So there's a boating equivalent to hiking the Appalachian Trail, called the "Great Loop":
https://www.atlasobscura.com/articles/loopers-great-loop-experiencehttps://oceanservice.noaa.gov/facts/great-loop.htmlStart in Chicago with your small boat - no more than 5 feet of draft because of all the shallow waterways you'll be on. Go up the Chicago River to the Des Plaines and then Illinois River to the Mississipi. Head south. You could go all the way to the Gulf, but barge traffic is usually too heavy, and there aren't that much in the way of facilities for your small craft. So at Kentucky, head up the Ohio River to the Tennessee River, which you will take south into Mississippi. Go via the Tennessee-Tombigee Waterway to the Tombigee River, and keep heading south to the Gulf of Mexico.
Follow the coast using the Intracostal Waterway (you can take a shortcut across Florida if you want) up to New York City. Go up the Hudson to Albany, and make a choice. North through Lake Champlain to the St. Lawrence Seaway, or west via the Erie Canal? Whichever route you pick, you'll just go along the shores of the Great Lakes back to Chicago.
If you're lucky and can time it right, you can do it in two months. A year is more common.