2019 marks the beginning of the long awaited Southwest flights to Hawaii. The first flight took off from Oakland to Honolulu in March 2019. At the time of this post, Southwest offers 4 direct flights from the mainland:
- Oakland (OAK) to Honolulu (HNL) on Oahu
- San Jose (SJC) to Honolulu (HNL) on Oahu
- Oakland (OAK) to Kahului (OGG) on Maui
- San Jose (SJC) to Kahului (OGG) on Maui
Southwest also flies to Kona (KOA) on Big Island via Honolulu. Besides Hawaiian Airlines, Southwest is the only other major commercial airline that flies inter-island routes*, which is great news for creating some competition in Hawaii!
For my trip this Memorial Day weekend, I flew to Kona (KOA). I purchased my ticket the day Southwest started selling tickets, but because of the days I needed to travel over the holiday weekend, I wouldn’t say my ticket was cheap – it was about~$400 from OAK to KOA on Southwest when competitors like American and United offered direct flights for ~$300 during the short-lived price war. However, if you choose the right dates that include flying out on a Tuesday, you could find tickets as low as $200! If you add a companion pass on top of this deal, you can fly to Hawaii for $100 a person! Unfortunately, the initial deals are gone and they are likely not coming back. The good news is – with another airline to Hawaii, there are opportunities for more deals in the future.
My Experience Flying Southwest to Hawaii – What to Expect
Overall I would say the experience was as expected. There was nothing special or fancy about this Southwest flight. It is still pretty much a “no frills” experience – no assigned seats, no upgrades, no special meals, etc.
BUT you do get 2 free bags! If you plan on going shopping in Hawaii (like I did), this could be a really useful perk!
On these flights, you DO get a special snack pack on your flight from the Mainland to Honolulu. It’s nothing fancy – Wheat Thins with cheese, fruit snacks, pretzels, tic tacs, and wet wipe – but it sure beats just a bag of pretzels! You still have to purchase your own drinks, so hopefully you have some Southwest drinks coupons to use! (You are going to Hawaii after all!) I couldn’t resist so I ordered myself a mimosa. The flight attendant brought me a bottle of champagne and a can of orange juice so I could mix my own drink. 🙂 Besides the usual drinks that Southwest offers, you can also order a Kona beer on these flights.
The flight from OAK to HNL takes almost 5 hours, so I was really grateful for the free messaging, live TV, and movies from Southwest. By logging onto the Southwest wifi, you can activate free messaging for iMessage and Whatsapp, and you also have access to all the live TV and available movies you want. What Southwest does not provide are seatback screens and power outlets, so be sure to fully charge your device(s) and/or bring a power bank.
The Southwest terminal in Honolulu is contained within the far end of the airport, so there is no need to run if you have a tight connection. If you need to connect, you simply have to go to the next terminal gate to scan your boarding pass and exit the same way you came in (you will be given a yellow boarding pass to make sure you are supposed to be boarding that flight).
The flight from HNL to KOA is very short (less than 30 minutes air time), so there isn’t much time for drink service. On this flight, Southwest only offers water and juice, and you will need to finish it very quickly. Given the short duration, there are no snacks.
Window Seats
I never sit in window seats, but for the inter-island flight, I had to sit there. The view was amazing – check it out!
View of Hawaiian Islands from Southwest 
View of Hawaiian Islands from Southwest 
View of Hawaiian Islands from Southwest
Advice – sit on the left side on the way to Big Island and on the right side on the from Big Island back to Oahu – you will get to see all the Hawaiian islands from your window!
How Did Southwest Do?
Southwest brings competition to the Hawaiian islands, and this is great news for travelers. I give them A+ on this.
However, it seems that Southwest still needs to work out its logistical issues. For my trip to Hawaii and my trip back from Hawaii, I experienced delays. The first delay was actually caused by a cancellation of my connecting flight from HNL to KOA with no reason at all, and this resulted a day of waiting as a standby passenger for other flights. On my way back from Hawaii, my flight from KOA to HNL was delayed, and this resulted in a mad dash to my connecting flight even though it was in the next gate over (I had to enter the terminal then exit again to get to my flight). Then, to top it off, I returned to Oakland, and my checked bag was nowhere to be found. When I asked the baggage agent about its whereabouts, the agent could not answer. He said Southwest doesn’t scan the bags until they reach their destinations. I would have to say Southwest’s baggage system is quite archaic! Based on my experience alone, I would give Southwest a D for logistics. I would hope they get better with more experience!
Overall, I would give Southwest a grade of C+.
*There are smaller airlines and private companies such as Go! Mokulele and Pacific Air that fly inter-island, in case you are wondering.
Did you fly Southwest to/from Hawaii? Leave a message about your experience!