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I lived in Chicago (in the city) for 30 years and can't opine on the suburbs. However for road riding, check out the Bicycle Club of Lake County's Ramble Ride. It takes place around Wilmot, WI and provides one of the few areas to ride hills near Chicago. I rode those routes endlessly in the summers. The website has good maps and you can easily follow the routes. The "Rustic Roads" in Wisconsin are country riding at its finest. Very few farm dogs!
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