What It’s Like to Fly Southwest to Hawaii: OAK to HNL Flight Review

This post is sponsored by Southwest Airlines. All opinions are my own.

Over a year and a half ago, Southwest Airlines announced its intent to fly to Hawaii. As frequent Southwest flyers and regular visitors to the Hawaiian islands already, this was very big news for my traveling family. We've been watching the news carefully ever since, waiting patiently for service to start. We made it a travel priority to fly Southwest's California to Hawaii routes as soon as possible after they launched.

As luck would have it, the stars aligned to make that a possibility. We already had spring break plans to travel to O'ahu to return to Disney's Aulani Resort for spring break this year. Southwest began its Hawaii service just two weeks before our scheduled vacation. The only route that was flying at the time was Oakland (OAK) to Honolulu (HNL) - the very route we needed to get us from our home in the Bay Area to the island of O'ahu.

My family of four flew to Hawaii on Southwest on April 1, returning April 7 (which just happened to be the same day the airline launched its second Hawaii route from Oakland to Maui). I've had so many friends, readers, and followers ask me what flying on Southwest to Hawaii was like, so a full flight recap and review seemed appropriate. If you are considering flying Southwest to Hawaii, here is what the experience entailed, along with my very best tips and tricks for Hawaii travel on Southwest.

(Trips With Tykes uses affiliate links which means I may earn a small commission if you purchase through links in this post. See our full disclosure policy here.)

Booking Flights on Southwest to Hawaii

If you aren't familiar with booking Southwest flights generally, it's important to know that you can only book flights on the airline at Southwest.com. Their flights are not available through third party online booking and search tools like Expedia, Orbitz or Google Flights. That means you need to use one of those other tools to scope other airlines that fly to Hawaii and then go to Southwest.com so you can compare prices and times.

Southwest normally releases its schedules in blocks once every couple of months, adding several weeks worth of flights in the wee morning hours. This happens about 6-9 months in advance. Schedule release dates are usually publicized in advance as well.

Because the initial Southwest Hawaii flights were a special late addition to the schedule, they came out in a block all their own and without pre-warning. The scramble was quick. Friends on the East Coast knew I was looking to book Southwest for a Hawaii trip and began frantically messaging me to wake up on the West Coast and get booked.

Southwest had some screaming deals during that initial release - flights as low as $49 each way from the mainland to Hawaii. I immediately jumped on my computer and saw seats on the very dates we wanted at $79 on the departing flight and $99 on the return. I booked three of us us with Rapid Rewards points in minutes. I then used my Companion Pass to book a free flight for my daughter as my companion. An hour later, the flight I booked was completely sold out. Nearly all the cheapest sale fares for spring and summer flying were gone.

One of the reasons I was able to snag such a great deal is that I was ready to pull the trigger immediately. I had all the pieces in place and executed. When Southwest adds more flights and extends its schedule (whether to Hawaii or otherwise), it is so important to act quickly. Sale fares sell out fast, and popular holiday travel dates will fill up.

Here are a few tips to keep in mind to have the fastest finger and snag the deals for your family too:

• Know your Rapid Rewards numbers: Make sure you have and know Rapid Rewards logins for everyone in your family. You'll need them in one place to book everyone quickly. I use AwardWallet.com to store frequent flyer numbers and passwords in one secure place.
• Save your payment information: Save a credit card to all of your Southwest.com account profiles so you aren't scrambling to complete payment at the moment you need to book.
• Add companions immediately: If you have a Companion Pass, add your companion to your flight immediately after you book your own flight. Otherwise you risk the flight selling out before you get a seat for that person.
• Book first and ask questions later: You can completely and totally refund any Southwest flight within 24 hours of booking. Don't wait to call your husband or wife in these crucial schedule release periods. Book. The. Flight.
• Take advantage of generous cancellation policies if you need to: After that 24 hours has passed, Southwest still has a super-generous cancellation policy. All Rapid Rewards points bookings can be totally refunded (so if you are unsure about a trip and have points, book with those). All cash bookings that are cancelled are given a full credit for use up to one year after the date of original booking.

For even more information, be sure also to read my guide to maximizing a Southwest Airlines fare sale.

Departure Day from OAK to Hawaii on Southwest

A few weeks after we booked these amazing deals, our big Hawaii travel day arrived. Our flight was scheduled at 8:20 am. We live only 15 minutes from the airport so we booked a 6:45am car service. Yep, we like to cut it close. OAK is such an easy airport that it's usually safe to do this unless you are traveling at peak Thanksgiving or Christmas times (see my guide to Oakland Airport with kids for even more information about the airport).

Upon arrival at OAK, we dropped our checked bags at Southwest's self-serve kiosks in Terminal 2. Bags of course fly free on Southwest, so we checked three for our family of 4 at no cost. Oakland's TSA checkpoints have family lanes, so we shortcut most of the lines and sped through security. It's a rare perk afforded to those of us who travel with kids.

Although Southwest is located in Terminal 2, it also operates out of some spillover gates in Terminal 1. The two terminals are connected post-security by a corridor. For now at least, Southwest seems to be operating all of its Oakland Hawaii flights out of these extra gates in Terminal 1. This means Hawaii travelers may need to plan on a walk of a few extra minutes to get to these flights. If you are originating in OAK and coming from the Terminal 2 TSA checkpoint, plan on a walk of about 8 minutes. If you are coming in on a connecting flight and have to walk from the far end of Terminal 2 to Terminal 1, plan on about a 12 minute walk.

When we arrived at the gate in Terminal 1, we found a Hawaii celebration in full swing. Even though Hawaii flights had been operational for two weeks, the gate agents at Oakland were determined to keep the inaugural fun going. There was a prize wheel for the kids to spin to win prizes from the "Heart Cart." Regina, my favorite Southwest customer service agent at Oakland was working the flight, so we gave her a big hug and got a few selfies, as always.

Boarding Southwest Airlines to Hawaii

And within minutes, it was time for boarding. Southwest boards in three groups (A, B & C), with family boarding between groups A and B. Families with kids ages 6 and under are able to use this perk, which helps immensely for snagging seats together (Southwest has an open seating policy).

Since it was a peak spring break week, the number of families in the family boarding line was pretty jaw-dropping. I've never seen more families with young kids on a Southwest flight ever, and that includes flights to and from Orlando. I wondered how the B & C groups would be affected on a completely full flight. These families are - of course - choosing seats together which includes middle seats, so not all the sought-after aisles and windows were claimed by the time Group B boarded. But it is definitely a very different pattern than frequent travelers on Southwest might be used to seeing.

My youngest is still 5, so we used the family boarding benefit since we were actually assigned early group B boarding passes. We had no trouble finding three seats together on the plane, but were not able to get my husband on an aisle directly across from us as we normally do.

As a result of what we witnessed, I would recommend that travelers who don't qualify for family boarding think very carefully about boarding strategy for Southwest's Hawaii flights. This is especially important if you are a family with older kids who wants to sit together.

What are your options? You can always check in exactly at 24 hours to get a good boarding position. I did this for this flight (to the exact second) for three of the four members of my traveling family. We got B8-10. Not too shabby.

For the sake of reporting (and because I knew we would use family boarding anyway), I checked my daughter in three minutes after the 24 hour window started to see how fast the boarding positions were being snagged. She got B58! So it just goes to show how many travelers were employing this same 24 hour strategy.

Consequently, this might be one time when it is worth it to purchase Southwest's Early Bird Boarding. Of course, Early Bird doesn't guarantee you an A group boarding pass (occasionally Early Birds are assigned early group B), so you may not beat the hordes of families on board. But your chances of a getting seats together are higher than with the 24 hour check in strategy.

I'd also recommend using a benefit of the Southwest Rapid Rewards Priority Credit Card if you have it (if you don't, find out more about it in my Southwest credit card comparison guide). This card comes with 4 upgraded boardings per year in the prime A1-15 spots. These boardings are subject to availability and can only be selected day of travel at the airport. They are a great way fix a bad boarding position when you forget to check in at 24 hours in advance and are stuck with the C boarding group. I have this credit card in my wallet. It provides a very nice Southwest boarding insurance policy, along with a number of other useful benefits.

In-Flight Southwest Hawaii Flight Experience

Enough boarding minutiae! How was the flight itself? We found that the in-flight experience is highly similar to every other longer Southwest flight we've taken: reliable and predictable, complete with signature Southwest friendliness and quality customer service. If you already fly Southwest to other destinations, it will probably look and feel quite familiar to you too.

What aircraft does Southwest fly to Hawaii?

Southwest is currently flying its ETOPS-certified Boeing 737-800 aircraft on the Hawaii routes. (No, this is not the MAX aircraft which are currently grounded, although Southwest likely plans to fly the MAX on Hawaii routes at some point in the future.) The 737-800 aircraft are longer 737 variants.

I personally find the aircraft provides a very comfortable ride for a single aisle plane. Our flight had the new interior and slimline seats which give 32-33 inches of legroom. This pitch is larger than pretty much any other airline flying 737s domestically.

What in-flight entertainment is available on Southwest to Hawaii?

The flight from OAK to HNL is scheduled at 5 hrs, 50 minutes long, so in-flight entertainment to pass the time is key. Luckily, Southwest has a system that works very well, as long as you know what to expect and prepare a tiny bit. You'll find the same system aboard all Southwest aircraft, including the airline's Hawaii flights. And best of all - it's all FREE!

On Southwest, there are no seatback screens -- everything requires using your own device. Find the Southwest WiFi on your device and go to SouthwestWifi.com to connect to the entertainment system (note that you do NOT need to purchase internet access to use the in-flight entertainment system). You'll find a wide variety of movies, streaming on-demand TV episodes, and live TV options. Messaging with either iMessage or What's App is also free. Some of the movies and on-demand TV episodes do require use of the Southwest app, so be sure to download that before your travel day.

My kids loved that there were quite a few kid-friendly entertainment options. Movies of interest to my kids on our particular flights included: Incredibles 2, Ralph Breaks the Internet, Small Foot, Teen Titans Go, and Johnny English. Among the the Live TV options is the Disney Channel.

If you do want to connect to the internet, Southwest flights are equipped with WiFi over the Pacific. The cost is the same $8 per day price that Southwest offers on every other flight. Mine worked quite well on my laptop on both of our flights. Of course, equipment working is never guaranteed so always be prepared with other things to keep you busy. Remember also that even when internet service is fully operational, it doesn't work for streaming services like Netflix or Hulu.

Southwest does not have in-flight power on any of its planes, including the ones operating on Hawaii routes. While my laptop battery lasted just fine for the length of flight, phones and tablets may run out. For this reason, I highly recommend that you bring a portable battery charger or two with you. We own several Anker PowerCore portable chargers. This smaller model can hold enough capacity to recharge an iPhone 11 Pro over 3 times.

To quickly summarize what you need to do to prepare to use the Southwest entertainment system before your day of travel, be sure to do the following:

• Download Southwest app to all devices you plan to use for in-flight entertainment
• Buy and charge up portable battery chargers (and pack them with their cords in carry on luggage)
• Pack compatible headphones for everyone (for kids, we swear by Kidz Gear)

What is there to eat and drink on Southwest's flights to Hawaii?

While most of what we experienced on our flight was identical to any other Southwest flight, there is one major different flyers can expect on Southwest's Hawaii routes: food and drink! On shorter flights, Southwest usually serves a bag of pretzels. On longer routes, they have pretzels and a selection of 2 or 3 packaged snacks like Oreos or Ritz cheese sandwich crackers.

But on Hawaii flights, you get more. Southwest provides a non-perishable snack box free of charge on Hawaii flights only. This box includes a bag of Southwest pretzels, a bag of Wheat Thins, spreadable white cheddar cheese, island-flavored fruit gummy snacks, Tic Tac mints, and a wet wipe.

Southwest doesn't have any hot food available for purchase but we found the snack boxes complete adequate. Bonus that the boxes have a lot of kid-friendly food. Our flight attendants were also glad to serve my pretzel-obsessed kids an extra few bags of pretzels mid-flight as well.

About an hour and a half before landing, the second drink service took place. At this time, flight attendants distributed a second snack - a small pack of two Milano chocolate sandwich cookies.

As for drinks, all of the usual Southwest choices are available, with a few extra on Hawaii flights only. Hawaii travelers can also order pineapple orange juice or purchase Kona Longboard Island Lager or a special spiced rum.

Landing in HNL

After a pleasant and well-entertained trip over the Pacific, Hawaii was in sight! Our flight landed about 15 minutes early at HNL. Passengers on the right side of the plane get the best views of the island of O'ahu on approach but we had some nice water views on the left upon actual landing as well.

 

 

 

 

 

 

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My little #avgeek looking out the window ready to yell “land ho!” as we approached the island of O’ahu yesterday. As many of you know, @southwestair began flying to Hawaii just two weeks ago - just in time for our spring break plans to visit @disneyaulani again. I’ll have a full review of the in flight experience very soon but suffice it to say that the flight had the usual Southwest reliability with a few extra aloha touches. Only OAK to HNL is flying right now but more routes are launching from OAK as well as SJC in the coming weeks, along with intraisland flights. AD #SouthwestSaysAloha #SouthwestStorytellers #Hawaii #HNL #oahu #clubwingtip #winglet #SouthwestHeart #swapic #familytravel #aviation

A post shared by Leslie Harvey (@tripswithtykes) on Apr 2, 2019 at 3:24pm PDT

Southwest gates at HNL do not have jetbridges, so we deplaned from the front of the aircraft into the warm and refreshing Hawaiian air. Southwest uses ramps at HNL for passengers to deplane, which is much safer than the stairs I've seen used in other tropical airports with similar setups.

We walked next into the gate area (the G gates in Terminal 2), which is fully indoors and air conditioned. After arriving into the gate area, it was a bit confusing and not well-marked where to head next after heading up an escalator to the main level. We knew we could either walk to the central terminal's baggage claim or take the "Wiki Wiki" shuttle there. Finding the correct shuttle stop required checking with two different airport employees. The G gates are very much under construction so hopefully signage will improve.

We waited only a minute or two for the Wiki Wiki once we found the right location. It was a very short ride to the main terminal which helped us (as we later found out) skip a decently significant walk.

Returning from HNL to the Mainland on Southwest

Sadly, all trips to Hawaii must come to an end. After 6 days in Hawaiian paradise, ours did too.

On our last trip to HNL, we experienced terribly long TSA lines. As a result, we definitely gave ourselves a bit of extra time this trip, arriving to HNL more than two hours before our departure time. Our taxi dropped us at the Southwest ticket counters at Lobby 6 which is a shaded but open air ticket counter near Air New Zealand and WestJet.

Before checking in for a flight, all passengers need to clear agricultural inspection. The machines are located to the left as you face the ticket counters. Just run your checked bags only through this machine where a representative will put a tag on the handle indicating clearance.

We then headed back to the Southwest ticket counters, where there are a number of new self-serve kiosks. Since Southwest only had two flights a day at the time of our return, the employee-to-customer ratio was pretty generous. There were absolutely no lines. A customer service agent helped us tag our bags after using the kiosk.

We proceeded through Security Checkpoint 3, immediately to the right of the ticketing counters. The line was longish but moved speedily. We were through in under 15 minutes. We did receive extra screening of our food items, which seems to be common at some airports these days, so be aware that your snacks may need to be separated.

After heading through security, plan for a bit of a walk to get to the Southwest gates at HNL. We chose to walk this time to compare to the Wiki Wiki bus experiecne. We stopped at shops and got food along the way, so our walk wasn't totally direct, but I'd estimate it at about 20 minutes with our kids if we had done it non-stop. Parts of it are open air, so you may get a bit sticky in the warm temperatures, especially if you are lugging bags. Watch carefully for signage directing you to the G gates - it's there, but it's small. And if you choose to take the Wiki Wiki, its location is not well-marked at all. We spotted its station up an escalator above the Delta Sky Club.

Our return flight was very much the same experience as our first flight. Boarding was quick and efficient with the usual Southwest practices in place, complete with the numbered boarding columns at the brand new gates at HNL. There were lots of kids during family boarding (although not quite as many as on the outbound).

The highlight of the return flight was undoubtedly the views at takeoff. From the left side of the plane, we could see all of Waikiki Beach and Diamond Head within close range. I've never snapped so many photos on a takeoff ever.

Thanks to tailwinds, the return flight from Hawaii is much quicker. Southwest scheduled ours at 5 hours, 5 minutes, but we made it in 4:15 due to extra favorable weather conditions.

The Bottom Line

So would I fly Southwest to Hawaii again? A million times yes. The predictable Southwest procedures, product, and amenities work for my family. The Hawaii routes are no different and in fact take the experience up a notch with a few extra amenities on the best planes in the Southwest fleet.

A lot is obviously going to change in the coming months as more routes and more airports are added to Southwest's Hawaii network. And you can bet I'll be watching closely here, ready to book another trip to experience even more of it and report back to all of you!

Disclosure: I'm a paid ambassador for Southwest Airlines in 2019. We paid for our family's Southwest Hawaii flights with our own Rapid Rewards points, but since I'm compensated in other ways by the airline and was asked to share our experience on this particular flight as part of that relationship, I wanted to give readers full transparency. All opinions are my own.