It would be helpful to know which weekend.
Chicago may have some weekend festival going on that interests you.
Have you thought of trying to go to Wrigley and see a Cubs game if they are at home?
what sort of budget are you looking at it terms of hotel stays?
You said planes/trains/autos---what about boats?
http://www.michiganmaritimemuseum.org/
http://www.glnmm.org/
Along Lake Michigan coast in Michigan you have a bunch of coastal towns and they have museums on boats and lighthouses. Same with Wisconsin.
You would be about 4 hrs from Detroit so you could drive up and tour one fo the auto museums there.
Ceder Point Amusement park is about 4 hrs drive away in Sandusky, Ohio along Lake Erie.
Green Bay is 3 hours away.
The National Railroad Museum is there
http://www.nationalrrmuseum.org/en-U...t/default.aspx
Madison and Wisconsin Dells area are also about 3 hrs away.