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Cleared for Takeoff: A family adventure in Oahu and Maui

June 08, 2021
14 min read
A beach in Maui, Hawaii
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Cleared for Takeoff is a weekly series showing readers like you the best ways to book post-pandemic adventures using points and miles. If you’d like tips on booking your own trip using miles, please email us with your preferred itinerary and current mileage balance.

Hawaii is a hot destination right now since Americans can travel there without major entry restrictions. COVID testing requirements imposed on travelers from the mainland have been reduced over the past month due to increased vaccination and declining case counts. With that in mind, reader LaKeisha Batts reached out to us asking the best ways to book a trip to Hawaii for her and her family:

"Hi! I would like to reschedule our post-COVID trip to: Hawaii (Maui & Oahu). My home airports are: HOU or IAH and there are 4 of us total (2 adults, 2 kiddos). I would love to fly First class, but am OK with economy too! Thanks so much for the help!"

LaKeisha has a stash of Chase Ultimate Rewards, Marriott Bonvoy and Southwest Rapid Rewards points to work with for this trip. Let's take a closer look at their balances and how they can use their mileage stash for a trip from Houston to Hawaii this summer.

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Current points stash

LaKeisha has a large stash of points across the three programs and more than enough for a family of four to go to Hawaii. Further, their points make it easy for them to cover a handful of nights on both islands in four- and five-star hotels. Here's a look at their current balances:

Related: The best elevated credit card offers to sign up for

Airfare to (and around) Hawaii

Business-class award space for four is hard to come by, so the Batts' best bet is to fly Southwest in economy class. (Photo by Phillip B. Espinasse /

This is a two-part itinerary: Houston to/from Hawaii and inter-island Hawaii flights. Here's a look at how LaKeisha can use their points and miles to book all legs of their Hawaiian itinerary with their stash of Chase and Southwest points.


LaKeisha didn't send us a timeframe for the trip, so we assumed they're OK with flying any time before the end of the summer. Unfortunately, business class award space to Hawaii for four can be hard to come by in the summer months. So, I assessed all their options and found that Southwest actually has the best award pricing for economy flights to Hawaii this summer. On the bright side, booking with Southwest points lets LaKeisha save her Chase and Marriott points for hotels in Hawaii.

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LaKeisha can book flights from Houston-Hobby (HOU) to Honolulu (HNL) for as little as 14,962 Southwest Rapid Rewards points one-way per person, depending on the date. Most flights go through Los Angeles (LAX), Las Vegas (LAS) or Phoenix (PHX).

Related: 6 versions of paradise: How to choose the right Hawaiian island for you

(Screenshot courtesy of Southwest Airlines)

Further, return flights from Maui (OGG) to Houston start at the same price, with the cheapest one connecting through Phoenix (PHX).

(Screenshot courtesy of Southwest Airlines)

I also recommend using Southwest points to book flights from Honolulu (HNL) to Maui (OGG). You can find nonstop Southwest award flights for as low as 2,240 points per person this August.

(Screenshot courtesy of Southwest Airlines)

If LaKeisha were to book the cheapest flights, they'd spend just 32,164 Southwest points per person on this Hawaii trip. This is a total of 128,656 Southwest points for the whole family, assuming they don't have a Companion Pass.

Related: I just traveled to Hawaii: Here’s what it’s like for tourists right now

How to book this award with points

Booking Southwest award flights is simple, with one caveat. Booking multi-city trips with Southwest is limiting since you cannot add more than two cities to your itinerary. So, LaKeisha needs to book their HOU-HNL, HNL-OGG and OGG-HOU tickets as separate one-way tickets.

Doing this is easy. Just head to the Southwest website and enter your desired itinerary into the search box at the center of the screen. Make sure to select the "points" option at the upper right-hand corner of the search box to book with your Southwest points. You can also click the Low Fare Calendar button to see a month's worth of award pricing at once.

(Screenshot courtesy of Southwest Airlines)

You'll see all available award flights and their respective prices at the center of the screen. Look through the options and click on the price for the flight you'd like to book. You'll notice that each flight has three prices: Business Select, Anytime and Wanna Get Away. I recommend sticking with Wanna Get Away fares for the best deal since the other two provide limited benefits for most flyers.

(Screenshot courtesy of Southwest Airlines)

Now, follow the on-screen prompts to book your award tickets. Do this for all three legs of the trip, and you're all set with airfare!

Related: 10 things to expect on Southwest flights to Hawaii

How to earn enough miles for this award

LaKeisha has more than enough Southwest points to book these flights. If you're looking to do the same, there are several ways to earn Southwest Rapid Rewards points, like transferring points from Chase Ultimate Rewards. The best way to earn them quickly is by applying for a Southwest cobranded credit card and earning the welcome bonus.

Here's a look at current offers:

Related: The best Southwest Airlines credit cards for family travelers

Hotels in Hawaii

LaKeisha can get a ton of value from their Chase and Marriott points when booking hotels in Oahu and Maui. (Photo by Clint Henderson/The Points Guy)

Hawaii has no shortage of amazing points hotels. Most major hotel groups have properties in both Oahu and Maui, and since LaKeisha has Chase and Marriott points to work with, they have plenty of flexibility. Let's take a quick look at some of their best options.

Related: TPG readers reveal their favorite points hotels in Hawaii

How to book hotels with points

I'd recommend the family redeems their stash of just over 280,000 Marriott points to book a five-night stay at one of the island's Category 7 hotels. These cost 60,000 points per night (or 70,000 on peak dates), but the family will save with Marriott's fifth-night free benefit.

Here are some of the best options:

  • Moana Surfrider, A Westin Resort & Spa, Waikiki Beach — 60,000 points per night
  • Sheraton Waikiki — 60,000 points per night
  • The Laylow, Autograph Collection (Category 6) — 50,000 points per night
  • The Royal Hawaiian, a Luxury Collection Resort, Waikiki — 60,000 points per night
  • Waikiki Beach Marriott Resort & Spa (Category 6) — 50,000 points per night
The pool at the Sheraton Waikiki is sure to impress the Batts' children. (Photo by Tomas del Amo /

Chase points instantly transfer to World of Hyatt at a 1:1 transfer ratio, so the family can use them to cover hotel stays in Maui. Hyatt has many great redemption options on the island, including some that will give the family over $500 per night in value.

Here's a look at some of the best Hyatt options in Maui, alongside their nightly award price:

  • Andaz Maui at Wailea Resort — 30,000 points per night
  • Hana - Maui Resort — 30,000 points per night
  • Hyatt Regency Maui Resort and Spa — 25,000 points per night
  • Kaanapali Alii — 30,000 points per night
  • Wailea Ekahi Village, A Destination by Hyatt Residence — 20,000 points per night
  • Wailea Grand Champions Villas, A Destination by Hyatt Residence — 20,000 points per night

Say the family wanted to book the most expensive option — the Andaz Maui — for 30,000 points per night. This would cost just 150,000 points for a five-night stay. The same stay this summer can cost as much as $5,700, giving them a massive 3.8 cents per point in value for their Chase points.

The Andaz Maui at Wailea Resort is an excellent deal at 30,000 points per night. (Photo courtesy of Hyatt)

How to book a Marriott hotel with points

You can book Marriott hotels by heading to the Marriott website. Enter your itinerary at the center of the screen and check the "Use Points" box at the lower right-hand corner of the search box to see award pricing.

(Screenshot courtesy of Marriott)

Look through the available hotels and find one you'd like to book. Then, click on "View Rates."

(Screenshot courtesy of Marriott)

Now select the room you'd like to book and follow the on-screen prompts to complete your reservation.

(Screenshot courtesy of Marriott)

If you're booking a five-night stay, the fifth-night free benefit will be automatically applied at checkout.

(Screenshot courtesy of Marriott)

Related: 5 ways to maximize Marriott Bonvoy award night redemptions

How to book a Hyatt hotel with points

To book a Hyatt hotel, head to the hotel group's website and enter your itinerary at the center of the screen. Make sure to check off “Use Points” to see award pricing.

(Screenshot courtesy of Hyatt)

Find the hotel you'd like to book and click on "View Rates" to see available award rooms. When booking high-demand hotels, you may have to play around with dates, as award availability can dry up quickly.

(Screenshot courtesy of Hyatt)

Select the room you'd like to book and follow the on-screen prompts to complete your reservation.

(Screenshot courtesy of

Related: 9 mistakes to avoid when redeeming hotel points

How to earn hotel points

Again, the family has more than enough points to cover their hotel stays in Hawaii. That said, if you wanted to book these hotels you could earn Marriott points quickly with a cobranded credit card from American Express or Chase. Here's a look at all available cards alongside their current welcome offers:

For Hyatt hotels, you can earn points with the following cards:

  • World of Hyatt Credit Card: Earn 30,000 bonus points after spending $3,000 on purchases within the first three months from account opening. Plus, up to 30,000 more bonus points by earning 2 bonus points total per $1 spent on purchases that normally earn 1 Bonus Point, on up to $15,000 in the first six months of account opening.
  • Chase Sapphire Preferred Card: Earn 60,000 bonus points after spending $4,000 on purchases in the first three months from account opening.

Related: My top 3 picks for the best cobranded hotel credit card

Bottom line

LaKeisha has more than enough points for an epic family vacation to Hawaii. While business class tickets to Hawaii are hard to find for a family of four, economy seats are more than made up for with points stays at five-star hotels. Consider replicating their itinerary this summer if your family is looking for a getaway to paradise.

If you have a destination in mind and need help figuring out your points strategy, send us an email to be featured in the next installment of Cleared for Takeoff.

Feature photo Pierre Leclerc /

Featured image by (Photo by Pierre Leclerc /
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.