The Princeville Kauai

Since rumors first began swirling about Southwest Airlines launching flights to Hawaii, there has been regular chatter about if/when it would happen, from what cities, and how much the flights would cost. Even once Southwest confirmed it would be flying to Hawaii, it remained perhaps the most highly anticipated announcement in domestic air travel.

Well, you don’t have to wait any longer. You can now book Southwest flights — with 2 free checked bags — to Hawaii and at some crazy low prices. Of course, this deal is even better if you have the Southwest Companion Pass.

Here’s what you need to know.

Southwest’s Hawaii Routes


Southwest will roll out 4 routes to Hawaii and 2 inter-island routes between March 17 and May 26, 2019. Here are the exact launch dates of each route:

  • Oakland (OAK) to Honolulu (HNL) – March 17, 2019
  • Oakland (OAK) to Maui (OGG) – April 7, 2019
  • San Jose (SJC) to Honolulu (HNL) – May 5, 2019
  • San Jose (SJC) to Maui (OGG) – May 26, 2019
  • Honolulu (HNL) to Kona (KOA) – May 12, 2019
  • Honolulu (HNL) to Maui (OGG) – May 12, 2019

Crazy Low Fares To Hawaii

Hawaii Sunset

With fares as low as $49 per one-way, if you’re considering a trip to Hawaii, you’d be crazy not to consider this option. There are also tons of flights available for $79 and $99.

Once you get into the heart of summer, many dates jump past $150 and even $200 for a one-way, but there are still plenty of sub-$100 dates in June.

Even if you live in the midwest or eastern part of the U.S., it might be worth taking a look at Southwest prices. With a quick search, I found a one-way out of Chicago Midway (MDW) for $133.

Inter-island flights can be found for as little as $29 per one-way if you want to hop around a bit. Also, if you can’t find a flight directly to Honolulu or Maui, you might be able to get there thanks to one of the connections for just a few bucks more.

Finally, you can transfer Chase Ultimate Rewards points to Southwest instantly if you want to book an award. Since Southwest has a revenue-based award program, the points required will be dictated by the cost. If you find a $49 flight, you’ll only need 1,950 Rapid Rewards points.

2 For 1 With The Southwest Companion Pass

Southwest Hawaii Flight

The Southwest Companion Pass is what really takes this from a crazy deal to an out of this world deal. Since the Companion Pass allows you to book 2-for-1 flights — cash or award tickets, all you have to do is cover the taxes/fees for the second person.

So, take one $49 ticket and pay the taxes/fees for a second — about $23 — and you’ll get 2 tickets for a grand total of $72 for a one-way. A round-trip for two would only cost $144 which is just insane.

To earn the Southwest Companion Pass, you need to acquire 110,000 Rapid Rewards points via flying Southwest, using any of the co-branded Southwest credit cards issued by Chase, using the Southwest shopping portal, or using the Southwest dining program.

Final Thoughts

If you live on the west coast, this is almost a no-brainer. Even if you don’t, though, we definitely think you should check prices from your home airport as you can still get some cheap flights right now.

Considering how difficult award space to Hawaii can be when you look at Alaska, American, Delta, and United, this really is a great opportunity to get yourself to Hawaii without breaking the bank.

Spencer Howard

Spencer Howard is a credit card rewards and award travel expert. He’s living proof that points and miles can unlock many of the greatest travel experiences and uses his skills to tick off new bucket...

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  1. Looking through October, there are no fares available at $49 one way from the west coast. Cheapest I am seeing is about $400+ round trip, with nothing available in March or April.

    1. With a great deal like this, I wouldn’t be surprised if most of the best fares have been booked by now. I’m still seeing some $119 on the outbound with the occasional $99 though.

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