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The city’s far northwest corner, where the grid gives up: streets that curve in circles by design, the oldest house in Chicago on its original rise, a drive-in with carhops since 1948, and a restaurant strip that fills up on Friday nights.
Norwood Park was platted in 1868 as a picturesque commuter village, and its planners deliberately broke the Chicago grid: the Circle, a full loop of curving streets around a small rise, survives as one of the few places in the city where you can get pleasantly lost. Edison Park, the city’s northwest tip beyond it, joined Chicago in 1910 and runs on its Metra stop and the short business strip around it.
Both feel closer to the suburbs than to Milwaukee Avenue, tall trees, deep lots, low buildings, while keeping city services and a rail line that treats downtown as twenty-some minutes away.
The Noble-Seymour-Crippen House at 5624 N Newark Avenue was built in 1833, before Chicago was a city at all, and its southern wing is the oldest building standing inside the city limits. It sits on a rise that was once a farm orchard and now serves as the Norwood Park Historical Society’s home, open for tours on a regular schedule.
Superdawg, the rooftop-hot-dog drive-in at Milwaukee and Devon, has been run by the same owners since 1948 and still sends carhops to your window. Edison Park’s strip along Northwest Highway and Oliphant holds a run of restaurants and taverns that draws from the whole Far Northwest Side, and its summer festival closes the street each year. Gladstone Park’s stretch of Milwaukee fills the gaps between.
Frame Victorians and foursquares on the Circle’s curves, brick Georgians and Cape Cods on the straight blocks, post-war ranches and split-levels toward the edges, and a steady trickle of new construction on teardown lots. Lots run wider here than the city standard, and garages face alleys less often, so check how parking and additions work block by block. Our home styles guide and zoning guide answer the questions these blocks raise most.
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