Milwaukee should sink into the lake.
Or your idea to join it with Chicago in a new rat state. ;d
But first, the western (Republican) parts of Kenosha and Racine Counties should secede from their respective counties and form a new county, Republican parts of Milwaukee County can join Waukesha County, GOP parts of Cook County and Lake County, IL can join DuPage or McHenry or something, and the Republican southern portion of Lake County, IN can join the county to its south. That way, only the heavily Dem parts of Milwaukee, Racine and Kenosha Counties from WI, Lake and Cook Counties from IL and Lake County from IN can form the über-Democrat State of Chicawaukee. : )