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Deal Alert: Southwest Flights to Hawaii From $99 or 5,848 Points One-Way

JT Genter
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JT Genter is a digital nomad who travels full-time.
Aug. 15, 2019
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3 min read
Waikiki Beach
Deal Alert: Southwest Flights to Hawaii From $99 or 5,848 Points One-Way
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Update: Some offers mentioned below are no longer available. View the current offers here.

Back when Southwest got approval to fly to Hawaii, it launched incredible deals with one-way flights between the mainland and Hawaii starting at just $49 one-way. But we haven't seen anything close to a deal on these high-demand Southwest flights since. That is, until now.

Southwest just put new Hawaii routes on sale, and Dan's Deals points out that prices are starting at just $99 one-way between California and Hawaii or just $29 one-way intra-Hawaii. To search, head to Southwest's website and enter your origin and destination cities. I'd recommend using the Low Fare Calendar to find cheap dates.

There are also cheap tickets from Hawaii back to the mainland, but they won't be as cheap as $99. You'll likely see them priced from $119 to $139.

Remember that Southwest has a value-based point system. That means when cash fares are cheap, points fares are also cheap. That means that you can book flights to Hawaii now for just 1,950 miles each way, blowing away your next-cheapest point option. If you need more Southwest points, you can transfer Chase Ultimate Rewards points to Southwest instantaneously.

Airline: Southwest
Routes: SJC/OAK/HNL/OGG to LIH/KOA
Cost: $29+ (1,379 points) one-way intra-Hawaii or $99+ (5,848 points) one-way between California and Hawaii
Dates: January-March 2020
Pay With: The Platinum Card® from American Express (5x on airfare booked directly with the airline), Citi Prestige Card (5x on airfare), Citi Premier® Card, Chase Sapphire Reserve, American Express® Gold Card (3x on airfare) or Chase Sapphire Preferred Card (2x on travel)

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Here are a few examples of what you can book:

San Jose (SJC) to Kauai (LIH) for $99 or 5,848 points one-way nonstop:

San Jose (SJC) to Kona (KOA) for $99 or 5,848 points one-way nonstop:

Oakland (OAK) to Kauai (LIH) for $99 or 5,848 points one-way nonstop:

Honolulu (HNL) to Kauai (LIH) for $29 or 1,379 points one-way nonstop:

Kahului, Maui (OGG) to Kona (KOA) for $29 or 1,379 points one-way nonstop:

Maximize Your Purchase

Don’t forget to use a credit card that earns additional points 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, 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 on maximizing airfare purchases.

Featured image by Getty Images
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.