Does Southwest fly to Hawaii? Yes! It’s true! The airline announced late in 2017 that they will begin Hawaii flights in late 2018 or early 2019!

2019 has arrived and it looks like we’re getting close :).

Imagine being able to fly to Hawaii using Southwest points combined with the Southwest Companion Pass, which lets you bring someone with you to fly FREE for up to two years! Now, that’s a deal!

Want someone to walk you through EXACTLY what you need to do to earn your 2019 Southwest Companion Pass — no guesswork required ;-)? Enroll in my online course, “How to Earn Your 2019 Southwest Companion Pass … Step by Step.” It comes complete with step-by-step checklists, case studies, roadmaps and everything you need to get your pass quickly and cheaply!


The Details

CEO Gary Kelly initially said the plan was to sell tickets in late 2018, though a tighter look by the federal government delayed things a bit along with the January 2019 government shutdown, which further delayed progress.

Hawaii - Southwest Airlines

On February 5, 2019, Southwest completed their first test flight to Hawaii, which means we should be super close! Southwest has repeatedly indicated that everything is ready to go on their end, but that they are just awaiting government approval.

The Southwest Hawaii flights will be from four cities in California, including:

  • Sacramento
  • Oakland
  • San Jose
  • San Diego

In April 2018, Southwest announced it will fly into Maui, as well as the Big Island of Hawaii, Oahu and Kauai. The airports they will serve include:

  • Honolulu International Airport (Oahu)
  • Lihue Airport (Kauai)
  • Kona International Airport at Keahole (Island of Hawaii)
  • Kahului Airport (Maui)

Kelly says the new Boeing MAX aircraft will be the plane they will use for Hawaii flights.

Southwest Airlines Hawaii

Credit Southwest Airlines

Here’s what he had to say when the new destination was originally announced in 2017:

“A day long-awaited by our customers, fans, and more than 55,000 of the world’s most-loved airline employees is finally within sight—a day that will showcase your hospitality, about as far Southwest as you can go in the U.S. Hawaii is an important place for Southwest Airlines because so many people count on us to take them everywhere they want to go reliably and affordably. We’re ready and excited to address a request we’ve heard for years.”

You can watch the announcement for yourself below:

You can not yet book flights to Hawaii, but we’ll let you know as soon as those are released.

What do you think?! Are you excited!! Who’s making plans to go to Hawaii already! (Hand raised…)

If you’re ready to fly to Hawaii RIGHT NOW, sign up for my Fly Free to Hawaii online course that walks you through the simplest way to fly up to four people to the Hawaiian islands completely on miles. It’s perfect for beginners or more advanced travel hackers.

If you’re looking for where to stay, here’s a review of Marriott’s Waiohai Beach Club on Kauai.

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