McCaskey's brother, George Jr., was the heir apparent for the franchise, but he died suddenly of a heart attack in 1979. As a result, McCaskey inherited an incredible nucleus of a team and was the owner when the Bears won their only Super Bowl. However, the team struggled in the 1990s and, since 1999 she has been a very hands-off owner. Her son Michael McCaskey was team president from 1983 to 1999 and is now chairman of the board. Team president Ted Phillips currently has operational control.
Halas's husband Ed McCaskey, a former jazz singer, was once the chairman and treasurer of the Bears. Although McCaskey never had any official share of ownership, he acted as co-owner alongside his wife. He died in 2003.
On January 21, 2007, she accepted the NFC Championship trophy, which bears her father's name. She called it "her happiest day so far."