Southwest cancels more than 200 Midway flights scheduled for Wednesday as airline struggles to get back on track

After a long weekend of winter weather that wreaked havoc on travelers’ plans, flight cancellations continued in Chicago Tuesday, driven largely by Southwest Airlines — and the carrier expected disruptions to continue into the coming days.

By about 2:30 p.m., Southwest had canceled 244 flights out of Midway Airport, accounting for every Midway cancellation but one. The carrier was also responsible for 42 of the 77 cancellations Tuesday at O’Hare International Airport, according to the flight-tracking website FlightAware.

The Chicago cancellations were part of a broader Southwest meltdown, as other airlines began to recover from a winter storm over the holiday weekend that left thousands of flights on many airlines canceled. The carrier had canceled more than 2,500 flights systemwide Tuesday.

The Southwest disruptions were expected to continue into the coming days, as the carrier said Monday it would fly about one-third of its schedule for “the next several days.” Southwest has already canceled more than 200 flights scheduled for Wednesday at Midway, according to FlightAware.

The Chicago Department of Aviation said there were no issues specific to Midway that were contributing to cancellations or delays Tuesday. Two gates were unusable during the winter storm days earlier — one because of an electrical wiring issue, and the other because of a door motor issue — but neither contributed “significantly” to delays or cancellations, and both gates were back online by Monday, spokesman Kevin Bargnes said.

CDA staff were being sent to Midway ticketing counters and baggage claim this week to provide extra customer service help, he said.

The cancellations drew the attention of federal authorities. The U.S. Department of Transportation announced Monday evening it was looking into the “unacceptable” level of disruption for Southwest customers and sought to ensure the airline was sticking to its obligations to stranded customers.

The union that represents the airline’s pilots, the Southwest Airlines Pilots Association, attributed the continued cancellations largely to technology that couldn’t keep up with the carrier’s complex flight system.

As the weather worsened, the technology used to schedule crews couldn’t keep track of pilots, flight attendants or planes, said Mike Santoro, vice president of the association, which is in negotiations with Southwest over a new contract.

Unlike airlines that operate a hub-and-spoke system, Southwest flies a point-to-point network, meaning crews can be scheduled to fly, for example, from an East Coast city to the Midwest and on to the mountains or West Coast, rather than flying in and out of a major hub city.

The system has benefits, but in this case it meant that crews and planes were out of place and couldn’t easily pick the schedule back up when the weather cleared, Santoro said. Then, the scheduling technology lost track of them.

“When things happen on a larger scale like what happened earlier last week with the storm, it just snowballed,” Santoro said. “And then it snowballed pretty much out of control. No one could keep track of where we were.”

Industry analyst Robert Mann said the scheduling technology issue was the last in a series of events that contributed to the cancellations, including increasing reliance on mandatory overtime for staff to meet the flight schedule.

“I think some of this was a self-created problem,” he said. “It’s an own goal, in World Cup terms.”

Moving airplanes back into the right place can be done in a few days, Mann said. The problem, for customers, will be finding space on increasingly full flights to be rebooked, especially when only a fraction of those flights are expected to be operating for the next several days.

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Southwest executives apologized in a statement issued Monday. They said they were working to reposition crew and aircraft, and rebalance the airline, which was fully staffed ahead of the holiday weekend.

“With consecutive days of extreme winter weather across our network behind us, continuing challenges are impacting our Customers and Employees in a significant way that is unacceptable,” the carrier said.

Adjacent to the line to claim suitcases at Midway, which hailed from across the country, was another long line to Southwest’s baggage services. Seemingly representing the dampened holiday spirit of many Southwest passengers, a blow-up of the Grinch stood in front of the desk to greet customers eager to know when they could catch another flight or where their bags were. The desk was also covered in a large fabric with a pattern of the Grinch’s face across it.

Kimberly Day and her two children got stranded in Chicago while trying to fly from Phoenix to Upstate New York to see a sick family member in hospice, “with only a few days left,” she said.

Day, who is five months pregnant, and her kids, ages 7 and 5, arrived in Chicago Monday. Southwest canceled their flight to Albany and rebooked them for Tuesday, then later canceled the Tuesday flight.

She said Southwest has now told her family the first opening for a flight to New York is Friday. To fly back home to Phoenix, they were told they will have to wait until Jan. 2., she said.

Amtrak was full and rental cars were hard to come by, she said. Rebooking on another airline could cost upwards of $1,000 per ticket. And Southwest’s customer service phone system is down, she said.

Her dad was visiting family in Ohio, and began making a five-hour drive to Chicago to figure out next steps. But now she can’t retrieve her family’s luggage, after she said Southwest employees told her it would be flown to Albany without them.

She said Southwest employees were doing the best they could, but she was frustrated the airline let the family fly into Chicago at all. Her daughters, dressed in sweatpants and red long-sleeved Christmas shirts, and she have no coats or winter attire as the city recovers from a sharp cold spell.

“I would have preferred to have been canceled in Phoenix and then been home,” Day said. “Now, we’re just stuck here for five days in a city that I know no one, nothing.”

The Associated Press contributed.

sfreishtat@chicagotribune.com