In sociology, the ‘boundary effect’ argues that policing maintains segregation by increasing presence at the borders of neighborhoods. Relatively few quantitative studies have attempted to explore the boundary effect. To address this gap, I turn to Chicago, Illinois, a city with high levels of segregation both historically and currently. I ask: is police presence greater at the boundaries of racially segregated neighborhoods in Chicago, Illinois compared to other locations in the city? Specifically, are African Americans more likely to be searched after being stopped at neighborhood boundaries? To explore this question, I use data from the Chicago Police Department and the American Communities Survey. I categorize over 68,000 police stops conducted in 2022 as occurring within 50, 100, and 200 meters of a neighborhood boundary. I run three logistic regression models that predict the likelihood that a stop results in a search given neighborhood segregation and whether the stop was made at a border. My results show that Chicago’s segregation has decreased 10% between 1980 and 2020. Although I find contradicting evidence for whether the odds of being searched were greater at the centers versus borders, my results support existing studies, which find that African American men have the highest odds of being searched. Furthermore, the odds of being searched are highest in less segregated neighborhoods with small proportions of African American residents. I suggest that policing maintains segregation by targeting racially integrating neighborhoods where small proportions of Black and white Americans live side-by-side.