Shahid Khan – Net Worth: $8 Billion – $8.3 Million, Chicago

At just 16, Shahid Khan traveled from Pakistan to the United States to study in college. He then transformed the car industry with a one-piece bumper design during the late ’70s and built auto parts juggernaut Flex-N-Gate. The billionaire now owns National Football League’s Jacksonville Jaguars and English Premier League’s Fulham Football Club. In 2006, Khan purchased this 9,000-square-foot Chicago penthouse that boasts a 360-degree view of Chicagoland, including Lake Michigan. He did not think twice about splurging $8.3 million on it because, after a year of looking, he immediately knew it was special since it captured the essence of Chicago.