3404 N. Southport Ave., Lakeview
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.
1658 W. Belmont Ave., Lakeview
Scooter's is a bit of a mom-and-pop shop: It's owned by husband-wife team Mardi and Denny Moore, who quit their corporate jobs in 2003 to start the family business. Mardi and Denny are both Chicago natives, so local is important to them, whether it's the milk they use (it all comes from dairies in Wisconsin) or the people who frequent their shop, many of whom they know by name. They specialize in frozen custard, which you can see pouring out of their machines all day long. The thing to order is the Boston shake, a milk shake with chocolate syrup and a mini custard sundae—whipped cream included—on top. It's fun to stop by on the last day of summer, when the whole neighborhood comes to hang out.
Bobtail Ice Cream
2951 N. Broadway St., Lakeview
Bobtail Ice Cream was born out of a business plan competition at The University of Chicago Booth School of Business, and inspired by the grandfather of one of the founders (Grandpa Wilcoxon) who sold ice cream door-to-door from a truck in his Ohio neighborhood in the 1950s. The ice cream here is hard-packed and homemade, a mix of expected flavors and specialty creations, like Merlot ice cream with dark chocolate chips. And for those cold, windy Chicago days, there are some more weather-appropriate options, like hot fudge on a warm brownie, ice cream lattes, hot chocolate, and white mocha.
2959 N. Lincoln Ave., Lakeview
We teamed up with Heritage as part of our Chicago pop. After all, this is the kind of family-run operation that can make all your bike-related dreams come true. Not only will they custom build one pretty much from scratch (Tassels? Glitter? No problem!), but they make great coffee, too. The original Lincoln Avenue outpost (owners Mike and Melissa Salvatore actually live upstairs) does both in addition to a sweet general store, while the newer Heritage Outpost in Uptown is devoted entirely to coffee. You'll find free Wifi, and a group of people working on laptops, at both locations.
3123 N. Broadway, Lakeview
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, Wicker Park, Millennium Park, Logan Square, and The Loop), offer free Wifi, and loads of seating options. Plus, you kind of have to love the theme-dressed baristas.