Southwest Inches Closer to Flying Redeyes


This is a post that probably could have been written a decade ago. After all, the idea that Southwest would eventually start flying redeyes always seemed like a foregone conclusion. It was just a matter of when. Now we seem to be getting a little bit closer to this being a reality with about 50 daily flights coming in the not-too-distant future.

When Southwest started flying, the idea of having a redeye was never even considered. The airline only did short hops around the country, so flying overnight just wasn’t an option. Southwest didn’t touch the East Coast until the summer of 1993 when it entered Baltimore. It wasn’t until 1995 that the average flight distance rose above 400 miles.

Average Southwest Flight Distance (in Miles)

T-100 data via Cirium

In 1999, Southwest scheduled its first flight over 2,000 miles, but it just dipped its toe in. That year it flew from Las Vegas to both Baltimore and Orlando as the extended range of the 737-700 started being put to use. With an average distance today of over 700 miles, Southwest is a different airline.

But Southwest’s bread-and-butter remains short- to mid-haul flying. In fact, it still doesn’t fly all that often on long-hauls. If we look at this entire year, including seasonal flight, Southwest has only 44 routes scheduled that are over 2,000 miles. Eight of those are from Baltimore, five are from the West Coast to Florida, another five are longer Latin/Caribbean routes, and then there are 3 random longer hauls (Atlanta – Oakland, Pittsburgh – San Diego, and Vegas – RDU). None of these are the catalyst here, however.

The catalyst came in 2019 when Southwest started flying from the mainland to Hawaiʻi. Those flights are all over 2,000 miles. This year, Southwest has 23 of those routes in the schedule making up more than half of the long-haul flights in Southwest’s system.

The unique problem with Hawaiʻi is that it is very, very far and many time zones away from the East Coast. If you don’t fly redeyes, it is particularly hard to connect people all the way back to the east at the end of their vacations.

Southwest has worked its way around this by having early morning departures from the islands. For example, you can leave Honolulu this summer at 8:30am and after 50 minutes in Phoenix get back to Baltimore at 1:40am. But that is a brutal way to fly, and it also only works for Southwest cities that have late afternoon options from Phoenix and Vegas to the east. Most cities in the Southwest network are cut-off if they’re in the Eastern Time Zone.

As someone who lives on the West Coast, prefers morning flights, and can’t sleep on airplanes, I do not like the idea of having redeyes ever. But there are people who feel the opposite. I remember my friend’s father from when I was a kid who would only fly redeyes. He thought that day-time flights were wasting productivity. I remember thinking he was insane, but that difference of opinion is what makes the world go ’round.

When it comes to Hawaiʻi travel, the number of people who would prefer a redeye goes up a lot. Anything they can do to maximize their time on the islands, they’ll do.

With this growing need for actual redeye flying, Southwest had to make changes. It had issues to solve in its labor contracts and technology in order to make redeye flying work, but as far as I know, those were all fixed long ago.

Some of these problems went deep. For example, I seem to recall that Southwest used to have to end the day and stop flying entirely to reset in order to start up the next day. I don’t recall which system required this, but I remember being floored that this was a thing. (Maybe some Southwest old-timers can confirm or correct me in the comments.)

Of course, with the increase in time zones served by the airline, it has gotten closer and closer to operating 24 hours a day anyway. And it does do that anytime there are delays. But according to the schedule, Southwest does still briefly shut down for the night. Take a look:

April 15, 2024 Southwest Flights in the Air by Hour (Pacific Time)

Data via Cirium

The day starts in the 2am hour Pacific Time when those 5am departures on the East Coast launch. And the day usually ends sometime just after midnight with some of those really late Vegas – West Coast trips. Keep in mind, this is an April schedule. In summer, it may have even less of a gap, but this will be ending when redeyes begin.

Like I said, I believe most of the real hurdles like this one are gone. Southwest has a modern reservation system and a pilot contract that deals with redeyes. So now it’s just a matter of fixing all the corner case issues and getting them ramped up.

The plan is apparently to start with Hawaiʻi flying, of course, but also some Las Vegas – East runs. All of those make too much sense as low-hanging fruit. It’s more about customer preference on those routes than it is about increasing aircraft utilization.

Over time, you can imagine this growing to serve some markets that may not make sense unless it’s as utilization flying where you assume the airplane is already paid for. That, however, isn’t something that I’d expect anytime soon. Southwest sees opportunity here to give customers more options… and in some cases, create the only options it can offer for people traveling across the entire empire. It’s a customer-focused move that can pay off for everyone involved.

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29 comments on “Southwest Inches Closer to Flying Redeyes

  1. You could see in the future where both MDW & DAL benefiting from this change as longer flights are routed through those hubs just like BWI.

  2. I just kind of assumed Southwest was already flying them. Quick check of last night (which did have terrible weather) but there were 11 SW flights which landed at BWI after 1 am, and 5 after 2am. So they’re inching there.

    Real question though is how will this affect Southwests on time record (computer systems notwithstanding). Many of those planes fly up to 6 or 7 legs a day. You can generally count on the first few flights being more on time, and advantage which may be negated with Redeyes.

  3. Southwest still resets its daily aircraft flows at 03:00 HERB/CT. If you convert their Hawaii flights times they all start and end before the 03:00 Herb reboot.
    WN from what I’ve heard originally planned on starting Red eyes this year with the Arrival of the Max7 ETOPS birds but Boeing and FAA just can’t seem to certify the aircraft that was used for the recertification of the MAX8 riddle me that on Batman.
    When WN ordered its first 38 NG800 Etops the original plan for Hawaii service was Red eye returns
    And Zero inter island service. Every westbound flight would arrive in Hawaii at 19:00 local tow off get cleaned then towed back to the gate around 22:30 and depart At 23:30 eastbound. All these times are within the 03:00 daily Herb system reboot. Similar times were planned for the now delayed DEN service. The original Hawaii service got pushed back 10yrs to focus on Buying AirTran instead.
    The recent Red Eye delay had to do solely with the SWAPA because during there most recent CBA they forced the company to do a complete rewrite of their contractual agreement. With their agreement passed and in place the final hurdle is with the Flight Attendants who also have new Red eye language in their pending TA which gets voted on starting April 10 and closes on April 24. If it passes WN is scheduled to announce its spring schedule for 2025 the following day on April 25. Which from everything I’ve heard will include Red eyes from Hawaii and LAS to the east coast and new service to DFW.

    1. Now AW at his time at Hawaiian loved Hawaiians most popular reverse Red eye service from LAS-HNL 01:55-05:25. These times would also work great for WN because they have a plethora of eastern and midwestern arrivals into LAS between 21:30-23:00 that could easily connect to 5 daily flights to Hawaii.
      Also that time of the night the aircraft wouldn’t have any High Heat weight penalties they suffer from LAS and also PHX in the summer.
      WN today in theory could fly 5 to 10 aircraft daily from Hawaii to the LAS and PHX departing Hawaii at 23:00-07:40+1 making a plethora of connections and with nightly flight to Hawaii from LAS-PHX departing at 01:55-05:25 getting a plethora of inbound connections without needing to add any additional aircraft during this period of Boeing delays.

    2. I assume you mean starting overall service to DFW, and not on a red eye from Hawaii? I don’t think WN has any aircraft that can make that nonstop.

      The problem WN will have at DFW is finding gate space. There are new gates coming with the expansions of A and C, and the construction of F, but none of that will be ready in April 2025.

      1. One other thought on WN in Dallas.

        They could still use a threat to move a bunch of flights to DFW to get Dallas to get rid of the 20 gate limit at DAL.

        1. You’re misunderstanding the Dallas Love Field drama.

          From day one of AAs operation at DFW SWA undercut them by offering cheaper and more convenient flights from DAL, something that AA just couldn’t compete with.

          AMR et al tried to get SWA out of DAL but the courts agreed with SWA. The Wright Amendment was put in place to rightfully ensure the success of the DFW hub as the O&D to support both/it just didn’t exist back then.

          Eventually AMR agreed to the Wright Amendment being amended as long as there was a gate cap at DAL. They did this knowing that fares in the region would collapse, and they did dramatically nosedive in 2014.

          AA has made it clear time and time again that they prefer to have SWA at DFW vs DAL. In fact they openly invited them to join back when they could legally serve it.

          As Southwest learnt the hard way in Atlanta (after the Airtran merger) it’s hard to be a no2 in the market.

          1. I am from Dallas. Took my first flight and a Cessna from love Field in the late 60s. I am very aware of the history of the Wright amendment.

            American, and Delta and Braniff before them, had to serve DFW. At that time, it was a significant advantage to serve the field. Love Field was much closer to the core business traveler. That was the heart of the fight over Love.

            But any need to “protect” Love Field is long gone. Due to the growth of the area, more people live closer to DFW than Love field, and it is a nightmare, trying to get to love field at rush-hour.

            WN wants more gates at Love so they can add service. They would likely rather have unlimited gate space in one airport.

            And Dallas has gone from fighting WN to realizing that they get lots of money from Love, and they don’t have to share it with Fort Worth. Further, people who fly into Love are going to rent cars, stay at hotels, eat, and shop…in Dallas. And not in Grapevine or Arlington.

            Dallas now has a good reason to expand Love and try to keep WN there if they can.

            1. Chicago makes it work with the larger ORD and smaller MDW. No reason Dallas metroplex cant do the same with DFW and Love. Dallas is lucky to have AAs global hub and Southwests hub at DFW and Love. The problem with adding gates at Love, is other airlines will demand them since SWA currently operates as a monopoly at Love.

      2. Yes new service to DFW with a 2025 start will be a completely separate service in addition to announcing Red eyes flying from Hawaii.

    3. > Southwest still resets its daily aircraft flows at 03:00 HERB/CT.

      If a delayed flight would miss the 03:00 “reboot” today, would WN cancel the flight ahead of departure? And how do they explain that to customers?

    1. Herb always said they should have kept ANC service.
      The Morris Air flights from SEA-ANC were always packed and carried a ton of Mail and cargo.

  4. At least some front facing ground employees on Southwest work the graveyard/overnight shift

    Back in 2019 I remember checking in at Midway for a 6:00am flight and chatting with the check-in agent who said she was about to end her shift which had started downstairs at the baggage office working on the late night arrivals.

  5. Redeye advocate here (why waste an entire day when flying east?). BUT, I think seat selection matters more on redeyes than most flights… wonder how that’ll factor in. Its either a nice upsell opportunity for WN or it’ll cost them some customers… or both.

    1. WN is festival seating. Without an F — which’ll never happen on Southwest — red eyes are asking for trouble.

    2. Former (recovering) red eye proponent:

      You day you (I) waste with a red eye is the one after the flight. :)

  6. Not (at all) a fan of the redeye flight as I can never, ever, sleep on a flight. Especially not in economy. Now, my father preferred the redeye schedule – dating as far back as the 1960s. He could sleep on the plane with no issue and liked having a drink upon leaving SFO or LAX and then waking up at (say) IAD after having a few hours of sleep. So, it is hard to dispute the usefulness of redeyes for people who prefer to be more efficient (and it is indeed efficient).

    I’m surprised that it’s taken WN so long to offer this option, but it’s good for them that they are. While I’m sure that connections between Hawaii and the east are one of the main drivers here, it’s attractive for west coast to east coast night flights, and can also be scheduled in other places in the interior west like LAS, PHX, SLC, BOI, etc. Perhaps they can reconnect OAK with some of the east coast cities they used to serve from there. Like OAK-PHL, which I flew back in around 2007 or so.

  7. They should restart the old HP/US Vegas bank of redeyes to every east coast city.

  8. Do any of you (including Brett) know the exact date the final Wright Amendment restrictions end next year?

    1. I don’t know the exact date. I know it’s 2025, but I never see a specific date referenced, so it might very well be Jan 1.

  9. WN’s biggest reason to note jump into redeyes right now is to restore labor peace and get everyone rowing in the same direction again. low earnings have cut profit sharing which is being somewhat restored by new labor contracts. When they get higher earnings, their employees will start making alot more money and the growth will come with younger employees that can fly redeyes if “the veterans” don’t like them. Like other airlines, WN will find that there are employees of all seniority levels that like working at night.
    And it will take employees across the company – not just pilots and FAs – that will have to be at work through the night for potential diversions, operational support etc.
    right now, WN can start the schedule early on the east coast and run it late into the early morning so the value of adding true redeyes is not as great as it might seem.
    Still, they are coming and WN will find that some people like them and they can use parts of their fleet more efficiently with them.

  10. “also some Las Vegas – East runs”

    Would be interesting if they reboot the old America West “Nite Flite ™” hub bank in Vegas

  11. Flying on a red-eye is miserable. Flying on a red-eye when you have no idea where you are going to sit is even more miserable.

    I like how Alaska, United, and Hawaiian have late afternoon flights that get me home in the evening or late evening. If it was a red-eye, I’d just go to bed when I get home because I’m non-functional for that day.

  12. Red eye flights from Hawaii to California have always been popular. I’ve know people who get off those night flights and go directly to work. A lot of people own a second home in Hawaii and those red eyes help make for quick weekend trips back and forth.

  13. No surprise that red-eyes are coming. Since sometime last year, Southwest has offered overnight itineraries where a passenger arrives at a layover airport late at night and then catches an early morning connecting flight. For example, one offered itinerary for SFO-HOU on 4/7 is 2051/2367. Flight 2051 departs SFO at 9:55 PM and arrives LAS at 11:25 PM. Connecting flight 2367 departs LAS at 5:00 AM (on 4/8) and arrives HOU at 9:50 AM.

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