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The “rebirth” of American cities is characterized by the dramatic revalorization of centrally located neighborhoods. But are these changes attributable to the distinct policy preferences of gentrifiers or broader transformations in urban political economy? This article uses an original survey of Chicago residents to assess whether gentrifiers hold distinct policy and candidate preferences from longtime residents of gentrifying neighborhoods. We find that gentrifiers are supportive of some aspects of a progressive policy agenda, including increased educational spending and expanded access to affordable housing. However, they are less supportive of aid to the poor, a living wage, and investing in public transportation. They are also more likely to support more moderate Democratic politicians. We argue that these divergent preferences are due, in part, to gentrifiers’ comparatively weaker connections to the city, their nationally focused media diets, and limited connections to neighborhood-level religious and labor organizations. Next, we use data from the Cooperative Election Study (CES) to assess whether similar trends are observable in gentrifying areas beyond Chicago. Our use of survey research, supplementing prior ethnographic work, highlights the role of individual attitudes and behaviors in the transformation of American cities.