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Any interesting sights from Chicago to Milwaukee/Lake Geneva?

I'm driving from Chicago to Milwaukee and from Chicago to Lake Geneva, and I'd love to find out if there are any kitschy, fun sights or stops along the way.

ALSO--I have a drive from Chicago to Columbus, Indiana (a very cool town architecturally) and I'm looking for the same thing--kitcshy sights/stops along the drive.

Thank you!!

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