Maximizing points and credit card sign ups for a trip to Hawaii

I recently received a great question from a friend. She wanted to take her family to Hawaii next year and wanted to know a good game plan. I think Hawaii is an awesome place for vacation, regardless if you have kids or not. There is so much good food and the beaches are amazing. Island life has a very chill atmosphere plus the weather is fantastic! The 5.5 hour flight is manageable if you’re traveling with little ones.

My eldest sipping POG juice while enjoying the view from our balcony when we stayed at the Hyatt Residence Maui in Spring of 2016.

Hawaii has always been one of our favorite destinations. We try to go once a year if we can since its a no fuss kind of place. I’m going to break this post down into two parts: airfare  and hotels but focusing more on airfare.

Airfare

I found airfare to range from $400 to $700 throughout the year. Sometimes airlines will have sales and you can score flights for $300 per person. There are so many options for you to score free or almost free tickets for Hawaii. If you have Chase points then you can transfer Chase Ultimate Reward points to their various airline partners listed below:

Chase Ultimate Reward Airline Transfer Partners

Transfer PartnersTransfer TimePoint Transfer Ratio
British AirwaysInstantaneous1:1
Fly Blue (Air France/KLM)Instantaneous1:1
Korean AirInstantaneous1:1
Singapore AirlinesSame Day1:1
SouthwestInstantaneous1:1
UnitedInstantaneous1:1
Virgin AtlanticInstantaneous1:1

The only issue with doing this is that some of these transfer partners require a lot of points to redeem a free flight. United, for example requires 45,000 points for basic economy. Chase points is valued at 2.2 cents per point by The Points Guy. So if you transfer 45,000 points to United, you’re only getting 1.1 cents per point ($509 roundtrip ticket/45,000 points). That’s not a good deal. I would save those Chase points for something else such as transferring to their hotel partners, Hyatt and Marriott.

A second option would be to book directly through the Chase Ultimate Rewards travel portal and get about 1.5 cents per point. This however is better than the previous option but still not that great. This may be a great idea if you’re booking a last minute flight and don’t want to pay top dollar.

The options that I would suggest include:

Southwest Airlines

The Southwest Companion Pass is a great option if you fly a lot of Southwest. You need to earn 110,000 Southwest Rapid Reward points in order to get your Companion Pass.

The pass is valid for the rest of the year in which you earn it plus the entire following year. That means that you could get nearly two years of use out of it by meeting the requirements in early 2017. That’s a two year value where someone in your family can fly for free with a purchase of another ticket every time!

Here’s how Southwest defines which points will count towards this minimum:

“Companion Pass Qualifying Points are earned from your revenue flights booked through Southwest Airlines, your points earned by making purchases with a Southwest Airlines Rapid Rewards Credit Card, and your base points earned from Rapid Rewards partners.”

There are currently two different Southwest cards out there with varying sign-up bonuses that can help you achieve the 110,000 points you need for the Companion Pass:

With both credit card sign up bonuses, you will accumulate 100,000 and plus the $5000 minimum spend, you will net you a total of 106,000 points, which leaves you 4,000 points shy. You would have to spend another $4000 to get to the 110,000. Do keep in mind that both cards come with a $99 annual fee.   These two cards option only make sense if you are able to meet the spend limit.  Don’t get the cards if you can’t meet the spend or have to spend beyond your means to get it.  That just wouldn’t make sense.  I always advise people to be financially responsible.

Alaska Airlines

Signing up for the Alaska Airlines Visa Signature Card and/or the Alaska Airlines Visa Business Card. Both cards come with a reasonable $75 annual fee. I chose this over Southwest mainly because I’ve had such bad experiences due to delays and cancellations with Southwest that I haven’t flown them for almost 4 years. This option is a little easier to obtain but not as lucrative as the Southwest Companion Pass.   Here are the perks for both of these cards:

  1. Alaska’s famous Companion Fare™ from $121 ($99 base fare plus taxes and fees from $22) every year on your account anniversary for Alaska and Virgin America flights booking on alaskaair.com with no blackout dates.
  2. Free checked bag on Alaska and Virgin America flights for you and up to six other passengers on the same reservation.
  3. Earn 3 miles for every $1 spent directly with Alaska Airlines and Virgin America purchases.
  4. Earn 1 mile for every $1 spent on all other purchases.
  5. No foreign transaction fees, plus chip enabled for enhanced security when used at chip-enabled terminals.
  6. No mileage cap.
  7. Miles won’t expire on your active account.
  8. 30,000 sign up bonus after meeting minimum $1,000 spend within the first 3 months
  9. Low Annual fee of $75

The key benefit to note here is the $121 companion pass. Southwest does have a more attractive deal of free companion pass each time you fly but this only pans out if you fly Southwest and like flying Southwest. Alaska airlines offers the once a year $121 companion pass. I also like Alaska because it partners with Virgin America, one of my favorite domestic airlines. The $121 companion pass is pretty lucrative if you use it towards a long distance trip such as SFO-JFK or SFO-HNL. Aside from Virgin American being its travel partner, Alaska Airline points are quite valuable. You can use them across multiple carriers such as Emirates, Cathay, JAL, American Airlines and many more.  If you do decide to get these cards, please contact me for the referral email.  

And if you do sign up for both cards, you will get TWO companion passes to use each year.

Hotels

After you’ve decided on how to get your family to Hawaii then you’ll need a place to stay. There are a lot of options available depending on which island you are going to. On Maui, we have stayed at the Hyatt Residence and come August we’ll be staying at the Andaz Maui at Wailea Resort.  I’ll post a hotel review once we check it out.   On Oahu, we’ve stayed at the Sheraton Waikiki and The Royal Hawaiian.  Both of these hotels are on located right on Waikiki beach and is central to shopping and food and activities in Honolulu.  I can talk more about these hotels in another post if anyone is interested, otherwise I won’t go into details in this post.

 

Disclaimer: Opinions expressed here are author’s alone, not endorsed by any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

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