I live in Chicago, my daughter attends school in Minneapolis, and my son's in Lawrence, KS. I've covered all of the territory in your itinerary. On the way up to Minneapolis there are a few wind farms on the west side of I-35. They are quite interesting to see from a distance.
We really enjoyed the Minneapolis sculpture garden. Try to get there if you have a chance. Grand Avenue in St. Paul has a great casual restaurant--Cafe Latte.
The quickest way to Chicago from Minneapolis doesn't really go through Milwaukee. We always take I-94 to I-90.
Sparta, Wisconsin has the world's largest bicycle. You can learn about cranberry farming near Tomah.
You could stop at the Wisconsin Dells for a few days. There are plenty of water parks, regular and mini golf courses, go cart tracks. They have these Ducks--vehicles that go on land and water. It's kind of like the Lake of the Ozarks area on steroids.
Madison, WI is the state capital. It's a really nice town. There's a place on the University of Wisconsin campus that sells ice cream that the school makes in their dairy.
If you stay on I-94 and go to Milwaukee, the Milwaukee zoo is a favorite of ours. If you like German food, there's no place better to get it than Milwaukee. In the summer they have a bunch of festivals along the lakefront--Summerfest is great if you're there while it's going on.
Lake Geneva, WI is a really cute town built around a lake. It's not exactly close to either highway. There's great food and boats for rent.
Before you get to Chicago, there's Six Flags Great America. They have a water park too. If not everyone is in to roller coasters, across from Six Flags is a enormous outlet type mall, Gurnee Mills.
On your way home from Chicago, if you go through Iowa on I-80, think about stopping at the Amana Colonies.
Midwest Living has a couple of travel books that have a few off the beaten path ideas. I'm sure they are available on
Amazon.com.
Have a great trip.
