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

May 13, 2021

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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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In This Post

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.

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

View from a Southwest plane over Oahu
(Photo by RandomHartz /

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

SAN to KOA Southwest ticket

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

SAN to KOA Southwest award ticket

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

Earn Southwest points quickly with a cobranded credit card. (Photo by Wyatt Smith/The Points Guy)

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 /

Delta SkyMiles® Platinum American Express Card

Earn 90,000 bonus miles after you spend $3,000 in purchases on your new Card in your first 3 months. Offer ends 8/3/2022.

With Status Boost™, earn 10,000 Medallion Qualification Miles (MQMs) after you spend $25,000 in purchases on your Card in a calendar year, up to two times per year getting you closer to Medallion Status. Earn 3X Miles on Delta purchases and purchases made directly with hotels, 2X Miles at restaurants and at U.S. supermarkets and earn 1X Mile on all other eligible purchases. Terms Apply.

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More Things to Know
  • Limited Time Offer: Earn 90,000 bonus miles after you spend $3,000 in purchases on your new Card in your first 3 months. Offer ends 8/3/2022.
  • 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.
  • 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 Miles on all other eligible purchases.
  • 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.
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