The Chicago Skyway and the Indiana Toll Road are the westernmost extensions of what I have always referred to as the "Eastern Turnpike Complex," which includes in addition to these two, the Ohio Turnpike, the Pennsylvania Turnpike, the New York Thruway, the New Jersey Turnpike (and in "guilt-by-association," the Garden State Parkway and the Delaware Turnpike), the Connecticut Turnpike, the Maine Turnpike, and the Massachusetts Turnpike.

Most of the planning for these highways predates the present Interstate system by a varying number of years. From what I originally understood (and if someone has differing data, please let me know), the system was set to run due westward from Chicago near Midway Airport and out toward Iowa. As a matter of fact, the Skyway ended at State Street in Chicago for a number of years at a literal dead end of the elevated roadway. The roadway was supposedly to continue westwardly through the city. When the Dan Ryan Expressway came through, a natural extension was to drop the elevated roadway into the depressed culvert that would become the Ryan.

To the east, the Skyway has had a couple of exits closed and associated lanes taken out (WB to Indiana Ave. - one way NB; and EB from Michigan Ave. - one way SB), due to dangerous conditions of the elevated roadway over adjacent rail yards. The Skyway passes the now-abandoned Falstaff Brewery on the far southeast side, just before crossing the state line into Indiana. In Indiana, the Toll Road has had a number of upgrades, most notably for out of state travelers is the notion of moving the point at which drivers acquire tickets from the West Point Barrier (now just past the state line, originally three miles further southeast at Calumet Ave.) about 25 miles east to the Willowcreek Barrier, at Willowcreek Road in Portage. West of that point, tolls are collected at individual exits, and at a full toll booth set at the West Point Barrier.

As always, corrections and additions are welcomed, and encouraged. The formatting is lifted (once again) from C.C. Slater's wonderful logs (if I have any say in it, this will become the standard for the exit logs on the net).