Deals and Steals: Fly To Hawaii for 8,967 Southwest Points (or $139)

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This morning I posted an article highlighting how 1TP reader Tosha redeemed her Southwest Airlines frequent flyer miles for a crafty award ticket to Puerto Rico and Florida for a mere $16.

Another subscriber has been watching the prices for travel to Hawaii. They noticed the prices had decreased over the next several weeks from their hometown (Oakland) and inquired if using Southwest Airlines points to travel to Hawaii were a deal?


It appears that everyone’s favorite Hawaii deal is back again!

Not only are these fares showing over the next few months but I’m seeing these fares well into November.

Beginning at $139 one-way (or $278 round trip), all the airlines appear to be in a price war departing from many West Coast cities including Oakland (OAK), Los Angeles (LAX), San Diego (SAN), San Francisco (SFO), and San Jose (SJC).


If you are tired of reading and just prefer bullet-points…

Airline(s): Alaska, American, Delta, Hawaiian, Southwest, and United
Route(s): OAK/SAN/SJC and other west coast cities to HNL/ITO/KOA/LIH/OGG
Cost: starting at $278 Roundtrip
Dates: April – November 2020


There is one major aspect to be aware of…many of the best fares are in basic economy. If you are not familiar with basic economy, it means different things to different airlines including (but not limited to): not being able to use the overhead bins for your carry-on bag, not being able to select your seat ahead of check-in, definitely won’t get an upgrade, or earn PQM/PQS/PQDs. However, it is possible to get around a lot of these aspects by having a cobranded airline credit card.

I told you credit cards pay for themselves. 😉

However, one airline that stands out for me is Southwest Airlines. They allow you to take 2 carry-on bags for free, and you can select any seat you want. They make flying simple and the cheapest award flights begin at just 17,934 Rapid Rewards points.

Here is an example of a flight that I found:

Oakland (OAK) – Honolulu (HNL) = $277 or ~17,934 points + 11.20 Roundtrip


To find the deals, simply head to Google Flights. I’ve also attached some links below to get your started. I recommend playing with the dates and user-friendly calendar function to find a city and price that works for you.


It’s worth noting that Southwest is an outlier (in a good way) and their prices do not appear on Google Flights so you will have to search them separately.

Again, I recommend using Google Flights to determine the dates that you want to fly.

If you’re buying a revenue ticket, make sure you are using a credit card that has a bonus category for travel such as the Chase Sapphire Reserve or Chase Sapphire Preferred.

To the individuals that have the Southwest Companion Pass… congratulations and make it work for you!!

Anyone planning a trip to Hawaii? What island is calling your name?

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