Looking at the trajectories, experiences, and aspirations of Cuban and Ecuadorian migrants living in Spain or who returned to their homeland following the 2008 economic crisis, this article focuses on the quandaries of comparison involved in the appraisal of different places, values, and visions of a “better life”. Our study leads us to move beyond comparison as a method and heuristic commonly based on the juxtaposition of community-based case studies, toward an analysis of how migrants with different backgrounds and trajectories themselves deploy comparison, which helps shed new light on the motives, stakes, and effects of their endeavors. The approach we propose contributes to advancing our understanding of how migrants cope with the dominant comparative scripts and hierarchies that migration activates, notably by either conforming, subverting, or unravelling them. It also draws attention to comparison’s entanglements with issues of choice, belonging, and its experiential and emotional effects, including the suffering it may elicit. A multi-dimensional exploration of the different ways in which comparison plays out among migrant populations opens promising research avenues to understand the ways it informs transnational living and shapes daily experiences and pursuits of a “better life”, while also raising ethical and epistemological questions for comparative field research on migration.