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I've been meaning to write this post for months now, but this ends up being better timing because January is the PERFECT time to earn this, and because Southwest is expecting to announce their flights to Hawaii in just days or weeks, and it's expected they will sell out fast. So…if you have ever dreamed of going to Hawaii, this is perfect timing because Southwest is the easiest airline I know of to earn free flights, and 2019 is the first time EVER that they will be flying to Hawaii.

Fly to Hawaii for Free with this Points Hack That Works Best during this time of year

If you are unfamiliar with Southwest's credit cards, they are one of the greatest travel hacks of all times, especially if you like getting free flights. Not only do you earn 40,000 bonus points for the sign-up bonus, but if you pair it with their business card, you can earn their companion pass and someone will fly free with you EVERY TIME YOU TRAVEL.

Flying Free with the Companion Pass

If you are unfamiliar with the companion pass, it is earned when you get to 110,000 points and it allows you to fly a companion free (just pay taxes which I believe is around $14 for U.S. flights), on every flight you take. Not only that, but once you earn the companion pass you have it during the year that you earned it, as well as the following year. So if you earn it towards the beginning of the year, you could have almost 2 years of a companion flying FREE! And you can change who that companion is up to 3 times!

If you don't own a business (I've heard of people qualifying for it even if they do something on the side like coaching, piano lessons, photography, etc.), and you just want to earn a free flight to Hawaii, then the next paragraph is for you.

 

How to Fly to Hawaii for Free

If you don't want to own both credit cards, you could probably earn a free flight to Hawaii (or anywhere they fly), or at least a good chunk of it with points on this particular card. Since Southwest hasn't announced their Hawaii fares yet, we don't know how many points a flight will require, but they are likely to offer some really competitive fares, and we have flown to California and Jamaica on our points, so I imagine we will be able to fly to Hawaii for free as well.

Now is a good time to sign up because they have the extra 20,000 points offer (through this link) on top of the 40,000 which only happens during a small time period (ends January 15th).

This is the card that our family used to fly to Disneyland for free (see my post How to get Free flights: How we earn free flights for our family of 5).

One of my favorite things about Southwest flying to Hawaii (besides the option to earn flights with points), is that they offer two free bags, which is awesome for a trip like Hawaii.

 

Tips Before you Fly to Hawaii

Not sure which island you want to go to? Need some more tips as you plan? Here are our guides that we published as we researched and visited each island:

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