The lives of Puerto Ricans in the neighborhood of Humboldt Park, Chicago, are often situated in a complex social field shaped by transnational cultural and political border crossing. We argue that artistic practices in this neighborhood are integral to building community and individual identities grounded in local meanings of the Puerto Rican diaspora experience. Interviews with three adolescent community residents and a high school art teacher indexed themes that exemplify community residents' purposes for artistic practice: (1) self-expression within practices of collective identity building; (2) cultural reclamation; and (3) political reimagining. We also discuss how such work invites new tensions for identity making, including who can participate, who is represented, and what forms those representations take. These tensions point backward in time, forward to the future, and across geopolitical space. Finally, we suggest implications for learning in schools.