$222 Find Cheap Flights from Kailua-Kona to Massachusetts

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Kailua-Kona to Massachusetts departing on 10/21. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Kailua-Kona to Massachusetts, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Kailua-Kona to Massachusetts, as well as popular online travel agencies
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Cheap Flights from Kailua-Kona to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Boston1 stop$464
Boston
Boston1 stop$464

Book Cheap Kailua-Kona to Massachusetts Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Kailua-Kona to Massachusetts that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Kailua-Kona to Massachusetts

Wed, Nov 5 - Tue, Nov 11
Delta Logo
9:30 pm - 4:22 pmKOA-BOS
13h 52m1 stop
Delta Logo
6:15 am - 7:25 pmBOS-KOA
18h 10m1 stop
$464Delta
Find Deal
Wed, Nov 5 - Tue, Nov 11
Alaska Airlines Logo
7:14 am - 6:00 amKOA-BOS
17h 46m1 stop
Alaska Airlines Logo
4:24 pm - 2:43 pmBOS-KOA
27h 19m1 stop
$468Alaska Airlines
Find Deal
Wed, Nov 5 - Tue, Nov 11
American Airlines Logo
9:35 pm - 4:18 pmKOA-BOS
13h 43m1 stop
American Airlines Logo
6:05 am - 4:47 pmBOS-KOA
15h 42m1 stop
$469American Airlines
Find Deal
Wed, Nov 5 - Tue, Nov 11
Delta Logo
9:30 pm - 7:30 pmKOA-BOS
17h 00m2 stops
Delta Logo
6:15 am - 7:25 pmBOS-KOA
18h 10m1 stop
$470Delta
Find Deal
Wed, Nov 5 - Tue, Nov 11
Delta Logo
9:30 pm - 4:22 pmKOA-BOS
13h 52m1 stop
Delta Logo
8:00 am - 7:25 pmBOS-KOA
16h 25m2 stops
$474Delta
Find Deal
Wed, Nov 5 - Tue, Nov 11
American Airlines Logo
9:30 pm - 5:02 pmKOA-BOS
14h 32m2 stops
American Airlines Logo
6:00 am - 4:47 pmBOS-KOA
15h 47m2 stops
$480American Airlines
Find Deal
Wed, Oct 15 - Wed, Oct 22
Delta Logo
9:30 pm - 10:43 pmKOA-BOS
19h 13m2 stops
Delta Logo
7:20 am - 5:30 pmBOS-KOA
16h 10m1 stop
$498Delta
Find Deal
Sun, Mar 1 - Thu, Mar 5
American Airlines Logo
10:40 pm - 6:18 pmKOA-BOS
14h 38m2 stops
American Airlines Logo
8:13 am - 8:12 pmBOS-KOA
16h 59m2 stops
$527American Airlines
Find Deal
Mon, Sep 22 - Fri, Sep 26
United Airlines Logo
11:00 pm - 5:13 pmKOA-BOS
12h 13m1 stop
United Airlines Logo
7:30 am - 3:46 pmBOS-KOA
14h 16m1 stop
$656United Airlines
Find Deal
Mon, Sep 22 - Fri, Sep 26
United Airlines Logo
7:40 pm - 5:47 pmKOA-BOS
16h 07m2 stops
United Airlines Logo
7:30 am - 3:46 pmBOS-KOA
14h 16m1 stop
$661United Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Kailua-Kona to Massachusetts flights

Get data-powered insights and trends into flights from Kailua-Kona to Massachusetts to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Kailua-Kona to Massachusetts?

The average price of all round-trip flights from Kailua-Kona to Massachusetts clicked on KAYAK for each day over the last 12 months.

For Kailua-Kona to Massachusetts, Monday is the cheapest day to fly on average and Saturday is the most expensive. Flying from Massachusetts back to Kailua-Kona, the best deals are generally found on Tuesday, with Friday being the most expensive.

Good to know

Low seasonSeptember
Cheapest flight$222
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 51% increase in price.
Flight from Kailua-Kona to Boston

FAQs - booking Massachusetts flights

  • How does KAYAK find such low prices on flights from Kailua-Kona to Massachusetts?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Kailua-Kona to Massachusetts.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Kailua-Kona to Massachusetts?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Kailua-Kona to Massachusetts is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Kailua-Kona to Massachusetts?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Kailua-Kona to Massachusetts with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Kailua-Kona to Massachusetts?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Kailua-Kona to Massachusetts up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Massachusetts?

    The cheapest time of day to fly to Massachusetts is generally in the morning, when round-trip flights cost $492 on average. The most expensive time of day to fly to Massachusetts is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $638.

Reviews of the top 4 airlines serving from Kailua-Kona to Massachusetts

 
See real verified KAYAK customer reviews for airlines flying from Kailua-Kona to Massachusetts. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Kailua-Kona to Massachusetts? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
Alaska AirlinesOverall score based on 10000 reviews
8.5Crew
7.8Comfort
7.1Food
8.1Boarding
7.0Entertainment
Airline reviews

It was not clear the check in shd be at Hawaiian Terminal 1. I got dropped off at Alaska Terminal 2. I did the long walk from terminal 2 to 1. Fortunately I didn’t have a check in bag.

8.0 ExcellentArnel, Sep 2025HNL - LAX
Read more Alaska Airlines reviews

It was not clear the check in shd be at Hawaiian Terminal 1. I got dropped off at Alaska Terminal 2. I did the long walk from terminal 2 to 1. Fortunately I didn’t have a check in bag.

Unfortunately 4 hour 40 minute delay because of airport then one hour into flight diverted back to Kona elderly man on plane got heart attack trying to get home some how

Hawaiian Airlines, like most US-based ones, constantly provide sub-par service and pack their planes to the max with all kinds of last-minute-purchase schemes. As a result, it makes every flight so uncomfortable and generates high health risk for its passengers. In one word, GREED rules the day!

I was sitting towards back of plane and the flight attendants I thought spoke unusually loud for an evening flight. They chatted and chatted all night long and it seemed odd to me that they didn’t try to lower their voices. It is annoying as a passenger to hear all their conversations.

Terrible airport. It took over one hour to pass checkpoint and security gate. We stood under the sun in the long line

Reserved seats and yet did not get my original seat because someone else was seating in them and the crew member did not try to find out what was going on with the issue. My wife and I did get similar seats. This created concern and unnecessary issues.

All airlines seem to be a scam with having to pay force assignment, baggage fees, and completely garbage food. Our flight attendants now seem to have a power trip complex. It’s clear they know we have no other choice if we want to travel so they don’t care and let you know it.

Tickets we booked together in January became two different connecting flights. VERY PISSED a about this and a terrible start to our bucket list vacation

I needed more space to sleep on an overnight flight.

Very good; ohana atmosphere and taking care of customer care

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

Love you guys are so friendly and kind and wonderful

Hawaiian airlines has awful customer service. Told me to keep a flight I wasn’t boarding, instead of rebooking me under two separate reservations, which caused my whole reservation to be canceled. Major issues with leadership and management. The staff at Hilo was reluctant to give me a refund, so I had to by a first class ticket in order to get on a flight the same time as my partner. The blame was pointed at me without sincere apology until the supervisor came out, who also apparently had no authority to refund me. Still waiting on correspondence from the airline days later.

I like that you have eliminated plastic cups, bottles and straws. The crew was conscientious about separating the used paper cups from the trash. This change to paper is a great move and makes me want to choose Alaska when I fly.

Attendants seemed un-engaged and indifferent when asked for assistance.

Overall it was a good flight. The thing I most appreciated was that you eliminated plastic cups and water bottles and stir sticks and had paper cups, wood stir sticks and cans. Plus, I saw that the airline staff were actually keeping the used paper cups separate and unfolding the used cardboard meal boxes and keeping those items separate from the trash. Good for them! This makes me want to support Alaska Airlines and fly Alaska again. Thank for taking this step in working to reduce single use plastics! Kudos!

Ok but why they need to sell the ear buds?

Our flight was delayed, which I know things can happen. The bathrooms were dirty and a mess. It took over an hour to get our bags after the plane landed. Every flight was on the same 2 baggage claims. You would thing if we spent over 5 hours on a flight we would get more then a tiny bag of pretzels. The movie and tv choices were mid.

The flight was very smooth and the landing was AMAZING! I have flight anxiety and it didnt peak once! :) Thank you to the pilots and crew!!

Pillows and blankets were nice since it was an overnight flight, but the seats should be larger and there should be more space between rows so we have more leg room.

I loved flying Hawaiian Air! We didn’t pay to sit together, but we were able to anyway. They had usb charging ports and even outlets in some seats. They served a hot sandwich that was not very good, but we were still pleasantly surprised. The staff was very nice. The seats really made my booty hurt but maybe I’m just not used to sitting so long. Also, the AC was really cold even though I was wearing pants, a hoodie, and a light blanket.

The newer screen was super cool and had the option to watch many different shows or movies. Crew was polite and helpful. However again, many children screaming bloody murder and kicking my seat, and parents doing nothing about it as usual.

Flight was good and crew was super polite. However, there were around 5 kids screaming the WHOLE 2 hours. I understand kids have to come but parents need to do something to control their children. They make the experience terrible, especially after finishing 16 hour shifts at the hospital I needed some sleep, which I did not get.

IAD with the archaic people movers is just a place to be avoided.

All of the United employees I interacted with were professional and courteous. The aircraft was clean, the food on the flight was good. No complaints here.

Armrest controller on my seat 35D and nextbooennseat 35E did not work right. Hard to press buttons to recognize and 35D had constantnpressure either upmost down somit was nearly impossible to make selections. .

I flew with my dog and had already purchased my dog’s ticket. Even that morning I had called costumer service to insure that my husband and I had seats together since the website was giving me an error when choosing our seats and the representative mentioned our dog. I showed up early to the airport and when I got to the gate and we started boarding I was help back and told that I was supposed to have a yellow tag and that I should have checked in at the counter for them to give me that tag. I was not aware of this, the representative on the phone did not say anything. Nor did I see it anywhere in the checking process online, so if you travel with a pet and are not checking in luggage, just know that you still have to go to the check in counter when arriving at the airport unless you want to be the last one to board and not have room for your carry on in the overhead bins. Other than that, I had a great experience.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

I understand stuff happens, but plane failures are likely due to lack of maintenance. Additionally, air conditioning wasn't working, no snack/drink service, no WiFi. Fortunately, the crew was communicative and light-hearted. United grabbed another plane and we were able to get to our destination.

There was no food available for this red eye... one little waffle cookie for a 6+ hour flight... thank God I was able to sleep some

It is clear that someone knew, and competent, is in charge of food at United Airlines at least for the international flights. I was flying in coach, but the choices of the dinner were excellent. Tasty, and appropriate size. I had the beef, which was a little bit like a shepherds pie, and it was good. Nothing comparable has been served on a United flight in years. It will not be confused with three star food, but it is very good for airline food. Even better was the breakfast choice between a cinnamon roll and a breakfast sandwich. I chose the breakfast sandwich which was absolutely delicious and which I would happily order again at my local Starbucks or Panera. It is clear that someone knew indifferent is in charge of the food and it’s about time.

Everything you need to know for your flight from Kailua-Kona to Massachusetts

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