Travel in Midwest
Lived in Chicago for 21 years so know the midwest area fairly well. Unfortunately, as the previous poster indicated not much is within driving distance that would be considered luxury level resort. However, that being said, a number of kid friendly places like the Wisconsin Dells and Door County within reasonable driving distance- 3 hours to Dells and 5-6 to Door County. Both can be "nicer" by either getting a condo or house for rent in the areas.
Chicago itself is a great city with much to see for the newcomer.