Most of the information you'll need will be found here: America's Great Loop
I'm going to make the Great Loop trip in my boat next fall and plan on leaving the Michigan shore to cross over to Chicago and then down the Illinois, Missippi, Ohio, Tennessee and TenTomm to Mobile in the fall.
You can also benefit from buying the "Skipper Bob - Cruising from Chicago to Mobile printed guide (about $20.).
If you draw more than 5', you will likely have a problem. Less than that and you may here and there, but it has been done by many sailboats in the past.
1965 Cal 30