Really there’s only one the i90, exiting chicago you have two options either the i94 or i90 but they converge in montana just east of billings, in fact you really only have the i90 out of chicago as the 94, heads up north to milwaukee then crosses wisconsin to meet the i90 at madison You could either take interstate 90 northwest out of chicago and enter wisconsin at beloit or you could just take interstate 94 north out of chicago. Chicago Milwaukee City Chicago City Chicago Illinois There’s one stop, newly renovated and more fantastically touristy than ever, that you don’t want to miss on this route, and it’s the mars cheese castle near kenosha, between chicago and milwaukee. Chicago to milwaukee scenic drive . I'll be coming from milwaukee to chicago on a weekday morning in july. 2:53 pm sheboygan stay for about 1 hour and leave at 3:53 pm drive for about 39 minutes. Not only will you get awesome views of the lake, but you'll meander through some of the oldest and most el...