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Day trips between Ontario and Chicago

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I am travelling from Norway to the US and Chicago in July. During my stay I would like to meet up with a friend of mine who lives near Ontario, Canada. Basically, we are looking for somewhere to meet half-way; preferably no more than 5 hours from Ontario and 3 hours from Chicago. She will be driving and my fiancee and I will be going by bus (preferably) or train. We are all in our early/mid twenties.

We welcome any suggestions you might have as to where we might meet up!

- Katrine

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