The F-18 crashed into a residential neighborhood near Cather Avenue and Huggins Streets in University City on approach to Marine Corps Air Station Miramar.
The Marine Corps admitted responsibility for the Dec. 8, 2008, crash that destroyed the Yoon home.
Killed were, 36-year-old Youngmi Lee Yoon; 15-month-old Grace; 2-month-old Rachel; and 59-year-old Seokim Kim Lee, who was visiting from Korea to help her eldest daughter take care of the new baby.
Ron Yoon was at work when the crash occurred.
The judge said the deaths of the two girls deprived their father of "the comfort, companionship, society and love a young child is capable of providing to a new parent and, then, in later life. By all accounts, the Yoon girls would have been raised with traditional cultural and family values emphasizing love and devotion to parents and family."
He ordered Yoon to be awarded nearly $10 million, and his father-in-law to be given nearly $4 million.
The rest should go to the father-in-law's three adult children for the loss of their mother, Seokim Kim Lee.
Yoon cried throughout his testimony, which came three years to the day after he buried his wife and baby girls in the same casket.
The Marine Corps blamed the crash on a mechanical failure and human errors.
The Marine Corps has said the plane suffered a mechanical failure but a series of bad decisions led the pilot, a student, to bypass a potentially safe landing at a coastal Navy base after his engine failed.
Low oil pressure killed the jet's first engine, and the second died when fuel stopped flowing from the tank.
Recordings of conversations between federal air controllers and the pilot of the F/A-18D reveal that the pilot at least twice was offered a chance to put down the plane at the Naval Air Station North Island in Coronado.
The base sits at the tip of a peninsula with a flight path over water.
Instead, the Federal Aviation Administration tapes disclose that the pilot decided to fly the jet, which had lost one engine and was showing signs of trouble with the second, to the inland Marine Corps Air Station Miramar, which is about 10 miles north of Coronado.
That route took him over the University City neighborhood, where the crash incinerated two homes and damaged three others.
The pilot ejected and told investigators he screamed in horror as he watched the jet plow into the neighborhood.
The military disciplined 13 members of the Marines and the Navy for the errors.