Booking a Trip to Oahu With Points (nearly free)

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Frequent travelers to Hawaii and those who are just starting to research a trip will know – the Aloha State is an expensive destination! According to our research, the average cost for a family booking a trip to Oahu for 10 days is $11,829, with over $6,500 of that being spent on airfare and accommodation alone. Source: HTA

Now imagine if you could get your flights and hotel room for free? We’ve had our fair share of amazing stays and free flights using credit card points for our trips to Oahu.

With a bit of knowledge of how to utilize points and some flexibility, you could be looking at a considerably discounted trip to Hawaii. These are our tips on booking a trip to Oahu with points.

Booking Flights to Oahu with Points

Having traveled back and forth from the mainland to Hawaii frequently, we generally find that flights to Hawaii are fairly reasonable price-wise, especially if you’re flying from the West Coast.

We have a five-step process for booking cheap flights to Hawaii that we use when we’re searching for and booking flights.

We prefer to use our points for free nights, as lodging will be your largest line item on your Hawaii budget.

Oahu has the most well-connected airport in Hawaii, making it one of your best bets for finding a good deal on tickets. The more flexible you can be with your dates, the better flight deals you can score. 

Still, if you’re dead set on using points for your flights, there are some good deals available with airplane-branded credit cards.

Southwest and Alaska Airlines cards both offer companion passes. These will save you the price of one ticket (plus a government fee of $5.60 to $11.20).

Let’s get into the details on how to make this possible when booking a trip to Oahu.

Southwest on Points

Southwest’s points value is based on the cash cost of the fare and fluctuates accordingly. Essentially, the points redemption value for tickets is similar to the actual price of the ticket. 

For example, we found a round-trip flight leaving LAX for Oahu on February 9th and returning on the 16th for just 19,000 points per person. That’s a cash equivalent of $274 + $53 fees.

Considering that the sign-up bonus for a personal Southwest card is 100,000 points (that’s their current special offer!), you could potentially fly your family of four to Hawaii for just the cost fees (which would come out to around $45)!

This fare also includes one free checked bag for each person flying as a perk of using the Southwest card. That’s the equivalent of $800. 

Perks like the Southwest Companion Pass, which you can earn by either taking 100 flights in a calendar year or by earning 135,000 Rapid Rewards in a calendar year, further sweeten the deal and are a wonderful way to reduce your travel costs.

Details! Here is our two-year lookback on having the Southwest Companion Pass for Hawaii.

You can earn a companion pass by signing up for a personal and business Southwest card, worth 180,000 Rapid Reward points. You most likely qualify for a business credit card.

We use our companion passes on every trip to Hawaii as we fly Southwest for Hawaii inter-island flights. Southwest and Hawaiian/Alaska are the two inter-island carriers with the most flights and the best rates.

Alaska Airlines on Points

Alaska, Southwest, and Hawaiian Airlines were the budget carriers to Hawaii. Now that Alaska Airlines has merged with Hawaiian Airlines, their combined reward programs make a free trip to Hawaii more likely for you.

Their new loyalty and reward program has a special online offer with its branded cards here.

The sign-up bonus is equivalent for one or two flights to Hawaii, plus a low cost companion fare ($99) or a companion award. Choose the card with a low annual fee or the card with a higher annual fee, but more points.

Premium Card for Free Flights to Oahu

Now, this airline-rewards strategy is a bit more complicated than getting an airline-branded card. But you will have greater flexibility in booking flights to Oahu with large mainland carriers like United. This is great for East Coast visitors!

Apply for our #1 favorite bank card, as the point transfer deals are excellent.

With the sign-up bonus plus the point multipliers (like 5X on travel), you can transfer your reward points to United, Southwest, or other carriers for free flights. You aren’t restricted to one airline.

Booking Oahu Hotels with Points

Oahu is the most visited island in Hawaii. Therefore, you have the largest selection of hotels to redeem points at.

We love a luxury hotel for less, but you can also book value hotels using points like AC Marriotts, Hilton Garden Inn, and Courtyard Marriotts. Honolulu is full of value hotels, except the North Shore Courtyard Marriott, which is at the Polynesian Cultural Center.

Hyatt Hotels in Hawaii continue to offer the best point redemption values. See our Hyatt vs Marriott Rewards in Hawaii for proof.

Lucky for you, booking a trip to Oahu means you can visit most of the Hyatt properties here. See our Hyatt Hotels in Hawaii and How to Book with Points for more options on where to stay with points.

Our two favorite options for booking a hotel on Oahu with points are the Hyatt Place Waikiki and the Sheraton Waikiki. Here are the best ways to exchange your points and free nights for a week in Waikiki.

More options for booking a hotel on Oahu:

• The 7 Best Luxury Hotels on Oahu
• 8 Best Beachfront Hotels on Waikiki Beach
• Where to Stay on Oahu: Best Locations and Hotels
• Where to Stay in Waikiki: 12 Best Hotels and Vacation Rentals
• 22 Best Family Resorts on Oahu
• Hyatt vs Marriott Rewards in Hawaii

The Hyatt Place Waikiki

The Hyatt Place Waikiki is something of a unicorn in the Hawaiian hotel points world. As a category 3 Hyatt Hotel, rooms here can be booked for as little as 12,000 points per night.

This is an incredible deal considering that other Hyatt hotels in Hawaii average about 22,500 points per night across the islands.

If you were to sign up for a Hyatt-branded credit card and earn the full 60,000 bonus points, you could hypothetically stay at the Hyatt Place Waikiki for five days, completely free!

Our preferred way of getting free nights at Hyatt hotels in Hawaii is to transfer points to Hyatt directly from our #1 favorite bank card. With the 75,000 sign-up bonus offer, you can get 5 nights free!

We transfer points from the bank’s travel portal to World of Hyatt. This gives us more flexibility on how we can spend our points.

Check out our complete guide to booking Hyatt hotels with reward points for the full scoop, where we’ll walk you through step by step on exactly how to do it. 

Overall, the Hyatt Place Waikiki is one of our favorite accommodation options on Oahu for the free breakfast buffet, walkable location, and their pet policy. Rooms are a bit more economical but still offer up views of the ocean and Diamond Head through the city, and a rooftop pool to boot.

The Sheraton Waikiki

While The Hyatt Place is a bit less flashy and more budget-friendly, The Sheraton Waikiki takes it up a notch with luxury vibes and an oceanfront location. Imagine an endless activity list that includes lei-making and hula dancing lessons, opulent pools that cater to both adults and children, and spacious rooms with private lanais overlooking either the sea or city. 

Booking The Sheraton Waikiki with points is a bit more difficult, and you’ll need to dish out quite a few more points to do it.

In the world of travel points, you don’t get nearly as much bang for your buck with Marriott properties, especially compared to Hyatt, but they do offer more luxurious properties. Our favorite strategy for utilizing points for a Marriott stay is to combine free night certificates with points.

The best card for free nights is our #1 bank card again, thanks to the 1:1 point transfer to Marriott Bonvoy.

The sign-up bonus can earn you up to three nights free if you spend enough on eligible purchases in the first three months. Free night certificates can be exchanged for nights at the Sheraton Waikiki.

As far as booking with points goes, Marriott uses a dynamic pricing system that is similar to a typical hotel booking portal in that the point value of rooms fluctuates depending on the day. Rooms at the Sheraton Waikiki typically range from 53,000 to 76,000 points a night, depending on the time of the week you book, as well as the time of year. 

One thing to keep in mind with the Sheraton Waikiki are $52 a night resort fees and the $55 self-parking fee or $65 a night valet parking fee (as of August 2025).

See our How to Avoid Resort Fees in Hawaii for tips!

We share over 31 hotels that are our preferred places to stay on points in our Where to Stay in Hawaii with Points.

Final Thoughts on Booking a Trip to Oahu with Points

Use those sign-up bonuses and hard-earned points to book your trip to Oahu! We focused on hotels and flights, as that is where you will get the most value using your points.

We share all of our Hawaii Travel Credit Cards and how to use them so you can take your dream vacation to Hawaii.

I’m afraid you aren’t done booking your trip to Oahu. But, we have done the heavy lifting for you! Grab our Oahu Wayfinder Itinerary for fully-planned excursion days, where to eat, and the best beaches. Learn more below.