I’ve been on THREE trips to Hawaii in the last year with free flights AND free hotels ALL booked using points and miles.

That’s:

One trip to Maui staying at the super swanky Wailea Beach Resort and doing my favorites like sunrise at Haleakala, the Road to Hana, and soooo much beach time.

One trip to the Big Island staying at the Mauna Kea Beach Hotel to visit Hawaii Volcanoes National Park, tour a Kona coffee farm, and see the manta rays after dark.

And one trip to Maui staying at the Ritz Carlton Kapalua to explore the west side beaches, drive the Kahekili Highway, and do a day trip to Lanai.

WITH FLIGHTS FOR TWO PEOPLE.

Some people call it “travel hacking,” but basically…it’s using credit card points & mile systems to cover travel experiences, usually in a more luxurious way than you would normally if you were paying cash.

I’m certainly no expert in this industry, and I’m sure there are people who do this WAY better than me (and on a bigger scale), but I do travel to Hawaii a lot and I’ve saved a LOT of money using points and miles. So I’m going to tell you how I do it ; )

Using Credit Card Points to Travel to Hawaii

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First of all, a BIG Disclaimer: You should NEVER go into credit card debt to do this. And you should never use this to justify spending more money on things than you normally would because you’ll “get points.”

Also, let’s be clear. Stringing together free stays and amazing deals isn’t as simple as applying for one credit card and getting a free trip. It usually involves a little more strategy and synchronization (and sometimes just time to accrue points).

But here’s how to start:

Pick an Airline

I like Southwest and they’re the only airline I fly to Hawaii anymore. They’ve also got BY FAR the easiest credit card point system to use plus bags are free I think they have the most flexible rebooking/cancellation policy.

I have this Southwest Premier Rapid Rewards Visa card through Chase. The current sign up offer is 50,000 points. Depending on where you live and fly from, that’s at least one completely FREE ticket to Hawaii and it could be two depending on the time of year (or more if you catch a crazy sale).

The card also gives you:

2 Early Bird Check-Ins per year (super nice when you’re going to Hawaii and the perfect seat is really important)

6000 anniversary points

3x points on Southwest purchases (more points for your next flight)

If you’re new to the “travel hacking” game, I think this is a REALLY good place to start. You’ll get some free flights right away and honestly, I feel like Southwest points rack up sooooo fast when you’re using the card for your everyday purchases.

Again, use >> this link << to get 50K bonus points when you sign up.

But my FAVORITE Southwest points feature is the Companion Pass. If you rack up enough points in a calendar year (through credit card spending and flights flown), you get a Companion Pass. For the entire year, every time you fly, you get to take somebody with you FOR FREE (whether you pay cash or book with points).

The Companion Pass is good for the rest of the year when you qualify plus the entire next year (for example: if you qualify in October, you get the Companion Pass for the rest of that year plus the entire next year)

So once you qualify for a Companion Pass, your points actually end up going twice as far.

It’s too good to pass up. Details >> here <<

For more info on how to maximize the benefits on this card (and how to fly Southwest to Hawaii even if you’re not flying from the west coast), read this post.

Pick a Hotel

Hotels and resorts are my FAVORITE thing to use credit card points on because there’s such a spectrum of what you could save. Flights cost what they cost, but using points on a luxury hotel could save you up to $1500 PER NIGHT.

My go to is Marriott. They have by far the most options available of any of the major hotel chains plus they’ve got a ton of luxury and boutique options (which are my favorite).

This Marriott Bonvoy Boundless card through Chase is probably my most used credit card.

As soon as you sign up for this card (and meet the minimum spend requirement) you get 3 FREE nights to use anywhere you want! The free nights attached to this card are good for hotels worth up to 50K points per night (plus you can add 15K points to each of those certificates) meaning you can book three nights at a hotel that’s valued at up to 65K points per night. There are quite a few hotels in Hawaii that will fall into that category (even more if you go during shoulder season – spring or fall).

Again, use >>this link<< to get 3 FREE nights when you sign up for this card.

For WAY MORE DETAILS on how I max out the benefits on this card PLUS the lowdown on the best Marriott properties in Hawaii (including which ones you’ll be able to use your free night certificates at), read this post.

The Big Guns: Chase Sapphire Reserve

Okay, we’ve talked about the two specific brand programs and cards that I use, but if you’re serious about travel hacking, you can’t ignore the Chase Sapphire Reserve.

This card operates with Chase Ultimate Reward points which are widely considered to be the most valuable and most versatile points in the travel industry. And it’s mostly because they’re part of a larger travel network.

Chase Ultimate Rewards has partnered with major travel brands like Southwest, Marriott, Hyatt, British Airways, etc. so you can transfer your points to those networks and book directly but they also have their own travel portal where you can book your travel and receive more value for your points.

BESIDES the amazing flexibility to earn and use your points, this card has some serious travel perks like: rental car collision coverage, baggage delay insurance, emergency evacuation and medical insurance, lost luggage reimbursement, trip cancellation insurance, etc.

The Chase Sapphire Reserve also comes with an annual $300 travel credit, Global Entry or TSA PreCheck fee credit, access to over 1300 airport lounges around the world, and credits and membership perks for brands like DoorDash, Instacart, Peloton, and Lyft.

But let’s talk about cost. The Chase Sapphire Reserve has a $550/year fee which is…a lot.

But let’s break that down. Remember, the Reserve comes with a $300 annual travel credit which immediately drops that to $250/year. So then you just have to decide if the increased point rewards, complimentary Global Entry/TSA PreCheck, lounge access, Instacart subscription, Doordash subscription, AND all of the travel insurance add up to the remaining fee.

All of the math suggests that it does, but it will just come down to if you’re comfortable with a card with such a high annual fee.

Here’s how I use the points:

Unless I’ve just opened a new card and I’m working to meet the spend requirement to get the sign up bonus (i.e. get 60K points when you spend $4000 in the first three months, etc.), I put all of my daily purchases on my Chase Sapphire card.

Then depending on what travel I’m looking to book, I either 1) Transfer Chase points to Southwest to book airfare, 2) Transfer Chase points to Marriott to book hotels, or 3) Book hotels through the Chase travel portal.

The Chase travel portal gives your Chase points a dollar value (1.5 cents for the Reserve) and you can use your points against the cash value of a LOT of different hotels.

I really like using this option to book luxury hotels like the Four Seasons or Montage or small boutique hotels which don’t have a credit card/loyalty program to collect rewards on.

For example, let’s say I have 400K Chase Ultimate Reward points saved up. At 1.5 cents/point value, that’s a cash value of $6000 that I can use to book a resort through the Chase travel portal on whatever hotel I want.

Use >>this link<< to get 60,000 bonus points when you sign up for this card.

Multi-Card Strategy

Points REALLY start to snowball when you start stacking cards to maximize rewards. The three cards I’ve mentioned above all work together really well since Southwest and Marriott are partners with Chase.

You can collect the sign up bonus (and program loyalty points) with the Marriott Bonvoy Boundless card and have the option to move your Chase Ultimate Rewards points over to Marriott Bonvoy too.

And the same for the Southwest/Chase Sapphire combo. Get the sign up bonus from the Southwest Premier Rapid Rewards card and you can transfer Chase Ultimate Reward points to your Southwest account.

So that’s like double points!

Two Free Nights at the Grand Wailea on Maui

Yes, yes, yes, I’m pretty loyal to Marriott. BUT here’s a “quick hit” that’s good to know about…

One of Maui’s most famous luxury resorts, The Grand Wailea, is a Waldorf Astoria hotel which is owned by Hilton. If you scout around a bit, you can usually find it available for as low as 110K points per night. Right now, the sign up bonus on this Hilton Honors (Amex) is 155K.

And one of the Hilton loyalty program’s stand out features (to me) is that members can transfer points to one another without a limit (Marriott caps the number of points you can transfer to someone at 100K per year).

If your travel partner (husband, wife, daughter, friend, etc) also signs up for the card and gets the bonus, one of you can transfer your points to the other and you’ll have enough points total to book 2-3 nights!

That’s probably not going to be your whole trip, but you can either pay cash for the remaining nights (a major way to lessen the bill), or use your free nights at the end of your trip (maybe you’re staying in an affordable condo) as a big splurge.

Again, use >>this link<< to get your 155K point sign up bonus when you sign up for this card.

Also, they’re not my cup of tea (too big), but a LOT of people really love the Hilton Hawaiian Village (Waikiki // Oahu) and the Hilton Waikoloa Village (Kona // Big Island) and those would also be available to book using these points (probably for less points than the Grand Wailea). And the Maui Seaside Hotel is currently undergoing major renovations and joining Hilton as part of their Tapestry Collection in 2026. When it opens, it’ll be a great (and less expensive) option that’s more of a basecamp/ “exploration” hotel.

Flying United Airlines to Hawaii

If you’re flying out of any of these cities, United is a great option for Hawaii:

Chicago (ORD) has flights to Oahu (HNL), Kona-Big Island (KOA), and Maui (OGG)

Denver (DEN) has flights to Oahu (HNL), Kauai (LIH), Kona-Big Island (KOA), and Maui (OGG)

Houston (IAH) has flights to Oahu (HNL)

Los Angeles (LAX) has flights to Oahu (HNL), Hilo-Big Island (ITO), Kona-Big Island (KOA), Kauai (LIH), and Maui (OGG)

New York Newark (EWR) has flights to Oahu (HNL) and Maui (OGG)

Orange County (SNA) has flights to Oahu (HNL)

San Francisco (SFO) has flights to Oahu (HNL), Kauai (LIH), Kona-Big Island (KOA), and Maui (OGG)

Washington Dulles (IAD) has flights to Oahu (HNL)

I’m currently working on the United Explorer MileagePlus (Chase) sign up bonus for an upcoming trip to Tokyo, but one of the things I’m most excited about is that if you book a cash ticket with United, you can use your miles to upgrade your economy seat to business class.

I don’t think that’s a big deal if you’re flying to Hawaii from the west coast, but if you’re flying from the east coast (even Houston or Chicago) it’s sooooo much nicer to fly in business or first class.

If you use >>this link<< to sign up for the card, you’ll get a 50K point bonus which could be enough to book a free economy ticket to Hawaii OR upgrade your economy ticket to first class.

The other reason I love this card is because United is one of Chase’s travel partners and my Chase Sapphire Reserve card is my go to travel card in general. So I can transfer my Chase Ultimate Rewards points to United to book directly if there’s a flight that works best for me.

And United is also in a bigger airline alliance so you have a lot of options to use your points on other airlines if you travel internationally.

Grab that United 50K bonus here.

P.S. I travel to Hawaii multiple times a year, and let me tell you a secret…I do most of it for FREE using credit card points and miles.

I have a somewhat intricate system that I’ve fine tuned over the years to maximize earning points and how I cash them in, but the short version is:

I use THIS Marriott Bonvoy Boundless card for free Marriott nights. The sign up bonus alone on this card will get you 3 (sometimes 5!) free nights at hotels in Hawaii like the Sheraton Maui, Royal Hawaiian (Oahu), Sheraton Kauai Coconut Beach Resort, and the Waikoloa Beach Marriott (Kona).

And I use THIS Southwest Premier Rapid Rewards card for free flights on Southwest. The sign up bonus will get you at least one round trip flight to Hawaii (possibly two depending on where you’re flying from).

The combo of these two cards will have you most of the way to a free trip to Hawaii right out of the gate. Again, you can sign up for the Marriott Bonvoy Boundless >> HERE and the Southwest Premier Rapid Rewards >> HERE
And if you’re really serious about getting into the travel hacking game, read this post for a more in depth look at how I maximize credit card points to book travel.

P.P.S. Here’s one more really important thing you need to know before your Hawaii trip…

You’ve got your airfare, hotel, rental car and your big activities booked, so you should be good to go, right? Wrong!

Travel is BOOMING in Hawaii and a lot of state and national parks have instituted reservation systems at some of the island’s most popular spots to help manage the crowds and make things a little more sustainable.

That means that there are now over half a dozen sites (beaches, trailheads, etc.) that require advance reservations. And some sell out well before you arrive on the island so you really need to have some sort of a plan.

I recently saw somebody in a Hawaii travel group post in a panic that they didn’t know they had to make reservations for things in advance…they thought they could just show up and “go with the flow.” I was tempted to say, well, “as long as the flow doesn’t take you somewhere that requires reservations, you can!” ; )

But I don’t want YOU to be that person, so I’ve pulled together a list of all the places you need to reserve entry in advance (plus all the details on booking windows, price, links, etc.) and a handful of popular tourist hotspots that book out really far in advance too.
Get that info >> HERE