I hate driving through Chicago more than is rational or healthy. When I do it I just bite the bullet and use the toll road of 294. It is by far the fastest way through and it is worth the insane tolls that they charge now (even taking into consideration how much I retch at paying tolls to IL).

The route over the Mackinaw and through da U-P is a very scenic drive, but VERY slow. Hwy 2 will take you right across to Superior/Duluth but is very winding and slow with a lot of small towns. Very enjoyable for a drive, but slow. Did I mention it's slow?

If you do take I90 to I94, I'd suggest taking Hwy 53 North @ Eau Claire instead of over to MN and up I35. It's basically an interstate @65 MPH but more direct and more scenic. The first time you come over a hill and see Lake Superior is memorable.

However you get there, may the breezes be gentle on your back.