This study explores the ways that two learning environments, located in structurally different spaces, provide low-income Latino adolescents with opportunities for critical civic development. Through two case studies, I explore the relationships between the characteristics and youth development outcomes of two critical learning sites. One of the sites is a community-based youth organizing group that addresses issues of educational injustice and the other is a high school social studies classroom with a social justice focused teacher. I highlight the characteristics of critical learning sites that promote engagement, which in turn fosters critical civic development. I examine critical civic development from an individual, site based and structural analysis. I provide a model for understanding and categorizing individual critical civic development, examine the site-based characteristics that influence youth development and explore the structural features that provided affordances and challenges to educator efforts to promote critical civic development in each site.