This paper harnesses two research projects on Chicago in order to analyze empirical articulations of freedom as staying. During the Chicago Freedom Movement of the 1960s, as the ghettoization that black Southern migrants encountered in Chicago dashed the prophetic hope that the Great Migration would follow the trajectory of the biblical Exodus from slavery in Egypt to freedom in the Promised Land, black Chicago Protestants rethought Exodus as staying in a way that generated spatially-oriented messianic and apocalyptic critiques of the tendency of civil rights movement leaders such as Rev. Martin Luther King, Jr. and Jesse Jackson to view freedom as a product and process of movement. In the current era, incarcerated folks in queer programming in a Chicago women’s jail division articulate conceptions of staying that contest the ways in which criminal justice reform and prison abolition discourses indicate that the solution to mass incarceration centers upon moving from spaces of incarceration to spaces of freedom. These expressions of freedom as non-movement in spaces of oppression, abandonment, withdrawal, capture, and in spaces deemed to be rife with cultural pathology suggest that the notion of wresting freedom from unfreedom in fact reinforces structural logics of anti-blackness.