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Amazing deal: Fly Southwest to Hawaii for under $300 round-trip this summer

May 13, 2021
6 min read
Southwest plane flying over a palm tree in Hawaii
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Southwest Airlines announced a slew of new routes to Hawaii this morning and is already offering great deals on these new routes.

Currently, you can book Southwest flights from many mainland U.S. cities to Hawaii for under $300 round-trip. These flights usually cost well over $800, presenting huge savings on a mid-summer trip to paradise. Plus, you can book the cheapest routes for less than 20,000 Southwest Rapid Rewards points.

Let's take a closer look at the deal.

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The deal

Airline: Southwest Airlines

Routes: Dozens of continental U.S. cities to Hawaii, roundtrip

Cost: From $286 or 18,256 Rapid Rewards points

Dates: Now through Fall 2021

How to book: Go to Southwest's website and enter your origin and select a city in Hawaii. Most deals route through Southwest's new Hawaii gateways in Las Vegas (LAS), Los Angeles (LAX) and Phoenix (PHX) or on one of the 15 new routes announced today. You'll find the cheapest flights on direct flights from these cities, but connecting tickets receive a nice discount too.

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Pay Taxes/Fees With: The Platinum Card® from American Express (5x on airfare booked directly with the airline; on up to $500,000 on these purchases per calendar year), Chase Sapphire Reserve (3x on travel) or Chase Sapphire Preferred Card (2x on travel) for travel protections on the award flight.

Related: Everything you need to know about the best seats on Southwest Airlines

Is it worth it?

As discussed, round-trip tickets to Hawaii usually cost well over $800 but can be even more expensive during the summer months. These cheap flights are an excellent way to plan a summer vacation and, if you'd like, burn some Rapid Rewards points in the process.

These deals are even more valuable if you have a Southwest Companion Pass. You can use this to bring a set friend or family member with you on all Southwest flights. This effectively doubles the value of your Rapid Rewards points and halves the price of Southwest flights when flying with your companion.

Chances are, this Hawaii won't stick around for long, so book now if you want to lock in a deal. Remember, Southwest flights are completely flexible too. It may be worth booking speculatively and changing your flights later if plans don't work out.

Related: How to quickly earn the Southwest Companion Pass

Sample itineraries

(Photo by RandomHartz / Shutterstock.com)

You can find deals from most Southwest gateways, but nonstop flights are the cheapest. Here's a look at a handful of the flights you can book with cash or your Southwest Rapid Rewards points. You may find cheap flights on other routes too.

San Diego (SAN) to Kona (KOA) from $286.60 round-trip

Las Vegas (LAS) to Maui (OGG) from $378 round-trip

Denver (DEN) to Honolulu (HNL) from $415.60 round-trip

Houston-Hobby (HOU) to Honolulu (HNL) from $429.90 round-trip

Chicago-Midway (MDW) to Honolulu (HNL) from $475.60 round-trip

San Diego (SAN) to Kona (KOA) from 18,256 points round-trip

Oakland (OAK) to Honolulu (HNL) from 28,209 points round-trip

St. Louis (STL) to Maui (OGG) from 29,048 points round-trip

Los Angeles (LAX) to Hilo (ITO) from 33,129 points round-trip

Related: TPG readers reveal their favorite points hotels in Hawaii

Boosting your Rapid Rewards balance

There are plenty of ways to earn Southwest points. The easiest is transferring Chase Ultimate Rewards points to the airline at a 1:1 transfer ratio or spending with a Southwest cobranded credit card. These cards let you earn Rapid Rewards on your everyday spending and include lucrative signup bonuses.

Here's a look at Southwest's current credit card offers:

Related: The best Southwest Airlines credit cards for family travelers

Maximize your purchase

Be sure to pay for your ticket with a credit card that earns bonus points on airfare and offers travel protections. Some of the best include The Platinum Card® from American Express, Chase Sapphire Reserve, or the Chase Sapphire Preferred Card. Each of these cards earns bonus points and will protect you if your flight is delayed.

For rates and fees of the Amex Platinum card, click here.

All screenshots courtesy of Southwest Airlines

Feature photo by Phillip B. Espinasse / Shutterstock.com

Featured image by (Photo by Phillip B. Espinasse / Shutterstock.com)
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

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How we chose these cards

Our points-obsessed staff uses a plethora of credit cards on a daily basis. If anyone on our team wouldn’t recommend it to a friend or a family member, we wouldn’t recommend it on The Points Guy either. Our opinions are our own, and have not been reviewed, approved, or endorsed by our advertising partners.
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TPG featured card

Best card for premium perks while traveling
TPG Editor‘s Rating
Card Rating is based on the opinion of TPG‘s editors and is not influenced by the card issuer.
4 / 5
Go to review

Rewards

2 - 10X points
10XEarn unlimited 10X miles on hotels and rental cars booked through Capital One Travel
5X5X miles on flights booked through Capital One Travel.
2X2 Miles per dollar on every purchase, every day

Intro offer

75,000 bonus miles
Earn 75,000 bonus miles when you spend $4,000 on purchases in the first 3 months from account opening, equal to $750 in travel

Annual Fee

$395

Recommended Credit

740-850
Excellent
Credit ranges are a variation of FICO© Score 8, one of many types of credit scores lenders may use when considering your credit card application.

Why We Chose It

The Capital One Venture X card is one of the best all-round travel credit cards ever launched. Not only is it offering a tremendous welcome bonus, but cardholders can earn tons of miles on everyday spending and receive a 10,000-mile anniversary bonus to boot. Its annual fee is $395, but cardholders can count on up to $300 in statement credits toward travel booked through Capital One Travel each year and other valuable benefits like access to Priority Pass lounges and Capital One’s own growing family of airport lounges.

Pros

  • Excellent welcome offer worth 75,000 miles after you spend $4,000 on purchases in the first three months.
  • Up to $300 in annual travel statement credits toward bookings make through Capital One Travel.
  • 10,000 bonus miles (worth $100 toward travel) each account anniversary.

Cons

  • The $395 annual fee might be expensive for some, but this card’s benefits provide much more value than that.
  • If you don’t travel frequently, this might not be the best card for you.
  • Earn 75,000 bonus miles when you spend $4,000 on purchases in the first 3 months from account opening, equal to $750 in travel
  • Receive up to $300 back annually as statement credits for bookings through Capital One Travel, where you'll get Capital One's best prices on thousands of options
  • Get 10,000 bonus miles (equal to $100 towards travel) every year, starting on your first anniversary
  • Earn unlimited 10X miles on hotels and rental cars booked through Capital One Travel and 5X miles on flights booked through Capital One Travel
  • Earn unlimited 2X miles on all other purchases
  • Unlimited complimentary access for you and two guests to 1,400+ lounges, including Capital One Lounges and our Partner Lounge Network
  • Receive up to a $100 credit for Global Entry or TSA PreCheck®
  • Use your Venture X miles to easily cover travel expenses, including flights, hotels, rental cars and more—you can even transfer your miles to your choice of 15+ travel loyalty programs
  • Named editors' choice for "Best New Credit Card of 2021" by The Points Guy
  • Earn 10 miles per dollar when you book on Turo, the world's largest car sharing marketplace, through May 16, 2023
Best card for premium perks while traveling
TPG Editor‘s Rating
Card Rating is based on the opinion of TPG‘s editors and is not influenced by the card issuer.
4 / 5
Go to review

Rewards Rate

10XEarn unlimited 10X miles on hotels and rental cars booked through Capital One Travel
5X5X miles on flights booked through Capital One Travel.
2X2 Miles per dollar on every purchase, every day
  • Intro Offer
    Earn 75,000 bonus miles when you spend $4,000 on purchases in the first 3 months from account opening, equal to $750 in travel

    75,000 bonus miles
  • Annual Fee

    $395
  • Recommended Credit
    Credit ranges are a variation of FICO© Score 8, one of many types of credit scores lenders may use when considering your credit card application.

    740-850
    Excellent

Why We Chose It

The Capital One Venture X card is one of the best all-round travel credit cards ever launched. Not only is it offering a tremendous welcome bonus, but cardholders can earn tons of miles on everyday spending and receive a 10,000-mile anniversary bonus to boot. Its annual fee is $395, but cardholders can count on up to $300 in statement credits toward travel booked through Capital One Travel each year and other valuable benefits like access to Priority Pass lounges and Capital One’s own growing family of airport lounges.

Pros

  • Excellent welcome offer worth 75,000 miles after you spend $4,000 on purchases in the first three months.
  • Up to $300 in annual travel statement credits toward bookings make through Capital One Travel.
  • 10,000 bonus miles (worth $100 toward travel) each account anniversary.

Cons

  • The $395 annual fee might be expensive for some, but this card’s benefits provide much more value than that.
  • If you don’t travel frequently, this might not be the best card for you.
  • Earn 75,000 bonus miles when you spend $4,000 on purchases in the first 3 months from account opening, equal to $750 in travel
  • Receive up to $300 back annually as statement credits for bookings through Capital One Travel, where you'll get Capital One's best prices on thousands of options
  • Get 10,000 bonus miles (equal to $100 towards travel) every year, starting on your first anniversary
  • Earn unlimited 10X miles on hotels and rental cars booked through Capital One Travel and 5X miles on flights booked through Capital One Travel
  • Earn unlimited 2X miles on all other purchases
  • Unlimited complimentary access for you and two guests to 1,400+ lounges, including Capital One Lounges and our Partner Lounge Network
  • Receive up to a $100 credit for Global Entry or TSA PreCheck®
  • Use your Venture X miles to easily cover travel expenses, including flights, hotels, rental cars and more—you can even transfer your miles to your choice of 15+ travel loyalty programs
  • Named editors' choice for "Best New Credit Card of 2021" by The Points Guy
  • Earn 10 miles per dollar when you book on Turo, the world's largest car sharing marketplace, through May 16, 2023