Probably the best solution in an urban area like Chicago, would be just what Chicago has done in the past....that is "piggy back" new railway construction with new highway construction, like the CTA did on the Dan Ryan and other expressways.
Of course, in today's reality, it seems even new highway routes are a thing of the past....
Here in NYC, when the Port Authority was considering route options for its JFK Airtrain, instead of reviving an old abandoned, LIRR Rockaway line that would have allowed one-seat fast rides from Penn Station to JFK, they finally settled on a new elevated automated train above the existing Van Wyck Expressway, that provided connections to the LIRR and the subways....