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For what you describe you want, I'd suggest a BnB or AirBnB or similar on the southwest coast of Michigan. You can get there in about two to two and a half hours from ORD in good traffic. Indiana also has some good options. I have no idea where outlet malls are, though. If you want something more inland-lakey, perhaps Lake Geneva. I'm not so well-versed on that kind of thing. I'd stay on Lake Michigan, though. "even the Cleveland area" sort of extends your range to basically the entire Great Lakes area - Cleveland is about a 5-6 hour drive from Chicago - so I'm not sure of your real range.
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'80 SC Targa
Avondale, Chicago, IL
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