An expressway along the alignment of the Eisenhower Expressway was foreshadowed by Daniel Burnham's plan of 1909, which described a west side boulevard. The passageway under the old Post Office was designed to preserve the right of way for the future road.
The Expressway is named for the former President Dwight D. Eisenhower; it originally was called the Congress Expressway because It begins on Congress Parkway in Chicago. The political columnist Mike Royko joked that it is Chicago's only Republican expressway, since the others all named after Democrats (though since that observation Bishop Louis Henry Ford, a non-political figure, had an expressway named in his honor). The first segment, 2.5 miles (4.0 km) in length opened from Mannheim Road to 1st Avenue in December 1955. On December 15, an additional 4 miles (6.4 km) was opened, from Ashland Avenue (1600 West) to Laramie Avenue (5200 West).
During the 1960s and 1970s, the Eisenhower Expressway was extended to Lake Street and North Avenue. In 1963, the first working example of ramp metering took place on the Eisenhower Expressway, based on successful metering through New York City tunnels and data from ramp closures in Detroit, Michigan. The first implementation utilized a police officer at the top of an entrance ramp, stopping and releasing vehicles onto the highway at a predetermined rate. Another section opened in 1972, to a north–south expressway in Addison, Illinois. At the time, this expressway was a short spur from the Eisenhower Expressway, and it was referred to as Illinois Route 53, which continued north to Schaumburg. Construction on Illinois 53 had finished in 1970.
Until 1978, the Eisenhower Expressway was marked as a part of Interstate 90. In 1978, the Interstate 90 designation was moved onto the John F. Kennedy Expressway and the Northwest Tollway, replacing Illinois Route 194. The Eisenhower Expressway was then renumbered as Interstate 290.
Because the segment from Interstate 294 to Illinois 53 was built last, that portion of the highway is referred to as the Eisenhower Extension. The Eisenhower Expressway, extension included, is 23 miles (37 km) long. If the Illinois 53 portion of Interstate 290 is added to that, the highway is actually 30 miles (48 km) long.