Save $4K on Hawaii: Flights & Hotels (Feb 2026)

Since I’m from New England, I’m used to the freezing cold temperatures and the gloomy days of winter. While I do love it when it snows and I’m able to frolic around a winter wonderland, I’ve always wanted to escape the cold for a bit.

When my family and I thought about what we wanted to do for the holiday season, Hawaii was brought up. Hawaii has been on our bucket list for many years, and we wanted to make our tropical winter vacation getaway a reality.

Unfortunately, the downside of traveling to Hawaii in the winter is that it can get very expensive. Hundreds of thousands of other people who live in the cold parts of the U.S., as well as Canada, have the same idea and want to flock to Hawaii to enjoy its lush beaches and warm weather year-round.

When I was looking into booking our flights and accommodation for the trip, I quickly realized that face value cash prices would run us up by thousands of dollars.

I strategically decided to get two new credit cards, and the benefits they provided me easily allowed me to save almost $4000 on my family’s round-trip flights, as well as a week’s worth of accommodation at hotels in O’ahu and Maui.

Saving on The Flights

Since my family and I needed to fly out of Boston (BOS), we would need to cover a distance of over 5,000 miles to make it all the way to Hawaii, warranting high flight prices. I was aware that Alaska Airlines and Hawaiian Airlines were some of the main flight carriers that operated flights between the mainland U.S. and Hawaii.

One of the credit cards I decided to get was the Atmos™ Rewards Ascent Visa Signature® credit card, as it offers a $99 companion fare as part of its introductory offer, as well as an annual $99 companion fare every year on your account anniversary. If you’re interested in learning more about the companion fare and how to use it, I have a whole article written about it.

In short, the companion fare is best used on long-distance flights that will often cost hundreds of dollars, as the companion fare will allow you to pay a heavily discounted fare for a travel companion after paying full price for the main traveler.

As this is my family’s first time going to Hawaii, we wanted to maximize the time we had there and visit two islands: O’ahu and Maui. Since the companion fare is valid on flights operated by Alaska Airlines and Hawaiian Airlines, I knew that I’d be able to book a multi-city itinerary where I’d fly into O’ahu, take an inter-island flight to Maui, and fly home from Maui.

When I applied the companion fare discount for a flight itinerary from Boston (BOS) to Honolulu (HNL), Honolulu (HNL) to Maui (OGG), and Maui (OGG) to Boston (BOS), I only needed to pay $932 for two people, saving $569 on the flights.

Additionally, since I booked the Main Cabin fare class, both the main traveler and the companion are eligible to receive 100% of the miles flown as Atmos™ Rewards points, which proves very useful when it comes to redeeming flights via Atmos™ Rewards, such as short-haul flights on American Airlines.

Saving on The Hotels

Staying for a week in Hawaii certainly isn’t cheap, especially when you want to visit during a peak tourist season. I’m usually a Hyatt loyalist, but when taking a look at the Hyatt hotels available that I could book with points, every hotel I saw cost at least 15,000 points a night, which is an exorbitant amount of points to fork over, especially for a week’s worth of nights.

The other credit card I decided to get for the trip was the Marriott Bonvoy Boundless® Credit Card. When I applied for the card, it was offering 5 Free Night Awards for redemption at Marriott hotels as its introductory offer.

Each of these Free Night Awards can be redeemed for a value of up to 50,000 points a night, and you can top off each night with an additional maximum of 15,000 points to book your stay.

Since my family wanted to visit O’ahu and Maui for a week, we decided to split our time between the islands, with 4 nights in O’ahu and 3 nights in Maui.

When I was taking a look at hotels in O’ahu, the Waikiki Beach Marriott Resort & Spa in Honolulu caught my eye. I wanted to stay in the Waikiki neighborhood of Honolulu as a first-time visitor, and the property seemed perfect as a more affordable resort option among the resorts in the area.

My four-night stay cost me 223,000 points + $261.17 in resort fees, which I split by redeeming two free night awards and 123,000 points I had earned from referral bonuses by referring other people to apply for the Marriott Bonvoy Boundless® Credit Card.

If I were to pay for this stay with cash in the same room that I booked using reward redemptions, it would’ve cost me $1,747 out-of-pocket, including the resort fees, meaning that I was able to save $1,500 on just the Honolulu accommodation.

For Maui, the Residence Inn by Marriott Maui Wailea caught my eye due to its location, highly-rated reviews, free breakfast for all members, and no resort fees. The Residence Inn by Marriott Maui Wailea is rare in the fact that it is located very close to the ocean, but is not considered a resort and thus does not incur resort fees on your stay.

Additionally, all Residence Inn hotels include complimentary breakfast in your stay, which is a major perk as I currently don’t hold any status with Marriott beyond Silver Elite, which is very basic.

For my three-night stay, I needed to pay 186,000 points, which I split by redeeming 3 free night awards and 36,000 points I had from the referrals I made.

If I were to pay for the stay out-of-pocket with cash, it would’ve run me $1665, meaning that I saved about the same amount of money I did for the accommodation in Honolulu.

When combining my savings with the flights and the two hotels, I saved a total of $3720 by utilizing the companion fare from the Atmos™ Rewards Ascent Visa Signature® credit card, the five free night awards from the Marriott Bonvoy Boundless® Credit Card, and point bonuses from referring the Marriott Bonvoy Boundless® Credit Card to other people.

This is an insane amount of money, and if it weren’t for the companion fare and the free night awards, my family’s trip to Hawaii wouldn’t be possible simply because of how expensive it would’ve been. $4000 is a luxury, and my situation goes to show how you can make your family’s dream vacation more accessible by simply taking advantage of credit cards.

Final Remarks

Traveling to Hawaii can feel out of reach when you see the sticker shock of airfare and hotels, especially during peak holiday seasons. But by pairing the right credit cards with thoughtful redemptions, I was able to save nearly $4,000 on flights and accommodations for a week-long trip to O’ahu and Maui.

This trip wouldn’t have been possible without leveraging the Atmos Ascent’s companion fare and the Marriott Bonvoy Boundless® Free Night Awards. These tools turned an expensive winter getaway into an affordable dream vacation.

If you’re considering a trip to Hawaii, or anywhere else, remember that the right mix of sign-up bonuses, loyalty programs, and travel perks can dramatically cut your costs. With a bit of planning and strategy, your dream destinations can become attainable realities.