I looked at going up though Wisconsin from western Chicago suburbs to Mackinac Island, but it takes SEVERAL hours more than biting the bullet and going I90/94/80.
When we go to Michigan or farther east to Virginia or New Jersey we just try to time it so we hit Chicago on off hours. Between 10am and 2pm, or later after 8pm and it isnt all that bad. There are CRAZY drivers no matter when you go through. The headache is worth the time saved to me.
There is always the ferry option to go across lake Michigan, but that is VERY expensive.
