Wicker Park Specialty
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.
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.