Wilson grew up in an athletic household, shaped by his parents' love for sports. His father, Dennis Wilson, was an ice hockey and football player from Canada, while his mother, Ruth Noel, was a gymnast from the United States. They met at Brigham Young University, where his father played football. Despite their athletic backgrounds, neither parent earned significant income from sports; instead, they worked modest jobs-his father for UPS and his mother as a seamstress who exposed young Chip to various fabrics.
When Wilson was five years old, the family moved to Calgary, Alberta, where he developed a passion for competitive swimming. At age twelve, his parents divorced, and both remarried. Later, Wilson attended the University of Alberta to play football but postponed his education to work in Alaska's oil industry before returning to Calgary. He eventually graduated with a bachelor's degree in economics from the University of Calgary in 1980.