Southwest Hawaii Flights: Flights ON SALE NOW!

The big day is finally here! I first published this blog post in the fall of 2017 when Southwest announced its intent to fly to Hawaii. A year and a half later, I’m finally happy to update it to announce that Southwest’s Hawaii flights are now officially on sale!!!! For all of you who have been hoarding Rapid Rewards points with palm trees and mai tais on the brain, you can finally take the country’s scrappiest and quirkiest little airline to get you to paradise.

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 beyond psyched about the addition of Hawaii to the Southwest route map for families. So psyched that I already booked flights from OAK to HNL for my family’s spring break (more posts about Aulani coming soon!)

So what do we know about these Hawaii flights?

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Where and When is Southwest Flying to Hawaii?

Sunset on the Big Island of Hawaii.

So, what do we know about these Southwest Hawaii flights now that the announcement is official?

We do know that the airline will eventually be flying the new 737-MAX on these routes (although it plans to start flying the 737-800 temporarily).

As for destinations, Southwest previously announced that would serve four Hawaii airports. These are the four largest Hawaii airports so the choices aren’t exactly surprising. They include:

• Honolulu (HNL)
• Kona on the Big Island (KOA)
• Maui (OGG)
• Kauai (LIH)

Southwest also previously announced that it would start service from four California cities. (I’m personally pretty excited that three Northern California airports, including my home airport of Oakland, made the cut.) Those include:

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

Of course, now that these flights are on sale, not all of these routes are launching at the same time, as expected. Some of the expected non-stops are not even on sale yet, even though Southwest’s calendar is open through October 1, 2019 right now. This Hawaii roll out is certainly going to be a bit of a slow roll.

The first route to launch starts March 17, 2019 with flights from OAK (Oakland) to HNL (Honolulu). Other routes won’t start until April, May, or later. Flights to OGG (Maui) will be next, with KOA (Kona) as the third destination added. There are currently no flights to LIH (Kauai) on sale yet. In fact, it isn’t even listed as a destination yet on the Southwest route map:

Exact launch dates for routes on sale as of March 4 are as follows:

• OAK to HNL: March 17
• OAK to OGG: April 7
• SJC to HNL: May 5
• SJC to OGG: May 26

Somewhat surprisingly earlier than predicted, Southwest is launching interisland routes in this first wave as well. HNL to OGG starts April 28. The interisland HNL to KOA route will be added on May 12, which will enable California flyers to make the connection on to the Big Island for their summer travel. There are no nonstop routes from the mainland to KOA on sale at this time, however.

Unfortunately for San Diego and Sacramento flyers, nonstop flights are not on the table as of yet. San Diego and other Southern California travelers can get to Hawaii on Southwest by connecting in the two Northern California airports. Sacramento flyers, however, will have to make the drive to OAK right now because there are no flights to position them to the OAK and SJC gateway cities.

What about everyone else in the rest of the country? Flyers in major West Coast cities with Southwest service have a lot of options. If you live in places like Phoenix (PHX), Salt Lake City (SLC), Seattle (SEA), or Denver (DEN) I’m seeing a lot of connecting itineraries on sale.

What about East Coasters? Because Southwest doesn’t fly redeyes, a lot of the flight schedules simply don’t line up in a way that makes the returning flights from the islands possible right now. In fact, I’m not even seeing flight options to make the connection possible for Dallas based flyers (sorry folks at Southwest headquarters!). We hope and expect that Southwest will start redeye service eventually. But for now, your only real option is to book two separate round trips – one that positions you into a California gateway city and then another one from that city to and from Hawaii. Remember to always leave room for delays or cancellations if you choose to go this route.

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 take advantage of these new routes? Here’s my advice.

Look Out for Deals & Fare Wars

So let’s talk cost! At the moment these flights were announced earlier this morning, there were some fare steals out of the gate — as low as $49/$79/$99 each way,  depending on the day of the week. As you might imagine, those promotional fares are mostly long gone just a few hours in. In fact, all the March OAK to HNL flights and many of the ones in early April are totally sold out. Clearly there was a serious demand here!

Prices before all the cheap fares sold out in the first hour.

But there are still some deals to be had, especially if your travels are after the peak summer family travel rush. And generally speaking, more competition is always good for the consumer. The addition of more flights to Hawaii should drive already pretty competitive fares downward a bit more across the board long term.

Looking at my home market of Oakland, both Alaska and Hawaiian have pretty extensive service that is usually priced fairly reasonably to Hawaiian destinations. With three airlines in the mix now at OAK, I expect prices to be very competitive once the dust settles, especially as we go into the fall.

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 and have been preparing and hoarding, you are in great shape.

But even 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. Check out the current offers on the Southwest cards here:

• Southwest Rapid Rewards Priority Credit Card
• Southwest Rapid Rewards Premier Credit Card
• Southwest Rapid Rewards Plus Credit Card

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). Chase points transfer almost instantaneously to Southwest in my experience, so you can make your moves quickly when you spot a deal.

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.

Fly to enjoy these views on Southwest now!

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.

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. 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 (including some of my own on other sites) 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.

• 5 Things Families Need to Know About the Southwest Companion Pass from a contributor whose name you might recognize at The Points Guy
• Southwest Companion Pass 2019 from Go To Travel Gal
• The Complete Guide to the Southwest Companion Pass from The Frequent Miler
• How to Earn the Southwest Companion Pass the Old Fashioned Way from Deals We Like

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. For now at least, it’s safe. In fact, I just used mine to book my daughter with me to Hawaii in April.

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

Disclosure: I’m was 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. 

Editorial Disclaimer:  The editorial content on this page is not provided by any of the companies mentioned, and has not been reviewed, approved or otherwise endorsed by any of these entities. Opinions expressed here are the author’s alone.