"I'm Gordon! Let's have dinner!" says the billboard overlooking the Stevenson Expressway.
It also displays his picture and the address of his own dating website, www.helpgordyfindlove.com.
Gordon Engle, a forty-something wealthy divorcee from Chicago, decided to spend money on the advertisement when he became disenchanted with online dating sites, 'New York Daily News' reported.
Engle, a self-made entrepreneur, said he was looking for love in all the wrong places, so he decided to try something new.
"You'll spend several thousand on education, a quarter-million on a house, money on a car, but what's your most important thing" he asked.
"Your significant other. You're going to go cheap on that" he said.
"There's not a lot of difference between a billboard and Match.com. I think [a billboard] shows a little more sincerity," he told Chicago's WGNtv.com.
Engle's innovative idea seems to be paying off. So far, the billboard has fetched between 15 and 20 'solid' applicants, he said.
However, gold diggers should stay away. Engle said he could spot them "within five minutes."