A few to check out: -Chicago: plenty to do there of course, so probably don't need to get into that. -Indy: Tour of Indy Motor Speedway is pretty cool, even if you're not a race fan. They have a museum as well. -Louisville- L'ville Slugger tour is fun, can pick up a new stick too! - Churchill Downs -Kentucky- Mammoth Cave tour, if you're into that - Fort Knox Not sure why you would go through Alabama, but I'm sure you have your reasons. Quite a bit out of the way though. -Nashville would be a good place to spend the night. Check out the bar scene. Also, obviously plenty of country music stuff to check out if you want. -New Orleans- A ton to see and do, of course. Tabasco tour is pretty cool. Then there are the swamp tours, haunted sites, etc. Bourban St is a must see, if you're into that scene or not. Plenty of great food, won't have a problem there.