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The urban planning ideas proposed by Jane Jacobs in the 1960s remain relevant to this day, promoting a perspective on the relationship between urban morphology and the community that takes into consideration the experiences of the people themselves in the planning of cities. With Jacobs’ ideas in mind, this article seeks to explore the urban territory of Santiago, Chile, and to assess the vitality of its neighborhoods with their diversity of morphological, architectural, and spatial characteristics. The results reveal a spatial reality that differs considerably from typical interpretations of this and other cities across Latin America, characterized by a strong radial center–periphery dynamic interspersed with sub-centers of high vitality, mainly in the form of rural towns and villages that, over time, became absorbed into the urban fabric of Santiago, along with social housing estates located on what used to be the urban periphery.