This nonexperimental study explored the relationships among individual differences, contextual variables, and reading achievement of English language learners (ELLs) in one large urban school district in the United States. The sample comprised 840 students in Grades 3–8 and 10 nested within 37 schools. Hierarchical linear modeling results indicate that English proficiency, metacognitive strategies, native language literacy, and school-quality indicators—four variables potentially under the control of the educational system—positively contributed to student reading achievement. The final model explained 36% of the within-school and 79% of the between-school variance in reading achievement. Controlling for other variables, ELLs with disadvantaged educational backgrounds appeared to perform on par with their more educationally advantaged counterparts. These results suggest that schools may play a greater role in supporting ELLs with disadvantaged educational backgrounds.