In this dissertation, I employ an institutional-based approach to immigrant incorporation based on over five years of ethnographic fieldwork that contributes to the emerging literature on the increasing significance of citizenship status in immigrant lives. In the context of a lack of comprehensive federal immigration reform since 1986, living “without papers” has led to the emergence of distinct status groups that I investigate in a particular fieldsite I call Chicharito’s Place and a social milieu I call Mexican Chicago. This fieldsite is an example of what I call an “ethnic safe space” and part of a milieu that people incorporate into and that allows the undocumented a certain degree of comfort within which to interact and exist. My dissertation argues for a distinct way of looking at the integration of Mexican Americans by highlighting the following: the power of undocumented status to alter incorporation trajectories, the multidimensional nature of the process generally that sees people moving forward in certain domains but not others, and the role that living within mixed-status communities plays in immigrant integration. In particular, I examine the experiences of two sociologically similar groups of children of immigrants: the undocumented 1.5 generation and their citizen-born, second-generation peers. I study these issues by delving deeply into a world where people are made similar by a sport and dissimilar when stepping outside these confines. It is society, our laws, and even our healthcare system that has worked to sharpen the distinction between and within this population. This institutional-based approach reveals spaces of belonging that add texture to theories and our understanding of undocumented life in the United States today.