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New, Different, downtown!

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Hi there. I am heading out to dinner tonight and would like to take my date somewhere he has never been. He's lived in Chicago for 11 years and claims to have eaten everywhere. Price range is open, would like something exciting, fun, trendy, hip, new and different. Location is also open, but would like to obviously stay in the city. So for someone who has eaten everywhere, where can I take him? :) Thanks so much!

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