I'm planning an un-supported cycling trip from Chicago to New Orleans this October (2015). I would love to hear any advice or tips from those that have done the ride before. I'm planning on following the MRT as well as the Adventure Cycling routes. If you have any interest in doing all or part of the ride contact me. I expect the ride to take ~20 days with rest days and enjoying the sites along the way, followed by several days in New Orleans binging on all that city has to offer. Will be flying or training back to Chicago.
About 1500 miles for me, I took the scenic route.
If you're looking for a place to stay in New Orleans look up the Petite Motel. About 15 minutes away from the French Quarter. Broad and Toulane. Clean, reasonably priced. Not a luxury motel, just a place to sleep.
Cross the river someplace, travel along the west side of the river through Louisiana. The Cajun territory is much more interesting than the Mississippi side.
Roughly my route, from Google Maps:
I've been down in that area several times. Once after taking a train to Texas, then on to New Orleans:
It's a great ride, no matter how you go. You get to see a lot, smell a lot, taste a lot, touch a lot, and experience a lot you wouldn't ordinarily do. Take pictures, and post a diary of your trip.