[2] She received a Bachelor of Science from the City College of New York in 1975,[3] working as a nurse before attending law school[2] and going on to receive a Juris Doctor from the John Marshall Law School in 1982.
In 1996, Cunningham was sworn in as an associate judge of Cook County Circuit Court where she was assigned to the civil trial division.
In 2006, she was elected as a justice of the First District Appellate Court, assuming office in December that year,[5] and she was retained by voters in 2016.
[3] In 2012, she ran for a seat on the Illinois Supreme Court, to permanently fill the seat left by the vacancy of Justice Thomas R. Fitzgerald[6] but lost the primary to then-incumbent appointee Mary Jane Theis.
[8] Cunningham is a member of the following organizations: Board of Trustees of Loyola University Health System, the Chicago Bar Association's Strategic Planning Committee, the Governor's Commission for Eradicating Poverty, the Board of Directors of the James R. Jordan Foundation, the Board of Directors of the Chicago Bar Association Media Organization, and is the Chair of the Associate Commissioners of the Illinois Supreme Court Historic Preservation Commission since 2010.