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Oak Park—20 Best Towns and Neighborhoods in Chicago and the Suburbs

The 74-year-old Lake Theatre
A suburban treasure: The 74-year-old Lake Theatre in Oak Park

Average house price: $447,515
Transportation * * * * (out of 4) Outstanding Metra and CTA options; Eisenhower Expressway lies along village’s southern border.
Schools * * * The Oak Park school district, with ten elementary or middle schools, performs well, and there are good options for public (Oak Park & River Forest) and private (Fenwick) high schools.
Shopping * * * * The primary shopping zones are along Lake, Oak Park, and Harlem avenues, with a smattering of smaller places throughout town.
Plus: The village’s rich cultural offerings—including outdoor summer performances by the Oak Park Festival Theatre (oakparkfestival.com)—are easily augmented by a quick train trip into Chicago.

It would be possible (though sinful) to remove all the houses designed by Frank Lloyd Wright from Oak Park and still leave behind enough architectural eye candy to populate two or three suburbs. With a century-long attention to good design, the town is layered with landmarks old and new. Oak Parkers shop and dine in the Prairie-style Scoville Square (a commercial building from 1908) and borrow books a block away in a glassy, angular public library from 2003.

Oak Park’s careful correctness may have irked its native son Ernest Hemingway—who famously (if apocryphally) dismissed the town as a place of wide lawns and narrow minds—but it has resulted in a place that is endlessly attractive, from the old horse fountain in Scoville Park to the bungalows south of the Eisenhower to the architectural buffet in the Ridgeland Historic District.

If Oak Park’s buildings are a feast for the eyes, its commercial districts offer a true banquet, with little bakeries, lively ethnic joints, and fine dining establishments all along Lake Street in the middle of town and at a scattering of other retail hubs. Diversity of races and incomes is also a hallmark of this mini-urban suburb, giving it a comfortably 21st-century mix.

Boundaries are porous; neighboring towns compensate for some of Oak Park’s deficits. Despite its name, the town is actually short on parkland—but Chicago’s historic Columbus Park, which includes a golf course, lies to the east across Austin Boulevard. Similarly, the picturesque older buildings downtown don’t accommodate big-box stores, but on the western end of town there was room for a few, with spillover into River Forest.

Add these amenities together, and it’s easy to borrow the name of one local landmark and use it as the town’s slogan. In 1897, the wealthy resident John Farson built a 30-room mansion (now a museum) at the corner of Pleasant Street and Home Avenue. Using the intersection as inspiration, he dubbed his residence Pleasant Home—and more than a century later, that moniker could still apply to all of Oak Park.

Dennis tours Oak Park with Rochelle Vayo Adkinson of WGN and CLTV’s HomesPlus.


Photograph: Courtesy of the Village of Oak Park


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