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The first class of eighth graders graduated from the School in June, 1984. There are currently more than 325 CCDS alumni. City Day graduates enroll in a variety of public, independent, and Catholic high schools throughout the Chicagoland area. Approximately 10% of the graduates of each class enroll in boarding school.

The School seeks to foster a continuing relationship between the alumni and the School. To this end, a bi-monthly online newsletter filled with current news about CCDS graduates and the School is sent to alumni. In order to stay in touch with former classmates and teachers, alumni are asked to call or write the School to relay current information about themselves.