Chicago’s East Lakeview neighborhood Boystown is home to one of the largest LGBTQ communities in the United States. That’s no surprise given it was one of the first gay neighborhoods to be officially recognized by a city government. In 1998, residents put up rainbow pylons to officially mark the area, a decoration that now serves as a key marker of the neighborhood.
Since the late 90s, the neighborhood has continued to boom with the additions of vibrant nightlife, creative boutiques and trendy restaurants, with many of the businesses owned by Boystown residents. Every year in June, the neighborhood comes alive for Pride weekend with one of the nation’s foremost celebrations: a parade that attracts 100,000 people from all over the country, along with live music, great food, drag shows and more.
But it’s not just the fun that makes this neighborhood so great. Locals make it a priority to support each other with places like the Center on Halsted — a community hub offering programs ranging from behavioral health support to career training and even team sports.
For a deeper dive into the neighborhood’s past, visit The Legacy Walk, an outdoor museum that pays homage to the many LGBTQ contributors throughout history and also seeks to help squelch bullying in youth.
Whether you’re in Boystown to shop, dine or party, here are some of the must-go-to spots.
Dance Into the Night at Sidetrack
Perhaps the best known bar in Boystown, there is always something fun happening at Sidetrack, from Lady Gaga lip sync and dance parties to show tune singalongs and LGBTQ storytelling. In the summer, party on the rooftop, where you’ll certainly come across a few people sipping on “Frozé” or frozen pineapple mai tais.
Catch a Show at the Kit Kat Lounge
Looking for a good time? Of course you are. This hip lounge has a stellar martini list, good grub and — the real highlight — a positively electric drag show. The Kit Kat Lounge is a popular spot for large groups. Shows run every 20 minutes, and the “divas” perform tableside, making it a truly interactive experience.
Eat Meat-Free at the Chicago Diner
Visitors might not flock to this neighborhood for vegetarian food, but locals know this restaurant has been in business since 1983, and with good reason. Even carnivores come here for the diner’s vegan milkshakes. The menu features every veggie comfort food imaginable, like country-fried steak and poutine, a Cuban sandwich or mashed potatoes and gravy.
Eat Delicious Food at Wood
Chef Ashlee Aubin creates seasonal American dishes that tempt people from all over Chicago to flock to Wood. Ingredients come from local farms, and even the meat is butchered in house. Dishes range from mushroom cannolloni to pork schnitzel, with a great weekend brunch menu to hit up, as well.
Sip on Cocktails at Elixir Lounge
For something a bit more low-key than the singing and dancing at Sidetrack or Roscoe’s, Elixir is a solid pick. This intimate lounge is perfect for pre- or post-dinner cocktails and intimate conversation. Choose a classic cocktail like a Manhattan or a sidecar, or something more inventive, like Lavender and Lace, made with lavender-infused ingredients, creme de violette, dry vermouth and a rinse of absinthe.
It’s Always a Party at Roscoe’s
A stalwart of the neighborhood, Roscoe’s is a great place to dance the night away. With an in house DJ and plenty of theme nights, the bar is bumping until the wee hours of the night. Karaoke Mondays and Dueling Piano Thursdays draw a crowd during the week, and weekends are always a party.