Southwest Expands Hawaii Service, Plus $29-$99 Fares!

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Alongside Southwest’s schedule extension this morning, they also enhanced their service to Hawaii. This is great for those on the west coast looking to jet off to one of the many islands are those throughout the country that can make a layover in California work.

New Routes

The new routes that were just introduced for flights starting January 2020 include:

From California to Hawaii:

  • Sacramento and Honolulu
  • Oakland to Lihue
  • Oakland and Kona
  • San Jose and Lihue
  • San Jose and Kona

Interisland service:

  • Honolulu and Lihue
  • Honolulu and Hilto
  • Hona and Kahului

a map of the island of hawaii

Book Cheap Fares Now!

Southwest has done a great job in keeping Hawaii fares low when they are initially introduced. Right now there are many new routes from the mainland to Hawaii pricing out at just $99 or just under 6,000 Southwest Rapid Reward points.

a screenshot of a flight schedule

Or, if you are looking for an intra-island flight, you can book for just $29 or just over 1,000 Southwest Rapid Reward points. This is an absolute steal!

a screenshot of a flight schedule

These fares are bound to go fast and I’d be surprised if they were even around by end of day today. This means, book now and think later! With Southwest you have 24 hours to cancel for a full refund back to your credit card. Or, if you need to cancel later on, Southwest has an extremely flexible cancelation policy. If you…

  • Paid for the flight… You will receive a voucher fare price to be used one year from the date the flight was originally purchased (NOT the date the cancelation took place). This voucher is non-transferable. The voucher will be tied to the confirmation number of the original flight. There is NO fee for this.
  • Booked your flight using points… The difference in points will go back into your account immediately. The taxes paid will go back to the credit card used. Again, there is NO fee for this. This is why I love booking Southwest flights using points!

Book Now, Add Your Companion Later

If you are going for the Southwest Companion Pass, where you can fly a companion 2-for-1, you can still book your flight now and add your companion later. Once you actually receive the pass, you can go ahead and add on your companion to your reservation. Remember, your the Southwest Companion Pass is essentially an unlimited BOGO certificate which allows your companion to fly for free, plus taxes/fees (which are nominal for flights to Hawaii).

Reminder: Points earned from the five Southwest credit card welcome offers will count towards earning the Southwest Companion Pass.


I absolutely love that Southwest is expanded their Hawaii service. This is a great addition for those looking for a Hawaiian vacation. While it doesn’t work out as well for those of us on the East Coast, if you are willing to do an overnight in California then it is absolutely a possibility. I must say I am definitely jealous of those living in California right now…

Anyone able to score any cheap Hawaiian flights? Which island will you be visiting?

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Gail Elkin Goldberg
Gail Elkin Goldberg
4 years ago

Hi Jen,
I’m coming up on the end of my (and my husbands) 4 years with a SWA companion pass. Two years with me as primary and 2 with him.
Is it possible to do it again and sign up again after. I think you said you’ve had it for 11 years.

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