Wicker Park Restaurants
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.
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 Tom Carlin 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.
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.
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 all the hot waiters in skater clothes and the blaring hip hop/heavy metal. 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.
1732 N Milwaukee Ave., Old Town
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.
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