Skipping I90 Chicago route going from MA to SD

Fleet Man wrote:
Have you considered avoiding the Chicago area completely and route yourself through Michigan, the UP and west to SD?

I'm open to anything that saves aggravation. I don't know the area at all which to make sense.

We want to get to SD as safe and quick as possible, we are not retired and have limited vacation time still working for the "man/woman". So I'm trying not to add too much time going around or through. I think we will go thru during the week day not weekend, not sure yet