Deal Alert: Midwest, East Coast to Hawaii From $539 Round-Trip

Jul 23, 2019

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Airfare deals are typically only available on limited dates. We recommend you use Google Flights to find dates to fly, then book through an online travel agency such as Orbitz or Expedia, which allows you to cancel flights without penalty by 11 p.m. Eastern Time within one day of booking. However, if you’re using The Platinum Card® from American Express, you’ll need to book directly with the airline or through the Amex Travel portal to get 5x MR points. Remember: Fares may disappear quickly, so book right away and take advantage of Orbitz or Expedia’s courtesy cancellation if you’re unable to get the time away from work or family.

It’s been a while since we’ve seen some solid prices to Hawaii. And when we do, it’s usually for flights from the West Coast. But as reported by The Flight Deal, there are currently low fares from cities across the Midwest and East Coast, including Boston, New York, Chicago and Baltimore from $539 round-trip.

The deals are available for travel from August through December and are being offered by American, Delta and Hawaiian. The low fares on Delta book in basic economy, meanwhile the ones on American and Hawaiian book into Main Cabin, meaning you’ll want to book with American or Hawaiian if you want to be able to pick your seat for free. Regardless of which airline you go with or which ticket type you book, you’ll be able to carry on a full-size bag.

Check out Get Your Guide’s suggestions for activities in Hawaii to maximize your time while on vacation.

To search, head to Google Flights and enter your origin and destination cities. Scroll through the calendar function to find dates and prices that work for you. Finally, click through to book directly with the airline or through an OTA like Priceline or Expedia.

Airline: American, Delta, Hawaiian
Cost: $539+ round-trip in economy 
Travel Dates:
August-December 2019
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 when booked directly with the airline) or Chase Sapphire Preferred Card (2x on travel)

Here are a few examples of what you can book:

Chicago (ORD) to Kahului, Maui (OGG) for $539 round-trip in Delta basic economy:

New York (JFK) to Kahului, Maui (OGG) for $548 round-trip on Hawaiian:

Boston (BOS) to Kahului, Maui (OGG) for $552 round-trip in American Airlines Main Cabin:

New York (JFK) to Honolulu (HNL) for $569 round-trip in American Airlines Main Cabin:

Baltimore (BWI) to Kahului, Maui (OGG) for $581 round-trip in American Airlines Main Cabin:

New York (JFK) to Honolulu (HNL) for $597 round-trip nonstop on Hawaiian:

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 photo by Summer Hull / The Points Guy

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