Southwest Hawaii Flights: Everything You Need to Know

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In the fall of 2017, Southwest Airlines first announced its plans to fly to Hawaii. Finally in March 2019, Hawaii planes took flight! I’ve been tracking all the developments, updates, and occasional bumps in the road with Southwest’s Hawaii flights in this post for over two years. There have been some curveballs, but I’m happy that the airline persevered and continues to expand to the Aloha State. I know a lot of you – like me – have been hoarding Rapid Rewards points with palm trees and mai tais on the brain. Luckily, you can take the country’s scrappiest and quirkiest little airline to a few more places in paradise, from quite few more originating mainland airports in late 2019 and early 2020.

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 have been beyond psyched about the addition of Hawaii to the Southwest route map for families. For my family’s spring break at Disney’s Aulani, we took one of the first OAK to HNL flights in March of 2019. Be sure to see my Southwest Hawaii flight review for all the in-air details. I’ll be hopping aboard the airline again with my kids in for our Thanksgiving travels this year to Hawaii’s Big Island.

So what do you need to know about Southwest’s Hawaii flights? Where are they flying to and from now? And how can you experience some aloha for less?

Where and When is Southwest Flying to Hawaii?

Southwest announces an extension of its flight schedule every month or two, and the last two schedule extensions have both resulted in increased Hawaii flight options from California airports.

As of the date this post was published, Southwest is now selling flights into five Hawaii airports, four of which have non-stop service from mainland airports. They include:

• Honolulu (HNL)
• Kona on the Big Island (KOA)
• Maui (OGG)
• Kauai (LIH)
• Hilo on the Big Island (ITO) – interisland only

Southwest previously announced that it would serve four California cities, although the rollout has only happened in three cities so far. Those include:

• Oakland (OAK)
• Sacramento (SMF)
• San Jose (SJC)
• San Diego (SAN) – service has not yet started/been announced.

I’m personally pretty excited that three Northern California airports, including my home airport of Oakland, made the cut. But I know travelers in Southern California are anxious for service to start there too! Unfortunately for San Diego 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 Northern California airports.

The current Hawaii route map looks like this:

Southwest’s calendar is open through April 13, 2020 right now. Some new routes are launching as early as November 10, 2019, with additional expansions happening in mid-January 2020 and March 2020. The newest Hawaii routes are summarized below:

Overall the non-stop mainland to Hawaii routes that are now available on Southwest include:

• Oakland (OAK) to Honolulu (HNL)
• Oakland (OAK) to Maui (OGG)
• Oakland (OAK) to Kona (KOA) – starting January 19, 2020
• Oakland (OAK) to Lihue/Kauai (LIH) – starting January 21, 2020
• San Jose (SJC) to Honolulu (HNL)
• San Jose (SJC) to Maui (OGG)
• San Jose (SJC) to Kona (KOA) – starting January 21, 2020
• San Jose (SJC) to Lihue/Kauai (LIH) – starting January 19, 2020
• Sacramento (SMF) to Honolulu (HNL) – starting November 10, 2019
• Sacramento (SMF) to Maui (OGG) – starting March 7, 2020

This Hawaii rollout has certainly been a bit of a slow roll, most notably due to the grounding of the 737 MAX. Southwest launched its Hawaii service with 737-800s, but the airline intends for the MAX to be the plane that flies to the islands. Presumably this latest Hawaii expansion means the airline is bullish on the aircraft’s return in the next several months. In the meantime, Southwest has done a lot of rejiggering of its overall flight schedules to free up more 800s to fly these routes.

Interisland Hawaii Travel on Southwest

Somewhat surprisingly earlier than predicted, Southwest launched interisland Hawaii routes. These flights are a great way for mainlanders to island hop on a vacation as well as for locals to fly between the islands for work or pleasure. Southwest is competing directly with Hawaiian Airlines (and to a lesser extent Mokulele) for this business. It does not yet have the flight frequency of Hawaiian but the schedule works for leisure travelers with less time sensitivity.

The inter-island routes that are available include:

• Honolulu (HNL) to Maui (OGG)
• Honolulu (HNL) to Kona (KOA)
• Honolulu (HNL) to Lihue/Kauai (LIH) – starting November 10, 2019
• Honolulu (HNL) to Hilo (ITO) – starting January 19, 2020
• Kona (KOA) to Maui (OGG) – starting January 19, 2020

Can I Fly to Hawaii on Southwest if I Live Outside of California?

What about everyone else in the rest of the country? While Southwest is only flying non-stop from California airports, travelers located elsewhere do have options to Hawaii too.

Flyers in major West Coast cities with Southwest service have the most choices. If you live in places like Phoenix (PHX), Salt Lake City (SLC), Seattle (SEA), or Denver (DEN), there are a lot of one stop 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 have not yet even seen flight options to make the return connection possible for Dallas based flyers (sorry folks at Southwest headquarters!).

We hope and expect that Southwest will start redeye service eventually, opening up more options for midwest and East Coast travelers. But for now, your only real option is to book Hawaii itineraries piecemeal as separate trips. For example, an East Coast based traveler could book two separate roundtrips – 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 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 the first Hawaii flights were announced last March, 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 were long gone just a few hours in and nothing quite that cheap has returned.

But 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. Because Southwest’s Hawaii flight capacity has been so small thus far, I don’t think the downward pressure on fares has really kicked in yet. That said, there are already some deals to be had, especially if your travels are not during peak periods like summer vacation, Thanksgiving week, and the winter holidays.

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.

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 personal credit cards below or review the details of them all on my Southwest credit card comparison guide:

• 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. Chase points transfer nearly instantaneously to Southwest in my experience, so you can make your moves quickly when you spot a deal. My family has had the following Chase cards to help us earn towards additional Southwest travel:

• Chase Sapphire Preferred
• Chase Sapphire Reserve
• Chase Freedom card (no longer available to new applicants. This card 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 is even more valuable if you need to fly on a more expensive route – like Hawaii during a major holiday period!

You have to earn 125,000 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 predicted that the addition of Hawaii to the Southwest route map would result in fundamental changes to the companion pass. I predicted a few changes when I first published this post, in fact! And as of mid-October 2019, Southwest did increase the number of points required to earn it (from 110,000 to 125,000). Although its a bit harder to earn, for now at least, the core notion of the companion pass is safe.

Are you excited about Southwest flights to Hawaii? Have you flown one of these flights yet? Share your thoughts and travel 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 is regularly updated with recent news. As always, all opinions are my own. 

Advertiser Disclosure: Trips With Tykes has partnered with CardRatings for our coverage of credit card products. Trips With Tykes and CardRatings may receive a commission from card issuers. 

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