The brutally honest pros and cons of flying Southwest Airlines to Hawaii

The brutally honest pros and cons of flying Southwest Airlines to Hawaii

I recently flew Southwest Airlines to Hawaii, and you know what? It went exactly how I thought it would.

I really liked how cheap it was. I also appreciate the fact that they only fly their newest airplanes out to the islands and back. They’re nice.

What I didn’t like was the anxiety brought on by not being able to select a seat at the time of booking. Why does Southwest continue to think that we enjoy traveling this way?

Sitting in a Southwest Airlines seat
FWIW, not knowing ahead of time where I would be sitting on a 5-hour flight might’ve taken a solid 2 years off my life. Anxiety is mofo – and it’s just one of the things you’ll have to deal with when flying Southwest out to Hawaii.

All the pros and cons of flying Southwest Airlines to Hawaii

Be sure to read my Southwest Airlines 737 MAX 8 review to see firsthand what my experience was like. The routing was from San Diego to Honolulu, and while I did say a few things about the Southwest Airlines Hawaii experience, I saved most of the juicy bits for this dedicated overview. Here we go with the “no holding back” pros and cons:


  • Because Southwest is so desperate to make their Hawaii flights successful, they’re often the cheapest option. (even if you go with a fancy-pants Business Select upgrade).
  • You can check two bags for free. Nope – there ain’t no other airline flying to Hawaii that will be so generous with all your stuff.
  • Southwest Airlines uses their Boeing 737 MAX 8 aircraft out to the islands and back. These are their newest and most state of the art aircraft.
  • Their streaming in-flight entertainment product is just as robust as what any other major US airlines offering.
  • Its true – leg room is actually fairly decent on Southwest Airlines. It’s not any worse than what any other major US airline is providing in economy class these days.
  • Not only does Southwest fly between the US mainland and the islands, they also do a fair bit of inter-island flying as well. It’s convenient to do your entire trip on one airline.
  • It’s extremely easy to redeem your hard-earned Rapid Rewards points for flights to Hawaii. There are no blackout dates or seat restrictions on any flight.
  • Changes are free on Southwest Airlines. There’s currently no other US airline allowing you to make changes without paying a fee. Cancelations are also free, but you’ll receive a flight credit (that you can use towards the purchase of another ticket) instead of a full refund on most base fares.
Southwest Airlines 737 MAX 8 empty interior
Weaseling your way to the front of the boarding queue with a Business Select ticket (and being one of the first to check in online) will negate the crippling anxiety I mentioned earlier. I can’t even put into words how baller it feels to be able to walk on a plane like this knowing that I can take any seat I want!
SANspotter manspread southwest airlines
Pro tip: a little bit of manspread goes a long way towards insuring that nobody will want to sit next to you.
Southwest Airlines in flight entertainment options
Yeah, all your friends will probably laugh at you when they found out you flew Southwest to Hawaii. What they won’t know is that you enjoyed the **** out of really nice perks such as high-quality in-flight entertainment.


  • At the time of this writing, power outlets aren’t installed on every Southwest Airlines aircraft. Even though there are plans to add them, it’s going to be a while before their entire fleet is retrofitted.
  • Southwest Airlines has an open seating policy, meaning that you can’t choose a seat at the time of booking. Once on the plane, it’s first come first serve. And that’s gonna suck if you’re not in one of the very first boarding groups.
  • There are no video screens in the seats. If you want to take advantage of the in-flight entertainment, you’re going to have to use your own device.
  • Speaking of the seats, they’re kinda hard (which makes them a not-so-good option for longer flights).
  • I’ve heard from other travelers that the streaming entertainment service doesn’t always work. It probably behooves you to have a back up plan – especially if you’re traveling with children.
  • The food they serve on flights between the US mainland and Hawaii is minimal. You’ll get a small packet of snacks (which is going to leave you feeling hungry and unsatisfied on those long five hour flights).
  • Southwest Airlines uses Concourse E (in Terminal 2) at the Honolulu International Airport. It’s dark, dumpy, and nowhere near as nice as some of the other terminals.
  • All seats on all Southwest Airlines aircraft are the same. There are no “better” seats with extra legroom to pay extra for. Note that the exit row seats have more legroom, but you’ll have to be one the first passengers on the plane to snag one of those.
Southwest Airlines seats to Hawaii
This is it. This is the only (and best) seat that Southwest is offering to Hawaii at the moment. The sad thing is that recently drove a clapped out 2018 Nissan Versa that was more comfortable than this. To be fair, the Versa couldn’t get me to Hawaii – but you know what I mean.
Southwest Airlines hawaii flights food
Good news: Southwest serves more substantial snacks on Hawaii flights. It’s not much, but at least you’ll hit the ground in Hawaii all jacked up on carbs (and ready for anything).

Two very good reasons why flying Southwest Airlines to Hawaii is a good idea

Spoiler alert: I don’t think I will ever fly Southwest Airlines to Hawaii ever again. That said, I can totally understand why some might think that choosing Southwest over any other airline for a trip out to Hawaii and back is a good idea:

1. It’s fairly likely to be your cheapest option

I’ve been watching prices for one-way and round-trip tickets between San Diego and Honolulu for a while now. Southwest is typically (but not always) the cheapest. Those low ticket prices, combined with free checked bags, means that you’ll be far likely to pay less than you would on any other airline.

Southwest Airlines airplanes at HNL
Technically, Hawaii is the most southwestern part of the US, so they’ve got every right to defend this territory as much as Hawaiian Airlines does (I guess). Either way, I love how the added competition is pushing prices down!

2. You won’t have to worry much about delays and cancellations

Love ’em or hate ’em, Southwest Airlines runs a pretty good operation. Yes, they have operational hiccups from time to time, but what airline doesn’t? Southwest Airlines has a fleet of over 770 aircraft serving 171 destinations. If something goes wrong, it won’t be hard for them to find you an alternate route to Hawaii. They’ll get you there.

SANspotter on Southwest Airlines flight
This is what I look like when I’m trying really hard to think of a third reason why anyone would want to fly to Hawaii on Southwest.

Two very good reasons why flying Southwest Airlines to Hawaii is not a good idea

So yeah. I stand by what I was saying about never flying out to Hawaii on Southwest ever again. Not because they’re a terrible airline or anything. I quite like them for short hops here in the continental US, but not for extended runs out to the islands and back. Here’s why:

1. They don’t offer an opportunity to upgrade to a better seat

All seats on all Southwest aircraft are the same. They’re all very thin, very stiff, and the leg room is so-s0. If Southwest offered me the opportunity to pay for a seat with more legroom, I’d throw my money at them with a smile.

But since all seats are the same, and I have to suffer the same as everyone else, I’ll choose another airline that allows me to do so. For the record, Hawaiian Airlines A330-200 extra comfort is a far superior “premium” economy choice IMHO.

Southwest Airlines 737 MAX 8 engine and wing view on flight to hawaii
What do the hungry ocean beasts think when they look up and see a Southwest 737 MAX 8 screaming overhead? I suppose the smart ones would assume that we are way off course and swim after us waiting for the crash. That’s what I would do.

2. The open seating policy is kind of stressful

It takes (at minimum) 5 hours to fly between the US mainland and the Hawaiian Islands. That’s a long time to be struck in a seat you’re not happy with, and the chances of that happening are much higher on Southwest than they are on any other airline.

Southwest Airlines gate area for Hawaii flight
T-minus 7 minutes until the flight to Honolulu starts boarding. No, I’m not taking a pic of the boarding area for the memories. I’m gathering the data I need to identify the weak (so I’ll know who to trample in the ensuing mad dash for the good seats).

I fully admit that the open seating policy thing works great for shorter flights. It takes less time to board the plane, and even if you do end up with a terrible seat, it’s a tolerable situation knowing that you won’t have to suffer long.

Chances are high that you’re not going to get a good seat on a Southwest flight out to Hawaii if you aren’t in the “A” boarding group. You might get lucky if you’re in the first half of the “B” group, but may God have mercy on your soul if your boarding pass says “B15” or higher.

Comments (5)

  1. Amy

    March 21, 2023
    • Scott (SANspotter)

      March 21, 2023
  2. Loren

    June 30, 2023
  3. Steve

    December 31, 2023
    • Scott (SANspotter)

      January 1, 2024

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