In this age of migration and transnationalism, it is imperative to take account of migratory experiences and lives of transmigrant teachers, who exhibit multiple ways of belonging and knowing. Informed by the theoretical framework of transnationalism and flexible citizenship, this study investigates two Asian transmigrant teachers who work in urban bilingual schools in the U.S. and examines how and why they are involved in their particular transnational mobility, professional choices, and educational activities. The findings show that transmigrant teachers' border crossings were motivated by economic as well as personal and educational necessities. After relocation to the U.S., they adopted specific residential and professional strategies to create transnational and multilingual networks with their homelands. They also demonstrated flexible attitudes towards citizenship, aspiring to continue their mobile lives. This study makes a contribution to the growing literature on contemporary migrants by shedding light on transmigrant teachers' personal, professional, and teaching lives, which are marked by spatial fluidity and ongoing transnational practices.