Southwest CEO Says “WEEKS AWAY” From Selling Flights to Hawaii – Here’s How You Can Save HUNDREDS on Your Tickets to the Aloha State

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I’ve never heard language this urgent from the Southwest about their upcoming flights to Hawaii.

We’ve known for a while that Southwest would begin service to Hawaii in Q1 of 2019.  In other words, the worst case scenario would mean you and me waiting until March 31, 2019, to buy a ticket.

But yesterday, CEO Gary Kelly said that Southwest is WEEKS away from selling flights to Hawaii.  In my mind, that indicates less than 2 months.  So folks with the Southwest Companion Pass (literally the best deal in travel) don’t have to wait much longer to start saving hundreds and hundreds on every visit to Hawaii!

If you want to know the moment Southwest begins selling flights to Polynesian utopia, sign up for our email newsletter!  You don’t want to find out after all the best travel dates are taken.

I’ll Be Flying Southwest to Revisit Oahu and Maybe Climb the Haiku Stairs Again

Southwest Unbelievably Close to Hawaii Service

Southwest’s CEO says that once the Federal Aviation Administration gives them the OK, their Hawaii marketing would launch almost immediately.  And actual flights would begin very soon after.

Based on his verbiage, we’ll likely see Southwest selling flights to Hawaii by early February 2019.  Plus, Southwest will offer service between the Hawaiian Islands, so you can hop around for cheap!

And if you’ve got the Southwest Companion Pass or a stash of Chase Ultimate Rewards points, prepare to save in a huge way.

The Companion Pass allows a friend or family member to travel with you for (nearly) free, whenever you travel on Southwest.  Even if you fly to Hawaii 300 times next year, your travel companion can come with you and receive 300 free flights.  And it doesn’t matter if your flight is booked with points or paid for with cash.

Emily and Keith both have the Companion Pass and use it all the time to bring their Sig-Os with them on their adventures.  You can read this post to see how surprisingly easy the Southwest Companion Pass is to earn!

Even for those of us without the Companion Pass, Southwest is likely to be our go-to Hawaii airline.  That’s because Southwest gives everyone 2 free checked bags, as well as free flight changes and cancellations.  Many on our team book free flights by transferring Chase Ultimate Rewards points to Southwest from cards like:

  • Ink Business Preferred
  • Chase Sapphire Preferred Card
  • Chase Sapphire Reserve

Just opening one of those cards will earn you between $750 and $1,000 in free Southwest flights.

We’re all anxious for these routes to Hawaii.  We’ll let you know when we hear another update!

Joseph Hostetler is a full-time writer for Million Mile Secrets, covering miles and points tips and tricks, as well as helpful travel-related news and deals.

Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)

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