This report from the University of Chicago Consortium on School Research and the To&Through Project examines two- and four-year college enrollment patterns among Chicago Public Schools (CPS) graduates over the last 10 years. CPS graduates' immediate college enrollment rates increased over the decade, with 63 percent of 2015 graduates enrolling in two- or four-year colleges immediately after high school, compared to 50 percent in 2006. Nineteen percent of 2009 CPS graduates delayed enrollment, with 40 percent of those who delayed eventually enrolling in two-year, and 12 percent eventually enrolling in four-year colleges. About 26 percent of CPS graduates who first enrolled in four-year colleges transferred to two-year colleges within four years. Sixteen percent of immediate two-year college enrollees transferred to four-year colleges within four years. Most 2009 CPS graduates who immediately enrolled in college enrolled in four-year colleges. The rate of two-year enrollment increased by 3 percentage points between 2006 and 2015. Rates of four-year enrollment increased since 2013. The growth in two-year enrollment was mainly at the City Colleges of Chicago. In 2015, CPS graduates' rate of enrollment in four-year colleges was equal to the national rate at 44 percent, and higher than some urban districts. Nineteen percent of CPS graduates enrolled in two-year colleges, compared to 25 percent of graduates nationally. Latino graduates had the lowest rates of overall college enrollment and the highest share of two-year college enrollment. Four-year college enrollment rates differed more by poverty level than two-year college enrollment rates. In 2015, 55 percent of graduates from high-income families enrolled in four-year colleges, compared to 39 percent of graduates from low-income families. Graduates with lower grades and lower ACT scores were less likely to enroll in college and more likely to enroll in two-year colleges. There was variability in the academic characteristics of students who enroll in both two- and four-year colleges. Half of two-year enrollees had at least a 2.5 grade point average (GPA) and 40 percent had at least an 18 on the ACT. There was considerable variability in GPA by institution attended, and students attending the same colleges had very different ACT scores. The differences in GPA and ACT profiles of CPS graduates were greater across four-year institutions than across two-year institutions. These findings suggest a need to better understand the myriad factors that inform students' college choices, as many students in the sample did not enroll in college, despite being qualified, while others enrolled despite relatively low levels of academic preparation. [Additional funding was provided by the Consortium Investor Council.]