Fly to Hawaii with Points: 5 Best Options For Families

This post goes over five sweet spots for flying to Hawaii with points. A Hawaiian vacation is a popular goal for families who are saving up miles and points. And for good reason! The islands are beautiful, you don’t need a passport to visit, and hotel prices can be high. Due to high demand, points redemptions to Hawaii can take more planning but are still possible — especially if you plan in advance and can be flexible.

We’ve been to Hawaii twice using points. Once to Oahu and once to Kauai. While we loved both trips, it will likely be a while before we return due to the distance and jet lag involved in going from Chicago.

Flights can be a major expense for families, especially as you are multiplying the number of tickets you need to buy. There are a few sweet spots when flying to Hawaii. Again — if you’re in the Midwest or on the East Coast, it is going to be harder to book your flights. There is more competition for award seats on the long haul flights to Hawaii from Chicago or New York. You’ll need to be flexible when looking for options.

Book on Southwest Airlines

Southwest flies nonstop routes to Hawaii from 8 airports. Here is a map that shows these routes:

Due to the times of connecting flights, coming from the Midwest or East Coast you may have limited options. With a long travel day to consider, one option is to fly to California, spend the night at an airport hotel, and then continue on to Hawaii the next day.

We did this in reverse in 2019 — we flew from Kauai to Oakland and spent the night at an airport hotel (using points of course!). The next morning we continued on east.

Points Needed to Book:

Southwest award prices are tied directly to the cash price of the ticket. Using this strategy the number of points you need will be a moving target. But the advantage here is that if you don’t have enough points to cover the ticket prices for everyone in your family, it is easy to book additional tickets for the same flight in cash.

Use Southwest’s Low Fare Calendar to find the cheapest dates to fly. And remember, if your flights drop in price, you’ll be able to change them for no fee to the lower priced ticket!

If you earn a Companion Pass, your flights will be even cheaper since your companion will be able to fly for $5.60 each way! Earning a Companion Pass is our favorite way to keep our flight costs down.

Southwest Companion Pass Tricks — Learn the easiest ways to earn the Companion Pass!

How to Earn the Points:

There are three personal cards and two business cards that earn points directly with Southwest Airlines. If you have a Chase Sapphire Preferred card (or Ultimate Rewards) you’ll also be able to transfer points to Southwest from that card.

If you earned a Companion Pass, in addition to the Companion Pass you’ll also have 125,000+ points to spend on flights!

Southwest Rapid Rewards® Priority Credit Card – Earn 60,000 bonus points

$149 annual fee
$75 annual statement credit for Southwest purchases
4 upgraded boardings per year
7500 points per year on your card member anniversary
3x earning on Southwest flights; 2x on local transit, internet, cable, phone services, and select streaming
1,500 Tier Qualifying Points for every $10,000 spent
Check your Companion Pass strategy before applying

Southwest® Rapid Rewards® Premier Business Credit Card – 60,000 point bonus

$99 annual fee
2 Early Bird Check Ins per year
Free in-flight wifi
1,500 Tier Qualifying Points for every $10,000 spent
3x earning on Southwest flights; 2x on local transit
6000 points per year on your card member anniversary

Learn how to apply

Chase Sapphire Preferred® Card: 6 0,000 points

Bonus: 60,000 points

Earn 60,000 Ultimate Rewards points after you spend $4,000 on purchases in the first 3 months from account opening.

Card Highlights

$95 annual fee
No foreign transaction fees
$50 annual Ultimate Rewards Hotel Credit
$15 per quarter statement credit for Instacart
Great transfer options to Hyatt, United, Southwest, and more
Earn 3x on dining, select streaming services, and online grocery

My Take

The Chase Sapphire Preferred is one of my top beginner cards for miles & points. This limited time bonus can get you at least $1000 of travel. The travel insurance it provides is top tier, too! Get this card early in your travel points journey, it’s a keeper.

Recent Bonus History

A publicly available online offer for 80,000 points ran from March 2023-May 2023. Another 80,000 point bonus ended in Fall 2022. Standard bonus is 60,000 points.

An offer for 100,000 points ended in Fall 2021.

Book on American or Alaska Airlines (via British Airways Avios)

This redemption allows you to leverage the OneWorld airline alliance to get a better deal on your flights. Both Alaska Airlines and American Airlines partner with British Airways through the oneworld alliance.

While American will charge 45,000 miles for a round trip MileSAAver fare to Hawaii, you might be able to book the exact same flight using British Airways Avios for as low as 26,000 Avios.

This sweet spot is most powerful for non-stop flights from the West Coast. That’s because British Airways prices partner award flights (on partners like American and Alaska Airlines) by distance and by segment. That means if you are on a connecting flight (Phoenix to LAX, LAX to Honolulu) you will be charged for two segments separately. Each segment is charged based on the distance flown.

Here are the routes that fall within this sweet spot:

Anchorage (ANC) – HNL, OGG, KOA
Los Angeles (LAX) – HNL, OGG, LIH, KOA
Phoenix (PHX) – HNL, OGG, LIH, KOA
Portland (PDX) – HNL, OGG, LIH, KOA
San Diego (SAN) – HNL, OGG, LIH, KOA
San Francisco (SFO) – HNL, OGG
San Jose (SJC) – HNL, OGG, LIH, KOA
Seattle (SEA) – HNL, OGG, LIH, KOA

The best way to search for this would be to use American Airline’s website to do the initial search. You will need to filter for non-stop flights. Flights that costs 22,500 points each way on American’s website should also be available to book this way.

In this example, I have filtered to Nonstop only and can see flexible dates for a month at a time that have available award seats for 22,500 each way.