If you consider that route pretty bad just consider this:
Kentucky and TN do not have Amtrack. [Well TN has a small segment on its western side that goes N to S but its pretty much a desert.
This means that if you wish to go from ATL, Raleigh/Durham, etc to Chicago, you have to make "connections" (good luck making that on amtrack) in either Charlottesville VA or DC. After that it is still 24 hrs at best.