How far North do you want to go and where will you have to commute to and from?
North from Chicago the First in line is Wilmette Harbor. It is a very small harbor and probably not live aboard friendly. I think there is very lengthy waiting list to get in there.
Sheridan Shore Yacht Club
Next is Waukegan. Its a very nice harbor with nice faculities, but located in a somewhat industrial setting. The harbor is in a nice park area, but the view from the lake is somewhat to be desired in my opinion. It’s also a long haul to drive back and forth to the city from there, only about 45 miles each way, but the traffic is terrible. 45 miles is not very far, but I am sure the commute would be well over an hour.
Next in line is North Point Marina at Winthrop Harbor. This is a very nice marina and a very large marina. They claim to be the biggest Mariana on the Great Lakes with over 1500 slips. Now you are probably over 50 miles away from the city and still stuck in the same traffic.
North Point Marina - Located on Lake Michigan in Winthrop Harbor, IL
Going further North and into Wisconsin are Kenosha & Racine both very nice facilities but now you are well over an hour drive each way in rush hour traffic.
Skipper Marine - Wisconsin : Skipper Marine - Wisconsin
Chicago itself, for as great as a city that it is, is not very boater friendly. If you’re looking for a nice, quiet, clean, showers, laundry, etc., I cannot recommend anything in the Chicago Harbor System. Others may disagree. If you want to try Chicago proper, Belmont, Montrose, & Burnham Harbors would be your best bet. They will also have a long waiting list. Facilities will be less than appealing. Monroe Harbor might fit you in, but there you will be on a mooring can. Chicago does have its appeal and is a great city to sail in and around with a magnificent skyline as your backdrop, but not a good choice for living aboard.
Chicago Harbors - Westrec Marinas
You might want to look at going East from Chicago. Michigan City, IN and New Buffalo MI are very nice friendly areas with a lot to offer. Be careful with draft if looking at New Buffalo. These two communities are about 60 and 70 miles from downtown Chicago but the commute is much easier in my opinion.
Courtney is My Hero
If a man is to be obsessed by something, I suppose a boat is as good as anything, perhaps a bit better than most - E.B. White
Last edited by sailortjk1; 07-29-2008 at 06:11 PM.