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My Bday in Chicago - what? where?

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I just found out I'm being treated to Chicago for my Bday arriving on Wednesday Aug 1st and flying out on the 5th. I've never been before. I need to get an itinerary together and I'm wondering about restaurants. I just read that they were packed in April. What will they be like in the middle of the summer? I'm a bit of a foodie so this is important but can't expect expensive every night. Any suggestions for my Birthday dinner? Also what should we not miss in the evenings. Second City? We are debating whether to book symphony tickets or go to a free jazz concert at the Park on Thursday. What else to do in the evenings? Which Blues club not only for tourists?What is 'very Chicago' that I should see/experience. A segway tour?
I work in design so am very excited by the architecture but can't see everything so what should I not miss with limited time? Which boat architecture tour is the best?

Ahhhh so many questions !

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