Southwest Hawaii Flights: Everything You Need to Know

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In the fall of 2017, Southwest Airlines first announced its intent to fly to Hawaii. Finally in March of 2019, Hawaii planes took flight. I’ve been tracking all the developments and occasional bumps in the road (government shutdowns, 737 MAX groundings) in this post for nearly two years. And I’m happy to report a further expansion to Hawaii just happened! For all of you who have been hoarding Rapid Rewards points with palm trees and mai tais on the brain, you can take the country’s scrappiest and quirkiest little airline to a few more places in paradise, from a few more originating mainland airports.

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. I took one of the first OAK to HNL flights last March for my family’s spring break at Aulani, so 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 to the Big Island.

So what do you need to know about Southwest’s Hawaii flights? Where are they flying to and from now?

BREAKING – New Southwest Hawaii Flights Added As of January 2020

Southwest just released its schedule extension through March 6, 2020. A number of new Hawaii flights will launch in mid-January 2020. In this schedule extension, Southwest has added its first Hawaii service from Sacramento (SMF) as well as its first flights into Kauai (LIH). Both San Jose (SJC) and Oakland (OAK) are getting new non-stop service to both LIH and Kona (KOA), supplementing the non-stop flights both airports already have to Honolulu (HNL) and Maui (OGG). The airline has added a variety of additional interisland flights as well. The route map as of mid to late January 2020 will look like this:

And the dates for the new routes and airports are as follows:

Where and When is Southwest Flying to Hawaii?

(Editor’s note: Some of the information below is now outdated. It is being updated shortly to reflect the most recent flight additions mentioned above. Come back later today for more updates.)

Sunset on the Big Island of Hawaii.

Southwest is now selling flights into five Hawaii airports, four of which have non-stop services 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 start service from four California cities, although the rollout has only happened in three cities so far. (I’m personally pretty excited that three Northern California airports, including my home airport of Oakland, made the cut.) Those include:

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

Southwest’s calendar is open through March 6, 2020 right now. Many new routes are launching in mid-January 2020.

This Hawaii roll out 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.

The first route to launch started March 17, 2019 with flights from OAK (Oakland) to HNL (Honolulu). Other routes were added in April, May, and throughout the summer of 2019, including flights to OGG (Maui) and KOA (Kona) as the third destination added.

Exact launch dates for the first routes that went 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 launched interisland routes in this first wave as well. HNL to OGG started April 28. The interisland HNL to KOA route was added on May 12, which enabled California flyers to make the connection on to the Big Island for their summer travel.

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 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. 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 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. 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. 

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