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Last October we learned that Southwest was going to begin service to Hawaii from California in 2018 on their new Boeing 737 Max 8 planes. We don’t yet know the exact routes yet, we did find out which cities will be served on the mainland as well as Hawaii.


Southwest will serve the following Hawaiian destinations:

  • Lihue, Kauai (LIH)
  • Honolulu, Oahu (HNL)
  • Kahului, Maui (OGG)
  • Kona, Island of Hawaii (KOA)


Southwest will serve Hawaii from the following cities in California:

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


Again, we don’t yet know what the routes will be–and it’s not likely they will begin when flights between Hawaii and the mainland start–but eventually Southwest intends to fly between the islands.


While Southwest has FAA authorization to fly between these destinations listed above, they are still waiting in approval to start selling tickets and commence service. Flights should go on sale at some point in 2018, and actual service might start before the end of this year.

Companion Pass and Points to Get There

The Companion Pass allows you to designate a companion who flies for just the taxes on every Southwest flight you fly. It’s easily one of the best deals in travel if you fly often domestically.

You can earn it by either…

  • flying 100 paid segments
  • accumulating 110,000 Rapid Rewards within a calendar year, which you could do by spending a ton of money on one Southwest Card, flying a bunch of paid flights, or opening and meeting the minimum spending requirements on two Southwest Credit Cards + some extra spending/shopping portal bonus earning
    • You cannot, however, open two personal Southwest cards at once, thanks to a new eligibility rule. One business card bonus + one personal card bonus is still a viable combo. You could open one business and one personal card, earn 105,000 Rapid Rewards from a 60k bonus + 40k bonus + 5k in non-bonused spending meeting the requirement, and then spend another $5,000 on one or collectively both of those cards.

The Companion Pass is good for the calendar year (January 1 to December 31) in which you earn the qualifying points as well as the following year, so timing when you earn it is wise if you want to fully maximize its potential value. To get two full years of Companion Pass benefits, you’ll want to meet the point requirement in the beginning of the calendar year so your companion can fly free for all of that year as well as the following. If you want the Companion Pass for flying to Hawaii, the timing should work out well with when service is expected to start (likely early 2019).

The Waimea Canyon on Kauai
The Waimea Canyon on Kauai

Whatever you do, if you want to earn a Companion Pass for all of 2018 and 2019, make sure you are careful about when you complete your minimum spending requirements as you want your points to post in 2018 and not 2019 (or else you’d get the Companion Pass for a few days in 2018 and 2019–not ideal). Read Timing the Southwest Cards for Companion Pass in 2018 & 2019 for more details about how/when points post and planning your strategy. That post refers to timing for the end of last year, but the same logic applies for timing at the end of this year.

More flights = more competition = lower prices. And I love Southwest’s lack of cancellation and change fees and two free checked bags on every flight, so I find all this to be excellent news. Not to mention Rapid Rewards are easy to come by as you can earn them directly via six separate Chase cards…

  • Southwest Rapid Rewards Plus Credit Card
  • Southwest Rapid Rewards Premier Plus Credit Card
  • Southwest Rapid Rewards Premier Business Credit Card
  • Sapphire Reserve (Ultimate Rewards transfer 1:1 to Rapid Rewards)
  • Sapphire Preferred (Ultimate Rewards transfer 1:1 to Rapid Rewards)
  • Ink Business Preferred (Ultimate Rewards transfer 1:1 to Rapid Rewards)

…or indirectly by three other Chase cards that also earn “Ultimate Rewards”, you just have to transfer them to (and therefore hold) one of the Ultimate Reward-earning cards above first…

  • Freedom
  • Freedom Unlimited
  • Ink Business Cash

Bottom Line

We now know where Southwest will be flying between in Hawaii and California, and that they intend on running interisland service as well. What we still don’t know is what the exact routes are and when service will commence. At the earliest flights will start at the end of this year. I think early 2019 is more likely.

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