Chuck was raised in Lafayette, Indiana, the youngest child of the late Charles Oberlie, a machinist at the Ross Gear Tool Company, and Virginia, an interior designer, along with his twin sisters. As a boy, he learned to fish and swim in the nearby rives and lakes, a favored activity he continues to share today with his family. Chuck worked in the summers for the Lafayette Park Department to help provide an opportunity for a college education.

While studying at Ball State University, he met Fran Tuholski. After graduating, they were married in 1968 and settled in Michigan City. Fran began her teaching career at Eastport School, and Chuck began as the assistant planner for the city. They have three grown children and four grandchildren.

Chuck worked 16 years in Michigan City's planning department, advancing to Director of Planning and Redevelopment. In 1984, the Michigan City Area Chamber of Commerce hired him as the city's first full-time Economic Development Director. Two years later, he was appointed president of the Chamber. Chuck also served as president of the Northwest Indiana Forum, then a seven-county economic development agency. In 1992, Mayor Bob Behler appointed Chuck as City Controller, a position he held during Mayor Sheila Brillson's terms of office.

Chuck has participated in many activities and organizations. He has served on Michigan City's Board of Public Works and Safety, the Plan Commission and the Urban Enterprise Association, as chairman (president) of the Michigan City Exchange Club, the Fair Housing Board, and the LaPorte County Convention and Visitors Bureau. Chuck has also served on the Boards of Michiana Industries, Michigan City Sports Corporation, St. Anthony's Hospital, Chancellor's Advisory Board at Purdue North Central University, Partners in Contracting, and the LaPorte County Chapter of the American Cancer Society. He has served as chair of the Crusade for the American Cancer Society and several Great Lakes States and Michigan City Special Olympic competitions. Chuck coached youth soccer, baseball and basketball. He is a lector at his church.