Southwest Airlines offering flights to Hawaii from $99 or 6,864 points into 2021

Sep 9, 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 (on up to $500,000 on these purchases per calendar year). 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.

As the travel industry reopens following COVID-19 shutdowns, TPG suggests that you talk to your doctor, follow health officials’ guidance and research local travel restrictions before booking that next trip. We will be here to help you prepare, whether it is next month or next year.

We know your 2020 Hawaii trip probably didn’t work out as planned — neither did ours. And while Hawaii remains closed to tourists with a mandatory 14-day quarantine upon arrival and spiking COVID cases on some islands, we haven’t given up hope that 2021 may bring with it the opportunity for some safe leisure travel to the Hawaiian Islands.

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With that hope for the future in mind, know that Southwest Airlines is offering flights to Hawaii for dates into April 2021 from just $99 or 6,864 Rapid Rewards points each way. And of course, if you have the Southwest Companion Pass, then two people can fly for that price, plus minimal taxes and fees.

While the cheapest fares are typically found on the nonstop flights between California and Hawaii, connecting flights from other mainland states start at about $163 or 11,544 points each way.

Related: The best Southwest Airlines credit cards

Should I book travel now?

Sadly, our crystal ball is a bit cloudy at the moment, so we won’t be able to tell you when Hawaii will reopen for tourism without a mandatory 14-day quarantine.

Even when the state does logistically reopen, there’s certainly a level of risk if you’re booking travel now, even if your flights are scheduled for several months out as there’s no guarantee when it will be 100% safe to travel again. The CDC states that, “staying home is the best way to protect yourself and others from getting sick.”

All that being said, Southwest Airlines is very lenient when it comes to rebooking travel.

If your plans change, you can redeposit your Rapid Rewards points without penalty. If you booked your reservations with cash and need to change your plans, you can use that amount toward future travel for up to one year from the date of purchase. Alternatively, Southwest is also giving travelers the opportunity to convert unused travel funds to Rapid Rewards points.

Related: How other airline no-change-fee policies stack up against Southwest’s policy

Southwest Airlines deals currently available

Airlines: Southwest Airlines

Routes: Mainland to Hawaii 

Cost: From $99 each way

Travel Dates: Select dates until April 2021

Pay With: The Platinum Card® from American Express (5x on airfare booked directly with the airline; starting Jan. 1, 2021 earn 5x points on up to $500,000 on these purchases per calendar year), Citi Prestige® Card (5x on airfare),  Citi Premier® Card (3x on airfare), Chase Sapphire Reserve (3x on travel), American Express® Gold Card (3x on airfare booked directly with the airline or 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.

You can also pay with a Southwest Airlines co-branded credit card, though that isn’t always the best option from a points-earning perspective. The highest-earning rate for Southwest flights via a Southwest credit card comes from the Southwest Rapid Rewards Performance Business Credit Card, which awards 3x Rapid Rewards points per dollar spent on Southwest airfare.

Related: What it’s like to fly Southwest Airlines in Hawaii

Sample itineraries

Here’s a look at some of the best deals you could book. This isn’t an exhaustive list, so you’ll be able to find deals between other cities as well.

Oakland (OAK) to Kona (KOA) for $99 or 6,864 Rapid Rewards points each way

Screenshot courtesy of


San Diego (SAN) to Honolulu (HNL) for $99 or 6,864 Rapid Rewards points each way

Screenshot courtesy of


San Jose (SJC) to Kona (KOA) for $99 or 6,864 Rapid Rewards points each way

Screenshot courtesy of

Related: The best way to fly to Hawaii with kids 

How to book

To book these Southwest flights, you’ll need to head to Southwest Airline’s website. The airline’s “Low Fare” calendar is very handy if you are looking to quickly spot the cheapest fares.

Screenshot courtesy of
Screenshot courtesy of

Related: How to decide whether to use cash or miles for your ticket 

Maximize your purchase

Don’t forget to use a credit card that earns bonus points or provides trip protections on airfare purchases, such as The Platinum Card® from American Express (5x on flights booked directly with airlines or American Express Travel), Citi Prestige® Card (5x on airfare), Chase Sapphire Reserve (3x on travel), American Express® Gold Card Citi Premier® Card (3x on airfare) or the Chase Sapphire Preferred Card (2x on all travel purchases). Check out this post for more tips on maximizing airfare purchases.

And of course, if a traveler in your group has the Southwest Companion Pass, then be sure and put that valuable travel perk to good use, too.

Featured image courtesy of Summer Hull

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