Well C.J.

If I were making that trip I'd get out of Chicago and go South on U.S. 55 through St. Louis where Highway 61 paralels U.S. 55. It may even be used as access road in some places South to Memphis where 61 separates and goes through Clarksdale Ms. (a fer sure stop dude!) then it continues to New Orleans.

Of course I wouldn't go to New Orleans, I'd just stay in Clarksdale a year or two and soak up what I could. :}

Have a good trip.