Hawaii - Southwest Airlines

Does Southwest Airlines fly to Hawaii? The answer is: Not yet. But it’s coming…

How great would that be?! We had plans to use miles and points to fly to Hawaii one spring break, but I gave up after it became too up in the air that we would find award availability on United using Singapore KrisFlyer miles. When you’re planning Spring Break for a family, you’ve got to be sure you have a plan in place. Unfortunately, most people can’t just book our trip a week ahead of time when award tickets become available.

Of course, that’s why I prefer to fly Southwest Airlines using points, because you can book any trip any time using Southwest Rapid Rewards points — no crossing your fingers and hoping that magic ticket appears. No waiting around for award tickets to be available! BUT if we want to get to Hawaii, right now Southwest is not an option.

Southwest Airlines and Hawaii

Southwest Airlines CEO Gary Kelly has said over the years that Southwest is considering adding Hawaii, as well as Canada and Alaska, to its list of destinations. Just this year Southwest added Grand Cayman Islands – yea!

A 2016 Chicago Business Journal article said, “Though Southwest has been rumored to want to add Hawaii for some time, [Gary] Kelly said weaving the island paradise into the carrier’s route system has been complicated by crew scheduling issues and the longer flying times involved.”

In October 2016 Kelly said, “Five years from now I’d love for Southwest to be in Hawaii, serving Canada, more destinations in the Caribbean and no doubt we’ll have more flights into Mexico.”

In a post on Million Mile Secrets, the bloggers at BeyondHonolulu.com said that flight attendants on one of their recent flights to Aruba “announced Southwest will be going to Hawaii soon.” Whoo hoo! Those bloggers did a complete analysis of what steps Southwest will need to take and what steps they have taken in order to add Hawaii as a destination. They give you all the facts thus far. Read their analysis.

It all sounds promising and like it WILL come to fruition, but I think we’ll just have to stay tuned to see WHEN it may happen. Can you imagine flying one person FREE to Hawaii using the Companion Pass? Yes please!

To learn how easy it is to earn the Southwest Companion Pass, which lets one person fly free with you for up to two years, and begin flying free on Southwest, download my free step-by-step guide.


I think we’ll wait to book any Hawaii trips until Southwest gets on board. What about you?

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