1732 N. Milwaukee Ave., Wicker Park
Some Chicagoans swear that Small Cheval has the best burgers in the city. And it just got easier to test the theory since they opened a third location in Old Town, near the Gold Coast and Lincoln Park (the other two are located in the downtown Loop). The burger they’re known for is the “double stack,” two patties with cheddar cheese, dijonnaise, pickles, and two slices of maple-glazed bacon. The food menu is small (hamburgers, cheeseburgers, fries), so don’t come here for a salad. But when you’re craving a summertime burger outside on a picnic table with a pitcher of locally-made Half Acre microbrew, there’s no place better.
1659 N. Damen Ave., Wicker Park
This progressive, impeccably curated natural beauty boutique stocks a wide range (more than 100) of nontoxic brands from around the globe, including top skincare and makeup products from de Mamiel, Ilia, Kjaer Weis, Kypris, RMS, Tammy Fender, and our very own goop by Juice Beauty. The original shop debuted in 2015 in San Francisco and quickly gained a huge following. Sister locations have since opened in Manhattan, Brooklyn, Los Angeles, and here in Chicago, where there is an exclusive Tata Harper spa, much like the other locations.
2018 W. North Ave., Wicker Park
The building itself is an art deco jewel that preserves much of the charm of its 1920s design, and its triangular footprint means each of the hotel's 69 rooms are filled with plenty of light.
1505 N. Milwaukee Ave., Wicker Park
This is the kind of ice cream shop that excels at slightly out of the ordinary, although not too outlandish, flavors: brambleberry crisp, churro, ylang ylang and fennel, Riesling poached pear sorbet, pink grapefruit buttermilk frozen yogurt. Jeni's started in Ohio, founded by Jeni Britton Bauer—James Beard award-winning author of Jeni's Splendid Ice Creams at Home, and has since expanded to other cities. There are two shops in Chicago (Lakeview and Wicker Park), which are both outfitted with modern communal areas to perch with your cones, and which also sell Intelligentsia coffee. (On that note, you should try Jeni's Intelligentsia Black Cat Espresso ice cream.) On the West Coast, there is also a location in LA.
Toast & Jam
3317 W. Fullerton Ave., Wicker Park
This adorably named DJ company specializes in weddings, and folks on their team of (mostly women) DJs are equipped with all of the highly specific skills that weddings entail. They have a “never” list of cheesy, eye-roll songs, and a reputation for being professional and efficient, and great at reading the crowd.
Dermatology & Aesthetics of Wicker Park
1765 N. Elston Ave., Wicker Park
The team of dermatologists working out of this massive, tricked-out office are the real deal (several friends have mentioned Dr. Karen Horn by name as the one to ask for). They offer facials and microdermabrasion as a complement to more extensive cosmetic dermatology treatments or a la carte. While the facials definitely err on the clinical side, they don't skimp on the massage. You can also pop in for a quickie "party peel" to prep for a special event.
1935 W. North Ave., Wicker Park
After picking up a gig at a local florist’s, college dropout Elizabeth Cronin fell hard for the craft and at twenty-three, went out on her own. Over the fifteen years she’s been in business, her space evolved into a goth-ish, fairy tale nook for everything from jewelry (Catbird, Ariko, and local Sarah Shikama are just a few standouts) to home décor (Santa Maria Novella candles, Leah Ball pottery) to vintage taxidermy—all deftly mixed with the fresh blooms that started it all. Asrai also has a second location—attached to the Ace Hotel in the West Loop neighborhood.
Apartment Number 9 (Closed)
1804 N. Damen Ave., Wicker Park
It’s weirdly appropriate for one of the most respected menswear stores in the Midwest to be owned and curated by chicks. Sisters Amy and Sarah Blessing do a stellar job of stocking their small-ish, slightly out-of-the-way shop with a heady mix of cool-guy closet staples (Band of Outsiders shirting, A.P.C. jeans, Billy Reid blazers) and heritage brands like Danner, Canada Goose, and Red Wing—arguably the best boots money can buy.
1935 W. North Ave., Wicker Park
After picking up a gig at a local florist’s, college dropout Elizabeth Cronin fell hard for the craft and at 23, went out on her own. Over the 15 years she’s been in business, her space evolved into a goth-ish, fairy tale nook for everything from jewelry (Catbird, Ariko, and local Sarah Shikama are just a few standouts) to home décor (Santa Maria Novella candles, Leah Ball pottery) to vintage taxidermy—all deftly mixed with the fresh blooms that started it all. Photos: Dan Paz
1531 N. Damen Ave., Wicker Park
Unlike so many of the city’s more popular watering holes, this indoor-outdoor Tex-Mex spot is bright, airy, and massive in size. It’s part of One Off Hospitality Group (Dove’s Luncheonette, Avec) and as evidenced by the deep tequila/beer/cocktail list and 2am closing time, values a good time above all. To balance out the copious amounts of booze, order tacos and lots of guacamole from the walk-up window—it's usually faster than waiter service.