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Chicago - where to stay

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I'm from the UK and taking my husband to Chicago for his 40th birthday as a surprise, I need help with where to stay for our few days. We like areas like Times Square in NYC where there is lots to see and do, shopping, restaurants and things to do at night, not necessarily bars and clubs. As it's his birthday I can spend up to $300 a night. We're arriving 6th September , thanks

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