The Best Southwest Rapid Rewards Redemption? Island-Hopping in Hawaii

Like many U.S. airlines these days, Southwest’s Rapid Rewards program uses dynamic award pricing to set redemption rates. Translation? The more a flight costs in cash, the more points it’ll cost you.

That limits just how much value you can get out of redeeming your Rapid Rewards points. Generally speaking, you can expect to get somewhere between 1.1 and 1.5 cents per point – like booking a $250 flight for 20,000 points or so. But there’s one glorious exception … and it might just be the single-best way to use your Southwest points for maximum value.

It’s in Hawaii, where Southwest somehow uses a flat award chart for inter-island flights. A one-way flight in a standard economy fare from Honolulu (HNL) to Maui (OGG) or Kona (KOA) to Kauai (LIH) always costs 4,000 points on Southwest – no matter the cash price.  

Better yet, Southwest charges the same 4,000 points whether you book the cheapest basic fare or a better “Choice” ticket – fares that include free seat selection and allow you to board earlier. That’s unique: Everywhere else in Southwest’s network, the airline charges more points to avoid basic fares.

Not here, though – despite the fact that the airline charges more for Choice fares when paying cash to fly between the islands, it’s the same, 4,000-point rate each way. Whether you’re flying nonstop or connecting through Honolulu en route to a smaller island, it always costs: 

• 4,000 each way for a Basic fare
• 4,000 each way for Choice
• 5,000 each way for Choice Preferred (including preferred seat selection and earlier boarding)
• 7,000 each way for Choice Extra (including two free checked bags, an extra legroom seat, and even earlier boarding)

Now, flights from Hawaiian island to island are typically quite cheap: Think under $100 each way and often closer to half that. This definitely isn’t the sexiest redemption. I get that.

But with stable award pricing, you’re almost always getting more value than you would redeeming points to fly from the mainland out to Hawaii – or anywhere else in the states, for that matter. 

For example, I can book this one-way flight from Kauai (LIH) to Honolulu for 4,000 points. The cash price for this exact same flight? It’s $75 for a Basic ticket and $95 for a Choice fare.

Doing some quick math, booking a Choice ticket with points (because there’s absolutely no reason to book basic here) means you’re getting roughly 2.2 cents per point. Start with $95, subtract the $5.60 in mandatory fees, divide that by 4,000, and voila: You’re getting double the usual value out of Rapid Rewards.

Compare that to this $293 Choice fare from Oakland (OAK) to Honolulu that same day, where Southwest is charging 25,500 Rapid Rewards points. That same math works out to roughly a 1.1 cents per point redemption – pretty typical and half the intra-Hawaiian example above.

And it can get even better in Hawaii.

Because these redemption rates don’t fluctuate with the cash cost, you can get even more bang for your buck (err, points) by booking inter-island flights – like last-minute or over the holidays, when Southwest charges more. 

For example, Southwest is charging $174 for a Choice fare tomorrow flying from Honolulu (HNL) to Maui (OGG). But switch to redeem points, and that exact same flight is – you guessed it – just 4,000 points. That’s getting you 4.2 cents per point in value!

Now that Southwest charges most passengers to check bags, it could be worth splurging for one of those 7,000-point Choice Extra fares – two free bags would save you another $35 each way.

This all begs the question: Why? Why is Southwest treating these inter-island Hawaii flights so much differently than … well, everything? Why is this such a good deal?!

The way I see it, there’s a two-part explanation:

• Ever since Southwest began island-hopping in Hawaii pre-pandemic, it’s been deadlocked in competition with Hawaiian Airlines (and now Alaska, post-merger) to ferry Hawaiian locals and tourists from island to island
• More importantly, Hawaiian flies Boeing 717s with just 128 seats between islands … while Southwest uses much bigger Boeing 737 MAXs with 175 seats. That’s a lot of seats to fill, so Southwest will take whatever passengers it can get.

Then again, I’m not about to complain about some cheap points redemptions that get you double (if not quadruple) the normal value!

Bottom Line

It’s certainly not the sexiest points redemption in the world, but Southwest’s incredibly stable award chart for inter-island flights in Hawaii makes it one of the best ways to use Rapid Rewards – if not the best, period.

For the first (and likely only) time, I’ll be transferring a few thousand Chase points to my Southwest account to put the finishing touches on a trip to Kauai next winter. 

Lead photo courtesy of Southwest Airlines