Is Getting the Southwest Companion Pass for Hawaii Worth It? (+ Bonus!)

Disclosure: This post may contain affiliate links, meaning if you decide to make a purchase through my links we may earn a commission at no additional cost to you. The Hawai’i Vacation Guide has partnered with CardRatings for our coverage of credit card products. The Hawai’i Vacation Guide and CardRatings may receive a commission from card issuers. Read about our affiliate policies here.

In 2023, we decided to get the Southwest Companion Pass for Hawaii to chip away at our travel spending a little. We fly to Hawaii frequently, and with family scattered around the country, the Companion Pass looked like an excellent fit for us. 

After almost two years of traveling with the Southwest Companion pass to Hawaii, here are our lessons learned.

We’re usually not big fans of using points to fly to Hawaii. In the past few years, airfare has been relatively low, while hotel costs have been sky high, so we’ve used our points to book some great hotel stays with points.

I got the two airline-branded credit cards that we share in our wallet below. I’d book our flights for me and our two kids. With one click on the reservation, I added Erica for free (plus a $5.60 government fee) on the Companion Pass.

But it’s not just the Southwest Companion Pass that helped us: we booked free flights for all of us using Southwest points. That felt wonderful.

In this article, we’ll cover:

1. How to fly to Hawaii for free with one sign-up bonus
2. Whether the Southwest Companion Pass is worth it for you

Pros for Getting the Southwest Companion Pass

After almost two years of flying with Southwest, we are grateful for the companion pass. Here are the reasons why we would get it again.

• We flew to Hawaii or another domestic location about every 1.5 months. Yes, we do a lot of travelling! Therefore, it was super convenient to have Erica fly for free for two years. That was an incredible savings for us.
• We accrued RapidReward points, rewarding us with more free flights with Southwest.
• We flew mainly from the West Coast to Hawaii over the past two years. Southwest has flights across the country, with a particular focus on the West Coast. As 60% of domestic passengers come from the West Coast, this is convenient.
• Southwest is perfect for inter-island flights in Hawaii. They are one of two carriers, and their prices are nearly identical. Therefore, getting a free one-way flight ($50 to $100 is typical) is a nice savings.
• Free checked bags. Although our Hawaii packing list is minimal, it’s a luxury to check our small bags at the airport, so we don’t have to carry kids and bags. Although Southwest has discontinued free checked bags, booking with their credit card still allows each passenger one checked bag for free.
• The annual fee on the two cards was offset by the Companion Pass savings. Yes, the annual fee was expensive, but it more than paid for itself in RapidReward points earned and free flights.

Cons for Getting the Southwest Companion Pass

Getting a pass wasn’t all sunshine and rainbows. Though we did see a lot of rainbows in Hawaii.

• Southwest flights aren’t always the cheapest or most convenient. We never blindly booked Southwest for our flights. We always shop around. For example, sometimes United was cheaper or had a less painful flight option. We can’t do Maui red-eye flights on every trip!
• A mainland flight to Hawaii is long! Southwest isn’t the most comfortable for those five to eight-hour flights. Bring lots of entertainment and snacks!
• East Coast flights to Hawaii on Southwest can be difficult. For our friends on the East Coast, check your local Southwest flights to see if booking with Southwest is a reasonable option.

Final Decision on the Southwest Companion Pass to Hawaii

Yes, the companion pass was a great deal for us over the past two years.

Our goal was to save money on travel, and it did just that. Although there were some minor discomforts with the boarding process and seating, the savings and convenience helped us save a lot of money.

Now that I have the credit cards, as described below, Erica can apply for additional credit cards that will help us obtain a Southwest Companion Pass for me for the next two years.

If you are planning an epic trip to Hawaii for the first time, or you are a frequent visitor, here’s what you need to know. You should consider applying for their credit cards.

Southwest Companion Pass: Hawaii Edition

The Southwest Companion Pass allows you to choose one person to fly with you, free of airline charges every time you fly.

Note: You are required to pay a $5.60 9/11 government fee every time you fly. The fee applies when you’re paying for your flight with dollars and/or points. 

The companion pass is good for the year in which you earn it! PLUS the entire next year.

So if you earn it in January 2026, it’s good for all of your travels in 2026 AND 2027. That’s just shy of two full years of having a companion travel with you for free. 

You can change the person designated as your companion three times in each calendar year that you have Companion Pass status. 

The Companion Pass is good for anywhere Southwest flies. So if you are booking a flight to Hawaii and you have earned Companion Pass status, you can bring a companion with you for just $11.20 round-trip.

The part that got me initially hung up was how to book the free companion pass. This is how you do it; it is super simple.

1. Book your flight for yourself and your kids. Do not book your companion. You will get a reservation number. So, I’d book three flights (Henry, Edith, and me). I would not book a flight for Erica. Yes, it feels weird.
2. Go to your reservation on Southwest. You will see an option at the top; they don’t try to hide it to add a companion.
3. Click to add your companion. They will charge you the $5.60 per-trip book fee. You will get a second reservation number for your companion. Erica, in our case.

More Hawaii with Points Resources:

• 9 Steps to Plan a Hawaii Vacation on a Budget
• Booking a Trip to Oahu with Points
• 7 Credit Card Myths About Reward Travel

Earning the Southwest Companion Pass

There are two ways you can earn the Southwest Companion Pass:

1. Take 100 qualifying one-way flights in a calendar year
2. Earn 135,000 Rapid Rewards points in one calendar year

We’re going to focus on the second option because you can earn Rapid Rewards points by signing up for an airline-branded credit card. Much easier!

Signing up for a personal card usually gets you 50,000 points, but at the time of publishing, they’re offering an elevated sign-up bonus of 100,000 points on all three of their personal cards.

They also give you 10,000 points towards your companion pass status (those aren’t points that can be used to book travel, unfortunately). That gets you over halfway there! 

After opening one card, you just have 25,000 more Rapid Rewards points to earn before you get your Companion Pass. You can do that through traveling, spending with your credit card, or by opening another credit card.

Points transferred to Southwest or points purchased from Southwest don’t count toward your Companion Pass points requirement. 

But here’s the catch: they don’t allow you to hold two personal credit cards at one time. 

If you want to earn the Companion Pass quickly and from opening up credit cards, you’ll need to open one personal credit card and one business credit card.

You don’t need to have a big business to sign up for a business credit card. A small side hustle (dog walking! babysitting!) can count. See our article on qualifying for a business credit card.

Our Southwest Companion Pass Strategy

I opened a personal card and a business card. Between those two cards, we hit the points requirement to qualify for the Companion Pass.

Remember: you only get the Companion Pass for the calendar year in which you earn it and the next calendar year. So you do not want to complete the award spend late in the year.

With my Companion Pass, Erica was my companion for two years, so we could automatically save 25% on all Southwest flights that we took.

Plus, the credit card welcome bonus points we received, along with the points we earned by booking flights and using our cards, helped us book our family of four two round-trip flights to Hawaii for free (well, technically paid $44.80 each time, but I didn’t complain).

We also had trips across the country to visit grandparents and cousins, so we put the Companion Pass to good use. 

Is the Southwest Companion Pass Worth it for Hawaii?

If you’re only planning to fly to Hawaii once, this isn’t the deal for you. If I were in this situation, I’d look for the cheapest fare on my flight and then focus on getting my hotel stays for free. Hotels are costly, and some of our favorite hotels offer exceptional points deals. 

If you plan to travel extensively with Southwest over the next two years and almost always with another person, it could be a significant cost saver!

Another great deal for free flights to Hawaii is grabbing our favorite travel card. That card enables you to transfer points to airline partners that go to Hawaii and more destinations around the world. We also use that card to offset our trips to Hawaii. Learn more below on traveling to Hawaii with points.