The school is diverse, drawing from many neighborhoods including Bridgeport, the South Side of Chicago, but also the west and southwest sides of the city. As a charter school, it admits applicants by random lottery. Approximately 80% of students qualify for free or reduced lunch, the nationally accepted indicator of poverty level in schools.
First located on the Illinois Institute of Technology campus, YWLCS has since moved into its own building nearby. Their first class graduated in June 2004; media personality Oprah Winfrey was the guest speaker. In 2005, the guest speaker at graduation was Michelle Obama.
The YWLCS founders drew inspiration from The Young Women's Leadership School of East Harlem, and the school maintains a loose affiliation with the network of Young Women's Leadership Foundation schools (TWYLS). Another TYWLS network school, The Young Women's Leadership School of Queens (New York) opened in September 2005, in the Jamaica neighborhood with a register of 81 students, under the leadership of new principal Avionne Gumbs.