I don't know what you mean by short drive. Do you have a length of drive that you want to do or a number of days in mind? The distance between Portland (Maine) and Chicago is a little under 1100 miles and 17 hours no matter which way you go. There are three main options. The shortest way by all of 9 miles goes through Albany (New York), Buffalo, and Cleveland The second option is that it is possible instead of going through Cleveland to go on the other side of Lake Erie into Canada and go through Flint The other route is the southern route which goes through Hartford and Scranton and goes south of Cleveland.