Hearing someone say they love a red-eye flight is like hearing someone say they love the middle seat - it just doesn't happen. Sleeping upright, with little legroom, within inches from a stranger's face is hardly ideal. But while fliers may loathe these overnight sleepovers in the sky, red-eyes are an opportunity for travelers to maximize precious time on the ground.
It may come as a surprise then, that throughout its 56-year history, Southwest has never operated them. That's right - the slightly offbeat, all-economy Dallas-based airline doesn't fly passengers overnight. It's one of the few major U.S. carriers without a single red-eye option.
But a recent comment from Southwest chief executive Bob Jordan on the "evolution" of their business hints that's set to change.
Red-eyes, at least in the United States, constitute west-to-east routes that depart from an origin at night and arrive at a destination in the morning. While Southwest mainly flies domestically, the carrier does offer flights to the Caribbean, Mexico and Central America.
Historically, Southwest didn't offer red-eyes because of technology constraints in its reservation system. In 2017, the airline moved to Amadeus, an aviation IT provider behind many of the world's most popular carriers. The option for red-eyes suddenly opened up.
"Before that shift, Sabre [the previous software] didn't have the capacity to allow Southwest to book red-eye flights," said Benét J. Wilson, a former aviation journalist and frequent Southwest Airlines flier.
Seven years later, Southwest finally made some moves. In July 2023, Southwest began to sell itineraries that involved an overnight layover - connections during the hours of midnight to 5 a.m. local time - at six airports nationwide. Those airports included Baltimore, Denver, Las Vegas, Phoenix, Chicago Midway and Oakland.
These weren't new Southwest flights being added; rather, they were existing flight options that Southwest made available for travelers on its website. For instance, a passenger looking to go from Los Angeles to Baltimore could now be given the option to have an overnight layover in Denver or Chicago Midway. Before July, this routing wouldn't even appear in the search results (for better or worse).
The next step from here? Red-eye flights. "It's a logical evolution for us," Jordan told the Dallas Morning News in a recent interview. "We have the aircraft; it's a great way to use an asset that you already have and use it more productively, which means more hours in the day. So, we will be doing red-eyes."
Edward Russell, an aviation analyst and reporter for Skift, believes that Hawaii and transcontinental routes should be the first red-eye options from Southwest.
"Both markets are long enough to make red eyes a logical addition to increase aircraft utilization - a low-cost way to grow since it uses aircraft an airline already has by flying them more often."
Southwest said in a statement to The Washington Post that red-eye flying will be deployed "to offer customers additional service from places they've requested" but a time frame wasn't given. Contractual agreements with pilots are one logistical hurdle, experts say. Therefore, it could still be years away.
"It won't be an insignificant amount of flights, but against our schedule of more than 4,000 flights a day, we're talking about a handful of origination points, primarily leisure markets, and with the structure of our network and our size in the western third of the United States, they likely will be in the west, along with some potential international flying," the company said.