The Ultimate Guide To Southwest Hawaii Flights

In case you missed it, Southwest’s flights to Hawaii are now on sale! And what a deal they were at too! Roundtrip fares were as low as $91 and one-way fares would cost you only $49 for the nearly 6-hour flight from Oakland. The inaugural Southwest flight to Hawaii will be taking off on March 17th from Oakland to Oahu. Although, at this time, the inaugural flight is completely sold out.

The Ultimate Guide To Southwest Hawaii Flights
Southwest’s inaugural flight to Honolulu from Oakland is sold out! Screenshot: Southwest

Interisland flights are set to start on May 12th with multiple daily frequencies between Honolulu to Maui and Kona. Tickets start at $59 for the inaugural flights to Maui.

The Ultimate Guide To Southwest Hawaii Flights
Southwest will begin interisland flights on May 12th. Screenshot: Southwest

Routes and Prices

Southwest will be offering nonstop service to Hawaii from Oakland and San Jose as of now. San Jose to Hawaii flights will be starting on May 5th. Southwest has indicated they would like to fly from Sacramento and San Diego nonstop to Hawaii, but have not announced when those routes will be starting.

Southwest Hawaii Initial Departure Airports
Southwest Hawaii Initial Departure Airports. Photo: Southwest

If you are looking to fly from either Oakland or San Jose to Hawaii, one-way and roundtrip tickets in May can be found for as low as $49 one-way, although it remains to be seen how long these fares last. Unless you plan on flying in July, you should be able to find flights for under $100 roundtrip per person, which makes for one heck of a deal to visit Hawaii! Not to mention the two free checked bags!

The Ultimate Guide To Southwest Hawaii Flights
With two free checked bags, Southwest is looking to disrupt the market to Hawaii. Photo: Southwest

If you want to fly from the East Coast or the Midwestern United States, Southwest does offer connections through Oakland or San Jose to Hawaii. You will be paying more than $91 roundtrip, but in many cases, you may find it to be a cheaper and better option if you’re looking for a cheap and convenient way to get to Hawaii.

Southwest still has to work on a few kinks as their website doesn’t show much availability to Hawaii when flying from Houston or Dallas. However, that could change.

If you’re looking to book fares now when they’re cheap, you could always look at positioning flights to the San Francisco Bay area. Combining Southwest flights to Hawaii from the Bay Area with a positioning flight on points and miles can be a great deal and make a vacation getaway cheaper.

Service Onboard

Southwest Airlines has worked to improve their onboard service as flights to Hawaii start. At 5.5-6 hours, these are long flights and giving passengers some more perks onboard (in addition to low fares and free bags) could just make Southwest the superior carrier to fly to Hawaii.

The Ultimate Guide To Southwest Hawaii Flights
Southwest Airlines will be offering free inflight entertainment onboard flights to Hawaii. Photo: Southwest

Southwest will offer gate-to-gate wifi for only $8 a day for each device. Compared to many other airlines, this is an excellent deal if you’re looking to stay connected with social media or Simple Flying en route to Hawaii 😉

If you want to stream some movies and remain disconnected from the world, Southwest will offer free inflight entertainment via their Southwest App. This will definitely help keep kids and family members entertained before deplaning.

If you’re looking to stay away from technology on your getaway, an overwing view could be quite entertaining!

The Ultimate Guide To Southwest Hawaii Flights
Southwest 737-800 from the cabin overlooking the wing after its first-ever landing in Honolulu. Photo: Southwest

On a six-hour flight, people are bound to get hungry. That is why Southwest will introduce a new complimentary snack bag for passengers. Southwest does not have ovens onboard so a hot meal would not be available on these flights.

In addition, Southwest has advertised pitch of 32-inches with 17.8 inches of width and 2 inches of recline. 32-inches is comfortable and a welcome relief from some of the tighter seats that can be found on other aircraft.

Will Southwest Launch More Flights?

As of now, Southwest is only flying nonstop to Hawaii from San Jose and Oakland. In addition, limited intra-island flights will follow from Honolulu to Maui and Kona. Southwest has indicated that Sacramento and San Diego will receive nonstop flights eventually, but as of now, no service has been announced. In addition, Southwest has not announced any service to Lihue, another popular destination in Hawaii.

The Ultimate Guide To Southwest Hawaii Flights
Southwest’s 737-800 and 737 MAX aircraft allow them to potentially start many more routes to Hawaii. Photo: Southwest

The 737-800 and 737 MAX series are versatile aircraft that can handle long hops across the Pacific in addition to the short inter-island flights. As such, it could be economically feasible for Southwest to launch more flights, maybe from Los Angeles, Long Beach, or even Las Vegas.

It looks like Southwest will operate a Hawaii “hub” from Honolulu, which is Hawaii’s most populous city. Southwest will face stiff competition from native Hawaiian Airlines….or will they?

Is Hawaiian Airlines Doomed?

Hawaiian Airlines certainly did not want Southwest to enter the Hawaii market. Hawaiian operates in a niche market, targeting passengers in Hawaii and beyond who are either originating or terminating their travels in Hawaii. In addition, Hawaiian dominates the intra-island flights and with Southwest’s introduction, they will now have to price fares competitively in order to remain a major player in Hawaii.

The Ultimate Guide To Southwest Hawaii Flights
Southwest’s Aloha to Hawaii could cause problems for Hawaiian Airlines. Photo: Southwest

Already, some airlines have begun pricing flights competitively or at least tried to. Dubbed the “Southwest effect”, we will have to see how this plays out in the Hawaiian market.

For passengers, Southwest’s entry to the market is a good thing and will provide more choices and options to get to Hawaii from the mainland U.S. and beyond. Currently, Southwest does not have any partner airlines. For international passengers looking to go to Hawaii, it would be easier for them to fly through another carrier like Hawaiian Airlines or a mainland legacy carrier.

I Want to Fly Southwest to Hawaii, When Should I Book?

If you’re in the Northeast or Midwestern United States, you’re probably sick of all the snow by now. If looking outside gives you the motivation to plan a trip to Hawaii, now is the time.

The Ultimate Guide To Southwest Hawaii Flights
Low fares on Southwest could be a driver to getting you out of the cold this winter (or next). Photo: Southwest

As ticket prices can vary on a daily basis, it is always better to book flights earlier rather than later. If you are looking to fly to Hawaii, Southwest could be a great way to get away. For more loyal Southwest fliers, this could be a great use of some Rapid Rewards points or a Companion Pass to finally get that island getaway you’ve been dreaming about.

The Ultimate Guide To Southwest Hawaii Flights
Could this be your next vacation now that Southwest flights to Hawaii are on sale? Photo: National Geographic


Unless you’re looking for a flat-bed or First/Business Class seat to Hawaii, Southwest is an airline that should be on every leisure traveler’s radar to fly to Hawaii on. With competitive pricing, Southwest will certainly shake up this market and it remains to be seen how far Southwest can expand and how much competition Hawaiian Airlines can sustain.

Have any other questions about flying Southwest to Hawaii? Ask us in the comments below and we’ll get back to you!