According to most reports, the lower Mississippi is a rather hostile environment
That's why most cruisers take the Tennessee/Tombigbee waterway. It runs from Mobile, Al. up to the Ohio
River. You then go downstream to the Mississippi and up the Miss. a short way to the Illinois River and to Chicago. There are issues right now with Asian carp and closing the Chicago canal. That situation is in flux.
Early spring can be troublesome with spring rains and runoff, creating strong currents and debris in the water
. Locks are sometimes closed because of this.
will have to come down. Many sailors truck the mast from Mobile to Chicago. You might be able to team up with some other sailors and share the expense of trucking the mast.