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@hippy
I don't know anything about Chicago.. but.. google I do know..
http://features.cityguide.aol.com/chicago/freebiesanddeals/
http://www.chicagotraveler.com/attractions.htm
http://www.propeller.com/viewstory/2006/09/19/do-stuff-for-free-in-chicago/?url=http%3A%2F%2Fwww.fodors.com%2Fwire%2Farchives%2F002094.cfm&frame=true
http://www.thelocaltourist.com/articles/chicagocheap.htm
http://gochicago.about.com/od/attractionsandlandmarks/tp/free_chicago.htm