This study examined rural–nonrural differences in postsecondary educational expectations and the attainment of expectations for grade 10 students attending rural and nonrural high schools in the Regional Educational Laboratory (REL) Midwest region and how these differences compare with rural–nonrural differences in the rest of the nation. For grade 10 students who indicated that they did not anticipate attaining more than a high school education, the study also examined rural and nonrural students’ reasons for not expecting to continue their education past the secondary level. Analyses drew on data from the Education Longitudinal Study of 2002 using descriptive statistics, chi-squared tests of association, and multinomial regression models with students nested in schools. The baseline model included only school locale, an indicator for region, and their interaction as predictors; subsequent models added student predictors, family characteristics, teacher expectations, and school contextual variables. Analyses reveal that rural students in the Midwest had lower educational expectations than their nonrural peers, yet similar levels of educational attainment after taking into account student, family, teacher, and school characteristics. For two-thirds of rural and nonrural students, educational attainment fell short of expectations. Importantly, participation in rigorous coursework, parent aspirations, and teacher expectations were more predictive of educational expectations and attainment than whether students grew up in rural areas in grade 10 in 2002. For grade 10 students who did not expect to go to college, both rural and nonrural students perceived financial barriers as the primary reason. Policymakers and other stakeholders in Midwestern states and the rest of the nation can use the results of this study to inform efforts to improve the educational attainment of rural students.