Andrew Benson was born and raised in Chicago, Illinois. He attended Georgetown University, where he earned his Bachelor of Arts in History and Classical Studies.

Upon graduating, Andrew returned to Chicago to attend the Loyola University Chicago School of Law. Andrew graduated from law school in 2012, where he was awarded his Juris Doctor with a concentration in Trial Advocacy. Andrew received a CALI award for earning the highest grade in Advanced Trial Advocacy with Courtroom Technology and made the Dean's List for his noteworthy academic performance.

While in law school, Andrew served as a judicial extern to the Honorable Dennis J. Burke in the Circuit Court of Cook County. After his summer with Judge Burke, Andrew interned with the Cook County Public Defender's Office in the Forensic Science Division and Homicide Task Force, where he tried his first murder case.

After graduating from law school, Andrew moved to Florida to begin his legal career. Andrew took a position with the Office of the Public Defender for the Fifteenth Judicial Circuit (Palm Beach County). During Andrew's five years with the Office of the Public Defender, he defended over 3,000 defendants in all aspects of trial litigation. Andrew tried over forty cases on behalf of clients charged with domestic assault/battery, violations of orders of protection, driving under the influence, murder, possession and sale of controlled substances, sexual offenses and other serious felony and misdemeanor offenses.

After leaving the Office of the Public Defender for the Fifteenth Judicial Circuit, Andrew joined the Law Offices of Jeffery M. Leving, Ltd., where he practiced matrimonial and family law at the highest level.