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You can try Galena. There are lots of little shops, antique stores, etc. around there, and apparently the leaves look good now. It's a quaint little town, and Dubuque's about 30 minutes away. It's not too bad a drive.
Going south there's not too much unless you want to see a U of I football game. They're doing ok this year, so that might be fun.
In Chicago the Frank Lloyd Wright tour is starting up soon. That's pretty cool. You could also take one of the gangster tours (good season for that!) to see the sites of various mob hits. Or you could try to go watch the field construction at Wrigley.
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