As the rain turned to snow more than an hour later, the plane once again readied for departure, finally pulling away from the gate at 7:39 p.m. But the weather rapidly deteriorated. By 8:10 p.m., visibility had dropped to about one-quarter of a mile due to heavy snow and fog, according to National Weather Service data.
The pilots headed back to be de-iced, joining a line of planes waiting between United's two main concourses. That was the story of the evening, say people who were on board the flight: Wait an interminable amount of time for de-icing, prepare to leave, repeat the process.
As the hours dragged on, the plane remained parked within hundreds of yards of United's terminal, Simmons said. It ventured out to the runway once, only to turn back when ice was spotted on the wings.
"You couldn't see out the window because we were encased in ice," said Simmons, a program director with a large non-profit group in San Francisco.
Passengers remained calm, watching the movie "The Prestige" and other programs broadcast on the plane's entertainment system. Mothers walked their small children up and down the aisles. Flight attendants served drinks, then all of the meals stowed on the flight, finally breaking out emergency food rations that United stows on all its aircraft for such delays.
Simmons read a book, strolling to the back of the plane occasionally to stretch his legs.
"I didn't get upset until about 7 hours into the flight," he said.
That's about the point when the plane's pilots finally decided they'd had enough. But it took the plane another hour to get back to the terminal: First they had to wait for city crews to move a pile of snow.
When passengers exited, it was after midnight, and the nearest customer service counter was closing at 1 a.m. Simmons lucked into a room at the O'Hare Hilton and got a seat on a United flight the next day.
What he can't understand is why United waited so long to cancel the flight.
"They should've canceled it at 5," Simmons said.
Medina says that was the pilot's call, although United is looking at how it handles operations in poor weather.
"As this was the last flight expected to get out that evening, we were hoping to get our customers where they wanted to go, and, unfortunately, the weather did not cooperate," she said.
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The Boeing 757 languished on the tarmac for seven hours before the pilots finally canceled the flight. It took another agonizing hour to get the plane back to the gate.
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