Wow, you left that one wide open.
I feel it would be to your advantage to pick a spot closer to the East Side of Michigan. Sure Lake Michigan has beautiful shoreline but that WOULD mean many trips to O'Hare, not that Metro is so much nicer, but rather driving in Michigan is much nicer than driving anywhere in Chicago.
Any place from Port Huron on down the St Clair River makes for very good Sailing. I'll also hook you up with the Lake St Clair Network, a community of Boaters that can help you with suggestions as well as a Social life.
Lake St. Clair Network, fishing, boating, marinas, destinations, forums, charts, weather water levels muscamoot bay photos LSCN These are good people and very diverese; from pleasure boating to fishing to enjoying the lake in any form. Check 'em out!