Chicago has a number of diagonal streets overlaying the grid. Most of them follow the routes of old trails. The diagonals can be useful shortcuts—except when you run into backups at triple intersections.
Perhaps these streets seem eccentric to rigid bureaucratic minds. For whatever reason, portions of several diagonals have been abandoned over the years. Let’s look at five of them.
We lead off with Vincennes Avenue. The street originally started at 35th and Cottage Grove, running southwest from there. It was a major highway for travelers heading downstate.
During the 1870s, Washington Park was laid out. Meanwhile, just to the south, rail yards were being established. Vincennes Avenue passed through the area, and portions of the street were abandoned.
Today, most savvy Chicagoans know Vincennes Avenue as an arterial street going from 69th Street to the city limits at 119th Street, and beyond. Yet there’s still a remnant of the old highway north of the park—Vincennes Avenue the side street, from 3600 to 5100 south.
Cottage Grove Avenue began at 22nd and Indiana, angling southeast to 39th Street. From there the route continued due south for seven miles to 95th Street, where it again went diagonal.
In 1955, as part of a renewal project, the city chopped up Cottage Grove between 26th and 33rd streets. A decade later, another stretch was abandoned during construction of the Stevenson Expressway. A few blocks of the old diagonal remained north of the expressway into the 1990s, when they were also built over.
Blue Island Avenue follows the first few miles of an old trail from Chicago to the town of Blue Island. The street began at the Harrison-Halsted intersection and ran southwest to 26th-Western. South of there, the trail became part of Western Avenue.
Two sections of Blue Island have been vacated in the cause of education. The section between Harrison and Roosevelt was abandoned in 1962, when construction began on the UIC campus. In 1973 one more block was cleared between 21st Street and Cermak Road to accommodate the new Juarez High School.
Milwaukee Avenue originally ran northwest from a starting point at Lake and Canal. Just up the street, from Fulton to Kinzie, a long viaduct carried Milwaukee over some busy railroad tracks.
In the 1980s the city reconfigured the area. The Milwaukee Avenue viaduct was torn down, and traffic diverted onto a new Des Plaines Street viaduct. In 2015 a single block of “old” Milwaukee Avenue still exists between Lake and Fulton.
Ogden Avenue was an old diagonal highway to the west, starting at Union Park. As early as the 1880s, planners were talking about pushing the street northeast to Lincoln Park. After twelve years of land clearance and construction, the Ogden Avenue extension was completed in 1934.
The extension didn’t last. Traffic on Ogden declined sharply once the expressway system was built. Between 1969 and 1993, nearly two-thirds of that expensive new street was abandoned. Today, north of Fry Street, the only Ogden remnant is an isolated block off Clybourn Avenue.