Visit Hawaii round-trip on Southwest from $278 or 17,934 points

Jan 16, 2020

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Southwest Airlines flights to Hawaii are on sale. Say no more.

As part of the airline’s current promotion, there are discounted fares to Hawaii from the continental United States. Flights are cheapest from the West Coast — between Oakland and Honolulu, or San Jose and Maui, fares are as low as $139 one-way or $278 round-trip.

We’ve found a good number of discounted flights from January to May, which is perfect for a last-minute escape from winter, a Valentine’s Day getaway (Southwest is known as the LUV carrier) or a spring treat for yourself before the kids get out of school.

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As always, Southwest doesn’t charge any fees for up to two checked bags per passenger. You can even substitute a surfboard for free as one of your pieces of checked baggage.

Southwest doesn’t serve meals on board, so bring a snack or lunch or be prepared to nibble on a complimentary snack box.

Not sure what to expect? Read our full review of the Southwest Hawaii flight experience

And of course, if you’re traveling over the Pacific for a Hawaiian vacation, you should visit more than one island. Flights between the Hawaiian islands begin at just $39 one-way. At these prices, you might as well visit them all, right?

To book, enter your origin city on and select your destination. These are the mainland cities from which Southwest flies nonstop to Hawaii:

Airline: Southwest
Cost: From $139 one-way from the continental U.S., or $39 one-way between Hawaiian Islands
Dates: January-May 2020
Pay with: Platinum Card® from American Express (5x on airfare booked directly with the airline); Citi Prestige® Card (5x on airfare); Citi Premier® CardChase Sapphire Reserve (3x on airfare); American Express® Gold Card (3x on airfare when booked directly with the airline), or Chase Sapphire Preferred Card (2x on travel)

The information for the Citi Prestige Card has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

Here are some examples of specific flights that are available:

Oakland (OAK) to Honolulu (HNL) round-trip in May on 17,934 Rapid Rewards points and $11:

or Oakland (OAK) to Honolulu (HNL) round-trip on the same dates in May for $278:

San Jose (SJC) to Maui (OGG) round-trip in February for $278:

or San Jose (SJC) to Maui (OGG) round-trip in February for $17,934 Rapid Rewards points and $11:

Maximize your purchase

Don’t forget to use a credit card that earns additional points on airfare purchases, such as the Platinum Card® from American Express (5x on flights booked directly with airlines or American Express Travel), Chase Sapphire ReserveAmerican Express® Gold Card Citi Premier® CardCiti Prestige Card (5x on airfare), or the Chase Sapphire Preferred Card (2x on all travel purchases). Check out this guide for more on maximizing airfare purchases.

Featured image by Getty Images.

Chase Sapphire Preferred® Card

WELCOME OFFER: 80,000 Points


CARD HIGHLIGHTS: 3X points on dining and 2x points on travel, points transferrable to over a dozen travel partners

*Bonus value is an estimated value calculated by TPG and not the card issuer. View our latest valuations here.

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More Things to Know
  • Earn 80,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. That's $1,000 when you redeem through Chase Ultimate Rewards®.
  • Enjoy benefits such as a $50 annual Ultimate Rewards Hotel Credit, 5x on travel purchased through Chase Ultimate Rewards®, 3x on dining and 2x on all other travel purchases, plus more.
  • Get 25% more value when you redeem for airfare, hotels, car rentals and cruises through Chase Ultimate Rewards®. For example, 80,000 points are worth $1,000 toward travel.
  • With Pay Yourself Back℠, your points are worth 25% more during the current offer when you redeem them for statement credits against existing purchases in select, rotating categories
  • Count on Trip Cancellation/Interruption Insurance, Auto Rental Collision Damage Waiver, Lost Luggage Insurance and more.
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