Hawaii on Sale! 4 Cities Round-Trip Starting at $499

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Hawaii on Sale! 4 Cities Round-Trip Starting at $499

Million Mile SecretsHawaii on Sale! 4 Cities Round-Trip Starting at $499Million Mile Secrets Team

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Update: One or more card offers in this post are no longer available. Check our Hot Deals for the latest offers.

Need some surf and sand this winter?

The Flight Deal reports folks in Boston, New York, Philadelphia, and Washington, DC, have their pick of 3 Hawaiian islands starting at $499 round-trip in coach through mid-March on Alaska Airlines!

Hawaii On Sale 4 Cities Round Trip Starting At 499
How Does This Look Right Now? Visit Hawaii From Boston, New York, Philadelphia, or Washington, DC, Starting at $499 Round-Trip Through March!

You can search for these fares using ITA Matrix or Google Flights, then book on the Alaska Airlines website.

Deals to Hawaii usually go quickly, so book soon if you’re interested!

How to Book It

Link:   ITA Matrix

Link:   Google Flights

Here’s how to use Google Flights to find sale dates.

If you book a ticket with an online travel agency like Orbitz or Expedia, you may be eligible for a refund within a short time of booking your ticket.  Check out my post on cancellation policies for airlines and online travel agencies for more details!

Visit Hawaii This Winter!

Via The Flight DealAlaska Airlines has tickets to Hawaii starting from $499 round-trip in coach.  You can fly from:

  • Boston
  • New York (EWR and JFK)
  • Philadelphia
  • Washington, DC

And you can fly to:

  • Honolulu (Oahu)
  • Kahului (Maui)
  • Kona (Hawaii)

I found flights from New York (EWR) to Maui later this month for $499!  Emily and I had a great time when we visited there for Spring Break!

Hawaii On Sale 4 Cities Round Trip Starting At 499
Under $500 From the East Coast to Hawaii Is a Steal!

These fares are valid through mid-March, and the price depends on the route.  Folks in New York get the lowest price, and it’s ~$30 to ~$60 more from other cities (which is still a good deal).

You must depart Sunday through Wednesday, and return from Hawaii Monday through Thursday.  Be sure to purchase your ticket 1 day in advance.  And keep in mind available seats are limited.

You can credit your flights to Delta, or several other partner airlines, to earn miles!

Remember, folks with the Alaska Airlines Visa Signature® Card can take someone with them for $99 plus tax with their annual Companion Fare certificate!  And they’ll get a free checked bag for themselves and up to 6 passengers on the same reservation.

What If You’re Not in 1 of These Cities?

Southwest – If you need more Southwest points, Chase Ultimate Rewards points transfer to Southwest.  Plus, if you have the Southwest Companion Pass, a friend can fly with you for (almost) free!

British Airways – If you’re a short flight away from an included city, you can save miles by using British Airways Avios points to book an award flight on American Airlines.

Chase Ultimate Rewards pointsAmerican Express Membership Rewards points, and Starwood points transfer to British Airways.

Pay With the Right Card!

Remember to pay with a card that will earn you bonus points:

Get Free Hotel Nights With These Cards

Link:   Hot Deals – Hotel Credit Cards

If you book a cheap flight, remember there are lots of ways to get cheap or free hotel rooms with points from credit card bonuses and spending!

Check out my post on how to decide where to stay in Hawaii using hotel points!

To find hotels that can be booked with points, I like using Hotel Hustle (which even shows you if rooms are actually available!) or AwardMapper.

Remember, you can transfer flexible points like Chase Ultimate Rewards or American Express Membership Rewards to different hotel programs.

Hawaii On Sale 4 Cities Round Trip Starting At 499
Don’t Forget You Can Transfer Points From Bank and Airline Programs to Hotels Like Hilton

Check out my posts on all the ways to earn Hilton and Hyatt points!

Note:  Folks who want to book paid stays could check out discount sites like Orbitz, Expedia, or TravelPony for deals.  But remember you won’t get stay credits or points (and might not have your elite status recognized).

Airbnb is a great way to save money on accommodations, especially for longer visits, or if you prefer a more local feel.  There are lots of places available on every Hawaiian island!

Read my tips on how to negotiate a better price on Airbnb!

Bottom Line

Fly from Boston, New York, Philadelphia, or Washington, DCto Hawaii starting at ~$499 round-trip in coach on Alaska Airlines.

Tickets are available through mid-March, and require a 1-day advance purchase.  The final price depends on the route, but folks flying from New York (EWR or JFK) get the best deal.

These flights will sell out fast, so book soon if you want to go!

Let me know if you plan a trip, and which island(s) you’ll visit!

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Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)

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