How to Fly to Hawaii for Free

If you read our last post, you know that we stayed in Hawaii for 7 nights for FREE, saving us over $6k on our trip!  I shared our strategy outlining how you can also get a 7-night stay for free.  In addition to having free accommodations, we also got free flights (with the exception of taxes and fees, which were $140)!

Since we were flying from the East coast (Ohio), we decided to break up our flights by flying to California first, before heading to Hawaii.  There were flights available from Pittsburgh to Honolulu with a short layover in Las Vegas, but the idea of an 11-hour flight with just a short layover just didn’t sound appealing to me.  We asked all of our kids what their preference was and they unanimously agreed on sleeping in California before heading to Hawaii.

Our trip consisted of 5 different Southwest flights:

• Cleveland to Los Angeles (layover in St. Louis)
• Los Angeles to Honolulu (direct)
• Honolulu to Maui (direct)
• Maui to Los Angeles (direct)
• Long Beach to Cleveland (layover in Denver)

We’ve flown on several different airlines, but for this trip, we decided to fly Southwest Airlines.  As with any airline, there are pros and cons, but the pros outweighed the cons in this situation.

What we LOVE about Southwest Airlines

FREE Bags

When you’re visiting places where you need to pack more than a backpack, Southwest is super convenient.  Not only can you bring a personal item, such as a backpack, but you can also check 2 bags per person for free AND bring carry-on luggage.  Our family of 5 traveled with two checked bags, one carry-on and our backpacks, which fit everything we needed for our 10-day trip.  Plus, they don’t make you stick your backpack in a bin to make sure it’ll fit under the seat like the budget airlines do!

FREE Cancellation + Changes

If you’re traveling on a budget airline, more than likely if you have to cancel, you lose your money.  However, with Southwest, you can cancel or change your flight up to 10 minutes prior to your scheduled departure time.  We were fortunate enough to use points to fly to Hawaii, but had we paid for these flights, they would have cost our family $3,572.  Now I certainly didn’t plan on canceling my trip, but if we needed to cancel for some reason, I wouldn’t have lost any money.  I love that Southwest gives you added piece of mind!

Get credited if you see a price drop!

Plus, I am not penalized for booking my flight early.  If I book my flight as soon as it’s released and notice that the flight cost decreases, I can easily update my flight on Southwest’s website and the points/money are credited back to me! 

When we booked our Hawaii flights, I booked them about 7 months in advance. I regularly watched prices and some of the segments never got any cheaper.  Other segments, however, did decrease in price/points prior to us leaving so I was able to rebook them.  The points I saved were put right back into my Rapid Rewards account to use at a later time.

FREE In-flight Entertainment

I love the ability to have in-flight movies, tv, flight tracker and more.  We typically download movies and books prior to leaving, but it was so nice to watch some new movies right on the Southwest App.

Companion Pass

One of the biggest ways to save with Southwest is to earn a Companion Pass.  When you earn a Companion Pass, you can select a companion to fly with you FOR FREE, for nearly two years (depending on when it’s earned).  You can read my post here about how to earn these BOGO Free flights!  This was a huge savings for our family on our way to Hawaii! 

Remember when I said the cost of flights would have been $3572 for our family of 5?  A Companion Pass would have saved $714 because my husband flew free on each of our flights!  And since we booked on points, we may not have saved money, but we did save the equivalent in points!

FREE Snacks

Ok…we don’t NEED snacks and are used to flying with airlines that don’t offer them for free, but it is nice. Southwest provides snacks (typically a snack mix) as well as drink service. There isn’t any extra food that you can purchase, but you can purchase alcohol. Since the flight to Hawaii is longer, you get a larger snack pack with a snack mix, Wheat Thins and a cheese dip. Then later in the flight, they bring Brownie Brittle.

What we don’t love about Southwest

Seating Policy

A lot of people either aren’t too familiar with or just don’t like Southwest’s seating policy.  If you’re not aware, Southwest has an open seating policy.  This means that no seats are assigned prior to boarding, which can be stressful for some people.  The good thing is, you don’t have to pay for your seats like you would on a budget airline.  However, if you end up boarding last, you could end up separated from your family members.

How does Southwest’s seating policy work?

When you check in before your flight (24 hours prior), you’ll be placed into one of three boarding positions—either A, B or C.  The group you are assigned is based on how soon you check in.  In the airport, you’ll line up according to your boarding position (each has 60 guests).

The plane is loaded by boarding position.  Those with A go first.  Then, they load “pre-boarders.”  These are guests traveling with children under 6, military or A-list (Southwest frequent flyers).  For anyone traveling with small children, this allows you to ensure you’re seated with your child. After pre-boards, they load group B and then finally group C.

If you are in group A up through mid-B, you probably won’t have issues finding seats together—even for larger parties of 5 or 6.  However, if you get the end of the B group or C group, you’ll likely be split up, especially if the plane is full or if there are a lot of pre-boarders.

For our flight home from Maui, we were in the end of group B/beginning of group C and there were so many kids who were able to pre-board; plus, the flight was completely full.  In this situation, we did get split up, but we were still paired together.  My youngest son and I were in row 13, seated together.  My husband was in row 14, by himself and my two older kids were seated next to each other in row 18.  This was totally fine for us—as long as we’re paired up, we’re good to go!

Ways to guarantee you’re seated together

Check in 24 hours before your flight

When I say 24 hours before, I mean 24 hours ON THE DOT!  Even a minute later will throw you into a later boarding position.

Pay for early check in

If you want an early boarding position and don’t want to deal with the 24-hour check-in, Southwest will do it for you, for a fee. If you have the Southwest Personal credit card, you can get 2 of these for free.

Pay for upgraded boarding

This cost is pretty hefty ($50/person) and is only available after check-in.  If spots are available, you’ll have the ability to upgrade to get group A 1-15 boarding.  If you have the Southwest Business Performance credit card, you can get 4 of these free.

Purchase Business Select or Anytime fares

There are four fares to book via Southwest.  When booking Business Select, you’ll get A 1-15 boarding position and Anytime fares, give you early check-in, which pretty much guarantee you’ll be with your family.

Bottom line

We’ve honestly just always checked in early and been able to sit together.  We did use an upgraded boarding when we were initially in group C, but that’s only because we have the Southwest Business Performance credit card and get this free.  We’re also used to flying cheaper airlines where we are likely to get completely split up so taking our chances on Southwest is really no different.

Southwest Flights can only be found/purchased on Southwest.com

I use both Skyscanner and Google Flights to check flight costs from my nearby airports.  I love that I can search and leave my destination open.  I’ve found awesome flight prices this way!  In September, our family of 5 flew round-trip to Fort Lauderdale for $181.50.  And that was our TOTAL for ALL 5 of us!  You can read more about that here.

Southwest doesn’t show up on these search engines though. You have to go to Southwest.com and search to find flight costs.  Just remember, when doing a price comparison between Southwest and other airlines, it’s important to take into consideration what you’ll pay extra for on other airlines. 

When we found our cheap flights to Fort Lauderdale, we didn’t choose to pay extra for our seats and we packed everything in we needed in our bookbags.  However, if we were set on sitting together and needed to more luggage, those flights would have been significantly more.  When comparing those airlines with Southwest, it’s important to go all the way through to see what the final cost will actually be.

How we got 5 FREE Roundtrip Flights

Just like we used our Hilton credit cards to get our hotels paid for, we used other cards to get our flights paid for.  The total cost of flights, in points, was 245,130.  However, remember that we got the Companion pass by getting the Southwest Personal Card and Southwest Business Performance Cards and meeting the minimum spend.  That means our total point cost for the 5 of us dropped to 196,104. This also included our island hop from Oahu to Maui, which was around 11k points.

Steps to earn your own FREE flights

Here’s how you can earn enough Southwest Points to purchase tickets for your family.  Flights were roughly 49k for roundtrip flights from Ohio to Hawaii + an inter-island flight to Maui.  If you factor in a Companion Pass, cost will be around 39k/person.

Southwest Credit Cards

Once you are approved for and meet the minimum spend of the Southwest Personal credit card, you’ll earn 70k points.  If you also get the Southwest Business Performance Card, you’ll earn another 80k points after hitting your minimum spend.  That means you will have 150k points to spend + earn the Companion Pass!

Chase Credit Cards

You can also earn Chase Ultimate Rewards by signing up for the Chase Sapphire Preferred, Chase Ink Business Preferred, Chase Ink Business Cash or Chase Ink Business Unlimited cards.  To get a “business card,” you do need to have a business; however, there are lots of ways to qualify as a business.  For instance, reselling items on Marketplace or other side hustles count as a business. 

Chase Ultimate Rewards points are different in that you can actually transfer them to a variety of airlines and hotel chains.  All of these points are earned by simply using these cards for your everyday spending.  Remember, you should only be putting charges to these credit cards that you can pay off monthly.  Otherwise, paying interest will just end up costing you more than you’ve earned.

Ready to start earning your next trip FREE?

It may sound a little overwhelming figuring out how to earn points and then spend them, but when you get to travel for nearly free, it’ll be all worth the learning curve!  Start small, earning one bonus at a time just to help offset costs.  Between flights and hotels, we saved almost 10k on our trip to Hawaii.  Those savings allowed us to take a trip that we didn’t think would be possible without years of saving.  And because we saved so much, we were able to spend our money enjoying actitivies and food without having to budget so much!

Up Next: How we planned our Oahu and Maui activities

Stay tuned for my next post to see what activities we did when we visited Oahu and Maui and how we saved.

Looking for other travel inspiration? Check out our posts about these destinations: Fort Lauderdale, California, Utah’s Mighty 5 National Parks, Universal Studios, Chicago