My sister has lived in Chicago the past few years and I have a ton of family there so i've been there more then a few times. In terms of places to eat.....i'm shocked that nobody has said GIORDANO's yet! BEST PIZZA EVER!!!!!!!!!! You have to try Giordano's Pizza. That is an absolute must. It's the best pizza i've ever had in my life.
In terms of other things to do........see if they have the boat tour that goes through downtown. It's a 1 hour tour and is worth it. They tell you about the history of Chicago and it's really neat. Also, go to the top of the John Hancock building as well. A great view for pictures etc and a lot of cool stuff up there.
You will have a lot of fun at the Cubs game! I went in '07 when Bonds was chasing the record and it was a blast. Amazing fans at Wrigley and an amazing atmosphere!
Last call there is 6:45 am so it's pretty nuts! The Hunt Club is a cool bar to go to (a lot of the Blackhawks go to that bar). We saw Patrick Sharp and Cam Barker there one night.
If you are into history, the Chicago History Museum is pretty neat as well.
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