Chicago's professional class has been a consistent South Florida buyer market for generations. The winters are the first reason. The taxes are the second.
Guide for Illinois buyers relocating to South Florida. Chicago to Fort Lauderdale, tax savings, escaping winter, and the Broward neighborhoods where Chicago buyers feel at home.
Chicago has been one of the most consistent feeder markets to South Florida for over 50 years. The pattern is well-established: Chicago professionals arrive in South Florida as winter visitors, rent for several years, and eventually purchase when they realize they are spending 8–12 weeks per year here and building no equity. The North Shore (Lake Forest, Winnetka, Glencoe, Highland Park) produces a specific buyer profile: families where children are grown, the large lakefront colonial is more home than needed, and the Illinois winters have compounded 30 years of motivation to move. The South...