Planning road trip in mid-October

[Ted$8roadFan]

I'm thinking of taking an extended road trip some time in mid-October (hopefully gas prices will be a bit more reasonable). By extended, I mean outside of New England and the Northeast Corridor and that lasts for a week or more.  Perhaps somewhere in the Midwest or South.  For the latter, I was thinking of Nashville or New Orleans; the former Chicago or Cleveland. Of course, I'm open to other ideas as well.  It's been a long time since I've traveled. Any tips/advice/places to go are welcome.