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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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TPG Editor‘s Rating
Card Rating is based on the opinion of TPG‘s editors and is not influenced by the card issuer.
3 / 5
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Rewards

1 - 3X points
3XEarn 3X Miles on Delta purchases and purchases made directly with hotels.
2XEarn 2X Miles at restaurants worldwide, including takeout and delivery in the U.S. and at U.S. supermarkets.
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Annual Fee

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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.

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Build your loyalty to Delta by applying for the carrier's mid-tier card option, the Delta SkyMiles Platinum card. The annual fee is quickly recouped by the card's travel perks, such as an application credit to Global Entry or TSA Precheck, annual companion certificate and so much more. Plus you can fast-track to elite status simply through card spend.

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  • Receive a Domestic Main Cabin round-trip companion certificate each year
  • Statement credit for TSA PreCheck/Global Entry fee (up to $100)
  • First checked bag free

Cons

  • Doesn't make sense if you don't fly Delta
  • SkyMiles aren't the most valuable airline currency
  • Earn 90,000 bonus miles after you spend $4,000 in purchases on your new Card in your first 6 months.
  • Receive a Domestic Main Cabin round-trip companion certificate each year upon renewal of your Card. Payment of the government imposed taxes and fees of no more than $80 for roundtrip domestic flights (for itineraries with up to four flight segments) is required. Baggage charges and other restrictions apply. See terms and conditions for details.
  • Enjoy your first checked bag free on Delta flights. Plus enjoy Main Cabin 1 Priority Boarding and settle into your seat sooner.
  • New: Card Members get 15% off when using miles to book Award Travel on Delta flights through delta.com and the Fly Delta app. Discount not applicable to partner-operated flights or to taxes and fees.
  • Earn 3X Miles on Delta purchases and purchases made directly with hotels.
  • Earn 2X Miles at restaurants worldwide including takeout and delivery in the U.S., and at U.S. supermarkets.
  • Earn 1X Mile on all other eligible purchases.
  • Enjoy a per-visit rate of $50 per person for Card Members and up to two guests to enter the Delta Sky Club when traveling on a Delta flight.
  • Fee Credit for Global Entry or TSA PreCheck® after you apply through any Authorized Enrollment Provider. If approved for Global Entry, at no additional charge, you will receive access to TSA PreCheck.
  • Earn up to 20,000 Medallion® Qualification Miles (MQMs) with Status Boost® per year. After you spend $25,000 in purchases on your Card in a calendar year, you can earn 10,000 MQMs up to two times per year, getting you closer to Medallion® Status. MQMs are used to determine Medallion® Status and are different than miles you earn toward flights.
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Apply for Delta SkyMiles® Platinum American Express Card
at American Express's secure site
Terms & restrictions apply. See rates & fees
TPG Editor‘s Rating
Card Rating is based on the opinion of TPG‘s editors and is not influenced by the card issuer.
3 / 5
Go to review

Rewards Rate

3XEarn 3X Miles on Delta purchases and purchases made directly with hotels.
2XEarn 2X Miles at restaurants worldwide, including takeout and delivery in the U.S. and at U.S. supermarkets.
1XEarn 1X Miles on all other eligible purchases.
  • Intro Offer
    Earn 90,000 bonus miles after you spend $4,000 in purchases on your new Card in your first 6 months.

    Earn 90,000 Bonus Miles
    50,000 Bonus Miles
  • Annual Fee

    $250
  • 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.

    670-850
    Excellent/Good

Why We Chose It

Build your loyalty to Delta by applying for the carrier's mid-tier card option, the Delta SkyMiles Platinum card. The annual fee is quickly recouped by the card's travel perks, such as an application credit to Global Entry or TSA Precheck, annual companion certificate and so much more. Plus you can fast-track to elite status simply through card spend.

Pros

  • Earn bonus Medallion® Qualification Miles (MQMs) and an Medallion Qualifying Dollar (MQD) waiver when you hit specific spending thresholds with your card within a calendar year
  • Receive a Domestic Main Cabin round-trip companion certificate each year
  • Statement credit for TSA PreCheck/Global Entry fee (up to $100)
  • First checked bag free

Cons

  • Doesn't make sense if you don't fly Delta
  • SkyMiles aren't the most valuable airline currency
  • Earn 90,000 bonus miles after you spend $4,000 in purchases on your new Card in your first 6 months.
  • Receive a Domestic Main Cabin round-trip companion certificate each year upon renewal of your Card. Payment of the government imposed taxes and fees of no more than $80 for roundtrip domestic flights (for itineraries with up to four flight segments) is required. Baggage charges and other restrictions apply. See terms and conditions for details.
  • Enjoy your first checked bag free on Delta flights. Plus enjoy Main Cabin 1 Priority Boarding and settle into your seat sooner.
  • New: Card Members get 15% off when using miles to book Award Travel on Delta flights through delta.com and the Fly Delta app. Discount not applicable to partner-operated flights or to taxes and fees.
  • Earn 3X Miles on Delta purchases and purchases made directly with hotels.
  • Earn 2X Miles at restaurants worldwide including takeout and delivery in the U.S., and at U.S. supermarkets.
  • Earn 1X Mile on all other eligible purchases.
  • Enjoy a per-visit rate of $50 per person for Card Members and up to two guests to enter the Delta Sky Club when traveling on a Delta flight.
  • Fee Credit for Global Entry or TSA PreCheck® after you apply through any Authorized Enrollment Provider. If approved for Global Entry, at no additional charge, you will receive access to TSA PreCheck.
  • Earn up to 20,000 Medallion® Qualification Miles (MQMs) with Status Boost® per year. After you spend $25,000 in purchases on your Card in a calendar year, you can earn 10,000 MQMs up to two times per year, getting you closer to Medallion® Status. MQMs are used to determine Medallion® Status and are different than miles you earn toward flights.
  • No Foreign Transaction Fees.
  • $250 Annual Fee.
  • Terms Apply.
  • See Rates & Fees