I'm going to be visiting Chicago next month for two weeks. I usually stay in a hotel, hostel or with a friend. But what about finding a boat in one of the marinas, Lincoln Park area-Montrose or Belmont-where the owner was not using the boat and would rent it to me for a couple of weeks? Just to live on at the dock and not take out. Probably not likely, but since I currently live aboard full-time with my better half in the Caribbean it would feel like home (except for the skyline). Interested in your opinions or leads. Thanks.
Chicago is a very difficult place when it comes to marinas and boat ownership. The public marinas along the lake are operated by the city and they have very strict rules regarding guests, transients, live'a'boards and the like. Some of the more ideal spots have a waiting list that takes many years to get into.
Here is an info sheet on slip rules to give you an idea.
I have read about a few live aboards, but not recently and they had to keep it on the down low when then did pull it off. You can try reaching out to some of the yachtclubs to see if you can arrange something, but don't get your hopes up. This city is also seasonal, so all boats need to be out of the water come Oct, its splash time soon actually.
There are some firms that do a time share deal on production boats, I think Sailtime is one of them, but I dont know what their policy is for long term possession.
Moving back to Chicago from South West Florida has really opened my eyes to how strict it is here. A real shame too as there is so much waterfront and so many rules. In Sarasota, there is a public Mooring field with old salts that row into the waterfront tiki bar every night for a drink, that culture does not exist here.
If you figure something out, please let me know. I'd kill for the secret.