2037 W Roscoe Street, 1 Chicago, IL 60618

The small enclave of Roscoe Village on the western side of Lake View has earned its name by offering a small-town feel in the heart of Chicago. It’s a neat-as-a-pin neighborhood with tree-lined streets, where you'll find sidewalks full of baby strollers, dogs on leashes, and kids on scooters. The closest L station, the Paulina Brown Line, is just five miles to downtown. The homes are mostly single-family row houses of the Midwestern Prewar fashion, with space for generous yards. That low-key vibe transfers into the dining and retail scene. Shopping is a quirky selection of locally owned boutiques, and while there are plenty of restaurants here, none require booking far ahead (if at all). Bars are locals’ haunts rather than the kind of places that rage until the wee hours. It’s a quiet place, and the villagers like it that way.