For many years, education was core to the work of the newly-arrived Sisters in Chicago. The founding mothers taught at St. Joseph School at Cass St. and Chicago Avenue near the center of early Chicago, but after the Great Chicago Fire of 1871, the order regrouped at Hill and Orleans Streets under the name SS Benedict and Scholastica Convent and Academy. The community incorporated as the Benedictine Sisters of Chicago in 1873.
St. Scholastica Academy in Chicago opened in 1907, where the Sisters taught girls from grades one through twelve until the 1940s, when it was limited to high school, operating that way until it closed in 2012. Today, the school building, auditorium, and athletic fields continue as a public charter school for neighborhood children.
The Benedictine Sisters of Chicago also taught in several Chicago parish schools, and mission schools in several locations in Colorado, including St. Scholastica Academy in Canon City which served as a day and boarding school for young women from 1890 until it closed in 2001.