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.
1545 N. Damen Ave., Wicker Park
COVID-19 update: Temporarily closed. 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.
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.
1373-75 N. Milwaukee Ave., Wicker Park
Locals love Filter because in a lot of ways it feels like a friend's living room—lived-in, mismatched couches, dim lighting, and good music. And with disco fries, wraps, sandwiches, and veggie options on the menu, it's pretty easy to set up shop for the day with no real need to leave.
The Wormhole Coffee
1462 N. Milwaukee Ave., Wicker Park
The first thing you'll notice here is the not-so-subtle '80s theme: A DeLorean, scattered Gremlin paraphernalia, and old-school Nintendo video games set the vibe. If that's not too distracting, it's actually a great place to hole up for a few hours of work (tons of outlets and good WiFi). They offer a revolving roster of guest roasters, most from the indy, small-batch end of the spectrum. Best part: It’s open until 11pm daily.
1609 W. Division St., Wicker Park
Chicago-based Intelligentsia ushered in a new wave of gourmet coffee shops, the kind where responsibly sourced and expertly roasted coffee is prepared using methods that, though time-consuming, result in a pretty perfect cup. As a rule, all outposts are aesthetically unique (five others are scattered in Old Town, Broadway, Millennium Park, Logan Square, and The Loop), offer free Wi-Fi, and have loads of seating options. Plus, you kind of have to love the theme-dressed baristas.