This article presents a case study with two transnational Mexican youth that came from a larger study of the digital media practices of young people in an urban high school. Our study takes a chronotopic (Bakhtin, 1981) lens to understand the youths' accounts of their digital communication. Analysis of interviews and observations with the youth when they described their online activities show that the youth employed digital literacies to vicariously "live" experiences and keep up with life away from their families in Mexico. The youth situated their activities in three distinct but dialogical chronotopes (family, hometown, and transborder) to create transnational connections and make sense of who they are. They drew on digital artifacts to narrate themselves, developed familial, cultural, and political knowledge, and expanded their linguistic repertoires in the process. The findings have implications for TESOL classrooms that seek to build on the border-crossing experiences and linguistic and multimodal resources of young people in their learning. We discuss how youths' digital practices and embedded artifacts serve to construct multiple contexts and vantage points for developing their transnational identities and knowledge, and how these practices could be recognized as agentic forms of narrative production and learning in the classroom.