New Orleans - Chicago

[61bluemoon61]

I am UK based and at the earliest stage of planning a tour from New Orleans to Chicago (or vice versa?) in late June / early July 2018. If anyone has any ideas, suggestions etc. on resources, routes and stops. North to South or south to North? I want to take in St Louis, Nashville and Memphis and believe I can do this and also do 2/3 of the Natchez trail. What other cycle paths would work?. All thoughts gratefully received. 

[RussSeaton]

Definitely ride South to North.  New Orleans to Chicago.  In the Midwest in the summer, the wind comes from the south and west.  You will have a much better chance of tailwind going south to north.  No guarantees of course.  You could have a headwind every day too.