How to score Hawaiian first class on the Dreamliner for cheap using points and miles

It’s no secret we love traveling in premium cabins here at TPG, and there’s no better feeling than redeeming your hard-earned points and miles for top-tier luxury travel experiences. Whether you’re booking business class or first class using points and miles, it’s so rewarding to know that you paid a fraction of the cash price.

However, there are times when frequent flyer programs offer a discount on purchasing miles or provide bonus miles on top of your purchase. These offers can provide great value, especially if you’re short on miles or saving up for more aspirational redemptions.

I recently utilized a Hawaiian Airlines HawaiianMiles sale to buy miles to upgrade to first class on Hawaiian’s new 787-9 Dreamliner for half the cost of a cash ticket.

Here’s how I did it — and how you can use another sale to do the same.

Related: Buy bonus points and miles with these promotions

HawaiianMiles sale

HawaiianMiles offered a lucrative sale on miles recently, giving members 100% bonus miles when they purchased between 3,000 and 100,000 miles. Although I had never utilized the HawaiianMiles program before, I looked into how to take advantage of this sale for an upcoming trip to Hawaii and East Asia.

I looked into purchasing miles to redeem for a one-way ticket to Honolulu outright. However, at the time, Hawaiian was charging 80,000 miles to fly on the Dreamliner. This would equate to purchasing 40,000 miles for $1,000 and, with the 100% bonus, receiving another 40,000.

Cash fares for first class hovered between $850 and $1,200 across my dates of interest, so that wouldn’t have been a great deal. In addition, I wouldn’t earn miles on a redemption, whereas I would on a cash ticket.

Upgrading a cash ticket with Hawaiian miles

The best-value option then became clear: purchasing an inexpensive Main Cabin cash ticket on the Dreamliner route and upgrading to first class using Hawaiian miles. Flights between the West Coast and Hawaii cost 25,000 miles to upgrade at the saver level (the A fare class).

My first step was to confirm that my preferred date did, in fact, have saver-level availability. For this, I turned to ExpertFlyer (owned by TPG’s parent company, Red Ventures) and searched for that date, looking specifically for a Dreamliner flight.

I then purchased three tickets for about $210 each for me and my family.

Because I was traveling in a group of three, I needed 75,000 miles for the upgrade. With the 100% bonus, that meant purchasing 38,000 miles (Hawaiian only sells miles in increments of 1,000).

Within minutes of the purchase, 76,000 miles (38,000 plus the 100% bonus) were deposited into my HawaiianMiles account.

Unfortunately, mileage upgrades on cash fares can only be made over the phone or via Hawaiian’s chat function.

After a quick call with a friendly customer service agent, all three of our tickets were upgraded to first class on Hawaiian’s Dreamliner. Each ticket cost a total of $532 — $210 for a cash ticket plus $322 in miles purchased with the 100% bonus during the recent sale. This saved me hundreds of dollars compared to the cash price of the flight.

Consider transferring Alaska miles to Hawaiian

Although the HawaiianMiles sale has ended, Alaska Airlines Mileage Plan is currently selling miles with a bonus through Monday. During this sale, you can earn up to a 60% bonus on purchased miles.

Remember, Alaska miles transfer to Hawaiian at a 1:1 ratio, and although this sale doesn’t offer a 100% bonus, it can still be worth exploring if you’re looking to book Hawaiian first class or other Oneworld partner award tickets.

Even if you’re not planning to fly Hawaiian anytime soon, Alaska Airlines offers a slew of sweet spot redemptions, so buying miles to book one of those award tickets could make sense, too.

Tips for upgrading Hawaiian Airlines flights with points and miles

If you’re looking to book Hawaiian Airlines first class, the best way is likely to locate saver-level availability and upgrade an economy ticket. According to Hawaiian’s upgrade chart, one-way upgrades to first- or business-class saver fares between North America and Hawaii are 25,000 miles.

The easiest way to find saver-level availability is through expertflyer.com using the “Award and Upgrade Availability” function.

Looking ahead to dates for spring break in 2025, there’s decent availability from New York’s John F. Kennedy International Airport (JFK) on March 9 and March 10. To upgrade a Hawaiian economy ticket to first class, you must be booked into Main Cabin.

A one-way Main Cabin ticket is $469, while a first-class ticket is $1,627.

By purchasing 18,000 miles through Alaska Airlines by Monday, you’ll receive a 40% bonus, giving you a grand total of 25,200 miles at a cost of $532.13 ($495 plus a 7.5% tax recovery fee). Combining the cost of the Main Cabin ticket and the cost to purchase miles, you could sit in first class for a flight of more than 11 hours for about $1,000 — or nearly 40% cheaper than paying cash for a first-class ticket on these dates.

If you’re set on flying the new Hawaiian Airlines Dreamliner, flights out of Los Angeles International Airport (LAX) in Main Cabin are as cheap as $179 one-way. With up to nine seats available to upgrade at the saver level, purchasing an economy ticket and upgrading to first could be as little as $711, a great price for a premium product.

Related: How to upgrade your seat on Hawaiian Airlines

Maximizing the Alaska Mileage Plan sale for other redemptions

Another way to maximize the current Alaska Airlines miles sale is to purchase miles for redemptions with Oneworld carriers or partner airlines through Mileage Plan. Alaska has a region- and distance-based award chart with several sweet spots that can maximize the value you get from purchasing miles.

For example, if you want to see Machu Picchu in 2025, you can fly from John F. Kennedy International Airport (JFK) to Jorge Chávez International Airport (LIM) for 35,000 miles one-way in business class.

By purchasing 24,000 miles with a 50% bonus, you’ll get a total of 36,000 miles for $660. That’s quite a deal, considering the cash fare for the same route is about $1,700.

Related: Best Alaska Airlines Mileage Plan sweet spot redemptions you can book

Another way to maximize the current sale is to redeem miles for interregional flights, such as flights within East Asia or Australia. A one-way flight within East Asia in business class is 15,000 miles, which would cost about $325 to buy with the current bonus. These are nearly four-hour flights that can cost anywhere from $500-800 for a paid ticket.

Alaska also has a generous stopover policy for award tickets, which can be a great way to maximize purchased miles. Despite the routing rules not being as flexible as those of Aeroplan’s stopover scheme, it’s still a great opportunity to get two trips out of one redemption.

Other ways to earn Hawaiian and Alaska miles

You can transfer American Express Membership Rewards points to Hawaiian Airlines at a 1:1 ratio, and transfers are usually instant.

The best way to earn plenty of Membership Rewards points is by utilizing the generous welcome offers on Amex cards. Here are some of our favorites:

• The Platinum Card® from American Express: Earn 80,000 Membership Rewards points after spending $8,000 on purchases in your first six months of card membership. However, some readers have been targeted for up to a 100,000-point bonus using the CardMatch tool (offer subject to change at any time). Terms apply.
• American Express® Gold Card: Earn 60,000 Membership Rewards points after spending $6,000 on purchases in the first six months of card membership.
• The Business Platinum Card® from American Express: Earn 150,000 Membership Rewards points after spending $20,000 on eligible purchases within the first three months of card membership.
• American Express® Business Gold Card: Earn 100,000 bonus points after spending $15,000 on eligible purchases in the first three months of card membership.

An easy way to boost your Alaska Mileage Plan balance, which you could either transfer to HawaiianMiles or redeem through Mileage Plan, is with the Alaska Airlines Visa Signature® credit card: New applicants can receive 70,000 bonus miles and Alaska’s Companion Fare ($99 fare plus taxes and fees from $23) after spending $3,000 or more on purchases within the first 90 days from account opening.

Bottom line

If you feel like you missed the ball on the HawaiianMiles sale and a chance to score cheap first-class seats to Hawaii, there’s still time to take advantage of the ongoing Alaska Airlines Mileage Plan sale. Thanks to the Alaska-Hawaiian merger, you can transfer miles between the two instantaneously and at no cost.

Earning up to 60% bonus miles is a great way to load up on Alaska miles, which are historically some of the hardest airline miles to earn. Don’t wait too long, as the sale ends Monday.

Related: Buy bonus points and miles with these promotions