The Federal-Aid Highway Act of 1956 spurred extensive construction around Chicago, but by 1960, the Crosstown Expressway was the only route included in the region's postwar transportation plans yet to break ground.

On February 25, 1967, the federal government proposed the Crosstown Expressway be redesigned as a "total development concept" that would integrate mass transit, high-rise apartment buildings, commercial and industrial zones, and green space.

Changing public opinion across the country on urban highway construction, the mid-1970s energy crisis, and rapidly escalating costs (from the total development concept additions and runaway inflation rates) ultimately undermined the expressway.

In the $1.916 billion in federal funds earmarked for the Crosstown Expressway and (never-built) Franklin Line Subway were then reallocated to Chicago's regional transit agencies, and to other road improvements across northeastern Illinois.

In 2001, Mayor Richard M. Daley announced plans for a Mid-City Transitway, using the alignment of the Chicago Belt Line Railway that the Crosstown Expressway route was to have followed.

Proposals for a Circle Line providing circumferential transit options closer to the Loop have been prioritized over investment in the Transitway project by city officials and the Chicago Metropolitan Agency for Planning (CMAP).