Well, you should on the whole drive US 61 and the roads that parallel it, the road the Bluesmen took on their way to Chicago.

Put this route into Google Maps, Greenville and Clarksdale in the Mississippi Delta, Memphis, St Louis, and Chicago. It will take you away from Highway 61 at some points, but in Mississippi you can follow the Blues Trail.

Get him a map of Mississippi and let him thrill to the names you will pass and pass through: Belzoni (pronounced "Belzona", as in 'Belzona Jailhouse Blues'; Rosedale, where Robert Johnson sold his soul to the devil; and Friars Point.

If he is interested in prison blues, Angola is not far northwest of Baton Rouge, just below the Mississippi line, and you will pass near Parchman Farm near Shelby but there is not a lot to see there, or wasn't when I was last there.

I would spend an additional night in NO as you will be too whipped to do much in three nights, and it is magical. In Mississippi eat at bait shop cafes, small roadside place that sell cooked breakfast and lunch along with gasoline, fishing bait, and general merchandise.

I would not take this trip later than mid-May. When I lived in Mississippi, every day from roughly May 15 to September 15 was about 93F which is something like 32 or 33C, and the humidity is challenging.

Have a wonderful trip!

For what it's worth, we did a similar trip (but in November - different weather concerns) a few years ago, documented here:

http://www.fodors.com/community/united-states/trip-report-long-beignets-bayous-blues-and-ducks-in-the-lobby.cfm

This is a spectacular report. Everybody has to ride on Highway 61, nobody has to _stay_ on 61.

The "blues economy" has apparently come a long way since 2003. Isn't it time to make another trip to Mississippi?

Before Doe's Eat Place became a franchise, you sat in the kitchen eating steaks that cost as much as a Sunday roast and were about as big while the locals lined up outside with gallon lard cans to buy tamales. Old Days in the Delta.

Memphis is a great blues city and is a must. St. Louis is nice and has some good blues places. Chicago has some good blues and jazz places. http://chicagovisitor.net/Music.html

St. Louis has produced some great musicans such as - Miles Davis, Scot Joplin, Chuck Berry and Ike (& Tina) Turner.

And it is a fun city to visit.