LUV It: Southwest Launches Flights To Hawaii From $49 Each Way

by Chris Dong

Southwest Airlines’ Hawaii service has been a long time coming. Well, the wait is finally over. After numerous delays, tickets are now available for purchase on Southwest’s website for travel beginning on March 18th.

Southwest Hawaii service will initially operate with daily service between Oakland (OAK) and Honolulu (HNL). Pricing starts at an insane $49 each way.

Shortly after the initial launch, Southwest will also have flights from Oakland to Maui starting April 7th, from $49. Flights from San Jose (SJC) will also commence this spring on May 5th.

Inter-island flights between Honolulu, Kona, and Maui start on May 12th.

Calendar for Oakland to Honolulu for March 2019: 


Summer dates from Oakland to Honolulu in June, lots of dates still at $49:

Oakland to Kona starting in May, starting at $79:

Oakland to Maui starting in April from $49

San Jose to Honolulu starting in May, also from $49 each way: 

Finally, here’s Los Angeles to Honolulu starting in March, from $88:

Southwest had received FAA approval for flights to Hawaii just last week so we knew sales would start happening soon. But it is a bit of a surprise that tickets would be released so suddenly.

Keep in mind Southwest doesn’t play with the OTAs (online travel agencies) so you must book directly on Southwest’s website.

The Upshot

Flights to Hawaii starting from $49 is an absolutely incredible value. Keep in mind Southwest is the only remaining airline to have free checked bags even for their lowest offered fares (two free checked bags, at that).

Example: A flight that is $49 on Southwest is running $249 on Hawaiian (the only other direct option from Oakland).

While $49 fares are by no means permanent, this bodes well for more competitive pricing from other carriers (known as “the Southwest effect”).

Will you be taking advantage of this Southwest flights to Hawaii starting at $49?

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Bill Shuman March 4, 2019 - 10:39 am

Sadly, it doesn’t look like those deals lasted long. I’m checking to rebook from another carrier and all I’m getting in June is ~$300.


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