Madison recently spoke to Us Weekly about the prospects of having a baby, saying "I've always wanted to be a mom, but I thought it would take longer!"
The pregnancy news comes just one month after she announced she was working with an adoption mentoring service called Hold My Hand to adopt a child from either Africa or South Korea.
Since 2009 when she left the Hefner and the Playboy mansion, Madison has headlined a Las Vegas burlesque show called "Peepshow" at Planet Hollywood. In June of 2012, she decided on not renewing her contract in an effort to move on to the next chapter of her life.
"I've wanted kids and that's something I'm definitely doing as soon as possible," Madison told People in June. "It is something that the time in my life is right for."
Madison's boyfriend Pasquale Rotella, 37, is the CEO of Insomniac - the company responsible for the up-and-coming Electric Daisy Carnival in Las Vegas. The three-day festival is the biggest, most-pyrotechnically trigger-happy music festival in North America. Last year, the festival generated $136 million in revenue and in 2012 launched a EDC New York edition.
The company also puts on popular summertime music festival's such as Nocturnal, Electric Forest, Beyond Wonderland, Escape From Wonderland and White Wonderland. He's been active in the industry since 1993.