Over the last four decades, comparative urbanism has flourished, triggered by a desire to identify, compare, contrast, or juxtapose parallel phenomena that happen in multiple sociospatial contexts and likely influence one another. Starting in the 1970s, a number of scholars began touting the need for comparative urban research that opens the eyes to broader urban phenomena that can be compared across municipal boundaries and national borders. Underlying comparative approaches carry the notion that urban imaginaries are “sites of encounters with other cities” mediated through travel, migration and the circulation of images, goods, and ideas. In more recent years, a transnational perspective has gained favor in urban studies, arising in response to criticism that comparative urbanism suffers from a static perception of the urban. Transnational approaches focus on interdependencies, movements, and flows across borders in regions and subregions, the goal being to understand urban settings and experiences, as composed by multiple regional, ethnic or institutional identities and forces. In other words, transnational urban studies wish to take down arbitrary divisions between entities so that both their interconnections as well as collisions become more apparent. There are three interrelated ways that urban humanities go beyond conventional comparative urban studies and contribute to our understanding of the urban. In this essay, the matter is fleshed out through a comparative study of Los Angeles and Mexico City.