[1] The Kennedy was originally constructed along the route of Avondale Avenue, an existing diagonal street, and the C&NW Northwest Line corridor, in the late 1950s and completed on November 5, 1960.

The American Recovery and Reinvestment Act of 2009 provided the necessary funding for the construction between Hubbard Street and the Circle Interchange, commencing in summer 2009.

[5] The only remaining short, limited-sight, left-side suicide ramp entrance is from Lake Street to the eastbound expressway (heading south).

In 2015, the American Highway Users Alliance named the 12 miles (19 km) of the Kennedy between the Circle Interchange and Edens junction the worst traffic bottleneck in the country.

Unlike other expressways on the south and west side of Chicago, areas around the Kennedy maintained much of their density despite the displacement caused by its construction.

Avondale residents view the Kennedy's underpasses' unwelcoming conditions as creating a barrier between the two halves of the neighborhood.

[11] Areas around the Kennedy Expressway are hotspots for air pollution, especially in the Avondale and Irving Park neighborhoods of Chicago.

Residents in these neighborhoods face significant exposure to fine particulate matter (PM2.5), a type of air pollution comprising tiny particles that can penetrate deep into the lungs.

[12] The Blue Line operates in the median of the Kennedy Expressway for about 10 miles (16 km) from O'Hare International Airport to just south of Addison Street.

The reversible lanes lie in the median of the highway from the Kennedy Expressway/Edens Expressway junction until just north of the Loop (at Ohio Street), a distance of about eight miles (13 km).

On January 25, 2014, a drunk driver broke through the safety gates and drove in the express lanes in the wrong direction, but was stopped by a snow plow; no injuries were reported.

The 2009–10 reconstruction between Hubbard Street and the Circle Interchange improved safety by increasing the lengths of most entrance ramps and reduced bottlenecks by better utilizing the existing space.

[citation needed] The Kennedy Expressway was the location of a large Magikist lips flashing sign which was a Chicago pop culture icon for many years.