Southwest Airlines has finally begun to sell flights to Hawaii, but with current prices and availability being limited, you should consider all your options before booking – including using transferred points from other rewards programs and looking into other airlines
Dear Cashing In,
I saw that Southwest has started flying to Hawaii. That sounds great, because flights to Hawaii are often expensive.
Is it better to use points and miles to fly there, or just to buy tickets? – Ruben
Southwest received a lot of attention recently when it put those Hawaiian flights on sale. The airline made some of the tickets available for as little as $49 each way, from Oakland and San Jose – among other routes on the West Coast.
Obviously, that is a tremendous deal, which is why those tickets sold out within hours.
See related: Southwest Airlines debuts flights to Hawaii
Flying to Hawaii on Southwest: Pros and cons
If you didn’t get in on that deal and still are harboring Hawaiian dreams, you still have options.
But it is important not to pin all your hopes on Southwest, at least for the moment.
- The airline’s schedule to Hawaii is still limited.
- It can be tricky to fly there and back from the East Coast.
- In many cases, the fares Southwest is offering are no better than the fares of competitors.
But if you are planning to use points or miles, the addition of Southwest does give you additional options.
Here are the flights Southwest is adding:
- Two flights a day between Oakland and Honolulu, beginning March 2019.
- Two flights a day between Oakland and Kahului (Maui) beginning April 2019.
- One flight a day between San Jose and Honolulu and San Jose and Kahului (Maui) beginning May 2019.
- Four flights a day between Honolulu and Kahului (Maui) beginning April 2019.
- Four flights a day between Honolulu and Kona (Big Island) beginning May 2019.
If you live outside of the Bay Area, you’re going to have to connect through Oakland or San Jose.
Because of the timing of the flights, especially coming back from Hawaii, there might be few options for tickets from other parts of the country.
You might have to book tickets on separate itineraries or build in a stopover in Oakland or San Jose.
How to take advantage of Southwest flights to Hawaii
Here are your options for taking advantage of the new flights:
1. Use Southwest miles
If you happen to have stockpiled Southwest Rapid Rewards points, you can use those for the flight to Hawaii.
However, the flights have been so popular that most of the cheapest fares have already sold out, including the popular “Wanna Get Away” fares.
And because the number of miles you need is linked to the cost of the ticket, you will probably need 30,000 or 40,000 miles or more per person for a round-trip, with few exceptions.
- If you don’t have enough miles, you might consider one of Chase Southwest Rapid Rewards cards.
- All three personal Southwest cards are currently offering a 40,000-point sign-up bonuses after spending $1,000 in the first 3 months, whereas the Southwest Rapid Rewards Premier Business Credit Card is currently offering a 60,000-point sign-up bonus after spending $3,000 in the first 3 months.
- Of course, you have to wait until the miles post before using them for a trip.
- If you earn 125,000 miles in a year – through a combination of spending, sign-up bonuses and flying – you qualify for the Southwest Companion Pass, which earns free travel for a friend or relative on your same itinerary.
- That can be valuable for Hawaii. Southwest and Chase ran a promotion earlier this year that made earning that pass easier, but it has expired.
2. Transfer miles from other programs
If you have miles or points in certain other programs, you can transfer them to Southwest. For instance, Chase Ultimate Rewards transfer on a one-to-one basis.
Some hotel programs also allow transfers to Southwest, though the terms are not as favorable.
3. Just buy the tickets
It’s not as fun as the idea of flying to an island paradise for free, but if you find a good deal, paying money for it instead of redeeming points can make some sense.
But beware that these Southwest fares might not be as cheap as you would like.
- The least expensive round-trip that I found between Oakland and Honolulu in June was $502.
- From Chicago to Honolulu (via Oakland), the cheapest I found in June was $990.
- In each case, there were cheaper alternatives on rival airlines.
Flying to Hawaii: Check all options first
For many years, Southwest’s competitors used to fear discount airlines entering their turf, because it meant they would often have to lower their fares to compete.
That might eventually happen with Southwest and Hawaii, and it is important for travelers to have another option.
But so far, there is no sign that Southwest’s Hawaiian flights are dramatically lowering the prices of flights.
If you’re considering a trip to Hawaii, don’t focus only on Southwest.
Look at your other options, take stock of your miles and points in different programs, and make the decision that’s best for you. Aloha!