$263 Find Cheap Flights from Boston to Kailua

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 9/15. 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.
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Cheap Flights from Boston to Kailua (BOS-HNL)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Boston to Kailua 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 Boston to Kailua

Wed, Aug 27 - Tue, Sep 2
Alaska Airlines Logo
7:45 am - 8:55 pmBOS-HNL
19h 10m1 stop
Alaska Airlines Logo
8:00 am - 5:40 pmHNL-BOS
27h 40m1 stop
$525Alaska Airlines
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Tue, Aug 12 - Wed, Aug 13
Alaska Airlines Logo
8:40 am - 3:30 pmBOS-HNL
12h 50m1 stop
Alaska Airlines Logo
12:55 pm - 7:30 amHNL-BOS
12h 35m1 stop
$526Alaska Airlines
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Tue, Sep 2 - Fri, Sep 5
Alaska Airlines Logo
7:45 am - 12:10 pmBOS-HNL
34h 25m1 stop
Alaska Airlines Logo
1:30 pm - 3:00 pmHNL-BOS
19h 30m1 stop
$540Alaska Airlines
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Wed, Oct 29 - Tue, Nov 11
Delta Logo
6:30 am - 7:50 pmBOS-HNL
19h 20m1 stop
Delta Logo
8:00 am - 5:58 amHNL-BOS
16h 58m1 stop
$596Delta
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Mon, Jul 28 - Wed, Aug 13
Hawaiian Airlines Logo
5:20 pm - 5:00 amBOS-HNL
17h 40m1 stop
Hawaiian Airlines Logo
12:55 pm - 7:30 amHNL-BOS
12h 35m1 stop
$612Hawaiian Airlines
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Mon, Jul 28 - Wed, Aug 13
Hawaiian Airlines Logo
8:00 am - 1:05 pmBOS-HNL
11h 05mnonstop
Hawaiian Airlines Logo
12:55 pm - 7:30 amHNL-BOS
12h 35m1 stop
$614Hawaiian Airlines
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Thu, Oct 30 - Tue, Nov 11
Delta Logo
6:30 am - 7:50 pmBOS-HNL
19h 20m1 stop
Delta Logo
8:00 am - 5:58 amHNL-BOS
16h 58m1 stop
$616Delta
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Thu, Oct 30 - Thu, Nov 6
American Airlines Logo
7:00 am - 4:56 pmBOS-HNL
15h 56m2 stops
American Airlines Logo
7:00 pm - 11:18 amHNL-BOS
11h 18m1 stop
$622American Airlines
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Sat, Aug 23 - Wed, Sep 3
American Airlines Logo
5:55 am - 4:18 pmBOS-HNL
16h 23m2 stops
American Airlines Logo
9:42 pm - 5:17 pmHNL-BOS
13h 35m2 stops
$628American Airlines
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Fri, Aug 22 - Sun, Aug 31
United Airlines Logo
7:30 am - 3:21 pmBOS-HNL
13h 51m1 stop
United Airlines Logo
1:30 pm - 9:56 amHNL-BOS
14h 26m2 stops
$687United Airlines
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Good to know

Low seasonSeptember
High seasonApril
Cheapest flight$263
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 2% increase in price.
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 05m.

  • How many flights are there between Boston and Kailua?

    2 direct flights run between Boston and Kailua on a daily basis. On average, there are about 15 departures each week.

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

    Consider leaving on a Wednesday and avoid Tuesdays 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 Southwest for $263. Alaska Airlines offered a round-trip connection from $525 and Delta from $596.

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 58 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 January.

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 10000 reviews
7.8Comfort
7.1Food
8.5Crew
7.1Entertainment
8.1Boarding
Airline reviews

Terrible check in experience, and they ended up losing our bag.

2.0 MediocreEmilie, Jun 2025KOA - OGG
Read more Alaska Airlines reviews

Terrible check in experience, and they ended up losing our bag.

they didn't fix a plane and we were delayed travelling an extra 12 hours.

This flight was how a flight should be. The flight from Hawaii to Seattle was terrible

Kayak and Alaska have our trusted traveller information stored in our profiles. But, that information never made it to Alaska when it came time to check into our outbound flight. As a result, we were not cleared for TSA recheck. I was able to add in that information for our return flight and we had TSA Recheck on the return. I really expected Kayak and Alaska to do a complete job with our booking given the amount of information you have on file.

Our big luggage never made it to Boston. Very crucial to get it ASAP as heart medication is in there.

Wish I got An email stating that I needed to check in at hawaiian even if I made my ticket thru alaska. I had to walk to terminal A from Terminal B.

It was all great all around. Will travel with Alaska next trip.

Long delay before boarding. By the time I was informed of the delay I was already at the gate.

One of the worst check-in experiences ever. Apparently, we were overweight and had to completely repack. They tried to charge us an extra $35 per bag on top of the standard checked baggage fee we had already paid in advance. Surprisingly, we managed to fit everything into our carry-ons and stayed under their precious 50-pound limit. (By the way, 23 kg is actually 50.7 lbs, so we couldn’t even go slightly over 50 according to the very unfriendly agent.)

Tight legroom. The breakfast was provided, which was a plus, and okay the taste.

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

I want to single out flight attendant Mitch who was in the Premium Economy section. When my wife’s hearing aide dropped through the cushion under the seat he was able to locate it and return it to her. Food was a different matter. Dinner was fine. Breakfast was another matter. They had a yogurt dish that the ran out of and the alternative was not very good according to those we talked to.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Great flight! Only complaint I had was that I didn’t get breakfast that morning because I don’t eat eggs for breakfast.. I ate an energy bar I bought in the airport which I had never done before. Otherwise, another great Delta flight!

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It was very pleasant. The staff and crew are very polite.

Hawaiian Airlines staff is always professional & quick & easy check in & boarding process

Customer service by Susan of Alaskan Air was outstanding. We missed our flight out of JFK. She got us rebooked the following day. Way to go Susan.

Bar code for checking luggage and boarding pass didn't work. Had to stand in long customer service line. Passengers at Oahu should be aware the Terminal for Hawaiian Air requires travel by shuttle. Budget an extra 20-30 minutes to get from the main terminal to the remote terminal.

Checking baggage at Honolulu was a real mess. No signs directing where to go.

We boarded an hour and a half late because a coffee maker leaked in the plane. Then we had to wait for awhile to get off the plane because another plane was in our spot at the terminal. I had plans when I landed that I had to skip so it was pretty disappointing.

We moved from the international terminal to a new location. I think there are still some bugs to work out . We didn’t receive check in notification and had to scramble to find it but i think it will work out

Not so good. The takeoff was aborted after reaching 100 knots due to a problem with the front tires. I do commend the pilot for a quick decision and preventing a potential disaster. We returned to the gate to put fresh tires on the front. Our flight was delayed for over 3 hours. The rest of the flight was okay. We were reimbursed by Hawaiian Airlines for only $50. Not too generous

Arrived at the gate with no seats assigned. Was told by gate agent the flight was full and we would not be on it. I asked the gate agent how could I be sold tickets when the flight was full. She replied, “Thats just how they do it.” I was able to get seats once I arrived at the gate. The flight itself was great. I’ll never purchase tickets without seat assignments from kayak or anyone again. Shame on kayak or Hawaiian airlines or all of you.

A cold sandwich would be much better than the warm gummy croissant.

United airlines, mediocre at best. No issues , nothing great . Worked for me

it was so bad. I tried to board my flight from vancouver to saskatoon. And to my surprise they did not board me cause the flight was changed and no email was send to me. and on my boarding pass which i got from seattle says different flight. I did not knew anyone from Vancouver, air canada crew was rude, i asked for today flight but they were rude and i had early morning dental appointment in saskatoon. I was so much in pain and my whole day is wasted today. and i suffered alot. They did provide me hotel but they did not provide me any food. I am really really disappointed first time had so bad experience with air canada. I may think twice to book it again. If i can get any reply or any composition that would be great. Thanks

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

Boarding was mayhem. Late boarding by 15 minutes because of lack of staff (missing 1 flight attendant. We had to wait for an arrival of another plane before we could board). Flight was a little rough, but cannot blame on airlines.

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

Very comfortable (upgraded to business class). The audio on my screen didn’t work, but I managed to play the audio through my phone while watching the screen.

Great experience…left a bit behind schedule but made up fir that in the air and landed 10 minutes early 😁

I was supposed to be on business class at first class from Denver back to Miami due to weather changes. I missed my connection and it’s put on a flight to Fort Lauderdale. Instead of honoring my business class/1st class ticket, they put me in coach, but there were two first class seats open. I think it’s absolutely disgusting that I paid for first class $1300 ticket and they put me in economy and they had to open seats available and I have still not been refunded the difference. I ended up having to eat a snack box instead of the meal I was supposed to get and did not get home till 2 AM so I think that’s a little pathetic that I had to live off crackers for dinner And my poor dog ate some cheese and salami. Oh yes, apparently when they switched me to the new flight they forgot to mention I had a service dog

Excellent service despite turbulence during the flight. Flight attendants were remarkable!

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

The check in and boarding process was a bit of a cluster. Two people at the counter to check in, three random lines that nobody knew which was for what, and people kept getting shuffled from one line to another for no apparent reason because then they’d get shuffled back and end up getting out further back in the line than they were originally. I only had to hand my already checked bag over and it took 45 minutes. I was never assigned a seat so when I tried to board I was pulled out of line again while someone had to try to manually assign me a seat. During the flight I got up to go to the bathroom, and there was an attendant in the aisle offering pillows etc and it was a 30 min wait unbuckled standing by the bathrooms because she said I couldn’t go past her. First and last time flying jet blue to be honest.

Communication since no reason or explanation was given for 3 hrs delay

Flight was delayed several 3 hours - no reason was given and no communication what so ever.

No overhead baggage room even though I was seated in row 2. Consequently had to check in my carry on bag. Baggage carousel was jammed. Took 45 min to get my bag.

Excellent from start to finish. All staff members were amazing!

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

It was too hot in the cabin. The AC did not help.

Except for the 28 minute delay leaving and the earlier reschedule to a later takeoff time the flight was good.

Loved the leg room and tvs screens on the seats and free WiFi. Wish the price was lower and could save by rebooking

Everything you need to know for your flight from Boston to Kailua

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