Uptown Specialty

While Dollop has expanded across Chicago over the past 10 years, it’s still very much the neighborhood coffee house at heart—there’s nothing slick or overwhelmingly modern about any of the cafes. At the original Uptown spot, the seating options include lived-in couches and upholstered chairs, which if you’re in it for the long haul, makes a difference. The food offering, while modest, will do the trick in a pinch. The Streeterville location is spacious and well suited for study groups or casual meeting. Want fresh-baked pie to go with your coffee? Evanston serves Hoosier Mama pie all day. Perfectly brewed Metropolis coffee is consistent throughout so check out the Downtown and Gold Coast outposts, too.

We teamed up with Heritage as part of our Chicago pop last year (we're currently in Sag Harbor, Dallas, and Aspen for the summer). 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 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.