NOLA to Chicago -- top 3 must sees
 

We are traveling north from New Orleans to Chicago in mid-late August.
Being unfamiliar with these areas, we would appreciate any suggestions -- interesting towns, restaurants, food festivals, regional foods, etc. Generally we'll drive through Memphis & St. Louis to Chicago, but we're open to ideas.
What would the top 3 "don't miss it" things to do be in these cities or in placs along the way?
Thanks!

Have you been through Nachez MS? That would be a good place to visit.

Are you interested in Chicago or "along the way". What kinds of food, activities, do you enjoy?

We're actually doing a giant loop, leaving from DE down to visit family in New Orleans, then driving up to Chicago. We might end up driving up through Detroit/Windsor across Canada to Maine, then back home. (Hope we'll still be talking to each other after this many miles!)
We could drive through Natchez MS on the way to New Orleans, which is a good idea (thanks).
We enjoy beautiful landscapes, hiking, interesting local restaurants, exploring areas, historical sites, not big on tacky junk. I haven't been to Chicago in many years and my husband's never been there -- theatre, shoppping, hotels, areas to avoid? We'll likely go through Memphis and wondered if anyone had other interesting "must see" places to recommend.
Thanks.

Natchez would be en route from NO to Chicago, rather than between DE and NO. Check out this link to the Natchez Trace Parkway. This would be an interesting route.
http://www.scenictrace.com/