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Kailua

$280+ Cheap flights from Boston (BOS) to Kailua, HI

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — HNL
Jan 29 — Feb 51
Thu 1/29
Thu 2/5
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Kailua are usually found in March or January, booked 20 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday

Cheap flight deals from Boston to Kailua

Cheapest flights from Boston to Kailua
Explore the most affordable flight options available from Boston to Kailua. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 30, 2025.

This United Airlines deal was found by Cheapflights users on 12/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/308:00 amBOS - HNL
1 stop14h 37mUnited Airlines
Wed 1/283:55 pmHNL - BOS
1 stop12h 19mUnited Airlines
Deal found 12/30$647
This Delta deal was found by Cheapflights users on 12/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 amBOS - HNL
1 stop15h 03mDelta
Tue 1/139:35 pmHNL - BOS
1 stop27h 39mDelta
Deal found 12/29$750
This Delta deal was found by Cheapflights users on 12/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:10 amBOS - HNL
2 stops29h 33mDelta
Fri 1/94:44 pmHNL - BOS
1 stop11h 25mDelta
Deal found 12/29$761
This United Airlines deal was found by Cheapflights users on 12/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:45 amBOS - HNL
1 stop13h 45mUnited Airlines
Wed 12/318:30 pmHNL - BOS
1 stop13h 44mUnited Airlines
Deal found 12/30$802
This Delta deal was found by Cheapflights users on 12/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:05 amBOS - HNL
1 stop15h 03mDelta
Tue 1/135:15 pmHNL - BOS
1 stop12h 36mDelta
Deal found 12/29$803
This United Airlines deal was found by Cheapflights users on 12/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:45 amBOS - HNL
1 stop13h 45mUnited Airlines
Wed 1/712:45 pmHNL - BOS
1 stop13h 36mUnited Airlines
Deal found 12/30$807
This Delta deal was found by Cheapflights users on 12/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:05 amBOS - HNL
1 stop15h 03mDelta
Fri 1/94:44 pmHNL - BOS
1 stop14h 35mDelta
Deal found 12/29$837

Find flight deals from Boston to Kailua

Keep the following information in mind while searching for Boston to Kailua flight deals. Data was last updated December 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$480
(Alaska Airlines)

One-way from

$280
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$991
Provider with most accurate pricing for Boston Logan Intl-Honolulu flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Honolulu flights.
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From Boston Logan Intl to Kailua
Search Deals
One-way flight from Boston Logan Intl to Kailua
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Boston to Kailua that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 30, 2025.
Use the filters below to find and compare flights from Boston to Kailua that are best for you.

Fly from

Boston

Fly to

Kailua

Route

Depart

Return

Price

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Thu 1/29

7:30 am-9:28 pm

1 stop18h 58m

Honolulu

Thu 2/5

1:55 pm-9:23 pm

1 stop26h 28m

$483

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Thu 1/29

4:20 pm-12:48 pm

1 stop25h 28m

Honolulu

Tue 2/3

12:58 pm-5:39 pm

1 stop23h 41m

$486

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Fri 2/6

4:20 pm-12:48 pm

1 stop25h 28m

Honolulu

Fri 2/13

12:55 pm-5:24 pm

1 stop23h 29m

$486

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Wed 1/28

4:20 pm-12:48 pm

1 stop25h 28m

Honolulu

Fri 2/6

8:00 am-4:20 pm

1 stop27h 20m

$486

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Tue 1/27

10:56 am-8:55 pm

1 stop14h 59m

Honolulu

Tue 2/3

8:40 pm-3:37 pm

1 stop13h 57m

$487

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Thu 2/26

7:15 am-5:05 pm

1 stop14h 50m

Honolulu

Thu 3/5

1:10 pm-6:50 am

1 stop12h 40m

$487

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Tue 2/24

9:02 am-10:06 pm

1 stop18h 04m

Honolulu

Fri 3/6

8:00 am-6:54 am

1 stop17h 54m

$487

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Thu 1/29

6:44 pm-11:18 am

1 stop21h 34m

Honolulu

Tue 2/10

9:50 pm-3:20 pm

1 stop12h 30m

$487

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Thu 2/5

4:20 pm-12:48 pm

1 stop25h 28m

Honolulu

Sun 3/1

11:59 pm-11:59 pm

1 stop19h 00m

$487

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Tue 2/24

9:02 am-10:06 pm

1 stop18h 04m

Honolulu

Mon 3/9

7:00 am-6:54 am

1 stop17h 54m

$487

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/29

Showing 1-10 of 23 results
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Best time to book a flight from Boston to Kailua

Have a flexible travel schedule? Discover the best time to fly to Kailua from Boston with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

How far ahead should I book a flight from Boston to Kailua?

Use this chart to determine the optimal time to book a round-trip flight from Boston to Kailua. Price data was last updated on December 26, 2025.

The best time to book flights from Boston to Kailua is 20 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Boston to Kailua?

Currently, January is the cheapest month in which you can book a flight from Boston to Kailua (average of $262). Flying from Boston to Kailua in July is currently the most expensive (average of $617). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Kailua

Get insights into the airlines that provide service to Kailua. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Kailua. Reviews last updated December 30, 2025.
See what other customers who have flown with Alaska Airlines, Delta, and Hawaiian Airlines from Boston to Kailua have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,575 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
Alaska Airlines
8.0
Very good
11,575 reviews
Alaska Airlines
8.0
Very good
11,575 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
Delta
7.9
Good
8,016 reviews
Alaska Airlines
8.0
Very good
11,575 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
Hawaiian Airlines
7.8
Good
2,821 reviews
Alaska Airlines
8.0
Very good
11,575 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
United Airlines
7.4
Good
9,124 reviews
Alaska Airlines
8.0
Very good
11,575 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
JetBlue
7.2
Good
2,903 reviews
Alaska Airlines
8.0
Very good
11,575 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.

Related info for your journey

Find useful and relevant information for your journey from Boston to Kailua. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Boston to Kailua?

    For a flight from Boston to Kailua, you will be flying from Logan Intl. Boston Logan Intl (BOS) is just 2.6 mi from the center of the city. Logan Intl is the only Boston airport and it handles 0 outbound flights to Kailua per day. 6 airlines have flights to Kailua from Boston Logan Intl on a regular basis.

  • How popular is this Boston to Kailua flight route?

    This flight path from Boston Logan Intl to Kailua was viewed by 17 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

  • How long is the flight from Boston to Kailua?

    A quick flight from Boston to Kailua can take about 18h 58m. Delta provides one of the quickest options available for as low as $483. The distance between Boston and Kailua is about 5083 mi.

  • What are the cheapest airlines to fly from Boston to Kailua one-way?

    One-way options have recently been found by users for as low as $247 on Delta. Other airlines that offer cheap prices include American Airlines from $258 and Alaska Airlines from $269 one-way.

  • What are the most reliable airlines from Boston to Kailua?

    The top 3 most reliable airlines when flying from Boston to Kailua are Hawaiian Airlines (67%), Alaska Airlines (64%) and JetBlue (60%).

  • What are the cheapest flights from Boston to Kailua?

    While on average a flight from Boston to Kailua is generally $3,008, our data shows the cheapest flight currently is $419. When looking at the most popular route, (Boston Logan Intl - Honolulu), you can expect to pay $453 for that flight.

  • Can I find deals for flights from Boston to Kailua that include hotel bookings?

    Yes. In addition to deals on Boston to Kailua flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Boston to Kailua?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to Kailua.

  • Can I find deals for business class flights from Boston to Kailua?

    Yes. Cheapflights offers flight deals from Boston to Kailua by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Boston to Kailua?

    Currently, January is the cheapest month in which you can book a flight from Boston to Kailua (average of $262). Flying from Boston to Kailua in July is currently the most expensive (average of $617). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top 6 airlines flying from Boston to Kailua

Discover the top 6 airlines that operate flights from Boston to Kailua. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$320Average$651FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$429Average$758FlexibilityNo cancel feeOn-time62%
Hawaiian AirlinesCheapest$459Average$742FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$507Average$768FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$517Average$794FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$530Average$754FlexibilityNo cancel feeOn-time75%

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