Dawn of a New Age: Southwest Launches Its First Redeye Flights

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Tl;dr – Southwest Airlines has started flying redeye flights for the first time in its nearly 60-year history, and more routes are in the pipeline.

Big changes keep coming at Southwest Airlines: The Dallas-based carrier now flies redeye flights, with its first few flights lifting off (and landing safely) last week. These redeye flights represent a significant shift in the airline’s operations. As activist investor and resident big bad wolf of Wall Street – Elliott Management – pushes for more changes to the airline’s business strategy, you can expect to see more redeye flights come online by the end of the summer. Let’s jump into the details. 

The First Five Southwest Redeye Routes

Thursday, February 13, 2025, marked the departure of Southwest Airlines’s first redeye – a flight from Los Angeles International (LAX) to Baltimore’s BWI airport. The next day, Southwest flew redeyes out of Las Vegas’s Harry Reid Airport (LAS) to BWI and Orlando (MCO). Additional redeye flown since have been:

• Los Angeles (LAX) to Nashville 
• Phoenix (PHX) to Baltimore (BWI)

In Southwest’s typical jolly fashion, the airline commemorated its inaugural Vegas redeyes with a party at the gate.

Now, at least you’ll be able to drift asleep in the air once your last few coins are fed to the airside slots!

What Can We Expect Next? 

By this summer, Southwest will fly 33 daily redeye flights. Unsurprisingly, BWI – Southwest’s largest hub on the East Coast will serve as the destination for many of these redeyes, though the number of departure cities will grow. By the end of June, Southwest will operate overnight flights to Baltimore from the following cities: Long Beach (LGB), Oakland (OAK), Ontario (ONT), Portland (PDX), Sacramento (SMF), San Jose (SJC), and Seattle (SEA).

You’ll also be able to fly on a redeye from Hawaii back to the mainland on two routes, Lihue (LIH) to Las Vegas (LAS) and Honolulu (HNL) to Los Angeles (LAX).

In addition to Baltimore, three other redeyes will originate in Seattle and head to Houston, Nashville, and Chicago, respectively. 

It makes sense that Las Vegas is featured prominently – it’s Southwest’s second busiest airport. Where, though, is Southwest’s first busiest airport – Denver? Nowhere to be found. Why? Snow. With redeyes, you need reliability. You can’t just hop on the next one leaving that night. Thus, since regions with heavy rain or snow can disrupt flight schedules and make reliable departures harder to maintain, it makes sense that Southwest didn’t want to risk delays or cancellations on its first week of redeye operations. That said, Mile-high city travelers need not worry. Flights from Denver (DEN) to Baltimore (BWI) will commence the first week of March.

My Take on These Redeyes and the Changes at Southwest in General

This development feels long overdue. Redeye flights are so common amongst other airlines that it feels like Southwest has been leaving money on the table for years by not offering more flexibility in its scheduling. 

Now, without a fleet that offers fully lay-flat seats and full onboard catering, Southwest probably isn’t going to poach business travelers and other loyalists who are accustomed to having a meal and catching some flatbed ‘Z’s’, but that was never the point. A bonafide cohort of travelers will enjoy boarding an overnight flight, falling asleep on one side of the country, and waking up on another – especially at the competitive price of a Wanna Get Away Fare. 

I would like to know where the redeye product will evolve from here. Will Southwest introduce robust catering? Dedicated seat assignments are the ground-zero move to make this a reality (you need to know where to deliver a pre-ordered meal), and we know those are coming soon. Do we see a retrofitting of planes? The introduction of a dedicated business class? Is that so unbelievable? When you take a step back, the reality is that every ten or so years, the makeup of what we ‘know’ in the domestic airline market is upended by mergers, consolidation, bankruptcies, and the emergence of a new (often budget) carrier. We’re very much in one of those ten-year shifts with the recent Alaska-Hawaiian merger, Spirit, Frontier, and Jetblue all trying to figure out which way is up, American Airlines sucking its thumb, and players like Breeze and Avelo continuing to emerge. If you tell me Southwest Airlines will be a completely different show in two years, I will believe you.

As mentioned earlier, I don’t fly Southwest very often these days. The ‘Great Operational Meltdown of 2022 Holiday Season’ was my official off-boarding from the LUV airline, and I haven’t been itching to rekindle the old flame. 

Still, there’s a bit of nostalgia surrounding all the Southwest news, as it was the first airline I chased loyalty with. I held the famed Companion Pass for three years. The Companion Pass fit my lifestyle (and my wallet), enabling Mrs. Blackbeard and me to jaunt all around the country, the Caribbean, and parts of Latin America on buy-one-get-one airfare. It was a ritual to grab the ‘two-seater’ exit row and wait for Mrs. Blackbeard to board the plane, somewhere around the late A group/early B group, depending on how disciplined we were with checking in exactly 24 hours before our flight. Flight attendants always seemed happier on Southwest, and fellow passengers more jovial. On one of those first-on-the-plane-cause-of-A-list-Preferred moments, a flight attendant shared her favorite thing about the job. As we watched the other passengers board, she smiled and proudly said – ‘Southwest will always ensure you’re home to a bed at night as they don’t fly redeyes.’ Welp,

Southwest will forever be the People’s airline for me, and I’ll fondly remember its quirkiness. Southwest Airlines – where every seat is ‘first class.’