Interestingly, Chicago's major arterial Expressways, the Dan Ryan, Stevenson and Kennedy (with it's NW Expressway/NW Tollway and Edens extensions) were built, in large part, adjacent to existing rail corridors which already divided communities (and in the Stevenson's case, was primarily industrial, which is why the planned rapid transit in the median never happened - we got the Orange Line to midway many years later instead). The remainder, the Dan Ryan, Congress (now Eisenhower, aka the Ike) and Kennedy have rapid transit in the medians, either supplementing or, to the NW, providing new subway service which eventually went to O'Hare. And in fact, through Oak Park, the trench is shared with active freight.
The freeway revolt came with the Crosstown Expressway was proposed - a north south arterial route from, more or less Midway Airport due north which would have tied in to the Edens was killed by neighborhood opposition. We still have fewer expressways than say, NYC or other big cities overall.