The twin Cessna 310 circled the airport for half an hour to burn off fuel, the plane landed just before 2 p.m. and came to a rest tilted forward on its nose.
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Emergency crews standing by on the ground rushed to assist the pilot and passenger, who emerged from the plane and hugged each other.
Small plane makes emergency landing in Wheeling
"We couldn't believe we landed an airplane and there wasn't a scratch on our body," said pilot Vartan Seferian.
Earlier in the day, Seferian took off from the Wheeling airport with a friend and headed to Janseville, Wisconsin. He had intended to drop off the friend and have lunch there.
But as soon as they took off, there were problems.
Seferian heard a pop.
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"I could see through the window that the gear wasn't coming up," he said.
Cruising at 2,000 feet, Seferian realized that he had to land on two wheels, not three. But with a full tank of fuel, he worried that a rough landing could be explosive.
Seferian contacted the control tower to connect him with someone who has landed a plane on two wheels. Other veteran pilots and mechanics talked to him through the process.
"I was coming in slower and Howard telling me, 'You're doing a great job, speed is perfect,'" Seferian said.
As he did land, he pulled the nose back to try and stay on two wheels, but it did scrape the runway.
As soon as they landed, they jumped out of the plane.
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"We were like, 'Wow, did we just land?'" Seferian said.
Smelling smoke, he thought to himself, "Let's get out of here before this thing blows up!"
Seferian said he was still in shock.
"All the money in the world I don't think if you gave it to me I would be able to do this again," he said.
No one was injured, but Seferian said the plane is totaled.