Having overnight flights is the norm rather than the exception these days. However, the airline of LUV has never operated them regularly, but are planning to. That’s great, as red-eye flights could be big for Southwest!
I’m sure many of you have read about this already from other places on the interwebs, such as the Star-Advertiser or TPG. However, they just graze the surface of this topic, especially as it relates to Hawaii.
Red-Eye Flights Could Be Big for Southwest
Southwest’s largest disadvantage has always been its technology. But, a few years back, that began to change, and will be changing more in the future after their embarrassing meltdowns these past couple of years. Those technological disadvantages have always been the carrier’s biggest barriers to offering overnight flights, especially because its reservation system simply couldn’t handle it. With that no longer being an issue, though, the airline is now eyeing a shift towards offering nighttime flights.
When it does begin offering them, red-eye flights could be big for Southwest, especially here in Hawaii. Outside of the economic benefit of utilizing their aircraft more – part of Southwest’s entire operating economics and why they offer free checked bags (quicker turns) – they could offer better scheduling. You see, for visitors to the islands, having the ability to spend a full day here, arrive back home early in the morning with enough time to change and head to work is quite popular. I don’t know how ya’ll do it, but you do you.
Just look at this departure schedule from Honolulu on Monday, March 25, 2024. In this brief 45-minute snapshot, you see the vast majority of the passenger airlines serving Honolulu with overnight departures to the West Coast and Mountain region. 
Earlier in the evening, you see flights to places like Texas and New York. So, clearly, the demand is there. Demand that Southwest is missing out on. However, direct flying is really only half the battle, here.
The other is connectivity.
Reaching Farther
The other reason why red-eye flights could be big for Southwest is that it could possibly open up the ability to connect across the U.S. For example, if you’ve ever tried to book a flight from HNL to LGA on Southwest, you may have noticed that you can’t. The inability to operate flights overnight (or at least ticket an overnight connection) is a HUGE reason why this is. For this route in particular, you’re either going to depart Hawaii during the day and take an overnight connection to New York, or you’re going to have an overnight flight to the West Coast and connect with a daytime flight.
Yes, I know airlines such as Delta and Hawaiian both offer direct flights to the East Coast, but that’s not the point. Both offer connecting flights, too, either on their own or with a codeshare partner (Hawaiian + JetBlue).
An example of this would be how I got to New York back in 2016 on Alaska:
- AS816 – departing HNL at 11:15 am and arriving in SEA at 8:13 pm
- AS22 – departing SEA at 9:55 pm and arriving in JFK at 6:13 am
Red-Eye Flights Could Be Big for Southwest, Final Thoughts
I know Hawaiian’s red-eye HNL-LAS flights are really popular, especially with all you degenerate gamblers out there (kidding, or am I?). Being able to arrive in Vegas early in the morning and depart at a ludicrous time of night is appealing to those that want to maximize their time in Sin City, especially since it doesn’t “waste a day” – getting in late afternoon/early evening, saving on hotel room costs, too. In fact, Mrs. Island Miler did this once, flying up with me for work on an overnight flight, spending the weekend, and flying home on the 2 am departure, arriving back in Honolulu at 5:30 am and driving straight to the office. Insane? You bet. Best use of time? Yes!
So, hopefully, Southwest will begin offering similar flights. And, more so, hopefully it’ll open up cross-country connectivity to and from Hawaii.
As you can see, red-eye flights could be big for Southwest in many different ways, and while we know that Hawaii and Las Vegas will be the first markets to see these flights, we don’t yet know when they’ll begin. I’d imagine Southwest needs to discuss this with their unions and figure out the logistics of transitioning to 24/7 flying, which is no small feat. But some estimates say it’ll take until sometime in 2026. Hopefully, it won’t take that long!