It''s my understanding that there is 51 foot clearance from the Mississippi to the Gulf. You would have to unstep the mast from Chicago to the Miss and for the Erie canal. Once you exit the Erie, you can either restep it, or leave it down and take one of the canals across Ontario.
Cruising Guide for the Tennessee, Ten-Tom Waterway and Lower Tombigbee River is a detailed and exhaustive tome for that part of the trip. Well worth the price if you go.