Southwest Hawaii Flights: What We Know Now & What’s Coming

What used to be the country’s scrappiest and quirkiest little airline is now ready to play with the big boys. Last fall, Southwest Airlines officially announced plans to fly to Hawaii. Last week, Southwest finally announced the 4 Hawaiian airports it plans to serve with its first flights. And today, we finally have learned the names of the California gateway cities where Southwest will base those first Hawaii flights!

If you are a regular reader, you know how much I adore Southwest airlines for family travel. With no checked bag fees, no change fees, early boarding for families (between Groups A & B), and a courteous and kind staff, flying Southwest with kids in tow is a much more pleasant experience than with other US airlines. It probably goes without saying that I am psyched about the addition of Hawaii to the Southwest route map for families.

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Where and When is Southwest Flying to Hawaii?

So, what do we know about these Southwest Hawaii flights so far? Although some Southwest Hawaii news is still to come, we do now know many details about Southwest’s plan to fly to Hawaii.

Last week, Southwest announced that it plans to serve four Hawaii airports: Honolulu (HNL), Kona on the Big Island (KOA), Maui (OGG), and Kauai (LIH). Those are the four largest Hawaii airports so the choices aren’t exactly surprising. That said, I personally was surprised that the airline is focusing on four airports right out of the gate. That means Southwest is truly making big play for Hawaii.

The big news for today is that we finally know the California cities where Southwest plans to position its first Hawaii flights. They include:

• Oakland (OAK)
• San Diego (SAN)
• Sacramento (SMF)
• San Jose (SJC)

Surprisingly, LAX was not one of the first four cities chosen, but could be in a second expansion phase down the road. I’m personally pretty excited that three Northern California airports, including my home airport of Oakland, made the cut!

As for timing, all we know so far is that the airline will begin selling tickets some time in 2018 “subject to government approval.” We don’t know when flights will start after that, although I’d expect several months at least between tickets going on sale and the routes actually starting to fly. Often that gap is 6 months or more, judging by other destinations Southwest has added in recent years (like its Caribbean and Mexico routes). So best case scenario seems like late in the year in 2018. More realistically, it could be as late as 2019.

The airline will be flying the new 737-MAX on these routes (although it plans to start flying the 737-800 temporarily).

What’s Next for Travelers Wanting to Fly Southwest to Hawaii

So what should family travelers looking to get into the Aloha spirit know and be doing to prepare to take advantage of these new routes? Here’s my advice (with a little speculation thrown in for good measure).

Look Out for Fare Wars

More competition is almost always good for the consumer. I’m hopeful that the addition of more competition to Hawaii will drive already pretty competitive fares downward a bit more. Looking at my home market of Oakland, both Alaska and Hawaiian have pretty extensive service that is usually priced fairly reasonably. With three airlines in the mix, I’m going to be hunting for deals now that we know that Southwest will serve OAK with these flights.

Time to Snag Southwest Credit Cards

So you wanna go to Hawaii on the cheap? Of course you do. If you already have a stash of Rapid Rewards points, save them up to redeem for award travel on these new routes.

If you don’t have a bank of Rapid Reward points, start building one up! One of the easiest ways to earn Rapid Rewards flights that you can redeem for free travel on Southwest is through the co-branded credit cards from Chase. My family regularly has one or two of them in our wallets. The current signup bonus for both of the personal cards (as of May 3, 2018) is 40,000 points for spending $1000 within three months (annual fee not waived). Sign up with my referral link for the Plus card here.

Remember also that Chase Ultimate Rewards points transfer 1:1 to Southwest Rapid Rewards points. So if you have one of the Chase cards that earns these valuable rewards, then you are all set too. My family currently has both the Chase Sapphire Preferred and Chase Sapphire Reserve cards as well as the Chase Freedom card (which doesn’t earn the same transferrable points when held by itself but can when paired with one of the premium cards).

Check out my recommendations for the 5 best credit cards for family travel for more details on credit card options that will help you get to Hawaii on Southwest.

Southwest Companion Pass Prep

If you are a veteran of the miles and points world, I’m sure you know all about the Southwest Companion Pass. If you are a regular person, that term probably means little.

The bottom line: the companion pass is a pass that allows a flyer to take a single companion with them on any Southwest flight totally free (plus taxes and fees). As you can probably imagine, it’s pretty valuable for saving money for couples and families who fly Southwest often. It might be even more valuable on these more expensive Hawaii routes. Many folks are rushing to earn one ASAP.

You have to earn 110,000 Rapid Rewards points in a single year to get a Companion Pass. Many people earn it by good old fashioned “butt-in-seat” flying. But it’s possible to do with a combination of several credit card bonuses as the miles and points world does. My word of warning – this method is not exactly for the beginner even though there are blogs that make it sound like a piece of cake. Believe it or not – I’ve never had a companion pass myself until this year (thanks to a targeted promotion for California residents). If you are ready to do some research and legwork, now certainly seems to be the time though.

A lot of ink has been spilled on the Southwest Companion Pass so I’ll spare you more. Here are a few of the more comprehensive guides out there if you think it might be for you and want to learn how to do it.

• How to Earn the Southwest Companion Pass in 2017 from The Points Guy
• The Complete Guide to the Southwest Companion Pass from The Frequent Miler
• Earning the Southwest Companion Pass: Timing and FAQ from One Mile at a Time

There are many gurus who are predicting the addition of Hawaii to the Southwest route map may result in fundamental changes to the companion pass. That is probably true long term, but I think the companion pass as we know it is a safe bet well into 2019 at least.

Are you excited about Southwest flights to Hawaii? Share your thoughts and plans in the comments.

Disclosure: I’m a paid #SouthwestStorytellers ambassador for the airline in 2018. This article was originally published in October 2017 before I was a brand ambassador and has been updated with recent news. As always, all opinions are my own.