Arable land has been continuously declining the the United States since 1970 and urbanization is one primary driver of this decline. This project attempts to quantify and visualize the relationship between cropland loss and urbanization in the Chicago Metro Area. To do this, land cover data from 1992 and 2016 were downloaded and then adjusted so the land cover classes lined up. The rasters were then combined to show change over time. Finally, the resulting table was imported into a python notebook where a transition matrix was calculated. The results show that the majority of urban expansion occurs on agricultural land, but that urbanization is only one of many drivers of cropland loss. Similar amounts of cropland were lost to forest, wetland, grassland, as to urban land, suggesting that the drivers of cropland loss in Chicago are more complex than initially assumed. More research is needed to further explore these other drivers of cropland loss.