Wicker Park

Originally developed by the Wicker brothers in the 1870s, Wicker Park was much sought-after by middle and upper-class families moving away from downtown after the Great Chicago Fire. Over the course of the next hundred or so years, the neighborhood became synonymous with a hip, bohemian lifestyle that’s still in evidence today—even if it’s been toned down some by a wave of gentrification that’s been on-going since the 1980s.

As a result, you can walk around the neighborhood and see resale and thrift stores existing comfortably side-by-side with sleek modern boutiques. Dive bars and craft cocktail lounges live together in harmony. Small venues host local music, larger venues pull in the touring acts, and musicians of every genre come together once a year for Wicker Park’s massive summer festival.

Now, although Wicker Park shares its northern border with Bucktown along the super busy and bustling North Avenue, the neighborhood has a second main drag along its southern edge on Division Street. Did I hear you say you want more options for dining, drinking and entertainment? I thought so, and here’s where you’ll find them.

Literally in the middle of all the action is an upwardly mobile, family friendly community filled with quiet, tree-lined streets that feature Victorian-era mansions, single-family homes, classic Chicago row houses, and—more recently—modern condominiums; it’s a surprisingly idyllic neighborhood.

And transportation couldn’t be simpler. The CTA kindly has four Blue Line stops running diagonally through the neighborhood, buses criss-cross all the main arteries, and the Kennedy Expressway more or less defines the eastern edge of this gem of a community. Wicker Park nicely balances all of the hip and trendy aspects of city life, while offering a place to take a break and recharge in whatever style suits you.

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