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What You Need to Know About Southwest’s Future Destinations: Hawaii, Canada, and More Are Up Next!

  • Million Mile Secrets

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    Lyn writes about how to fly free on Southwest and has a free guide that shows you step-by-step how to earn their coveted Southwest Companion Pass.  The pass lets 1 person fly nearly free with you for up to 2 years.  The Million Mile Secrets team agrees it’s THE best deal in travel.

    We’ve asked Lyn to share the latest news on where Southwest is headed next, including that ONE destination we think everyone is interested in: Hawaii!

    Lyn:  While we do know for sure that Southwest will be flying to Hawaii, CEO Gary Kelly has recently thrown around a lot of other destinations as well, like Canada, South America, and even Europe.

    I Can’t WAIT to Be Able to Use My Companion Pass to Fly to Hawaii!

    According to an article in the Orlando Sentinel, Kelly said, “Southwest is eyeing a host of expansion opportunities within the next 25 years, with as many as 50 additional North and South American route expansions under consideration.”

    Here’s the latest scoop on what he’s said and when you can look for tickets to go on sale to Hawaii.

    Get Ready to Hula in Hawaii

    I know lots of readers are antsy to fly to Hawaii on Southwest – and better yet – use their Companion Pass to bring someone with them for free.  Now that’s a deal!

    When the airline first announced they’d be flying to Hawaii, we all hoped flights would start in time for summer vacations in 2018.  But clearly, that was a no-go.

    Me in Hawaii in Fourth Grade! Here’s Hoping I Can Fly There Again, This Time on Southwest With My Own Kids!

    Instead, in many interviews and investor meetings, Kelly has repeated that they will sell tickets to Hawaii by the end of 2018 and begin flying there in early 2019.  The next release of flights will be June 28, 2018, when they will open their calendar for booking flights through March 6, 2019.  We can all hope, just maybe, Hawaii will show up. 😉

    Here’s what we do know:

    Stay posted to Southwest’s Hawaii page, Million Mile Secrets, and Go to Travel Gal for updates and information.

    Oh, Canada!

    It looks like Hawaii isn’t the only upcoming destination Southwest has set its sites set on.  According to ch-aviation, at the company’s annual shareholder meeting in May 2018, Kelly indicated he’s interested in flying to Canada from Baltimore.

    One Day (Hopefully Soon!) You Might Be Able to Fly to the Beautiful City of Toronto on Southwest!

    He even said that Baltimore could be a launching point for transatlantic flights to Europe, as well (drooling over here…that would be amazing!).

    Would you fly to Canada on Southwest?

    Serving South America

    Southwest has already expanded its footprint to destinations across Mexico, the Caribbean, and Central America, currently flying to:

    Southwest Now Flies to Grand Cayman. What’s Next for the Airline?

    So it makes sense that South America could be the next logical destination for them.  A CNBC article suggested possible destinations include Colombia, Ecuador, and Peru.

    Despite all these exciting possibilities, Kelly has indicated that Hawaii will be the focus for 2019.  So don’t look for any of this to happen before then.  In fact, according to CNBC, he is quoted as saying it could take 25 years!

    Where do you wish Southwest would fly?  Paris, anyone?

    Bottom Line

    While Southwest has always been a great airline to fly nearly anywhere in the US, they are taking their low fares and outstanding customer service and expanding to more and more destinations.  Hawaii should be coming online before year’s end, and then we’ll see what comes next: Canada, Peru, London?

    Want more ideas on how to earn the most miles and points for free travel?  Sign-up for our newsletter and follow us on Facebook and Twitter so you never miss another travel tip or trick!

    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! :)