Since the early 1800s, Chileans have imagined their nation’s history and destiny through an ever-changing array of transoceanic connections with the rest of the planet. At a deeper level, Chile’s relationship with the Pacific Ocean is built upon myriad collective memories and aspirational identities. The long arc of Chile’s linkages with the Pacific World—or the peoples and ecosystems in and around the Pacific Ocean—has yet to be fully explored by historians. This article fills this lacuna by analyzing five diverse historical episodes that span more than two centuries: first, Valparaíso’s growth into a Pacific commercial hub during the early 1800s; second, Chile’s role in the Californian and Australian gold rushes of the mid-1800s; third, the Chilean victory in the late-19th-century War of the Pacific; fourth, Chile’s burgeoning commercial relationship with China, which began in the years following the Second World War; and, finally, the emergence of a Chilean-Pacific variant of neoliberal ideology in the final decades of the 20th century. These five developments reveal a litany of ambiguities and antagonisms in Chile’s complicated, ongoing association with its western ocean.