Home to one of the largest Pride Parade events in the world, Chicago’s Northalsted neighborhood is the country’s oldest officially recognized gay neighborhood.

Things to do in BoystownWhere to shop: Unabridged Bookstore, Beatnix, Cram FashionWhere to eat: Chicago Diner, Big Gay Sal’s Pizza, Bites Asian Kitchen + BarWhat to see: Legacy Walk, AIDS Garden Chicago, Center on HalstedWhere to go out: Sidetrack Chicago, Progress Bar, Elixir Lounge, and HydrateAlso known as Boystown, this enclave in the Lakeview East neighborhood vibrates with energy and LGBTQ+ pride. Come visit this exciting stretch of shops, nightclubs, restaurants, and bars for a day of nonstop fun.

Coffee and book browsing

Unabridged BooksKick off your day with a hand-crafted brew or tea at one of the oldest independent coffee roasters in Chicago, The Coffee Tea Exchange. Sip on a monthly special like the Ginger Judas, filled with butterscotch and gingerbread flavor to spice up your afternoon.

Walk down the street to Unabridged Bookstore and browse through the hand-written staff recommendations and extensive sale section.

A vegan diner and LGBTQ+ history

The Chicago AIDS Garden; photo courtesy Chicago Parks Foundation

The Legacy Walk Fill up on a healthy brunch at Chicago Diner, a vegan and vegetarian mainstay that serves up delicacies like seitan steak eggs and cinnamon roll French toast.

Grab a sugary pick-me-up at Windy City Sweets, a childhood dreamhouse of classic candy, gourmet chocolates, homemade fudge, and ice cream. Don’t miss the chocolate-covered Twinkies.

Soak up the neighborhood’s history with a stroll through the Legacy Walk, adorned with 40 bronze plaques honoring activists, artists, and individuals who are significant to the global LGBTQ+ community. Located along Halsted Street between Belmont and Grace, the markers make up the world’s only outdoor LGBTQ+ museum.

Finally, take the short walk (or hop on the bus or a Divvy bike) to the lakefront. Enjoy green space and sculptures at the AIDS Garden Chicago, which memorializes the history of Chicago’s HIV epidemic, a block south of Belmont Harbor.

Lunch and local boutiquesGrab some retail therapy at Beatnix, a boundary-pushing boutique filled with vintage finds and glittery accessories. Nearby, Cram Fashion for trendy menswear and an underwear lounge.

For lunch, sample an array of pizza slices, including chicken mole and taco twirl, at Big Gay Sal’s Pizza or opt for savory Asian fusion like soft-shell crab sliders and roast duck bao at Bites Asian Kitchen + Bar.

After lunch, drop by the historic community hub, Center on Halsted, to view artworks by LGBTQ+ artists in the buildings two art galleries on the second and third floors.

Drag, dinner, and neighborhood nightlife

Kit Kat Lounge Supper Club

Prepare yourself for the neighborhood’s famous nightlife with a cocktail at the iconic Roscoe’s Tavern.

After, head to Drew’s on Halsted for a leisurely meal of elegant American fare like oven-baked crab cakes and a pork chop with blueberry balsamic vinegar. Reservations are recommended at this neighborhood gem, but if you can’t snag one, Joy’s Noodles Rice is another fave with open seating.

With your fortification in place, grab an early show at the Kit Kat Club, which hosts some of the city’s most entertaining drag performers. Don’t miss their inventive martinis like the Britney, Bitch (citrus vodka, elderflower liqueur, lemon, orange, and sparkling wine).

SidetrackDive into the heart of the party scene, starting at gay mecca, Sidetrack Chicago, which spans multiple floors and seven separate bar areas.

Cross the street and dance to the resident DJs spinning at Hydrate, and then move to Progress Bar, with weekly drag shows, DJs, and specials.

Close out the night at Elixir Lounge and sip a signature libation like the aptly named Bloody and Bruised (Jim Beam Black, blood orange puree, lemon juice, simple syrup, fresh basil).