While recent years have seen many analyses of techniques to reduce urban heat island, nearly all of these studies have either been evaluations of real small scale applications or attempts to model the effects of large scale applications. This study is an attempt to analyze a real large scale application by observing recent vegetated and reflective surfaces in LANDSAT images of Chicago, a city which has deployed a variety of heat island combative methods over the last 15 years. Results show that Chicago’s new reflective surfaces since 1995 produced a noticeable impact on the citywide albedo, raising it by about 0.016