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

Jan 16, 2020

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Airfare deals are typically only available on limited dates. We recommend you use Google Flights to find dates to fly, then book through an online travel agency such as Orbitz or Expedia, which allows you to cancel flights without penalty by 11pm Eastern Time within one day of booking. However, if you’re using The Platinum Card® from American Express, you’ll need to book directly with the airline or through the Amex Travel portal to get 5x MR points. Remember: Fares may disappear quickly, so book right away and take advantage of Orbitz or Expedia’s courtesy cancellation if you’re unable to get the time away from work or family.

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: 2X points on all travel and dining, 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 toward travel when you redeem through Chase Ultimate Rewards®.
  • 2X points on travel and dining at restaurants worldwide, eligible delivery services, takeout and dining out & 1 point per dollar spent on all other purchases.
  • 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.
  • Get unlimited deliveries with a $0 delivery fee and reduced service fees on orders over $12 for a minimum of one year on qualifying food purchases with DashPass, DoorDash's subscription service. Activate by 12/31/21.
  • Earn 5X points on Lyft rides through March 2022. That’s 3X points in addition to the 2X points you already earn on travel.
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Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of 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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