Chicago is easily my favorite US city and I am lucky to be there often on business travel. If you are checking out some sporing events and do a few of Canada 02 suggestions you'll have a great time. The architeture of the skyscrapers is amazing.
Make sure you check out Giordano's or Gino's for some deep dish pizza as well. Italian Village in The Loop downtown (I believe on Adams St) is good italian food and used to be a favorite eatery for Al Capone back in the day.
A tour up the Sears Tower or John Hancock Tower is also a must. I prefer John Hancock becuase you they have a good restaurant to eat while you enjoy the view but both are good.
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