Displacement has marked the individual and collective lives of Puerto Ricans in Chicago, especially those who migrated in the 1950s and 1960s. For these older persons, the arrival of the gentry and the yuppies of yesterday, the hipsters of today, and the disappearance of familiar faces in their current neighborhoods are not new phenomena, but rather parts of a profoundly familiar process. They came of age in displacement. Today some Puerto Rican older adults have achieved housing security and are able to age in place because they live in low-income senior housing. Yet a sense of displacement still looms large in their daily lives with the upscaling of and new-build gentrification in their current neighborhood. This work sheds light on the meaning of place for older adult Puerto Ricans who have experienced what psychiatrist and urban studies scholar Mindy T. Fullilove calls a history of “serial displacement.” Through life history narratives and ethnographic snapshots, this paper highlights the neglected reality of “aging in displacement,” or the experience of growing up and growing older in a context of repeated socio-spatial dislocation and how individual and collective life histories of community upheaval texture the spatial and social meanings of place.