We live near Cincinnati. I would suggest you skip Chicago and plan to make it a separate trip. Not knowing where in Ohio you are, I would suggest I 70 till you get west of the Mississippi river. You can do that with 1 overnight. From there you have several options 90, 80, 70, or farther south.
As far as Chicago goes, it can easily be a 1 day or less drive from any where in Ohio. Take your car and find a suburban hotel or motel and take the commuter train into the city. Spend a whole day or more and head back home.