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I went to Chicago this summer for a mini vaca, you'll have so much fun!
As soon as you get there you should open up the guide book at your hotel. They list all of the best clubs, comedy shows, places to eat etc.. Our first night there we did one of the dinner and a shows thats offered ( it had some mob theme, I can't think of the name of it though) it was a blast, everyone had a really good time. They also do a tour of the city and show you all of the places where all of the mob related history went down in the twenties. It was a lot of fun and you got to see the whole city- I think it was like twenty bucks for an hour and a half tour- definetly worth it.
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