I can't help much from Chicago to this area:
Long first day to the Kingsport, TN local. There are so many nice roads in the area above it is hard to fit them all in. It is really a lovely part of the country. The company I am part owner of is in Morganton, NC and I spend two weeks a month there. I have driven all through Boone, Banner Elk, Spruce Pine, LS, etc. many times on Sunday drives.
Once you get past I40, do try and drive back roads to Lake Lure. My Sister has a house outside Brevard and when I go see her from Morganton I like to drive through there. Touristy but cute.