The 46-year-old was once a regular customer of Direct Air, a U.S.-based charter airline that ferried passengers to their destinations at rock-bottom rates.
Flynn, his wife, and three children had taken advantage of the company's traditional discounts as recently as last week. They jetted off to Florida for some March Break relaxation at just over $200 a ticket.
Less than a day before they were to return to their home in Kingston, Ont., however, the bubble burst. Direct Air grounded all its planes on Tuesday, saying operational issues prevented the airline from flying again until at least May 15.
"We were in horror, to be honest with you," Flynn said in a telephone interview. "I think we were all pretty pale when we read the news."
Direct Air has not offered any explanation for the sudden suspension of operations, but multiple media reports suggest the airline couldn't keep up with payments on its fuel bills.
The carrier's parent company, Southern Sky Air & Tours LLC, filed for chapter 11 bankruptcy protection in Massachusetts late on Thursday, citing debt of up to US$50 million.
Direct Air _ based in Myrtle Beach, S.C. _ opened for business in 2007 and served 17 smaller cities throughout the U.S. at the time of the suspension.
Rescheduling the return trip became a family affair for the Flynns, with Sean making frantic phone calls, his wife scouring the internet for suitable flights and the kids pitching in with mobile technology to research alternate routes.
The family struck gold upon discovering a flight that would return them to the airport in Plattsburgh, N.Y. where their car was parked. The circuitous route that saw them travel from Fort Myers, Fla. via Charlotte, N.C. and Boston was a far cry from the direct flight they had originally booked, but was preferable to landing at a far-flung airport with no means of getting back across the border, he said.
Flynn's credit card company also delivered some timely good news, agreeing to reimburse the original tickets and cover off the cost of the rescheduled flights.
"It was sort of a really big relief, because otherwise we'd be out pretty close to $3,000, not to mention the half-leg of the trip that was cancelled," he said.
When all was said and done, Flynn and his family made it home a mere eight hours behind the schedule they had originally planned. Despite their good luck, however, Flynn isn't inclined to forgive Direct Air.
Just 24 hours before leaving passengers in the lurch, he said, the company was sending out promotional emails touting membership deals and discounted fairs.
"That was really the biggest thing that bothered me," he said. "You wonder how many people actually paid for that membership even in that 24-hour time frame."
The experience has soured him on discount airlines, which he wryly acknowledges may always have been too good to be true.
Next time the family goes on vacation, he said, their travel plans will look quite different.
"I said to my wife as we were driving to the airport, 'I think I'm going to drive down next year.'"