What Can Stranded Travelers Expect From Southwest?

Will passengers who booked flights on other airlines be reimbursed for those flights?

They are in a more complicated category.

Though Southwest said in its email that it would honor “reasonable requests” for “alternate transportation,” Southwest typically does not rebook passengers on competitors’ flights, unlike legacy carriers like Delta Air Lines and American Airlines, among others.

But Mr. Buttigieg said in his letter that “Southwest has stated that it will honor reasonable requests for reimbursement for alternate transportation, such as other airline tickets, Amtrak, or rental cars.”

“It will be a case-by-case basis,” Mr. Mann predicted. Booking an expensive flight might indicate to the airline you had a serious obligation you couldn’t miss, he said. “My advice is to hold onto your receipts, use the Southwest tool, and see how it goes,” he said.

“I had to rebook on United,” said Michael Quidort, 32, who was traveling home from Raleigh, N.C., to Chicago when his Southwest flight was canceled. He said he paid United $295, but his original flight was $140, and when he tried to submit a claim, the Southwest system kept crashing. He plans to keep trying, but said he is “not that hopeful” that he’ll get reimbursed. “Everything has just been a mess with them and I don’t have a lot of faith in them turning this around any time soon,” he said.

What about the cost of the vacation I wasn’t able to take?

Reimbursing passengers for meals and alternate transportation is one thing, but there is also a human cost to the airline’s meltdown, said Katy Nastro, a travel expert with Scott’s Cheap Flights, which alerts members to airfare deals. “Some people don’t get the flexibility of being able to take time off whenever they want,” she said. “Your holiday period is one of the only periods you can rely on and plan and save for a trip.”

How people could be compensated for those losses is unclear.

Ms. Nastro also wondered whether passengers who incurred nonrefundable expenses — including for Airbnbs and all-inclusive hotels — would be covered under Southwest’s vague reimbursement policy. “I don’t know,” she said, “but there are a lot of cases like this.”

What about missing bags?

Caroline Neary’s flight from Houston to West Palm Beach, Fla., wasn’t canceled or delayed. But while the Ph.D. student arrived home on time, her baggage still has not arrived; she ended up wearing her mother’s clothes for the…