SHR), was founded in Chicago. Then, in 1962, Illinois decriminalized consensual same-sex sexual relations—the first state to do so. There’s a reason why Chicago has one of the highest LGBTQ+ populations in the country. Queer folks have long recognized Chicago as a place to live in community, particularly in neighborhoods like Wrigleyville (aka Boystown) and Andersonville (once referred to as Girlstown). 

But hey, we’re not only here to discuss history. Chicago’s current reputation as a queer haven is well-known—from cocktail bars and cabarets to museums, music festivals, and world-class dining. There is a lot to enjoy about Chicago for a queer woman, so let us take you around some of the city’s hottest sapphic spots. 

The Loop and South Loop

When visiting Chicago, the first stop on your list will likely be the Loop, aka Downtown, which is where you’ll find the city’s top tourist attractions. Kick things off by going on a walking tour to listen to some Downtown LGBTQ Stories, which will also help you get the lay of the land. You’ll learn about a Nobel Peace Prize-winner’s secret, lesbian romance, the country’s first Gay Liberation March, and much more for only $25 a ticket.

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Then decide for yourself what kind of adventure you want. Art-loving queer gals will certainly want to make a stop in the Art Institute, which some of you might recall if you ever had a crush on Sloane Peterson from Ferris Bueller’s Day Off. You’ll find plenty of LGBTQIA+ art here, including the renowned Felix Gonzalez-Torres piece, “Untitled” (Portrait of Ross in L.A.).” 

Check out the aquatic animals at the nearby Shedd Aquarium, explore the stars via the Adler Planetarium, or dive into natural history at the Field Museum. All three host Pride events annually and are great for exploring solo, with your partner, or even with kids. If you’re planning to enjoy a few attractions, it may be worth it to purchase a CityPass, which grants you admission to five of these Chicago experiences for one flat rate.

If you’re in town during the WNBA season, you’ll definitely want to snag tickets to see the Chicago Sky play at Wintrust Arena. Whether they win or lose, you can always celebrate (or mourn) right after with some food, drinks, and a show at Lips. One of the city’s best-known drag show spots, Lips has a robust menu (including plenty of vegetarian and vegan-friendly options) to choose from. Come for dinner and a show Thursday through Sunday, or stop by early for their fabulous Drag Brunch Saturday and Sunday.

For comfortable and queer-friendly accommodations, I can attest to StayPineapple – The Loop. Housed inside a National Historic Landmark building, this hotel features all the usual amenities, comfortable beds, and is conveniently just 2 blocks from the L (aka the “elevated train” system) and surrounded by plenty of eats. It’s also a short walk from the Chicago Cultural Center and Millennium Park—both free attractions and worth a visit. They even have a special Pride offer every summer for those of us visiting during Chicago Pride. 

There’s plenty of food in the area to grab, but The Dearborn—co-owned by out queer woman Amy Lawless and her sister Clodagh—is a great spot for brunch, lunch, or dinner. They have a wide array of offerings on the menu, like Midwest fried chicken, a mushroom melt sandwich, crispy Brussels, shakshuka, and tons of yummy cocktails to choose from. 

Andersonville (aka Girlstown)

Once known as Girltown, Andersonville still remains one of the best spots for queer women to find community in Chicago. About a 20-minute drive north (or 30-minute ride on the L)  from The Loop, this neighborhood is absolutely charming in every way. 

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If you’ve only got a few hours to spend, make sure to head over to Clark Street, the neighborhood’s commercial main street, full of shops, restaurants, bars, and more. Consider starting with a pick-me-up from Eli Tea Bar. It’s a delightful queer-owned tea shop that also serves lemonades, coffee drinks, and other tasty libations. Bonus: it stays open late, serving as a great nightlife alternative for the sober and sober-curious community. 

Feeling crafty? Head north and you’ll find The Dropped Stitch, a woman-owned yarn store with a slew of classes to choose from. A couple of blocks south, you’ll then run into Rattleback Records, a queer-owned record store where you can find your favorite albums fro Chappell Roan to Brandi Carlile. 

Afterwards, snag some scones, cupcakes, or other sweet treats from A Taste of Heaven bakery. Or if you’re feeling a bit hungrier or hankering for a beer, Replay, a sports and arcade bar serving up classic American fare, is just across the street.

If shopping is what you’re after, you’ll find plenty of great spaces here, like Paper & Pencil, a sweet stationery store owned by a gay couple, as well as the Andersonville Galleria, where you’ll find tons of artwork and other gifts from local artists, including LGBTQIA+ ones. The well-known, women-owned Women and Children First Bookstore is perfect for finding books and gifts of all kinds from your favorite feminist authors. And of course, if you’re on the hunt to add some new toys to your collection, Early to Bed is a fun and sexy women-owned and queer-friendly adult toy shop. 

Not far from Andersonville is Garden Of Studio, a new sapphic co-working space in Ravenswood where you can spend a few hours working and networking with other queer women in the area. Garden Of Collective also hosts classes and events—from sapphic clothing swaps to Only Come Alone socials (where you’re encouraged to show up on your own and meet new friends) to their upcoming Gaysgiving, where food and fun abound!

As for nightlife, you can never go wrong with Nobody’s Darling. This Black-, queer-, and women-owned cocktail bar is one of the city’s best. Order up a Giovanni’s Pride & Passion (or a Pay It No Mind for a refreshing mocktail) while you schmooze during their monthly singles’ mixer. Of course, you could also head to the lesbian-owned Whiskey Girl Tavern and split a flight of scotch with your traveling companion during trivia. 

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While there are no hotels directly in Andersonville, you could always book a stay at the Magnolia Studios, located inside an LGBTQ+ friendly brick coach house, complete with a fully equipped kitchen and en suite bathrooms for plenty of privacy. 

Northalsted (aka Boystown) and Uptown

While Northalsted is certainly still living up to its reputation as Boystown, there’s still plenty for queer women to enjoy in this neighborhood. 

Opened by two lesbians—co-owners Rose Pohl and Judi Petrouski—in the late 1970s, The Closet is a longstanding neighborhood bar. Though it’s now under new ownership, it’s still a solid LGBTQIA+ bar in which to order up a beer, shoot some darts, sing karaoke, and do it all again the next day. 

If you’re feeling like dinner (or brunch) and a show, Kit Kat Lounge and Supperclub is considered top-notch for entertainment. While you’re in the area, visit the Chicago Diner, a popular vegan restaurant opened in 1983 by couple Mickey Hornick and Jo Kaucher (they also have a location in Logan Square).  

Over in Uptown, there are two must-visit places: Big Chicks and Carol’s Pub. The former is run by Michelle Fire and serves up delicious bar food plus cocktails, beer, wine, and plenty of people-watching, not to mention game nights. The latter is a honky-tonk bar where you can practice your line dancing, belt out some Dolly Parton, or drink an Old Fashioned whenever you want. 

If you’re Cali-sober (no drinking or drugs, just cannabis), don’t sleep on Sway, Northalsted’s queer- and BIPOC-owned dispensary. It’s the perfect place to pick up pre-rolls, gummies, and even disposable vapes. Once you’ve got your goodies, go have an even better time at Sidetrack (owned by some of the same owners of Sway), a welcoming LGBTQIA+ bar and nightclub that hosts tons of events, including Sapphic Saturdays on the last Saturday of each month.

Once you’re done with the revelry, you’re free to go pass out in your cozy room at Dorothy’s Guesthouse, an adorable LGBTQ+ friendly bed and breakfast, or their sister property, The Villa Toscana.  

West Side for all the rest

There are plenty more neighborhoods to discover on the West Side, from Logan Square and Pilsen to Wicker Park, the list goes on. But here is my non-negotiable: you must visit lesbian cocktail bar Dorothy’s in the Ukrainian Village. This classy joint hosts everything from cabaret nights to silent book clubs, comedy nights, and queer karaoke—you name it, they probably have a night for it. 

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Started by rugby co-captains and best friends who wanted to create a dedicated space solely to women’s sports, the new Babe’s Sports Bar in Logan Square is currently making a splash you won’t want to miss. Speaking of Logan Square, make sure to grab a bite (maybe an ice cream sundae a la Sydney on The Bear) at the iconic Margie’s Candies while you’re in the neighborhood. 

A few more gems: drop in for a visit to the National Museum of Mexican Art in Pilsen. This museum is always free, and you can also check out some gorgeous murals nearby, not to mention tasty Mexican cuisine—my personal pick is 5 Rabanitos. And finally, keep your eyes locked on social media, too—groups like the Lesbian Social Club host events around town you’ll want to add to your list. Check out their Sapphic Slasher event on Halloween at TAO Chicago (which has been transformed into “Camp Tao” for the frightfully fun night). Whether you’re looking to party and play or are hoping for a more laid-back adventure, Chicago’s got something for you (as long as you promise to never put ketchup on your hot dogs, that is).