Chicago is actually one of the best cities to visit in the fall, so you won't find a shortage of things to do. There's local family-friendly novelties like apple-picking and pumpkin festivals, more traditional fare like tailgating at a Chicago Bears game, or something more urban like any of the great concerts that come to Riviera Theatre and the United Center.
I think it's also important to know when enough is enough. We all have heard of or know of someone that has gone under the knife once too many. Like that one lady that looks like a cat...what's her name?
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