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Chicago has a large under city
Chicago is known for its crime rate, which is not enviable, in fact, Chicago is the birth place of Al Capone and other famous gangs, but more importantly Chicago is one of the most surveilled cities in the United States. Chicago has a certain intrigue and mystery to it, and as such it was the perfect setting for Ubisoft to set the Watch Dogs world in. Sure they could have gone with a fictional city, but Chicago has something which adds to the dynamism of the game.
