Columbus, OH, is interesting. Shopping, restaurants, Ohio State, historical things, German Village, etc.
A cute summer getaway town is Saugatuck, MI--on Lake Michigan, lots of B&B's, art galleries, etc. Very picturesque.
For a smaller town in IL, try Galena. B&B's in town or the Eagle Ridge Resort about 6 miles east of town (golf, tennis, spa, lake). However I don't know if they have been affected by the flooding. I love Galena--fun shops and cafes, not far from the Mississippi.