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For those of us who are frequent Southwest fliers and Southwest fans, the question of when will Southwest fly to Hawaii has been a big question.  Southwest has often said that it’s no longer a question of IF they will fly to Hawaii but now WHEN Southwest will fly to Hawaii.  A few weeks ago, Southwest announced publicly that they were flying to Hawaii, but… didn’t really give any details about when Southwest would start flying to Hawaii.  There are also no known Southwest Hawaii destinations – so we don’t yet know if they will fly to Honolulu, Maui, Kauai or anywhere else.  We don’t even know where Southwest will fly to Hawaii FROM, though California airports like SFO, OAK, SJC, LAX or SAN seem to be most people’s best bets.

Winter escape to Hawaii

Image courtesy of Jason Francisco

Easy Southwest Companion Pass for California residents

Yesterday’s news and notes post contained information about how California residents are being targeted for an offer where they can receive the Southwest Companion Pass by signing up for one of 3 Southwest credit cards and making only ONE purchase (rather than the regular offer which requires earning 110,000 Rapid Rewards points in one calendar year.  This offer came out a few weeks ago but was targeted – now though it is open to ALL California residents.

[Southwest Companion Pass: What is it and how to get it]

You generally do have to be under Chase 5/24 to be approved for a Southwest card, though it is not 100% clear to me at this point if you would be eligible for the Companion Pass offer if you’ve gotten a signup bonus on the Southwest card you apply for in the past 24 months (I assume you wouldn’t earn the signup points but would you still get the CP?)

The Southwest Companion Pass you earn through this promotion would be good through the end of 2018.

Speculation wondering when will Southwest fly to Hawaii

When I shared the news on this California Southwest Companion Pass offer over on the Points With a Crew miles and points Facebook group, one of the people I thought about was Leslie from Trips with Tykes.  Similar to PWaC, Trips with Tykes is a blog that covers both family travel and miles and points.  I’ve met Leslie a few times and she is my go-to expert on all things Disney as well as (if you’re a blogger like me) Pinterest.  She replied with something that I found interesting


I think that speculation on when will Southwest fly to Hawaii is very good one and has a decent shot at being right.  Southwest’s initial Hawaii announcement said that they hoped to start selling TICKETS to Hawaii in 2018, but that doesn’t mean those tickets are for FLIGHTS that will happen in 2018 :-).  California is a crowded airline market with American, Delta, Virgin / Alaska and Southwest all heavily invested – so getting a jumpstart in the hearts and minds of California residents before starting Hawaii service seems like fairly sound marketing strategy

We still don’t even know if the Companion Pass will be good for flights to Hawaii, or if it may come with additional restrictions (an additional copay on Southwest flights to Hawaii?)

Readers what do you think?  When will Southwest fly to Hawaii? Do you think the California Companion Pass offer is part of their Hawaii marketing strategy?

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