Wicker Park
Establishment
neighborhood
Small Cheval
1732 N. Milwaukee Ave., Wicker Park
Some Chicagoans swear that Small Cheval has the best burgers in the city. 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.
Credo
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.
The Robey
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.
Jeni’s
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.
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.
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.
Big Star
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.
Mirai Sushi
2020 W. Division St., Wicker Park
"Unfussy" is probably the best word to describe the fresh fish at this sexy little sushi joint. All the chefs are traditionally trained, so while the more out-there rolls and daily specials are great, it’s the beautifully cut sashimi and nigiri that steal the show. It’s also important to note that while the offering is topnotch, the atmosphere is decidedly low-key, just right for a weeknight dinner. Both this location and the one in Gold Coast offer delivery and takeout.
Dove’s Luncheonette
1545 N. Damen Ave., Wicker Park
A working jukebox, padded stools, and counter seating…aesthetically speaking, everything about this smallish Wicker Park restaurant screams retro luncheonette. The menu, on the other hand, is the farthest thing from greasy diner food. Chef Ryan Piotrowski turns out an impressive selection of Southern-inspired Mexican comfort food (red chile enchiladas, grits, and a bunch of yummy chicken dishes) and a tequila-heavy drink menu to match. The seating situation is a tad unconventional and doesn't really accommodate large groups comfortably. That said, it’s ideal for a low-key one-on-one.
Schwa
1466 N. Ashland Ave., Wicker Park
The absolute highlight of any Chicago trip is eating at Schwa. Chef Michael Carlson and his staff are so punk rock that they don’t even answer the phone, which makes getting a table difficult, yet weirdly fascinating. From the outside, Schwa looks like it has been condemned. Inside, the dining room is small and spare yet cozy. The formality of the service and menu (no orders taken until the whole party arrives, and the elaborate tasting menu) is juxtaposed by the waiters in casual clothes and the blaring music. The food is sublime. It’s classic American comfort food by way of Ferran Adrià/Banksy/Tony Hawk. It’s off the hook. Try the 9-course tasting menu.