Neighbourhood Watch: Chicago’s Boystown

America’s first designated gay neighbourhood remains one of its most vibrant

Boystown feels like a world of its own, and you’ll know you’ve arrived when you encounter one of the rainbow pylon landmarks prominently displayed throughout the business and residential district. Well established as the heart of Chicago’s LGBQT community, the portion of the North Side neighbourhood of Lakeside known as Boystown was in fact the first recognized gay village in the United States.

Visitors are attracted here by that proud history, and the fact that the Chicago Pride Parade – which is one of the largest in the world – travels throughout the neighborhood on the last Sunday in June.

Adjacent to Wrigleyville (home of Chicago Cubs), Boystown’s boundaries are Irving Park Road on the north, Broadway on the east, Wellington Avenue on the south and Sheffield Avenue on the west.


For live comedy, skip the Second City and head instead to Annoyance Theater & Bar for no-holds barred improvisation, sketch comedy, cabaret and original musicals. Most performances are raw and experimental, but there are a few that are appropriate for families.

While Boystown is best known for lively nightlife and dining venues, its Center on Halsted is the heart of the community. It balances all the late-night partying with LGBQT-oriented programs, health-awareness workshops and more. There are also free weekly yoga classes (a $5 donation is suggested).

Those looking for an all-out scene should head for Wang’s, the Chinese-inspired live music venue with lots of attitude. The cocktails are strong and often the crowd is far more entertaining than the performances onstage

Food and drink

You can find great fried chicken all over Chicago, but in Boystown, one Korean BYOB eatery reigns supreme. Crisp boasts four different types of fried chicken, with the signature “Seoul sassy” a highly recommended dish. Marinated for hours in a secret sauce that includes a base of ginger, soy and garlic, the chicken is then deep fried. This recipe has been handed down for a few generations. The fried chicken is best accompanied by deep-fried mushrooms, onion rings or traditional kimchi.

Dive Bar features a nautically and island-inspired theme inside a narrow dining room and sprawling backyard patio. Favorite dishes include seared tuna nachos, Cajun mac and cheese with shrimp and crawfish and signature “boomboom” shrimp that’s tossed in a spicy, creamy sauce. The cocktails are tiki-inspired; the “walking the plank,” for example, is made with mango rum, Cajun-spiced rum and a flaming rum float.


Dive Bar

The craft cocktail-focused Elixir is where neighbourhood types prefer to hang for a low-key evening in Boystown. In addition to its laid-back vibe, with no televisions or deejays, Elixir offers a comprehensive cocktail menu showcasing old-school and original drinks. That includes an exceptionally made negroni.

With craft breweries and distilleries popping up in every trendy Chicago neighborhood, it should come as no surprise that Boystown boasts one. DryHop Brewers focuses on hop-centric ales, thereby setting itself apart from other breweries in the city. It also attracts a loyal following for featuring seasonal gourmet pub grub and artwork by local artists.


DryHop Brewers

The grilled barbecue cheddar burger at tiny vegan gem Kitchen 17 is so tasty that even the hardcore carnivore may be deceived. The house-made patty is comprised of ground and roasted zucchini, carrot, onion, garlic and rosemary, so it’s flavourful on its own. Loaded nachos, pizza topped with pepperoni-flavored seitan and the Philly cheesesteak also come highly recommended. Those dining with four or more should arrive during off-peak hours because the restaurant only seats 16.


Among a few lodging options in Boystown is Villa Toscana Guest House, a fashionable Victorian-style home that’s been transformed into a European-inspired bed and breakfast. Located next door to Dive Bar, the two-level structure houses eight sleeping rooms, living room, eat-in kitchen and outdoor deck. Villa Toscana is located right in the heart of the action on Halsted Street, and pretty much everything is in walking distance. The parade route also passes by the residence.

Neighbourhood Watch: Chicago’s Boystown
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