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Road trip Chicago Milwaukee Door County Mackinac Help Pleasd

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The plan is to fly to Chicago, drive to Milwaukee, Door County, Mackinac Island, Traverse City
My questions are: Is the Fairfield Inn on E. Ontario St. in Chicago a good choice?
Shoud we stay by the Historic Old Third Ward in Milwaukee?
Which village in Door County is the best place to stay so that we can see all in a couple of days?
How long would it take to drive from Door County to Mackinac - Triptik says 6 hours.
Where to stay on Mackinac?
Thanks for any help.

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