As often happens when a hurricane develops in the Caribbean, high pressure develops over the Midwest and Great Lakes.  So for the coming days, while Ian moves N/NE up the west side of Florida into Georgia, Chicagoans will have a good deal of sunshine during the days and cool, possibly even frosty nights. This weekend Chicago will experience fair skies and mild temps.
The National Hurricane Center forecast has the center of Hurricane Ian slamming into the west central coast of Florida around Tampa on Wednesday with potentially 110-120 mph winds.  Before that time a steady lowering of clouds, increasing winds and rainfall, and rising storm surge will occur.  Heavy flood producing rains will continue to spread north over the remainder of Florida into Georgia by this weekend.