Chicago's LGBTQ Neighborhoods: Boystown

Where to eat, stay, shop, and play in one of the most vibrant LGBTQ communities in the world.

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By Amber Holst of Concierge Preferred

Home to the annual Chicago Pride Festival and Parade, Boystown is home to one of the most vibrant LGBTQ communities in the world. The neighborhood offers much more than gay bars, though. Here's your guide to the best of the neighborhood, just in time for Pride Weekend.

Where to Eat

HB Home Bistro

Among the many gay-popular restaurants along Halsted Street and elsewhere in Lakeview (such as Chicago Diner, Lark, and Nookies Tree), HB Home Bistro stands out for its remarkably tasty, inventive, and well-priced contemporary American (with Mediterranean accents) cuisine. There's also a quite popular Sunday brunch. 

Angelina Ristorante

This Italian bistro's two dining rooms are as sweetly ornate as a jewelry box, with candles and flowers, gauzy curtains, and softly painted walls. It's a favorite spot for fettuccine norte or veal marsala at good prices. Rumor has it this is Madonna's favorite Italian restaurant in Chicago.

Wood

Whether you like to indulge in a weekend brunch, or a few cocktails and a fabulous meal on a weeknight, this neighborhood hang is for you. Chef Ashlee Aubin, who comes with Alinea credentials, is a big fan of local and seasonal ingredients and it shows in his super high-quality food.

Where to Shop

Chicago Male

Unlike its name suggests, this Boystown spa welcomes dudes and ladies for cuts, color and special treatments. Saddle up for a quick trim or buzz cut or enjoy something a bit more indulgent, like a scalp balance treatment or dual exfoliation peel facial.

Egoist Underwear

Like its name suggests, this Boystown boutique is a one-stop shop for underwear, swimwear and athletic wear. Stocking specialty brands like Diesel, Andrew Christian and Aussiebum, it's the best place to find everything you'll need to update your underwear drawer.

Hollywood Mirror

After you get over the initial insanity of Hollywood Mirror, you'll realize that the massive store has tons of great goodies. The eclectic collection of vintage clothing, toys and accessories includes everything from fleece-lined jean jackets to sweatshirts to cowboy boots.

Ragstock

Ragstock is a Boystown staple. With an entrance in the alleyway, it occupies the second floor and basement of the same building as Hollywood Mirror. You can grab some funky sweaters, $5 sunglasses or a trendy outfit without breaking the bank.

What to See

Center on Halsted

This home for the LGBTQ community opened in 2007 as a LEEDS-certified eco-friendly delight. The Hoover-Leppen Theater hosts LGBTQ-themed events and doubles as a house of queer-friendly worship on Sundays while the Billie Jean King Recreation Hall beckons sports enthusiasts, but it's the wide array of social services that lures LGBTQ youth, seniors and minorities from the South and West Sides.

The Legacy Walk

Beginning in 2012, North Halsted Street became the world’s first LGBTQ outdoor museum as the Legacy Project began installing a collection of placards on the street’s rainbow-colored pylons (erected in 1998 by then Mayor Richard M. Daley), honoring heroes like Oscar Wilde, Harvey Milk, Antonia Pantoja, Frida Kahlo and Alvin Ailey. New placards are rotated in every year on National Coming Out Day, October 11.

Annoyance Theatre

Annoyance put itself on the map with its famously distasteful gross-out musical Co-Ed Prison Sluts. Three decades later, it still cranks out bizarre, unconventional comedy. Its new home on Belmont, established in 2014, gives it two performance venues and classroom space all in the same building.

Where to Play

Elixir

At this shoebox of a cocktail bar, the drinks are skillfully prepared, the crowd is kept to a minimum by the doorman, and the music never gets too loud so you’re still able to converse. The clientele is mixed in age but not in gender—and everyone is on their best behavior, which makes it an altogether more sophisticated and adult experience than Elixir’s next-door sister, Hydrate.

Hydrate

Hot and sweaty boys pack themselves in for all-night dancing at this thumpin’ after-hours club. A rotating menu of entertainment includes the Honeys on Halsted Drag Show, RuPaul’s Drag Race viewing parties, and more.

Kit Kat Lounge

Regular strut-through performances by talented female impersonators are a draw for straight and gay patrons alike at this popular night (and brunch) spot, as is the lengthy (and potent) martini list.

Sidetrack

This huge Boystown hot spot gets packed, but there are six big rooms, an open-air courtyard and a lush rooftop deck, so you can move around till you find a spot to sip your slushy drink. A longstanding anchor of the Halsted strip, Sidetrack also plays host to a number of community fundraisers and events throughout the year.

Berlin

This come-one-come-all dance destination built its reputation back in the mid-’80s with a mix of German new-wave music and freak-friendly shows. Today, it’s still quirky, but more retro, with diva-tribute, disco, and ‘80s nostalgia nights.

Roscoe’s Tavern

This long standing landmark has multiple bars, a dance floor, an outdoor patio and is known for playing all of your favorite diva jams. The drink specials are among the best in the neighborhood, with $15–$17 cocktail pitchers, $5 shots and bombs each day, and $1 Miller Lites on Sundays. Roscoe’s is also a favored venue for visits by current and past RuPaul’s Drag Race personalities.


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