This dissertation is an empirical investigation of educational policies, practices and organizational settings that shape the schooling experiences of Chicago Public School (CPS) students. The first chapter, "Educational Choice and Student Participation: The Case of the Supplemental Educational Services Provision in Chicago Public Schools," examines the Supplemental Educational Services (SES) provision, a market-based educational reform introduced under the No Child Left Behind (NCLB) Act. I employ multilevel cohort and longitudinal analyses to explore the characteristics of students participating in SES from 2004-2005 to 2007-2008. My findings suggest that students with higher observed cognitive achievement were less likely to participate in SES while students with better non-cognitive performance were more likely to participate in SES. The second chapter, "Does Greater Autonomy Improve School Performance? Evidence from a Regression Discontinuity Analysis in Chicago," explores the decentralization of decision-making authority in CPS. I describe the nature of the autonomy granted to principals and employ quasi-experimental methods--regression discontinuity and instrumental variables techniques--to identify the causal impact of autonomy on school performance. My findings suggest that principals were more likely to exercise autonomy over their school budget and curricular and instructional strategies. My findings confirm the view that greater autonomy poses a short-term risk to school performance--greater autonomy adversely impacted math (but not reading) achievement after the first year, with relative improvements in school performance after two years of autonomy. The third chapter, "Student and Teacher Safety in Chicago Public Schools: The Roles of Community Context and School Social Organization," explores the nature of the problems around school safety in Chicago and the neighborhood and school factors that produce safer schooling environments. This chapter is concerned with how factors under the control of schools--their social and organizational structure, and particularly the relationships among adults and students--mediate the adverse influence of neighborhood disadvantage on school climate and safety. Key among the findings is that the quality of relationships between school staff, students and parents most strongly define safe schools in Chicago. Indeed, disadvantaged schools with high-quality relationships are found to be as safe as advantaged schools with low-quality relationships. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]