If you mean proper Sailing Directions, Google
"Sailing Directions" + "Chicago to Maine" and "Maine to the Bahamas". Include all the areas you're interested in. I am not sure if they exist for those inland waters, but there are Sailing Directions for all the oceans and their included islands.
If you're planning to do the loop, the post above this one's link should do you.
You might add what kind of boat
and its size, too. People can adjust their answers to some of your questions when they have that info.