K.L.
Galena, IL. Not only will it be a beautiful drive this time of year but they have the lovliest little B&B's. It's a beautiful town to walk around, there's a river and great little shops and restaraunts. Here's a link to Galena info: http://www.galena.org/
Another great idea would be to have brunch at the Signature Room 100+ floors up in the John Hancock building. You can stay at the Drake for $100 a night and then walk to the Hancock building and go to a jazz club in the evening or Navy Pier and a horse drawn carriage ride. That's what hubby and I did the weekend we got married. Loved it! Lovely weekend trip. Have fun!!!