Hawaii Just Got a Lot Easier to Reach With Points

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Following a brief, government shutdown-imposed delay in certification, Southwest finally put its long-awaited Hawaii flights up for sale this morning, and prices start at less than a ticket to a luau.

The first flights take off between Oakland and Honolulu on March 17, with additional routes between San Jose, Maui, and Kona launching in April and May. Limited inter-island service also starts between Honolulu and Maui on April 28, and Honolulu and Kona on May 12. The airline also plans to add service to Lihue on the island of Kauai (the best island), with additional routes from San Diego and Sacramento, though those dates are not yet available.

Some flights were briefly available starting at $49 earlier in the day, but it seems like most flights in the first few weeks of each route have already sold out completely. Still, as Southwest continues to add routes, this could present a new, best way to get to Hawaii on points, following the demise of Chase and Korean Air’s points transfer relationship. Here’s why:


Southwest Rapid Rewards points are fairly easy to accrue.

You’ve got a few different options if you want to rack up a bunch of Southwest Rapid Rewards points quickly. The airline offers a trio of its own credit cards through Chase, all of which currently offer a 40,000 mile welcome bonus after spending $1,000 in the first three months. Their 2x bonus earning categories are limited to Southwest purchases, unfortunately, but the welcome bonuses plus various included perks (below, and detailed here) make any of them a fine addition to your wallet.


More likely, you’re going to be transferring points earned through Chase Ultimate Rewards to your Southwest account at a 1:1 rate. That means you can sign up for a Chase Sapphire Preferre Card or Chase Sapphire Reserve (both of which currently offer 50,000 point welcome offers, after spending $4,000 in your first three months), earn bonus points on travel and dining purchases (2x for the former, 3x for the latter), and transfer as many points as you need to your Southwest account to book your Hawaiian getaway. And as we’ve covered before, you can also add the no-annual-fee Chase Freedom and Chase Freedom Unlimited cards to your arsenal to earn even more points, assuming you also have one of the Sapphire cards.

You can book any seat with points

Though the redemption rate varies a bit, Southwest Rapid Rewards points are generally worth about 1.5 cents when used towards flights (according to The Points Guy’s latest valuations), with no blackout dates, and no limit to the number of available award seats on any given flight. On particularly cheap fares, you can sometimes get an even better rate of return. For example, those $49 Hawaii flights were priced at 1,950 points each way, a valuation of about 2.5 cents per point.


At that price, you could fly a family of four roundtrip to Hawaii—twice!—with just a 40,000 point credit card welcome offer, and still have nearly 9,000 points left over. I wouldn’t expect to see too many 1,950 point fares going forward, but Southwest does run frequent sales, which apply to award bookings as well.

No change or cancelation fees

Worried that you’re booking too early? If you book a Southwest flight with points, and find a lower rate later (either on the same flight, or on a different flight), you can change your flight at any time with no fee, and get the difference in points refunded to your account.


That same trick works with cash bookings as well, but unless you booked a pricy, fully refundable fare, your refund will come in the form of a travel voucher good for one year. With refunded points, there are no such restrictions beyond Southwest’s requirement that you have some activity on your account every 24 months.

Just remember that if you transferred Ultimate Rewards points to your account, you can’t move them back to your Chase account; you’ll have to use them on Southwest once you transfer them.


Free checked bags

Hopefully, you’ll be spending enough time (and buying enough souvenirs) in Hawaii that a carry-on won’t cut it. Southwest’s famous policy of offering two checked bags for free applies to its Hawaii flights as well, which can add up to serious savings on a family trip.

Companion pass!

While you can no longer earn Southwest’s companion pass with a single credit card welcome offer, if you fly enough to earn it through conventional means, you can bring your companion to Hawaii with you for free (save for taxes and fees), including on award bookings. No other airline offers anything comparable.


Whether you’re booking with points or with cash, Southwest’s incursion into Hawaii is undiluted good news for leisure travelers. Even if you don’t end up flying Southwest to Hawaii (as of now, it’s difficult or impossible to book return flights to the east coast, since Southwest doesn’t offer red eyes), their presence alone is already forcing other airlines to compete on price—great news if you’re booking with points through a credit card travel portal—to which we say mahalo.

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