I've driven around Chicago eastbound from Milwaukee more times than I can recall. When in a car, I almost always take I-94 south through the city proper and then the Chicago skyway. Traffic is usually hideous, but manageable in a car. I took the Beaver around Chicago this May. I elected to take the I-294 bypass and found that to be a relatively easy drive in the coach. I-94 in Michigan had construction and reduced lanes from about the state line to Michigan City. I-80, which we took on the return trip, also had construction and reduced number of lanes.
Larry