ABC7 Chicago is told the single-engine RANS S6 plane landed on the Drive near Jackson shortly after 6 a.m.
It appeared the pilot suffered only minor injuries and was OK. He was the only person aboard the aircraft.
The Chicago Fire Department says the plane had a mechanical issue with tail control. The pilot then watched for a gap in vehicular traffic on Lake Shore Drive and made an emergency landing near Buckingham Fountain.
"I was just doing a routine flight, a recreational flight. I was over Willis Tower, and all of sudden, 'Boom!' The plane was shaking vigorously," pilot John Pedersen said. "You prepare for it . When you fly, you look for a place to land at all times."
"I'm on the ground. I'm alive. That's history. That's my God looking out for me," Pedersen also said.
Two cars hit the plane's wing and then took off. No one on the ground was hurt.
Fire department crews pushed the plane from the pavement onto grass nearby.
Pedersen, who has been flying for five years, said he was making calls to get the plane towed. He said he planned to get the plane repaired and fly again.
Pedersen says he started having trouble about 20 minutes into his flight, which originated in Schaumburg.