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Find cheap flights from Boston to Kailua from $279

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to Kailua departing on 8/19. 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
0 bags
Thu 7/11
Thu 7/18

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Good to know

Low season

November

High season

April

Cheapest flight

$279
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Boston to Honolulu

When to book flights from Boston to Kailua

Are your dates flexible? Find out the best times to travel from Boston to Kailua based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Boston to Kailua

  • Which airports will I be using when flying from Boston to Kailua?

    When flying out of Boston you’ll be using Boston Logan Intl. Kailua does not have its own airport so you’ll be flying into nearby Honolulu airport, which is 13.0 mi away.

  • How long does a flight from Boston to Kailua take?

    Direct flights cover the 5,083 miles separating Boston and Kailua in about 11h 10m.

  • How many flights are there between Boston and Kailua?

    1 direct flights run between Boston and Kailua on a daily basis. On average, there are about 10 departures each week.

  • What’s the cheapest day of the week to fly between Boston and Kailua?

    Consider leaving on a Wednesday and avoid Mondays if you are looking for the best rates. For your return to Boston, you’ll find the best rates on Tuesdays and the most expensive ones on Fridays.

  • How does KAYAK find such low prices on flights from Boston to Kailua?

    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 Kailua.

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

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

    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 to Kailua with an airline and back to Boston with another airline.

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

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

  • Which airlines provide the cheapest flights from Boston to Kailua?

    In the last 72 hours, the cheapest one-way ticket between Boston and Kailua found on KAYAK was with Hawaiian Airlines for $279. Delta offered a round-trip connection from $440 and American Airlines from $461.

See more FAQs

Top tips for finding cheap flights from Boston to Kailua

  • There is no airport in Kailua. Instead, you’ll be flying into Honolulu Airport when flying between Boston and Kailua.
  • The cheapest flight from Boston to Kailua was found 24 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be May, June and July. The cheapest month to fly is November.
See more tips

Top 5 airlines serving Boston to Kailua

Need help choosing which airline to fly with from Boston to Kailua? 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 9267 reviews
7.3Entertainment
7.3Food
7.9Comfort
8.2Boarding
8.6Crew
Airline reviews

The crew members were wonderful. When we encountered a little turbulence, the pilots let us know and provided an estimate of how long it would last. Another nice amenity: every seat has AC power outlets and USB ports. It was a 6-hour flight, which seems a bit much for a single-aisle jet: over 200 passengers with access to only 3 restrooms (assuming you time it right and won't be blocked in by beverage carts); food is mediocre, over-priced, and (if you failed to reserve a meal ahead of time) the flight attendants have to process food/meal sales in the aisle. To access any entertainment, you must use your own device to log on to the plane's wi-fi (or bring your own entertainment).

8.0 ExcellentNolan, Jun 2024SEA - HNL
Read more about Alaska Airlines reviews

The crew members were wonderful. When we encountered a little turbulence, the pilots let us know and provided an estimate of how long it would last. Another nice amenity: every seat has AC power outlets and USB ports. It was a 6-hour flight, which seems a bit much for a single-aisle jet: over 200 passengers with access to only 3 restrooms (assuming you time it right and won't be blocked in by beverage carts); food is mediocre, over-priced, and (if you failed to reserve a meal ahead of time) the flight attendants have to process food/meal sales in the aisle. To access any entertainment, you must use your own device to log on to the plane's wi-fi (or bring your own entertainment).

Great first time experience for me. The gate agent at the Anchorage location was so helpful. Definitely will be booking more on Alaska.

Delayed an hour and sat without updates. Ended up an hour late to destination

The flight was decent again if there was a place that you could put crying children that would be great. Or maybe make a rule against allowing infants on the plane.

Smooth. Courteous. Fun. One problem: the wheels on my checked roller back were broken when I picked up baggage at destination. Must have happened during flight baggage handling but I don’t know where.

Overall good flight, smooth and on time and comfortable. Disappointing that food is not served and you can't purchase the snack packs on the plane.

Comfortable seat, plenty of leg room which is so rare, overhead bin comfortably accommodated my carry-on bag. Deli box was tasty, service was good, bathrooms were clean. Uneventful flight, which I appreciate. Departed on time and landed early.

The maintenance delay was seemingly handled very poorly... Little to no information was provided to the passengers sitting on board for an extended period of time. On a brighter note, at least the cabin crew (flight attendants) did the best they could. They seemingly were provided very little information with regards to the delay. Unless absolutely beyond my control, I can’t imagine buying a ticket on Alaska airlines again, based on this and a previous experience my wife recently had, along with complaints overheard from other passengers.

Honestly, there was not much they could do. Due to wind, the flight was delayed for several hours because we had to be diverted to San Jose where we needed to refuel before departing to Hawaii. Wish they had offered some snacks during the delays/diversion because we had to wait such a long time to finally get our food served during the flight after leaving California.

Alaska continues to provide one of the best domestic US airline experiences.

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Liked all aspects except boarding notification. Long delay with little support in knowing about change in boarding gates .

I liked my seat and the boarding was seamless once I arrived at the gate. The food was not good and they didn't have any vegan options. Some of the crew members were lacking empathy or personality

Well organized staff friendly and great attitude. Little awkward and slow to check a bag in Lihue but otherwise a pleasant experience

The flight was so cold from Vegas to Hawaii. Everyone was so cold they put on goodies. They made us buy blankets for $13 each for 4 people. The plane was like an icebox. Now on the way back you made me pay extra so my family can sit together. Will not use you again.

The crew was quick and efficient. The flight was uneventful and arrived slightly early.

My seat was broken I couldn’t put it back I have really bad back issues , the flight was 5 hours delayed and there was a drink dude harassing the entire flight

No food or entertainment because it was a short flight. Unfortunately the takeoff was delayed more than an hour

Parents with kids should all be in the same area. Sounds rude but who what's to fly 6hrs with crying and bratty kids. Just my opinion.

Ok, so I didn’t have seats, so got there very early. I was first in line only to be told, listen for your name for seats. The flight was boarding before they gave me a middle seat, way after others showed up who were given more favorable treatment. Ok, so , don’t show up early and obey all the rules??? Clearly, your gate clerks did not. What gives???

Short flight but delayed. Since its a short flight no food or entertainment necessary

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

Original plane sidelined. Had to wait an hour for replacement.

Crew was very cooperative and professional. Passenger's first checked in bag should be free.

No real agent onsite helping you for missing luggage there. Not like the other airline next to UA desk, they have staff attending in their desk assisting answer/helping luggage issue, even after midnight.

Horrible, the flights kept delaying, so it is obvious that we won't be able to make it to the next connection. No easier/real agent on site to help you figure this out. UA agent on other counters refuse to assist you and direct us to use the QR code/call customer service. So inefficient and poor. While technology seems convenient, but it's not the best interest/experience for customers need help while there is active issue need assistance.

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

My window shade didn’t work. So I missed coming into my city. ☹️

Flight was delayed in the gate by 5 hours and ultimately cancelled- rebooking service by United agents was terrible

Flight was delayed due to the late arrival of the catering truck, which is quite unacceptable. There was a beverage service, but no pretzel, or cookie, or nuts were served in coach.

Not worth the price of premium class ticket paid, felt more like steerage.

Paid for premium economy had no tv the whole time the crew tried to reset/reboot but would not work they said they would put a trouble ticket in for it. We had 3 seats my tv was the only one that didn't work. They cancelled our flight re worked us on another that left us at airport over night on the floor I have a ten year old and a 78 diabetic mother which also had shingles and suffers from nerve pain in legs and back. Requested wheelchair service at all airports after the re route NO wheelchair service was there to help. WORST experience we have ever had. Went to American airlines assistance it was closed. I AM FURIOUS!!! I expect some sort of compensation from this traumatic experience and no need for flying points we don't plan on using American airlines again!!!!

This is by far the worst experience I have had with American Airlines. The start of this trip was a complete disaster. I purposely planned my trip so that I would weather any delays so that I could make very important meeting at the Pentagon. My flight was cancelled because of maintenance and I was put on the first flight the next day but I was late to the meeting. After a long week at the Pentagon I just wanted to go home and my flight home which was early in the day was delayed. Eventually the flight was delayed until the next day. I was not authorized a hotel room because DCA was my point of origin. So I paid for a hotel out of pocket. The flight this morning was boarded then deplaned because the aircraft was hot. The flow of information was not happening in DCA and made it worse when the news was bad. I am going to take a break from American for my next few military flights. Hopefully whatever has been going on with American Airlines will be resolved.

We had a 2 hour delay. The seats were smaller than most other airlines. The person in front of us wanted to lay back and we had to stop her because she was pressing against my girlfriend’s legs. We had to ask her to sit up and not lay back due to the lack of room.

Everything was fine once we actually got on our flight. It was more then annoying they canceled (delayed) our flight. We lost out on a day of our trip along with money on our stay. Plus we had to book another hotel. So expensive.

This flight was canceled and delayed several times without explanation. The plane was freezing cold and no wifi for messaging. Getting off the plane was terribly unorganized and felt like it took forever….

The flight was delayed several times without explanation. The seats were terribly uncomfortable and wifi isn’t included. All these make for a less than ideal flight.

The flights was delayed by hours and it was the firmest landing I have experienced in my life. My back is still sore.

Internet service was erratic. Crew service was poor and slow. My luggage on this non-stop flight was lost and not recovered

Worst experience flying American Airlines. I fly with them often, so I was super disappointed in the service I received at gate 30 in LGA on May 24, mid-day. The flight was delayed twice. I was patiently waiting in the American Airlines lounge when I received the notice on my app that the plane was boarding 45 minutes before its newly re-scheduled take off of 4 pm (from the orginal 1:45 pm then 3:00 pm). It took me 5 min to travel from the lounge to the gate and when I arrived there at 3:20 flight gate attendant told me the flight had closed and that they announced for passengers multiple times. I showed them the notification on my app and they were really rude and unempathetic. The person who rescheduled my flight at customer service wasn't any happier but was at least helpful in getting me on the next flight.

Crew were attentive and friendly. Flight was smooth and early! I enjoyed the less crowded plane. Thank you!

Book cheap flights from Boston to Kailua

Recent round-trip flight deals

9/11Wed
1 stopDelta
16h 59mBOS-HNL
9/19Thu
1 stopDelta
12h 35mHNL-BOS
$440
8/24Sat
1 stopDelta
16h 53mBOS-HNL
9/3Tue
1 stopDelta
11h 25mHNL-BOS
$460
9/11Wed
2 stopsAmerican Airlines
18h 29mBOS-HNL
9/19Thu
1 stopAmerican Airlines
15h 07mHNL-BOS
$461
11/2Sat
1 stopAlaska Airlines
34h 40mBOS-HNL
11/15Fri
2 stopsAlaska Airlines
26h 04mHNL-BOS
$464
11/6Wed
1 stopAlaska Airlines
21h 59mBOS-HNL
11/15Fri
2 stopsAlaska Airlines
26h 04mHNL-BOS
$465
9/11Wed
2 stopsAmerican Airlines
17h 19mBOS-HNL
9/19Thu
2 stopsAmerican Airlines
13h 42mHNL-BOS
$466
9/14Sat
nonstopHawaiian Airlines
11h 10mBOS-HNL
9/23Mon
nonstopHawaiian Airlines
9h 45mHNL-BOS
$519
8/14Wed
1 stopHawaiian Airlines
16h 54mBOS-HNL
8/20Tue
1 stopHawaiian Airlines
18h 20mHNL-BOS
$536
9/18Wed
1 stopUnited Airlines
13h 27mBOS-HNL
9/28Sat
1 stopUnited Airlines
12h 41mHNL-BOS
$555
8/17Sat
1 stopUnited Airlines
13h 50mBOS-HNL
9/16Mon
1 stopUnited Airlines
12h 17mHNL-BOS
$566

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Recent one-way flight deals

8/19Mon
nonstopHawaiian Airlines
11h 10mBOS-HNL
$279
7/5Fri
nonstopHawaiian Airlines
11h 10mBOS-HNL
$310
8/16Fri
1 stopAlaska Airlines
16h 52mBOS-HNL
$311
7/10Wed
1 stopAlaska Airlines
17h 55mBOS-HNL
$325
8/16Fri
2 stopsAmerican Airlines
17h 08mBOS-HNL
$341
7/16Tue
1 stopUnited Airlines
15h 43mBOS-HNL
$368
7/5Fri
1 stopUnited Airlines
19h 03mBOS-HNL
$370
7/12Fri
1 stopDelta
15h 08mBOS-HNL
$409
7/9Tue
1 stopDelta
17h 45mBOS-HNL
$410
6/16Sun
2 stopsAmerican Airlines
16h 58mBOS-HNL
$418

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Last minute flights from Boston to Kailua

Last minute flight, train and bus deals

6/14Fri
nonstopHawaiian Airlines
11h 05mBOS-HNL
6/26Wed
nonstopHawaiian Airlines
9h 50mHNL-BOS
$752
6/15Sat
multi-stopUnited Airlines
13h 06mBOS-HNL
6/17Mon
multi-stopUnited Airlines
12h 47mHNL-BOS
$780
6/15Sat
multi-stopUnited Airlines
15h 05mBOS-HNL
6/17Mon
multi-stopUnited Airlines
16h 00mHNL-BOS
$785
6/15Sat
multi-stopUnited Airlines
19h 31mBOS-HNL
6/17Mon
multi-stopUnited Airlines
16h 00mHNL-BOS
$790
6/14Fri
multi-stopUnited Airlines
14h 20mBOS-HNL
6/16Sun
multi-stopUnited Airlines
12h 47mHNL-BOS
$794
6/14Fri
nonstopHawaiian Airlines
11h 05mBOS-HNL
6/19Wed
nonstopHawaiian Airlines
9h 50mHNL-BOS
$795
6/14Fri
multi-stopAmerican Airlines
13h 59mBOS-HNL
6/19Wed
multi-stopAmerican Airlines
14h 16mHNL-BOS
$801
6/14Fri
multi-stopAmerican Airlines
14h 37mBOS-HNL
6/19Wed
multi-stopAmerican Airlines
14h 16mHNL-BOS
$806
6/14Fri
nonstopJetBlue
11h 05mBOS-HNL
6/26Wed
nonstopJetBlue
9h 50mHNL-BOS
$925
6/15Sat
nonstopJetBlue
11h 05mBOS-HNL
6/17Mon
nonstopJetBlue
9h 50mHNL-BOS
$970

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