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Chicago Walks

An urban exploration.

Chicago is big, in square-miles and spirit alike. Visitors can expect a certain busy urban grandiosity: people drive big cars down wide, tower-lined streets. This is the Midwest, after all, where urban developers took advantage of the seemingly limitless inland space—space that cramped Atlantic seaboard cities, with their finicky peninsulas and islands, could only dream of. Yet despite its intimidating size, Chicago is a great city to walk about. Visitors who travel by foot will be rewarded with the discovery of delightful little neighbourhoods tucked within the city’s bustling whole.

The Gold Coast: One such treasure is the Gold Coast. True to its name, the Gold Coast is one of Chicago’s most affluent neighbourhoods. With its combination of townhouses and mid-century modern luxury towers, it is also the closest the Midwest gets to feeling like the Upper East Side of Manhattan. Mansions punctuate the tightly knit towers, including the original Playboy Mansion notorious for hosting decadent parties in Hugh Hefner’s pre-L.A. heyday. The Lake Michigan coast is nearby too, but the dozen or so lanes of Lake Shore Drive allow for few access points. Fortunately, there is always the alternative of ending one’s walk at a different kind of watering hole: The Drake Hotel—which houses the legendary Coq d’Or bar and lounge, where stiff drinks have been served since prohibition was repealed in 1933.

Wicker Park: Developed after the Great Chicago Fire in 1871, Wicker Park is Chicago’s take on a Victorian neighbourhood, where leafy lanes are lined with gorgeous homes and some of the city’s most vibrant commercial streets can be found. Three of them meet at the gobsmacking six-point intersection of North, Damen, and Milwaukee Avenues. As a new arrival, you’ll be forgiven for losing your sense of direction. No matter—pick any street, explore, and repeat. Be sure to stop into Myopic Books with its three floors and 80,000 titles; it is open late (for a bookstore) every night. If the “L” (“elevated”) trains fascinate you, find a seat in La Colombe Coffee Roasters next to the Damen transit station and watch the bustle from a soothing distance.

Pilsen: Chicago’s Lower West Side features one of the city’s great diverse neighbourhoods: Pilsen. Initially settled by Eastern European migrants 150 years ago, the neighbourhood has become a hub for the Latino community. Solid rows of old homes and commercial buildings create a walkable streetscape of varied styles with the interesting feature of sidewalks that are raised higher than some homes, which, in turn, boast charming “front doors” on second floors. Wandering the rapidly gentrifying neighbourhood, you’ll find independent shops, cafés, and plenty of authentic Mexican and Italian restaurants. Keep an eye out for murals and mosaics scattered throughout the area’s nooks and crannies; they are the work of the Resurrection Project, a community endeavour to revitalize Pilsen, 25 years in the making.