I agree with staehpj1, there are lots of nicer places to ride than around Milwaukee. Rocky Mountains anywhere, Pacific Coast anywhere, parts of Utah & Arizona. Also, which month are we talking about here, that makes a difference!
The problem with riding to Milwaukee is that a lot of your tour is in the vicinity of Milwaukee - personally I found the midwest / plains states to be the least appealing of my cross country tour. That said, the Wisconsin River valley was OK.
West is best & the higher the better.