What it’s like to fly Southwest to Hawaii: Impressions & thoughts


A couple of months ago, Southwest Airlines began flying to Hawaii, starting with routes to Honolulu and connecting onward to Maui and Kona. I spent a week in Honolulu earlier this month, flying there and back on Southwest Airlines. Here are seven thoughts & impressions.

1) It’s just like flying Southwest anywhere else

The most obvious conclusion is of course that flying Southwest to Hawaii is just like flying Southwest anywhere else: either you like (or more likely tolerate) open boarding and all-economy class or you don’t. Southwest already flies some transcontinental routes, and if you’ve ever flown between the coasts, the flight time to Hawaii isn’t substantially different. The most obvious conclusion out of the way, it’s worth a reminder that…

2) It isn’t all that different than flying anyone else in economy

These days, economy class passengers don’t get many frills on the major US carriers. Southwest doesn’t get major frills either — though on the plus side, I do find their crews to be a bit friendlier than other US carriers (on average). In fact, during the announcements on the way to Hawaii, it was notable when a flight attendant said, “We’re here for your safety and service”. I don’t think I’ve heard that last part — and service — in quite a while. It was a nice touch. I think that they were training new crew members on our flights and I imagine the Hawaii routes are in high demand from an employee perspective, so perhaps it was just a product of the crew putting its best foot forward, but everyone was friendly and pleasant.

That goes a long way in keeping the passenger experience positive, especially when you’re cramming everyone into economy class seating and not offering meal service. However…

3) They offer better snacks on these routes

We flew from Oakland to Honolulu and a family member flew from San Jose to Honolulu and we found snacks served to be the same: a snack pack that included wheat thins, spreadable cheese, fruit snacks, pretzels, and tic tacs for the first service and then a package with 2 Milano cookies for a second snack service before landing. They also have pineapple-orange juice on the Hawaii routes. Hey, it’s no lobster thermidor and Krug, but you probably didn’t have those expectations when you booked Southwest. One thing you do expect when you fly Southwest is free checked bags, and that means that….

4) Inter-island flights are a terrific value
Advertising at Ala Moana shopping center to remind everyone that this is a pretty big deal for inter-island flights.

I’ve had the good fortune of visiting Hawaii twice this year. I wish I had taken screen shots of the inter-island flight prices on my first trip this year (before Southwest started service), but you’ll have to trust me: I looked for months and the price was about $103 each way every day of the week. Now Southwest fares start at just $29 or less than 2,000 Rapid Rewards points each way.

But what’s more is that *bags still fly free*. In January, on top of paying $103 each way, we also had to pay for bags: $15 for the first checked bag and $25 for the second for members of the Hawaiian Miles Frequent flyer program. If you travel with two checked bags, your cost on the routes Southwest serves just went from $143 each way to $29 each way. That’s an unbelievable change. And Hawaiian Airlines has noticed: you’ll now find fares on Hawaiian from around $59 each way.

5) This nearly obliterates the value of the Hawaiian Miles credit cards (in my opinion)

I used to say that the card was worth it for inter-island fights alone since each 7500 miles could save you the approximatey $100 cost of an inter-island flight. A 60K new cardmember bonus could get you 8 inter-island flights and that was not a bad savings.

Now, a 60K Southwest offer could get you around 30 inter-island flights (at about 2K each).

6) Scheduling could use some improvement

There was a schedule change that took me off of my originally-planned flights. We ended up on a flight from Las Vegas to Los Angeles to Oakland to Honolulu on what was an 11 hour itinerary.

It didn’t make a lot of sense to me as Southwest had a Las Vegas-to-Oakland option without the stop in LA, but at the time they weren’t selling that one connected with the flight to Honolulu.

We ended up calling the day before our flight to change to a 5:15am departure, which wasn’t ideal either but cut a few hours off the travel time and didn’t involve a stop in LA. They’ve since eliminated the itinerary that required the extra stop at LAX, so they are improving.

It’s just worth keeping in mind that Southwest definitely has some kinks here that need to be worked out, and the grounding of the 737 Max isn’t doing them any favors. Keep an eye on the details when reserving and an eye peeled for any schedule change emails.

7) Don’t forget, you end up here.

While some will invariably look at flying Southwest with dread, it’s worth a reminder that even if you’re slightly uncomfortable, the juice is likely worth the squeeze. It had been about 10 years since I’d spent time in Oahu and I’d forgotten how beautiful it is.

If you go to Oahu, I can’t recommend Haleiwa Joe’s in Kaneohe highly enough. Your view during dinner is the stuff of tropical paradise dreams.

And the food was arguably better than the view.

It opens at 4:30pm and they don’t take reservations. Get there early. we arrived around 5:15 and the wait was about 45 minutes. It was well worth the wait.

Bottom line

Those who don’t mind flying Southwest domestically will be pleased that the experience flying to Hawaii isn’t much different. For those who haven’t flown Southwest lately, I’d say this: having flown American, Alaska, Delta, and United in economy class over the past few months, I don’t find flying Southwest to be substantially different (apart from the boarding process) in any negative way. In fact, two free bags, whether inter-island or from the mainland, enhances the deal with Southwest. And for those who would never set foot on a Southwest plane, take comfort in competition. While Southwest’s prices to Hawaii are pretty expensive right now, they are expected to extend the booking calendar to January 5, 2020 today. I don’t know for sure whether there will be Hawaii deals to be found since the future of the 737 Max is still up in the air, but if you’re looking to fly to Hawaii, Southwest is a decent way to get there.

Please enter all required fields Click to hide
Correct invalid entries Click to hide
Notify of

This site uses Akismet to reduce spam. Learn how your comment data is processed.

newest most voted
Inline Feedbacks
View all comments