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

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.

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

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:

• Southwest Rapid Rewards Priority Credit Card – Earn 75,000 bonus points after spending $3,000 on purchases in the first three months.
• Southwest Rapid Rewards Premier Credit Card – Earn 75,000 bonus points after spending $3,000 on purchases in the first three months.
• Southwest Rapid Rewards Plus Credit Card – Earn 75,000 bonus points after spending $3,000 on purchases in the first three months.
• Southwest Rapid Rewards Premier Business Credit Card – Earn 60,000 points when you spend $3,000 on purchases in the first three months of account opening.
• Southwest Rapid Rewards Performance Business Credit Card – Earn 80,000 bonus points after you spend $5,000 on purchases in the first three months of account opening.

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