Here are some ideas I would consider if I were you:
1) Starved Rock State Park, maybe 100 miles or so SW of Chicago. You could even get a room at the lodge, or rent a cabin, if you wanted to make it an overnight trip. Lots of trails through the woods, and it's a perfect time of year for that.
2) Someone already mentioned Galena, IL. Lots of shops, including a winery you can tour, and some very historic sites.
3) Visit downtown Naperville. There are some great restaurants, a riverwalk trail, plenty of shops, and is just a quick drive down I-88.
You could also go to your local Barnes and Noble or Borders bookstore and look in the "local" section. There are quite a few books with roadtrips and daytrips one can make from Chicago.
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Coimhéad fearg fhear na foighde!!!!
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