From 2000 to 2019, the number of Black residents in Chicago dropped 25 percent. In this study, we sought to understand how Black Chicagoans make meaning of out-migration, their desires for the city and its future, and the factors they use to navigate questions of whether to stay or leave. We conducted focus groups and interviews with 80 Black Chicagoans who reported either having close friends and family who departed the city or themselves harboring a strong desire to leave. We find that a complex web of factors—a sense of being displaced by White residents, struggles in education, challenges with employment, a sense of declining public safety, and limited access to services—contributed to participants’ sense of the city as increasingly unlivable. We argue that this out-migration constitutes a slow-motion disaster in which cumulative disinvestments interact with socioeconomic vulnerabilities to create a catastrophe for Black Chicagoans.