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Kailua

$306+ 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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — HNL
dic. 6 — dic. 131
sáb. 12/6
sáb. 12/13
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Kailua are usually found in January or March, booked 20 days in advance, depart on a Wednesday or Tuesday and return on a Friday

Find 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 noviembre 6, 2025.

This Alaska Airlines deal was found by Cheapflights users on 11/3. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/36:52 pmBOS - HNL
2 stops25h 43mAlaska Airlines
mié. 12/101:45 pmHNL - BOS
2 stops20h 52mAlaska Airlines
Deal found 11/3$579
This Alaska Airlines deal was found by Cheapflights users on 11/3. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/56:52 pmBOS - HNL
1 stop33h 58mAlaska Airlines
vie. 12/1210:36 pmHNL - BOS
1 stop12h 01mAlaska Airlines
Deal found 11/3$586
This United Airlines deal was found by Cheapflights users on 11/3. 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.
mar. 12/28:30 amBOS - HNL
1 stop13h 55mUnited Airlines
sáb. 12/65:00 pmHNL - BOS
1 stop12h 38mUnited Airlines
Deal found 11/3$587
This Delta deal was found by Cheapflights users on 11/5. 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.
mar. 12/97:45 amBOS - HNL
1 stop19h 03mDelta
lun. 12/1511:23 pmHNL - BOS
1 stop26h 32mDelta
Deal found 11/5$588
This Alaska Airlines deal was found by Cheapflights users on 11/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/36:52 pmBOS - HNL
2 stops23h 42mAlaska Airlines
sáb. 12/131:45 pmHNL - BOS
2 stops20h 52mAlaska Airlines
Deal found 11/4$589
This Alaska Airlines deal was found by Cheapflights users on 11/5. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/86:52 pmBOS - HNL
1 stop21h 08mAlaska Airlines
jue. 12/187:00 amHNL - BOS
1 stop12h 23mAlaska Airlines
Deal found 11/5$593
This United Airlines deal was found by Cheapflights users on 11/4. 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.
mar. 12/29:40 amBOS - HNL
2 stops16h 23mUnited Airlines
mar. 12/92:25 pmHNL - BOS
1 stop12h 11mUnited Airlines
Deal found 11/4$594
This Alaska Airlines deal was found by Cheapflights users on 11/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/36:52 pmBOS - HNL
2 stops23h 42mAlaska Airlines
vie. 12/1210:36 pmHNL - BOS
1 stop12h 01mAlaska Airlines
Deal found 11/4$595

Cheap flight deals from Boston to Kailua

Keep the following information in mind while searching for Boston to Kailua flight deals. Data was last updated noviembre 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$579
(Alaska Airlines)

One-way from

$306
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$625
Provider with most accurate pricing for Boston Logan Intl-Honolulu flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Honolulu flights.
Search Deals
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. 0% potential increase in price ($2 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 noviembre 6, 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

mié. 12/3

4:40 pm-9:55 pm

1 stop34h 15m

Honolulu

mié. 12/10

8:00 am-7:29 am

2 stops18h 29m

$584

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

sáb. 1/31

7:00 am-10:30 pm

2 stops20h 30m

Honolulu

mié. 2/4

12:58 pm-5:39 pm

1 stop23h 41m

$590

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

mar. 12/2

5:45 am-3:28 pm

1 stop14h 43m

Honolulu

lun. 12/8

8:00 am-5:27 am

1 stop16h 27m

$621

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

mar. 12/2

8:05 am-9:03 pm

2 stops17h 58m

Honolulu

lun. 12/8

10:50 pm-7:26 am

1 stop27h 36m

$667

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

dom. 12/7

7:45 am-8:37 pm

2 stops17h 52m

Honolulu

lun. 12/22

6:10 pm-10:52 am

1 stop11h 42m

$667

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

mar. 12/2

7:00 am-9:03 pm

2 stops19h 03m

Honolulu

mar. 12/9

10:50 pm-7:26 am

1 stop27h 36m

$667

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

dom. 11/9

11:10 am-8:15 pm

1 stop14h 05m

Honolulu

dom. 11/16

2:00 pm-3:30 pm

2 stops20h 30m

$669

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

lun. 12/29

7:45 am-6:48 pm

2 stops16h 03m

Honolulu

lun. 1/26

12:45 pm-7:21 am

1 stop13h 36m

$673

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

dom. 1/11

7:15 am-6:29 pm

1 stop16h 14m

Honolulu

dom. 1/18

1:17 pm-6:50 am

1 stop12h 33m

$674

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

jue. 1/8

5:20 pm-12:40 pm

1 stop24h 20m

$311

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

Showing 1-10 of 21 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 October 31, 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 $223). Flying from Boston to Kailua in July is currently the most expensive (average of $456). 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.

What is the cheapest time of day to fly from BOS to K4I?

Find hourly flight availability from Boston to Kailua. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated noviembre 6, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 12% on flights from Boston to Kailua by exploring options for tickets at noon.

What is the cheapest day to fly from Boston to Kailua?

Use this chart to determine the cheapest time to fly round-trip from Boston to Kailua. Price data was last updated on November 2, 2025.

Travelers seeking maximum savings on their Boston to Kailua flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 noviembre 6, 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
11,246 reviews

Entertainment

7.0

Food

7.1

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
11,246 reviews
Alaska Airlines
8.0
Very good
11,246 reviews

Entertainment

7.0

Food

7.1

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Delta
7.9
Good
8,001 reviews
Alaska Airlines
8.0
Very good
11,246 reviews

Entertainment

7.0

Food

7.1

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Hawaiian Airlines
7.8
Good
2,804 reviews
Alaska Airlines
8.0
Very good
11,246 reviews

Entertainment

7.0

Food

7.1

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
United Airlines
7.4
Good
9,007 reviews
Alaska Airlines
8.0
Very good
11,246 reviews

Entertainment

7.0

Food

7.1

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
JetBlue
7.2
Good
2,907 reviews
Alaska Airlines
8.0
Very good
11,246 reviews

Entertainment

7.0

Food

7.1

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

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 21 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 14h 43m. Alaska Airlines provides one of the quickest options available for as low as $621. The distance between Boston and Kailua is about 5083 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    The top 3 most reliable airlines when flying from Boston to Kailua are JetBlue (82%), Alaska Airlines (79%) and Hawaiian Airlines (68%).

  • What are the cheapest flights from Boston to Kailua?

    While on average a flight from Boston to Kailua is generally $2,231, our data shows the cheapest flight currently is $269. When looking at the most popular route, (Boston Logan Intl - Honolulu), you can expect to pay $466 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 $223). Flying from Boston to Kailua in July is currently the most expensive (average of $456). 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 noviembre 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$305Average$634FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$340Average$701FlexibilityNo cancel feeOn-time62%
Hawaiian AirlinesCheapest$399Average$731FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$456Average$757FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$495Average$783FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$518Average$751FlexibilityNo cancel feeOn-time75%

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