This paper seeks to uncover the fiscal relationship between public transportation access, particularly the rail stations of the Chicago Transit Authority, and the Chicago housing market. In addition to determining the fiscal relationship between public transportation access and housing in Chicago, I’ll analyze how crime rates at the Chicago Transit Authority (CTA) stations impact their usage. To solve these questions, I built multivariable regressions for each research question. The regression for the first research question had variables Median Home Value in USD, CTA Station Present Y/N, Cumulative Crime by Zip Code, High Crime Dummy Var, and Station & High Crime. The regression for the second research question had variables Cumulative Ridership Total, Cumulative Crime by Station, Usage/Pop Density by ¼ Mile, and Median Household Income. The data for these variables came from Social Explorer and the Chicago Data Portal. To determine the number of crimes by zip code and by ¼ mile radius of each CTA rail station, I used the geospatial software QGIS to accomplish this. The results from my first regression found that CTA rail stations will always have a positive fiscal impact on the housing market within that zip code, regardless of the number of crimes in that zip code. The second regression found that crime actually increased the number of riders per station. From a Public Policy perspective, this study reinforces the importance of public transportation access for Chicago residents and recommends two policies that will improve the efficiency of operating the Chicago Transit Authority rail system.