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Airfare deals are typically only available on limited dates. We recommend that you use Google Flights to find dates to fly, then book through an online travel agency, such as Orbitz, which allows you to cancel flights without penalty by 11pm Eastern Time within one day of booking. Remember: Fares may disappear quickly, so book right away and take advantage of Orbitz’s courtesy cancellation if you’re unable to travel.
Deals to Hawaii are particularly rare, especially from the East Coast. Alaska, American, Delta and United are currently competing for customers on Hawaii-bound flights from New York, Boston, Washington, D.C. and Philadelphia. We’re seeing fares as low as $539 round-trip from Boston and $549 from New York, with prices increasing depending on which island you want to fly to.
If you’re a Citi Prestige cardholder, you can use Thank You points to book your tickets. With Citi Prestige, ThankYou points can be redeemed at 1.6 cents per point towards any American Airlines flight — meaning this booking would cost you just over 36,000 points, and you would still earn AAdvantage miles because it would technically be booked as a revenue ticket.
Furthermore, since American would consider it a “special ticket”, you would accrue miles distance based not revenue based. This means that on a flight from Washington, D.C. to Hawaii, you could earn over 5,000 redeemable miles (50% of the distance flown). If you booked directly with American, the same flight would earn less than 3,000 redeemable miles based on the revenue price of the ticket.
Airline: United, Delta, American, Alaska
Route(s): East Coast to Hawaii
Cost: $539+ round-trip in economy
Dates: August – December
Elite Mileage Earning: 10,500+ elite miles possible with 1 stop.
Booking Link: Orbitz
Pay With: American Express® Gold Card, Citi Prestige or Chase Sapphire Preferred
Here are a few examples of what you can book:
Boston (BOS) to Honolulu (HNL) for $539 round-trip on United in August:
New York (JFK) to Kona (KOA) for $549 round-trip on Alaska in December:
Washington, D.C. (DCA) to Honolulu (HNL) for $583 round-trip on American in September:
Philadelphia (PHL) to Kona (KOA) for $583 round-trip on Alaska in December:
Washington, D.C. (DCA) to Honolulu (HNL) for $557 round-trip on Delta in September:
Maximize Your Purchase
Don’t forget to use a credit card that earns additional points on airfare purchases, such as the American Express® Gold Card or Citi Prestige (3x on airfare) or the Chase Sapphire Preferred Card (2x on all travel purchases). Check out this post for more on maximizing airfare purchases.
H/T: The Flight Deal
If you’re able to score one of these tickets, please share the good news in the comments below! The Points Guy Assessment: The Chase Sapphire Preferred is a great pick for the beginner and the frequent traveler. The CSP has superb travel benefits, double points on certain purchases, and a 50,000 point sign up bonus. The $95 annual fee is waived the first year so this puts it as one of the less expensive cards, while still allowing you to earn one of the most valuable point currencies.
The Points Guy Assessment:
The Chase Sapphire Preferred is a great pick for the beginner and the frequent traveler. The CSP has superb travel benefits, double points on certain purchases, and a 50,000 point sign up bonus. The $95 annual fee is waived the first year so this puts it as one of the less expensive cards, while still allowing you to earn one of the most valuable point currencies.