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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. American Airlines has put the island of Maui on sale, with discounted fares from New York (JFK) and Boston (BOS) from just $599 round-trip, valid for departures from early August through early October 2016. If you’re a Citi Prestige cardholder, you can use Thank You points to book your tickets. With the Citi Prestige Card, ThankYou points can be redeemed at 1.6 cents per point towards any American Airlines flight — meaning this booking would cost you just over 37,000 points, and you would still earn AAdvantage miles because it would technically be booked as a revenue ticket.

Airline: American
Route(s): NYC and BOS to OGG
Cost: $599+ round-trip in economy
Dates: August – October
Elite Mileage Earning: 10,500+ elite miles possible with 1 stop.
Fare Class: Q
Booking Link: Orbitz
Pay With: Premier Rewards Gold Card from American Express, Citi Prestige or Chase Sapphire Preferred

Here are a few examples of what you can book:

New York (JFK) to Maui (OGG) for $599 round-trip on American in August:

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New York (JFK) to Maui (OGG) for $599 round-trip on American.

Boston (BOS) to Maui (OGG) for $609 round-trip on American in August:

Screen Shot 2016-06-23 at 9.29.28 AM
Boston (BOS) to Maui (OGG) for $609 round-trip on American.

New York (JFK) to Maui (OGG) for 37,000+ Citi Thank You Points round-trip on American in August:

Screen Shot 2016-06-23 at 9.32.56 AM
New York (JFK) to Maui (OGG) for 37,000+ Citi Thank You Points round-trip on American.

Maximize Your Purchase

Don’t forget to use a credit card that earns additional points on airfare purchases, such as the American Express Premier Rewards Gold 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!

Chase Sapphire Preferred® Card

With great travel benefits, 2x points on travel & dining and a 50,000 point sign up bonus, the Chase Sapphire Preferred is a great card for those looking to get into the points and miles game.

Apply Now
More Things to Know
  • Earn 50,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. That's $625 toward travel when you redeem through Chase Ultimate Rewards®
  • Named Best Credit Card for Flexible Travel Redemption - Kiplinger's Personal Finance, July 2016
  • 2X points on travel and dining at restaurants worldwide & 1 point per dollar spent on all other purchases.
  • Earn 5,000 bonus points after you add the first authorized user and make a purchase in the first 3 months from account opening
  • No foreign transaction fees
  • 1:1 point transfer to leading airline and hotel loyalty programs
  • Get 25% more value when you redeem for airfare, hotels, car rentals and cruises through Chase Ultimate Rewards. For example, 50,000 points are worth $625 toward travel
  • No blackout dates or travel restrictions - as long as there's a seat on the flight, you can book it through Chase Ultimate Rewards
Intro APR on Purchases
Regular APR
16.49% - 23.49% Variable
Annual Fee
Introductory Annual Fee of $0 the first year, then $95
Balance Transfer Fee
Recommended Credit
Excellent Credit

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