Ya know it gets 20+ below zero here in the winter. Brrrrrrrrr! Oh yea and the water freezes, that might be a problem.
If you are just wanting to liveaboard during the sailing season Monroe Harbor is your best bet and most affordable, I know cans are available. You will be on a mooring can, but they have a good tender service pizza delivery A Binkys liquor store that will deliver to the marina. You will defiantly want a dinghy, so you don't have to depend on the tender service to get you ashore as well as a good battery charging system. If I didn't have 2 dogs I would liveaboard in the summer I work about 2 blocks away. Chicago Harbors - Westrec Marinas