Travel Hacking: How I Get Free Flights & Hotels in Hawaii
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 <<
Later in this post I’ll get into logistics about picking the best airline that makes sense for YOU to fly (based on where you’re flying from) and I’ll layout options with Southwest, American, United, Delta, Hawaiian, and Alaska.
So keep reading!
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.
But I have a “go big or go home” philosophy when it comes to travel, so I like to DOUBLE DIP on Marriott Bonvoy rewards with the Marriott Bonvoy Business Amex.
If you’re self-employed, a freelancer or contractor, a gig economy worker, if you own rental properties, etc…you qualify for a business card. (And you don’t need to be registered as an LLC or corporation. You can apply as a sole proprietorship with just your social security number.)
This card comes with three free 50K nights (the same as my Marriott Bonvoy Boundless through Chase) so right out of the gate, that’s SIX FREE NIGHTS.
Plus having both really gives you a jump on hitting an “elite status level” where you get perks like free breakfast, room upgrades, late check out, etc.
AND with each of these cards…every year on the anniversary of the date you opened your card, you get a free 35K/night free night certificate. I just used a couple of these to stay at the new AC Hotel Wailea!
Later in this post I’ll get into the logistics of which Marriott properties on which islands will give you the best options for using free nights plus which properties are most “aspirational” (AKA which ones I would save up a bunch of points to spend on).
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…
Maui’s flagship luxury resort, 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.
More about Flying to Hawaii ON POINTS
Okay, now that you know about my favorite airlines for points, here’s what you need to know LOGISTICALLY about flying to Hawaii:
Flying Southwest Airlines to Hawaii
Here’s what Southwest flights to Hawaii look like.
You can fly direct to Hawaii on Southwest from:
Las Vegas (LAS) to Maui (OGG), Oahu (HNL), Kauai (LIH), Big Island (KOA)
Oakland (OAK) to Maui (OGG), Oahu (HNL), Kauai (LIH), Big Island (KOA)
Phoenix (PHX) to Maui (OGG) and Oahu (HNL)
Sacramento (SMF) to Oahu (HNL)
San Jose (SJC) to Oahu (HNL)
Los Angeles (LAX) to Oahu (HNL)
Long Beach (LGB) to Oahu (HNL)
San Diego (SAN) to Oahu (HNL)
If you live in one of those cities, you are GOLDEN. You’ll be able to find flights fairly cheap (and low miles) and it’s an easy 4-6 hour flight.
If you do not live in one of those cities (hi, it’s me), you’ll need to do a little research into which (if any) you can fly directly from your city to.
For example, flying from Tulsa, OK, I can get direct flights on Southwest daily to Las Vegas and Phoenix, making those options for me to get to Hawaii (Southwest won’t sell you a through ticket with more than one connection).
Now, the flight times have to line up so you’ll be able to do it all in one day, but I can usually make something work even if it’s just on certain days of the week.
Maybe you noticed that from Las Vegas you can fly to all four of the main Hawaiian Islands, and that’s not by accident.
First of all, Las Vegas is a wildly popular destination with Hawaiians so there’s always demand for those flights.
Second, most mid-sized cities in the US have direct flights to Las Vegas making it the perfect “hub” for Southwest to use for people who don’t live in one of the cities with a direct flight and need to make a connection.
Live in Minneapolis, Dallas, Denver, Memphis, Albuquerque, Charlotte, Chicago, Columbus, Pittsburgh, etc? You can probably get a direct flight to Vegas which opens up Hawaii to you.
So flying to Hawaii from Las Vegas, Oakland, Phoenix, Sacramento, San Jose, Los Angeles, Long Beach, or San Diego will generally be fewer points (and a cheaper cash price) than if you have to make a connection, but you’ve got options. And that’s not even taking into account a sale.
PLUS…when Southwest entered the Hawaii market, they also added a TON of interisland flights so even if you can only get to Oahu from the mainland, you can easily island hop once you get there.
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.
Flying American Airlines to Hawaii
If you’re flying out of any of these cities, American Airlines could be a good option for Hawaii:
Dallas (DFW) has flights to Maui (OGG) and Oahu (HNL). These two routes are AA’s “Flagship” Hawaii routes meaning they fly a widebody aircraft more commonly seen on international flights. You’ll get a full meal plus the option for premium economy seating and lie flat seats in business class. These flights are usually more $$$ even in economy.
The rest of these routes are just standard domestic flights:
Los Angeles (LAX) has flights to Oahu (HNL), Kauai (LIH), Kona-Big Island (KOA), and Maui (OGG).
Phoenix (PHX) has flights to Oahu (HNL), Kauai (LIH), Kona-Big Island (KOA), and Maui (OGG).
*AA used to fly some routes to Hawaii from Chicago and Charlotte, but those aren’t currently offered.
Flying Delta Airlines to Hawaii
If you’re flying out of any of these cities, Delta could be a good option for Hawaii:
Atlanta (ATL) has flights to Oahu (HNL) and Maui (OGG).
Detroit (DTW) has flights to Oahu (HNL).
Los Angeles (LAX) has flights to Oahu (HNL), Kauai (LIH), Kona-Big Island (KOA), and Maui (OGG).
Minneapolis (MSP) has flights to Oahu (HNL).
New York (EWR) has flights to Oahu (HNL).
Salt Lake City (SLC) has flights to Oahu (HNL).
Seattle (SEA) has flights to Oahu (HNL).
Delta also offers interisland flights so you can connect to another island through Honolulu.
Flying Hawaiian Airlines to Hawaii
If you’re flying out of any of these cities, Hawaiian Airlines could be a GREAT option for Hawaii (get those aloha vibes going before you even get there ; )
Austin (AUS)
Boston (BOS)
Las Vegas (LAS)
Long Beach (LGB)
Los Angeles (LAX)
New York (JFK)
Oakland (OAK)
Ontario, California (ONT)
Phoenix (PHX)
Portland (PDX)
Sacramento (SMF)
Salt Lake City (SLC)
San Diego (SAN)
San Francisco (SFO)
San Jose (SJC)
Seattle (SEA)
Hawaiian Airlines also offers an extensive network of interisland flights.
Flying Alaska Airlines to Hawaii
This west coast based budget carrier isn’t something that’s ever on my radar (since I fly from the middle of the country), but if you’re flying out of one of these cities, they’re usually very competitively priced.
Anchorage, Alaska (ANC)
Portland (PDX)
Los Angeles (LAX)
San Diego (SAN)
Seattle (SEA)
San Francisco (SFO)
San Jose (SJC)
Always Book Directly with the Airline
Whichever airline you choose, be sure to follow the cardinal rule of air travel. ALWAYS BOOK DIRECT. Under no circumstances should you ever book airfare through a third party company like Expedia, Travelocity, and I hate to say it but even Costco. Air travel is WILD. Wildly undependable.
Flights get delayed, they get canceled, plans get derailed. And when you’ve booked through a third party, you can’t deal with the airline directly. You can literally be in the airport at the gate and depending on what the problem is (flight canceled, flight delayed and you’re going to miss your connection, etc) the gate agent may not be able to help you.
You haven’t known frustration until you’re literally standing in front of a human that handles flight changes for the airline and they can’t help you because you have to call Expedia and be on hold with them for 6 hours instead. When you book with a third party, THEY hold the reservation, not you.
Here’s the other thing…these booking sites hardly ever have prices any cheaper than the actual airline anyways. Do your research using Expedia or whoever you like to shop and then go directly to the airline to book.
More about Using Marriott Points in Hawaii
Besides the traditional Marriott marquis hotels, Marriott’s brands in Hawaii also include Sheraton, Westin, Ritz Carlton, Courtyard, Residence Inn, Marriott Vacation Club, and the Luxury Collection & Autograph Collection (collections of boutique hotels like the Royal Hawaiian, Moana Surfrider, Mauna Kea Beach Hotel, and the Laylow – these are some of my favorites ; )
So there are a LOT of great hotel choices in Hawaii under the Marriott umbrella – whether you’re looking for a once in a lifetime destination resort, a boutique hotel with fun vibes, or a good bang for your buck hotel.
Hawaii Hotels to Use 50K Free Night Certificates
In Hawaii (depending on dates), that could work at hotels like:
Oahu: The Laylow, Royal Hawaiian, Moana Surfrider, Courtyard Waikiki Beach, Sheraton Princess Kaiulani, Waikiki Beach Marriott, Renaissance Honolulu Hotel, AC Hotel Honolulu, Residence Inn Kapolei, and Courtyard North Shore.
Maui: Sheraton Maui Resort, Westin Maui Resort, AC Hotel Wailea, Courtyard Kahului (in August 2024 the Wailea Beach Resort has redemptions for 55K/night!!)
Kauai: Sheraton Kauai Coconut Beach Resort, Sheraton Kauai Resort
Big Island: Courtyard King Kamehameha’s Kona Beach Hotel, Waikoloa Beach Marriott
But I’ve saved my favorite thing about using Bonvoy points to book Marriott hotels for LAST:
When you book four nights using points, you get a FIFTH NIGHT FREE. So after I use my free night certificates (that have max point values like 50K or 35K per night), I only use my Marriott points for “big” stays where I have enough points to book four nights and get the fifth free. It’s by far the best way to max out the value on your points.
Side note: You cannot combine free night certificates with points to take advantage of the fifth night free promo.
Last year, I cashed in 325K points to stay for 5 nights at the Mauna Kea Beach Hotel on the Big Island. And I’m getting ready to stay at the Ritz Carlton Kapalua for 5 nights for 330K points.
And obviously, if you’re not staying at premium luxury properties, you can get stays for a LOT less. Or stay a lot longer ; )
I mentioned a list of hotels above that are good places to get the best “bang for your buck” on points and use free night certificates above, but if you’re like me, and you have a “bucket list” of great hotels, here’s also a list of the top aspirational Marriott properties in Hawaii (places that are worth hoarding your points for a big splurge):
Wailea Beach Resort (Maui)
Ritz Carlton Kapalua (Maui)
Koloa Landing Resort (Kauai)
Mauna Kea Beach Hotel (Big Island)
Royal Hawaiian (Oahu)
Moana Surfrider (Oahu)
Turtle Bay Resort (Oahu) ***This hotel JUST joined the Ritz Carlton brand earlier this year!!
P.S. Thanks for sticking around and reading this whole post! If you have ANY questions about planning your trip to Hawaii, you can join my free Facebook group here. I’m there answering questions every day and there are 7500+ other friends who have a ton of Hawaii information to share!
Also, if you want to follow along on my travel adventures in real time, you can follow me on Instagram (@caitylincoln). My post captions are full of travel tips and I have a ton of story highlights and videos with great info. And please share my account with your friends that are headed to Hawaii! Your support really helps me keep this blog running!