Drawing from personal and institutional archives and the oral histories of Estrella Alamar (the founding president of the Filipino American Historical Society of Chicago) I interrogate the ways in which one’s location, gender, socio-economic status, and generational positioning shape the contours of Filipina American diasporas. This interdisciplinary study combines ethnography with cultural and social history as I trace major moments in Estrella’s life: living in tenement housing on the West side during the 1930s and 1940s; moving to the South and Southwest sides of Chicago during Urban Renewal; becoming the first ever Filipino American teacher in Chicago and first person of color at McKay Elementary during the 1960’s; and lastly, her establishment as the first second-generation community leader in Chicago-based Filipino American organizations and founding president of the Filipino American Historical Society of Chicago. While earlier studies on Filipino Americans reveal important insight on how immigrant families create transnational homes and how geographical location plays a determining role in the shaping of Filipino diasporic communities, they are told almost exclusively through immigrant narratives, often uphold heteropatriarchal cultural norms, and are predominantly limited to cities in the west coast where easily locatable ethnic enclaves exist, such as Manila Towns. As the daughter of immigrants who were amongst the first to settle in Chicago during the 1920’s and 1930’s, Estrella’s stories of growing up in between two major eras of twentieth century Asian migration and growing White/Black racial tensions provides a history that is at once unique to Estrella and illustrative of how Filipina American history in Chicago emerges out of legacies of colonialism and slavery in gender and class-specific ways.