Young professional, ship captain- looking for a summer home in Chicago

I live an adventurous life.  I recently ended my contract working on a superyacht in Baja Mexico and I enjoy working the boat summer scene here in Chicago.  I don't smoke, do drugs, and drink a glass or two on occasion.  I'm very clean, organized, and responsible but I'm not a hardass.  Think of an ideal young yacht captain, and that is me.  I keep a healthy lifestyle, but am not looking to break the bank with accomodations.  My plan is to head back South in October, with my job cooling off after labor day.