The Best Ways to Use Miles for Hawaiian Island-Hopping in 2019

a view of a body of water

If you have picked Hawaii as your vacation destination — congratulations! You made a great decision and now almost can’t go wrong with whatever you choose next. Hawaii is (more than) worth the effort no matter what you do when you get there (but please do yourself a favor and don’t just stay on Waikiki the whole time).

a canyon with Waimea Canyon State Park in the background: Kauai’s Waimea Canyon: the Grand Canyon of the Pacific. (Photo via Getty Images)

Since the islands of Hawaii are so diverse and unique in their own ways, it can be tempting to want to visit multiple islands on the same trip by island-hopping. As long as you have enough time during your vacation to Hawaii to do the individual islands justice (I’d vote for at least five to seven days per island), we give Hawaii inter-island travel a big thumbs-up. Here are some logistics to note about island-hopping in Hawaii that you’ll want to familiarize yourself with first. With that out of the way, here are the best ways to use your miles for island-hopping in Hawaii.

Hawaiian Airlines World Elite Mastercard: Earn a 60,000-mile bonus for a limited time (after spending $2,000 on purchases in the first 90 days).

water next to the ocean with Molokini in the background: Molokini Crater with West Maui in background. (Photo by M Swiet Productions / Getty Images)

You Now Have Options

Until recently, Hawaiian Airlines all but had a monopoly on inter-island travel in Hawaii. But now in 2019, Southwest Airlines is a formidable option on some inter-island routes. Currently, Southwest operates inter-island routes from Honolulu to Kona (Big Island) and Maui, but additional inter-island routes are on the way to cities such as Hilo, and hopefully Lihue on Kauai before too much longer.

Those lucky folks who have the Southwest Companion Pass have a great advantage of being able to fly two people on these inter-island routes for the price of one ticket plus taxes/fees. Here’s a play-by-play of my recent experience island-hopping with Southwest Airlines.

a large passenger jet sitting on top of a tarmac: (Photo by Getty Images)

Check the Cash Price

Naturally, airfare prices vary, but flights between the Hawaiian Islands can be found in economy starting at around $39 each way, though prices can get up to about $200 one-way. Distances also vary — from Hilo on the Big Island to Lihue on Kauai is a little over 300 miles, though flights from Honolulu to Maui clock in at just 100 flown miles.

If the flight in Hawaii that you want costs about $100 or less and is operated by Hawaiian Airlines, your best play is likely using cold hard cash, or fixed-value points to cover the cost of the relatively inexpensive ticket.

For example, you could purchase a $59 ticket and use 5,900 miles from your Capital One Venture Rewards Credit Card to cover the cost. Or, you could book that ticket via the Chase Ultimate Rewards booking site using your Chase Sapphire Reserve and spend just 3,933 Ultimate Rewards points at a value of 1.5 cents each.

However — in my searches, I noticed a trend that the cheapest island-hopping flights on Hawaiian Airlines aren’t always available for booking via third-party sites (like the Chase Travel site or Expedia), so you may need to book directly with Hawaiian to get the cheapest flights. You would then use the best fixed-value card in your wallet to pay for the direct booking and use the points from that card to offset the cost.

If you are booking with Southwest, the equation shifts. The Southwest Rapid Rewards program uses an award pricing model that ties the number of points required for the flight to the cash price. For example, on my recent hop from Honolulu to Kona, the options were spend $39 or about 2,100 Rapid Rewards points — both of which were great choices.

Free Island-Hop Via the United Excursionist Perk

If you want to get a Hawaii island-hop in “for free,” book your trip to Hawaii using United miles. For example, you could fly Houston – Honolulu (stop) – Lihue (stop) – Houston for the same number of miles as just Houston to Honolulu and back (45,000 in saver economy). Since Hawaii is in a different award chart region than the Lower 48, it works for a free stopover using the United Excursionist Perk on a round-trip booked with United miles.

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Here are the best credit cards for flying with United miles. If you do book your island hop with United, you’ll need to get your Hawaiian Airlines confirmation code from them to select your seat directly with Hawaiian.

Use Airline Miles for Inter-Hawaii Travel

You can use a variety of airline miles to island-hop Hawaii, but most of them bring you right back to the same Hawaiian Airlines flights. But, not every airline charges the same number of miles for flights on Hawaiian so it pays to shop around with the miles you have available. And, of course, if you are flying on an inter-island route operated by Southwest, then you have yet another set of choices. Here’s a rundown of some popular options, prices listed as one-way except where noted.

American miles to fly Hawaiian: 7,500 miles in economy, 15,000 in first

Delta miles to fly Hawaiian: 7,500 miles in economy

Hawaiian Airlines: 7,500 miles in economy, 15,000 in first

If you have the Hawaiian Airlines World Elite Mastercard, your first checked bag will be free if you book directly with Hawaiian using the card, you’ll have access to discounted awards and more.

JetBlue points to fly Hawaiian: 6,000 miles in economy, 12,000 in first

You can transfer points from Chase Ultimate Rewards to JetBlue at a 1:1 ratio if you have cards such as the Chase Sapphire Reserve and Chase Sapphire Preferred Card. Citi ThankYou now also has a 1:1 transfer ratio to JetBlue. Those with the JetBlue Plus Card get 10% of their redeemed points back.

Note that JetBlue awards on Hawaiian Airlines must be booked over the phone with JetBlue, but in our test call, availability lined up roughly with what United displayed as available.

Korean: 10,000 miles in economy, 20,000 in first (round-trip required)

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Sadly, you can no longer transfer Chase Ultimate Rewards points to Korean but you can transfer Marriott Rewards points at a 3:1 ratio (with a 5,000-mile bonus for every 60,000 points you transfer). Korean can be a good deal, but there will probably be some extra paperwork involved when booking for the family.

United miles to fly Hawaiian: 7,000 miles in economy

Virgin Atlantic miles to fly Hawaiian: 7,500 miles in economy, 15,000 in first (infants 2,000 miles in economy/10,000 in first)

A benefit of Virgin Atlantic miles is that they are easy to earn, as you can transfer from Amex Membership Rewards, Chase Ultimate Rewards, Citi ThankYou Rewards and even Marriott Rewards. We’ve also seen periodic transfer bonuses from both Amex and Citi in the past, so your award rates could be discounted even further by transferring during these promotions.

Southwest Airlines: Many inter-island fights on Southwest are currently available for 2,000 to 4,000 Rapid Rewards points each direction. You can earn Rapid Rewards points from Southwest credit cards, such as the Southwest Rapid Rewards Plus Credit Card. You can also transfer your points in on a 1:1 ratio from Chase Ultimate Rewards and cards such as the Chase Sapphire Preferred Card. On Southwest, you’ll get two free checked bags and access to in-flight streaming entertainment at no charge (on your own device).

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Bottom Line

You may not need to use airline miles for an inter-island trip in Hawaii if cash prices are low enough. We recommend doing the math to make sure you are getting a decent value for your points. But when prices cross that $100 threshold, miles become a deal worth considering. This whole island-hopping equation may change dramatically once Southwest has its Hawaii game fully operational, but for now, start your Hawaiian island-hopping planning by checking cash prices and then turn to some of the mileage options listed if cash prices leave a sour guava juice taste in your mouth.

Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

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