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A Field Guide to


Where gay culture, quirky shopping, and Michelin Bib Gourmand dining meet

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Above:Sidetrack Photo: Beth Rooney/Chicago Tribune

As you can tell by the name alone, Boystown has long been a nexus for Chicago’s LGBT community. But word of this pocket of East Lake View’s awesomeness has spread, and the stroller contingent now brings its A-game on weekend mornings. It’s no surprise: the neighborhood boasts excellent restaurants, kitschy shops, and beautiful architecture—all close to the lake.

Boystown map
Illustration: Michael A. Hill
Chicken and waffles at Kit Kat
Chicken and waffles at Kit Kat Photo: Courtesy of Kit Kat Lounge & Supper Club

1. The Annoyance Theatre & Bar

You just might see the next Stephen Colbert or Jane Lynch, both alums of this renowned comedy spot. theannoyance.com

2. Hawthorne Place

This street between Broadway and Lake Shore Drive may be only one block long, but, oh, what a beautiful stretch of mansions it is.

3. Kit Kat Lounge & Supper Club

Where else can you catch a drag queen diva show with a side of comfort food? (Avoid the Saturday night bachelorette party crowds and hit Burger & Beer Bitch Tuesday.) kitkatchicago.com

4. Lake View Presbyterian Church

This John Wellborn Root–designed building offers inclusive services and outdoor concerts. lakeviewpresbyterian.org

Beatnix Photo: Nancy Stone/Chicago Tribune

5. Beatnix

Looking for some cheap cowboy boots? Find ’em here. Want a studded leather mask with a leash? Yep, that’s here too. beatnixclothing.com

6. Hollywood Mirror

You can spend hours in this hodgepodge of pop culture detritus, which includes unicorn backpacks, used bikes, and packs of Flintstones trading cards. hollywoodmirror.com

7. Paired Wine Co.

Hit the affable (and knowledgeable) staff at this wine shop to find exactly which Pinot Noir goes with that pork belly recipe you’ve been perfecting. pairedwine.com

8. Reckless Records

Vinyl lovers’ Shangri-la, where you’ll find bands such as TV on the Radio performing live in the store. reckless.com

9. Unabridged Bookstore

This indie spot specializes in LGBT lit and frequently welcomes scribes such as Jonathan Safran Foer, Dave Eggers, and Anne Lamott. unabridgedbookstore.com

Eat & Drink
Lunchbox at Hollywood Mirror
Lunchbox at Hollywood Mirror Photo: Courtesy of Hollywood Mirror

10. The Chicago Diner

Lady Gaga is a big fan of this institution, where everything on the menu is vegan but can be made with dairy on request. veggiediner.com

11. HB Home Bistro

A cozy, modern American restaurant that’s this good and BYOB? No wonder it’s perpetually packed. homebistrochicago.com

12. Sidetrack

One of the biggest gay bars in the Midwest. Visit on Monday for the vodka- slushie-swigging crowd belting out show tunes. sidetrackchicago.com

13. Wood

Alinea alum Ashlee Aubin’s elevated wood-oven-cooked cuisine ensures the four-time Michelin Bib Gourmand winner is always busy. woodchicago.com

14. Yoshi’s Café

This Chicago favorite draws raves for the roasted Japanese pumpkin filled with tofu, mushrooms, and veggies. yoshiscafe.com

Did You Know?

Those rainbow pylons throughout Boystown aren’t just decorative—they feature plaques commemorating LGBT history and icons, including the Stonewall riots, Keith Haring, and Oscar Wilde.

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Tour Boystown with Joel Reese

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If You Want to Live Here

Population Median houshold income Median sale price (house)
(78% white, 9% Hispanic, 7% Asian, 4% black)
$63,300 $400,000
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