Since the great Chicago heat wave of 1995, the city government has enacted a large number of policies under the pretense that it is combating its urban heat island.  While much investigation on the subject thus far has focused on either the local benefits of policies or broad descriptions of the entire region, few studies have evaluated whether the small-scale benefits of policies have begun to collectively impact the larger heat island.  This study addresses this issue by using LANDSAT imagery to observe changes in Chicago’s vegetated and reflective surfaces in relation to changes in surface temperature since 1995. This is accomplished using two images from early June of 1995 and 2009 with similar air temperature and atmospheric conditions.