Don't Forget Chicago
This year I moved my Catalina 30 to Montrose Harbor in Chicago from Waukegan, where I had kept it for two years. First, you should consider Waukegan if you are looking for a non-Chicago option. It's a big, friendly marina with good services and it's much closer to most of the Chicago area than Racine. One consideration if you plan to keep your boat in a slip: Waukegan's docks are fixed, so the current low water levels make for some dicey docking conditions.As for Chicago, I've had a totally different experience than Bob. Parking is only a problem at Montrose on July 4; otherwise there is always room in a reserved lot directly across from my slip. It takes about 5 minutes to dingy out to the stardock and 1 minute to motor over to the touch & go to pick up passengers, etc. For me, coming from Evanston, that saves 30 minutes travel time over going up to Waukegan. Then I go out to sail past one of the most beautiful skylines in the world. Sure there is more traffic than in Waukegan (or Racine), but you can get away from most of it by going out a few miles, especially if you are leaving from one of the northern or southern marinas rather than a downtown location.Two other things: I paid $500 more for a slip in Waukegan, and they hit you for the extras too, like a ladder to deal with the afore-mentioned low water. Also, contrary to everything I was told to expect, I got a slip in Montrose, my first choice harbor, the first year I applied.I think it's all a matter of how you feel about the city. If you sail to get away from the madness, you'll probably prefer Waukegan or Racine. But if you're here for what the city offers, you'll probably enjoy sailing in it too.