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Driving from Va to Milwaukee - need help

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We're thinking about driving this summer from SE Virginia to Milwaukee for business (but taking kids and sitter too) for my husband (he works for Northwestern). We'll stop in Chicago to visit friends. We know nothing about WI. Are there any reasonable places to stay in Milwaukee? We're B&B fans but would consider anything decent that is $100 or less, if that is possible. While we're up there, what would be within a few hours drive that we should see? We're not into shopping or really touristy places and love hiking and culture (sports are fun too). Kids are 3 and 5 and sitter is Dutch so she'll love the culture. Really think this will be our 2006 vacation so we may as well see / experience some areas of the country that we have not. Also, is it worth driving any particularly scenic routes there or back? Thanks!

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