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 knowing that the seats are really hard. Why does Southwest continue to think that we enjoy traveling this way?

Sitting in a Southwest Airlines seat
In the olden days (prior to 2026), the anxiety of not knowing ahead of time where I would be sitting on a 5-hour flight would’ve taken a solid 2 years off my life. Their switch to assigned seating was a much appreciated improvement. Like, finally, bro.

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.

Pros

  • Because Southwest has been so desperate to make their Hawaii flights successful, they’re often the cheapest option (even if you go with a fancy-pants Extra Legroom seat).
  • 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 offering extra legroom seats at the from top the plane.
  • Their streaming in-flight entertainment product is just as robust as what any other major US airlines offering.
  • Its true: main cabin 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.
  • For anyone needing / wanting additional legroom, the Extra Legroom seats offer approximately 3 more inches (right where it counts). My review of the Extra Legroom Experience on the 737 MAX 8 has all the juicy deets.
  • 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.
  • There are USB charging ports at every seat (both USB-A and USB-C).
Southwest Airlines 737 MAX 8 empty interior
Another pro: Southwest has assigned seating now, which eliminates the crippling anxiety I always had about scoring a decent seat. No more worries about ending up next to the toilet way in the back!
Southwest Airlines gate area for Hawaii flight
The switch to assigned seating also eliminated the need for scanning the gate area to identify the weak (so I’d know who to trample in the ensuing mad dash for the good seats). I’m kinda bummed about this, because that was kinda fun.
Eating snacks on Southwest Airlines
Even the snacks are kinda good!
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.

Cons

  • 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’ll probably behoove 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.
Southwest 737 MAX 8 extra legroom seats
This Extra Legroom seat is the best seat that Southwest is offering to Hawaii at the moment. Yeah, it looks nice, but it’s not all sunshine and roses. The sad thing is that recently drove a clapped out 2018 Nissan Versa that was more comfortable than this. Ok, yeah, the Versa couldn’t get me to Hawaii. But you know what I mean.
Southwest Airlines hawaii flights food
Good news: Southwest serves snacks on Hawaii flights. More good news: 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.

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 800 aircraft serving 117 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. The seats are kinda hard

All seats on all Southwest aircraft are the same. They’re all very thin, very narrow, and very hard. That said, now that they offer the opportunity to pay for a seat with more legroom, I’m happy to throw my money at them. I might even smile while doing it.

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. Hawaiian Airlines offers a better experience IMHO

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 without video screens and a less than enthusiastic cabin crew based out of Baltimore or Dallas.

I mean, if you’re going to Hawaii, it’s a lot more fun to do it in a seat with a video screen while being served by a cabin crew trying their damnedest to put you in an island mood the moment you step on the plane. Just sayin’.

Hawaiian Airlines A330-200 economy class
The Hawaiian Airlines A330-200 economy experience. Video screens! And guava juice! And softer seats!

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7 Comments

  1. Lots of great points here Scott! I’d add something else from my perspective…one thing I like about getting to choose seats on Southwest is knowing who I’m sitting next to. When you select a seat in advance, you have no idea who that might be. That is especially crucial for longer flights.

    1. That’s a very good point Amy – I’m totally guilty of being picky about who to sit next to on a Southwest flight. And I’m sure there have been lots of people who felt the need to steer clear of me as well lol.

  2. Am I the only person who brings food on planes nowadays? Honestly everytime I’m flying southwest and it’s more than a quick jump across California or to something like Phoenix/Vegas I always bring some food with me. Could be a few snacks or it could be a sandwich (obviously nothing pungent) if it’s longer like SD to Nashville (which I’ve done). Once you get that and a fully powered up (to the hilt) device, it’s really pretty easy to do long runs in SWA.

  3. Personally i wont be flying on a narrow body jet, especially a 737 max, 5 hours across the pacific ocean. I do not trust the FAA or any etops certificate they issued post max disasters. Ill take the clapped out a330 or 767s doing the same route with 20k more cycles anyday, but thats just me.

    1. Hey Steve – I’m slowly coming around to liking the MAX (a lot). There are so many of them flying now, and there haven’t been any issues, so it appears that they have fixed whatever the problem was. I just flew on an Alaska Airlines MAX 9 from San Diego to Fort Lauderdale (a 4 1/2 hour flight), and never once was I worried about anything going wrong.

      I understand your concern though! My prediction is that the 737 MAX will end up being one of the most significant aircraft in aviation history (in a good way lol).

  4. Have you seen the video of different ways to get a free row all to yourself? Man, some of the tactics are just wild, like the “fake breakup” (where some guy pretends to yell into his phone). Southwest’s open seating policy always leaves me scratching my head and going “huuuhhhh? Why’d they do that?” But Southwest has their reasons, I guess.
    Thanks for the tips!

    1. Oooh, sounds like I need to give that a try next time! lol But yep – the open seating policy is the primary reason why I don’t fly Southwest more often.

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