If you’re interested in going to Maui, Hawaii and not looking to pay the $650 – $850 per ticket sticker price, you’ve come to the right article. 

Today I’d like to share exactly what I did to book Maui flights for my husband and I for $22.40. 

That’s $11.20 per ticket or $5.60 each way that must be paid by cash or credit card per person.

The rest of the airfare was covered by credit card points.

Here’s how:

1. Sign up for a Southwest Rapid Rewards Credit Card
2. Get the sign-on bonus by spending (and paying off) the minimum spend
3. Get the Southwest Companion Pass
4. Pay bills, gas, groceries, etc. to build up even more rewards points
5. Find the best time and flight prices to spend your bonus on
6. Book flight
7. Add your Companion to your flight itinerary for free

Get the Southwest Rapid Rewards Plus Credit Card

First, I signed up for the Southwest Rapid Rewards Plus credit card.

Southwest credit cards provide a variety of perks for credit card holders.

Obviously flying with Southwest is the best way to earn AND redeem points.

Big secret there… so that’s exactly what I did.

Southwest cards are uniquely beneficial for Hawaii trips too because the airline tends to have some of the most competitive prices for flights to the island.

Key Tip: Make sure to read about the benefits, bonus offers, and requirements of the Southwest Rapid Rewards Plus card before signing up.

For me, it made sense because we were already looking at going to Hawaii, but if you plan to fly outside of the country, even the excellence that is the Companion Pass won’t help you reach your goals.

Hit the Sign on Bonus

The next step is to hit the minimum spend and get the Southwest sign-on bonus.

The strategy I used to hit the $5,000 in 3 months minimum spend without spending money on things I didn’t really need or going out of the norm of our normal accounted-for spending, was to prepay bills.

Granted, our regular bills and spending could have been enough to take care of most of the amount, but to speed up the process and ensure I could hit the $5,000, I pre-paid our internet bill for the rest of the year and then pre-paid our vehicle insurances for 6 months.

This took care of a little over $2,000 of the amount.

This strategy works if you have savings enough to be able to pre-pay bills and if you’ve worked hard to keep your regular bills as low as possible.

The sign-on bonus for the Southwest card at the time was 35,000 bonus points.

This is admittedly very low as far as most credit card sign-on bonuses, but the deal also came with a promotional Companion Pass sign-on bonus.

The bonus prior to this deal was 100,000 point (which I missed at the time) and the bonus now is at 75,000 bonus points.

Southwest Companion Pass

The Companion Pass is one of the best travel perks on the market.

The perk allows a card holder who achieve’s Companion Pass status to select a companion who can fly free with the exception of taxes and fees.

Waiting for the right sign-on bonus is a strategic step in getting free flights, so once Southwest released its companion pass promo bonus, it was an easy decision for me to sign up.

For all my planners out there, I know it may be a tough idea to wait on booking / planning your vacation until you can sign up for the most advantageous credit card sign-on bonus, but it is worth it.

Also, with Southwest, you shouldn’t have to wait very long, as Southwest rolls out new sign-on bonuses from every quarter to ever couple of months.

There are other ways to qualify for the Companion Pass as well.

• By getting 125,000 bonus points in a calendar year

• Or by flying 100 qualifying Southwest flights.

The qualifying points example works when the sign-on bonus of a credit card is high. For instance, in December of 2021, Southwest ran the 100,000 point sign-on bonus deal.

I could have hit the minimum spend by Feb. or March 2022 and got those bonus points.

Then, I could have spent strategically to get another 25,000 points in swipes by my regular grocery spending and by using the Southwest shopping portal.

The bonus of hitting the Companion Pass this way, is it is good for the remainder of the year in which you get the Companion status and for the entire calendar year the following year.

Get Swipes and Play the Points Game

Once I got my 35,000 bonus points and Companion pass, I was a couple of hundred dollars away from completing paying for my ticket.

35,000 bonus points are equal to about $490.00 dollars.

To acquire more points, I made sure my husband and I used the Southwest card for all gas, groceries, and bills spending.

I also hopped on the Southwest portal and took advantage of some bonus point opportunities Southwest was running. The Thrive Market 15 points per dollar incentive helped me reach my points goals for the Maui flights as well as some health goals during our Month of Whole 30.

Find the Best Flight Prices

This is going to sound a little extreme, but to find the best flight times and prices for our trip, I made a couple of trips to the local library.

I think I ended up running to the library a mile up the street four evenings before I was ready to book.

Why the Library you ask?

Didn’t you pre-pay your internet?

Yes, I did, but since I have yet to figure out the VPN game and hiding flight searches, I go to the library to avoid the inevitable price hikes that comes with repeatedly visiting a flight itinerary.

Once we settled on the best time to take off of work and the best flight prices, which also happened to be the first week of September for Labor Day, we were ready to book the flights.

Booking the Flight

Booking the flight with points is a matter of searching for your predetermined itinerary and selecting the points filter in Southwest’s flight portal.

I was still short 6,000 points or $84 dollars at the tie of booking, so I ended up transferring points from another credit card to my Southwest card.

I have the Chase Sapphire Preferred card, which is also a Chase card, so the points transfer went through in minutes.

It’s important to note that since I was short just under 7,000 points, I still had to transfer 7,000 points as you have to round up to the nearest 1,000 point. I didn’t lose but 240 points in the transfer though.

And while many travel gurus will tell you it’s not the best idea to transfer points to Southwest, it was the best route in this particular care.

I’d contend that even though Southwest Points aren’t as flexible as Chase Sapphire points, the points in Rapid Rewards for this particular itinerary were worth more cents than if they were to stay in the Chase Sapphire card side.

I ended up booking through the Southwest website instead of over the phone like the Points Guy suggested because the customer service rep couldn’t guarantee that I would have the same cancellation flexibility as I would with booking through the Southwest portal.

So, instead of take chance of losing all the points should something happen in a couple of months, I sacrificed the 5x Chase Sapphire points PLUS the 2x points for Rapid Rewards by booking through the Chase portal and booked through the Southwest website.

Add Companion to Itinerary

The last step after I booked my flight was to go to the ‘My Trips’ section of Southwest and simply add my husband to the itinerary. He was added in seconds and all I had to pay was another $11.20 for the taxes and fees for his round trip flight.

I hope this quick guide helped give you some ideas on how you can potentially save money on a trip in the future. The rules and perks and sign on bonuses are always changing, but they don’t stray too far from the bonuses and perks discussed here, so this article is a good step in the direction of getting your barrens in the travel hacking space.