How to fly Southwest to Maui for free and 10 photos that will make you want to go there.
Is Hawaii on your bucket list of places to go on vacation? You’re not alone! Each year almost 10 million people visit the Islands (not counting 2020), but as I’m sure you know, it’s not cheap. Good news, though. I’m going to share with you how you can fly on Southwest to Maui and any other Hawaiian island for free!
Well, almost free. So completely cheap, it’s practically free. Hang with me and I’ll explain what I mean in just a bit.
But first, let’s get our Hawaiian juices flowing with a few photos to remind us why people fall in love with Hawaii to begin with.
If you’re anxious to learn how to fly to Hawaii for free, skip the pictures and get straight to it! Then, we’ll lay out the plan so you can see exactly what you can do to fly on Southwest to Maui (our favorite Hawaiian island!) for free!
There is just something so dreamy about Hawaii that makes the rest of the world (and all it’s responsibilities) seem far, far away.
Probably because it is far away. In our case, Hawaii is 2665 miles from Seattle to be exact.
That’s not a cheap plane ticket even if you live on the west coast like we do. Most of the time you’re doing good if you can find a roundtrip ticket for less than $500.
Since most people don’t travel alone, that’s at least $500 multiplied by however many people you’re bringing with you.
If you’ve read my post on how to score a Southwest Airlines Companion Pass, you’ll know I’m a big fan of using credit card sign up bonuses to rack up miles and points. These miles and points are like gold when it comes to getting free flights and hotel stays!
If you’re just starting to learn about this, believe me when I say you’re going to feel like a kid in a candy store once you realize how easily it can be done.
Related: 27 Tips for First Time Flyers
How to fly to Hawaii for Free using points.
You can read all about how to get the Southwest Airlines Companion Pass here. For now, let’s use that airline as an example to show how you can fly to Hawaii on Southwest Airlines for free.
Currently, a round trip ticket from Seattle to Maui in May of this year costs $515.40.
However, that same flight is 35,000 points if you use Southwest’s Rapid Rewards program. If you used the two card method to earn your companion pass, you’ll be sitting on at least 138,000 points to use toward free flights and you get to fly one person with you for free!
That means you can fly a family of four to Maui on Southwest for 105,000 points. That’s $2,061.60 worth of flying that you’re not having to pay. How cool is that?
Now, I do need to mention that even tickets “bought” with points are subjected to the US 9/11 Security Fee of $5.60 per flight. So each roundtrip ticket actually costs $11.20. With that in mind, a family of four using points to buy their tickets can fly to Hawaii and back for $44.80 out of pocket expense.
That’s the same as paying for four pizzas from Costco.
About Credit Cards
Before we go any further, I want to put out a big ol’ disclaimer and say that if you are not in a position to pay off a credit card every month, this is not something I want you to get into.
Clearly, if you know you have a hard time keeping track of expenses and aren’t certain you can pay your balance off at the end of the month, you need to figure that out first. To be even more clear, there’s no vacation in the world that’s worth racking up debt and potentially ruining your credit.
Rodney and I have spent a good bit of time over the years helping people set up budgets and teaching them how to be fiscally responsible. Credit cards are not bad, but abusing credit cards is.
Now, back to the good stuff and figuring out how to fly to Hawaii for free. I mentioned the Southwest Airlines Companion Pass and all the points you’ll accumulate in the process of getting it. There are several other cards worth mentioning you could get and use the sign up bonus points to fly to Hawaii for free. (Same $11.20 per round trip ticket applies.)
At the time of this writing, here are some current bonus offers by a few specific cards. You can find more on this Best Offers page.
Chase United MileagePlus Explorer Card – 60,000 bonus points when you spend $3,000 in the first three months. You’ll get an estimated value of $800 in free travel. (If you and a partner team up and each get a card, you’ll end up with 120,000 miles to play with!)
American Express Platinum Delta SkyMiles – 80,000 Delta SkyMiles Points after you spend $3,000 in the first 3 months. You’ll get an estimated value of $900 in free travel.
Chase Sapphire Preferred Card – 60,000 Chase Ultimate Rewards Points after you spend $4,000 in the first 3 months and you get an estimated value of $750 in free travel.
Even more perks
In addition to the sign up bonuses, some of these cards offer other perks such as $100 credit toward signing up for Global Entry and TSA Precheck and additional bonus miles on your one year anniversary. Most have an annual fee, although they are offset by the bonuses. Be sure to read all the details to decide which one is best for you.
I hope I’ve given you an idea of how to get started with your travel planning. It’s not something you can decide you want today and then book it tomorrow. However, with a little strategy you can put together some pretty awesome vacations to take in the not-so-distant-future, including flying to Hawaii for practically free!
Using Credit Card Bonuses for Free Hotel Stays
Did you know there are also credit cards that offer sign up bonus points you can use to stay free at hotels? We’re not talking Motel 6, either.
Coming soon, I’ll share some examples of exactly how you can stay in Hawaii for free! With free flights and a free hotel, you’ll have earned yourself a free trip to Hawaii!
Until then, I’ll be dreaming about waking up to this view every morning and planning my next trip…for free, of course!
If you want more sure fire ways to save money on travel, be sure to sign up for our weekly email list!
PS. I use TravelFreely to keep track of all my award programs. I love having my points info all in one place! They also make it very easy to know which credit cards are best to help reach my goals and to make sure I don’t mess up the Chase 5/24 rule. It’s free to use, so be sure to sign up!