$308 Find Cheap Flights from Boston to The Big Island - Compare and Save

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Cheap Flights from Boston to The Big Island

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Kailua-Kona
13h 11m2 stops
from $610per person
Hilo
14h 25m4 stops
from $645per person
Waimea (Big Island)
18h 00m4 stops
from $1,042per person
Booking Insights

KAYAK's insights & trends for Boston to The Big Island flights

Get data-powered insights and trends into flights from Boston to The Big Island to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Boston to The Big Island?

No, with an average price for the route of $567, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Boston to The Big Island?

The cheapest month for flights from Boston to The Big Island is January, when tickets cost $553 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of round-trip tickets is $882 and $822 respectively.

How far in advance should I book a flight from Boston to The Big Island?

To get a below average price on the flight from Boston to The Big Island, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.

Good to know

Low season

September

Cheapest flight

$308
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Boston to Kailua-Kona

FAQs - booking The Big Island flights

  • How does KAYAK find such low prices on flights from Boston to The Big Island?

    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 Boston to The Big Island.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Boston to The Big Island?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Boston to The Big Island 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 Boston to The Big Island?

    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 Boston to The Big Island 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 Boston to The Big Island?

    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 Boston to The Big Island up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from Boston to The Big Island

 
Need help choosing which airline to fly with from Boston to The Big Island? 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.
7.9
Alaska AirlinesOverall score based on 12925 reviews
7.8Comfort
7.0Food
8.1Boarding
8.5Crew
7.0Entertainment
Airline reviews

It was about as poor as it could be!!! Delayed not once but multiple times

2.0 MediocreAnonymous, Sep 2026
Read more Alaska Airlines reviews

It was about as poor as it could be!!! Delayed not once but multiple times

The crew at the airport and in flight were excellent, the seats were a bit cramped but I am tall so maybe someone shorter wouldn’t care. Not many food options unless you know to pre-order. I would definitely fly them again but would pay for emergency row and bring food. Flight was perfect, arrived a little early.

It was delayed seven hours and we did not take it

The delays were the real problem. The crew and staff were amazing and kept us informed and taken care of but what should have been a 6 hour flight with 1.5 hour wait ended up being a 13 hour day in the airport and in the plane waiting to board then waiting for takeoff. Great flight once we got in the air. Pilots and flight crew were awesome 😎.

The flight boarded and landed on time. There were frequent snacks & beverages, The pilot spoke in a clear calm voice, The leg room was cramped and there were no screens (entertainment) on this long ~6 hr. flight.

We had the bulkhead seats in back of the first class section and there was a rigid plastic barrier which made it very hard to get in and out of our seats. We paid extra for the bulkhead and got neither extra room nor he's getting up. We were very disappointed.

Zero refreshment offered for the whole 6 hrs flight is a turn down

Nice to get moved from a middle seat to an aisle seat upon request, but why wasn’t I put in an aisle seat to begin with? The flight was not full.

The merging of Kayak & the airline’s website was not always clear. Both on their own provided adequate Information about the flight. I had some challenges retrieving the boarding pass. I relied on the agent & may have paid the baggage fee twice.

Hello, Our flight arrived late, and the flight we were to connect to the departure time was moved up. At first our flight was scheduled to arrive at 10:40, but it arrived at 10:56. Our connecting flight was scheduled to leave at 11:25, and it was moved to 11:20. Also the terminal was moved from N to S. N would have been in the same terminal as the one we arrived in-- to get to S we had to take 3 trains to get to. And when we arrived at the gate, around 11:15, they said the gate was closed and would not open it. We had come from a funeral in Boston, and the person that helped us get new tickets said, "did you come from a girsl trip?" No, we did not. We were coming from a funeral. This experience was not what we expected/wanted. My friend, because she had to run to S, got a migraine and turned pale. In addition, I paid an extra $70 for an aisle seat that was more upfront, to make sure I can get off the plane faster and make the connecting flight. The fact that the plane not only did not wait, but left earlier, is absolutely unacceptable. This was a terrible experience, and I hope that I can be refunded for this horrible experience.

Could have been on time and not missed my connection

Flight Staff: Always great! Checking back vs carry-on: I typically check my bag since so much time is spent stowing the bag, it's heavy, maybe not enough room. Delta is charging $45 to check bags. Yet, the people who have multiple carry-on bags are then asked to check their bags and are offered this service for free. This does not seem fair to a person who is trying to be proactive in improving the process . Boarding: Boarding is always slow and exhausting. With the exception of First Class, Economy, why not board the zone in the back of the plane first??? Seats: Why cross the seat belts? I get that it looks nice, but people waste so much time moving them or sitting on them and then having to move. Seats: On both my flights the seat did not recline. Not a big deal. Smell: There was a horrific smell like the restrooms on my first flight. I thought I was going to be sick. Most flights do not smell great. Does Delta use air purifiers or anything?

Terrible - the flight was delayed taking off after boarding. Then the flight circled lga before landing. Significant delay

The flight was delayed at the very last minute and no information, both of my round trip flights were delayed at least the BNA to Boston was informed earlier but the return one was horrible

Delayed, then set on termac before taking off for 45 minutes. After landing had to sit on termac for another 30-40 minutes. Total disaster of a flight

Stewardess was not accommodating when I requested a second drink.

Although I know the Airlines cannot control the situation when there’s a ground stoppage, it would’ve been nicer if we would have had more up-to-date information clarity around the delays. Additionally, I think the delays also took a toll on the Cabin crew, particularly the lead flight attendant in first class. She was not very friendly when we boarded the plane for many of the passengers. Number one she refused to hang a garment bag in the front closet for a first class passenger, she was unwilling to dispose of an empty bottle in the trash as I was boarding (despite drinking a bottle of water herself and needing to disregard), and she was very combative with a passenger, who needed to access something from his bag that was Gate checked. Frankly, it was really unfortunate as I’ve never seen a flight attendant behave that way directly to the passengers, particularly when none of us had done anything wrong.

Flight from Savannah arrived very late and we did not take off till 2 hours after scheduled departure!

It is usually very pleasant. Good service for the price, international flights are even better

Flight attendant was very poor in taking care or showing attention. I slept up front for a few and missed the snacks. She saw me many times, went by me many times and never once asked if I needed anything. The whole 2 hours flight. And this is to a Diamond member in first.

Omg the disaster at the security was on another level! “Go to this end, sorry closed now, go to that end”. Ridiculous! This took over an hour! As far as the airline was concerned although I booked nearly a year ago I couldn’t get my bag tag - stand in another 15 minute line or my seat on Hawaiian Airlines- 5 more minutes! Then my TSA status was denied. Like what the heck! Makes a person not want to travel with this amount of incompetence

Fabulous if you have a portable wheelchair. They can store it in the galley and you can just walk out with it. Really nice and the flat seats are just incredible, very nice. iPads for movies, also pretty nice,

No charging outlets worked. Other than collecting trash attendants didn’t come around. No one could hear flight attendants announcements during the flight. Seat pads were horrible. Sitting on a board for 5 hours. What happened to Hawaiian airlines comfort, hospitality, and extras? Our pilots did an excellent job trying to minimize turbulence and incredible job in landing in windy conditions.

Flight attendants were friendlier than on previous flight from HNL-BOS

My only complaint with JetBlue is that they have Pepsi products instead of Coke and the snacks are not great. The crews are almost always outstanding, and their planes are fantastic

The attendant was rude. The headphone port didn't work well. The entertainment screen didn't work, only half the screen was responding. Seats were very uncomfortable and I could feel the knees of the person behind me in my lower back.

Jet Blue lost my bags after charging me to connect with HAL.

Very friendly crew. Food was good and several rounds of snacks, drinks, meal. Boarding process was smooth. Pilot communicated frequently to explain what to expect and what their plan was due to weather issues around Boston.

Didnt get seat i booked Extra leg &so bags go under seat in front .couldnt! needwheelchair to board .nNnChair f when boarding no chair needed extra help from Busy flight attendant So want refund fo extra leg and no seat in front fo bag Suport back Not Using kayak 😤 air line good 👍✈️

Hawaiian Airlines was great but we had a connecting flight from Boston to JFK using their partner airline JetBlue. Once we got to JFK in order to get from JetBlue to Hawaiian Airlines we had to go through security again which was a huge inconvenience and very frustrating.

Very disappointing that on an international business class flight they would not give me access to the lounge in Boston. They said it was because it was a codeshare flight. International business class should include lounge access regardless of codeshare.

Great, except the canon was so cold. Even the flight attendants put jackets on

The app logs you out right when you are boarding requiring all passwords and reservation number for the flight. Super annoying

The pre-order only approach for fresh food is really challenging

Flight was 2.5 late. Maybe not United’s fault but late none the less. We were late as well on the first leg. WiFi quit working with an hour left.

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

Food was great. Staff was phenomenal. Seats were a bit hard and could use a lot more entertainment options as far as movies to choose from. WiFi was good. Overall great trip.

The flight was delayed, they didn’t even have water for the toilets or for drinks

It’s always a great time flying with united airlines.

I've flown American several times this summer and I have yet to get a flight that leaves on time. However, a delay is better than a cancel. So far I have had four canceled flights and two delayed flights

The flight was delayed in 30 minute increments for a total of 4 hours and 30 minute delay. All other flights to Chicago left on time except for this one flight. If there is an issue with the inbound flight, just let customers know so they can find another flight right away, Once we got on the plane there was another 30 minute delay taking off at 10:30 at night which is very unusual that a flight wouldn't be ready to take off

They have overselled the ticket and kicked me out from boarding, All my Plans were collapsed and important network meeting missed.also I booked direct flight i have to go through an 1 stop and it was frustrated.

Horrific. We were delayed due a flight attendant stuck in traffic en route to the airport. Over 100 people were then stuck in Charolette. Then I ran to make my layover only to find that my connection didn’t have a plane anymore. Waited 2.5 hours without any updates. On the flight we had to beg for even a pretzel option.

Terrible boarding and first class experience. Nice staff but overall disorganized, dirty plane.

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

Early departure meant on time arrival. Only real problem was free internet had issues, although chatting with the internet help desk (you can do this via aainflight.com) got the issue resolved.

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

Found that the plane used for this short flight is smaller and therefore the seats are really squeezed tight.

Great experience. Good dinner and service. FA's were very nice and attentive.

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