The Chicago Police Department (CPD) suffers from a strained relationship with the city it serves as a result of broken trust from numerous scandals. In this study, I utilized Police Sentiment Scores from the Chicago Data Portal to determine key predictors of police legitimacy in Chicago. I investigate three categories of independent variables: safety (perceived safety and crime rates), police intrusion (use of force incidents, investigatory stops, and complaints), and race (percent black, Hispanic, and Asian). I found that while perceived safety and race are significantly correlated with police legitimacy and should be focused on for future reform, actual safety and police intrusion are not significant predictors of legitimacy. An increased sense of perceived safety was associated with better perceptions of legitimacy, while higher proportions of all three major racial minorities were negatively correlated with perceptions of legitimacy. These results held for perception of respect and receptiveness regarding the CPD.