The original eastern terminus was at the intersection of Jackson Boulevard and Michigan Avenue in downtown Chicago in 1926.
In a later alignment, the terminus was moved east two blocks to the intersection of Jackson Drive and Lake Shore Drive after the latter was designated as U.S. Route 41.
It remained there until the eastern terminus of Interstate 55 was completed at Lake Shore Drive, and then that also became the eastern terminus of Route 66 until I-55 completely replaced the route in Illinois and Route 66 was decommissioned.
Jackson Boulevard was the original Route 66, but it is now a one way street heading eastbound, towards Michigan Avenue and Lake Shore Drive.
As a result of changing two-way streets to one-way traffic, you can come into Chicago on the original Route 66, but you have to leave by way of Adams Street (one way westbound).
Adams Street begins at the entrance to the Art Institute of Chicago.
Compiled by Neil Gale, Ph.D.