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Kailua

$296+ 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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — HNL
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
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 18 days in advance, depart on a Tuesday or Wednesday and return on a Friday

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 septiembre 16, 2025.

Round-trip from

$537
(Delta)

One-way from

$296
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$622
From Boston Logan Intl to Kailua
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One-way flight from Boston Logan Intl to Kailua
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Highest demand for flights based on searches. 14% potential increase in price ($117 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 septiembre 16, 2025.

This Hawaiian Airlines deal was found by Cheapflights users on 9/14. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/228:00 amBOS - HNL
Nonstop11h 10mHawaiian Airlines
dom. 9/282:15 pmHNL - BOS
Nonstop9h 45mHawaiian Airlines
Deal found 9/14$518
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/158:00 amBOS - HNL
Nonstop11h 10mAlaska Airlines
dom. 9/211:10 pmHNL - BOS
1 stop12h 50mAlaska Airlines
Deal found 9/14$526
This JetBlue deal was found by Cheapflights users on 9/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/228:00 amBOS - HNL
Nonstop11h 10mJetBlue
dom. 9/282:15 pmHNL - BOS
Nonstop9h 45mJetBlue
Deal found 9/15$536
This United Airlines deal was found by Cheapflights users on 9/16. 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. 9/236:02 amBOS - HNL
1 stop16h 03mUnited Airlines
mar. 9/305:15 pmHNL - BOS
1 stop11h 47mUnited Airlines
Deal found 9/16$537
This lastminute.com deal was found by Cheapflights users on 9/14. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/69:00 amBOS - HNL
Nonstop11h 17mJetBlue
lun. 10/203:10 pmHNL - BOS
Nonstop9h 50mJetBlue
Deal found 9/14$547
This Hawaiian Airlines deal was found by Cheapflights users on 9/15. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/234:00 pmBOS - HNL
1 stop13h 46mHawaiian Airlines
dom. 9/282:15 pmHNL - BOS
Nonstop9h 45mHawaiian Airlines
Deal found 9/15$548
This KAYAK deal was found by Cheapflights users on 9/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/308:00 amBOS - HNL
Nonstop11h 18mAlaska Airlines
mar. 11/49:55 pmHNL - BOS
1 stop14h 28mAlaska Airlines
Deal found 9/14$552
This Rumbo deal was found by Cheapflights users on 9/16. 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 Rumbo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/139:00 amBOS - HNL
Nonstop11h 17mJetBlue
lun. 10/272:18 pmHNL - BOS
Nonstop9h 42mJetBlue
Deal found 9/16$555
This Delta deal was found by Cheapflights users on 9/15. 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.
jue. 9/186:05 amBOS - HNL
1 stop14h 38mDelta
mar. 9/233:05 pmHNL - BOS
1 stop13h 30mDelta
Deal found 9/15$557
This Hawaiian Airlines deal was found by Cheapflights users on 9/15. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/288:00 amBOS - HNL
Nonstop11h 18mHawaiian Airlines
mié. 11/53:18 pmHNL - BOS
Nonstop9h 42mHawaiian Airlines
Deal found 9/15$558
This Delta deal was found by Cheapflights users on 9/16. 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.
jue. 10/306:15 amBOS - HNL
1 stop16h 53mDelta
mar. 11/411:15 pmHNL - BOS
1 stop15h 12mDelta
Deal found 9/16$559

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 septiembre 16, 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

jue. 9/25

6:05 am-2:43 pm

1 stop14h 38m

Honolulu

lun. 9/29

3:05 pm-10:35 am

1 stop13h 30m

$537

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

jue. 9/25

11:45 am-7:32 pm

1 stop13h 47m

Honolulu

dom. 9/28

9:40 pm-5:54 pm

2 stops14h 14m

$542

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

jue. 11/6

8:00 am-2:18 pm

Nonstop11h 18m

Honolulu

mié. 11/12

3:18 pm-6:00 am

Nonstop9h 42m

$558

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

lun. 10/6

8:00 am-1:17 pm

Nonstop11h 17m

Honolulu

lun. 10/20

2:10 pm-6:00 am

Nonstop9h 50m

$558

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

mié. 11/12

4:24 pm-12:25 pm

1 stop25h 01m

Honolulu

lun. 11/17

3:04 pm-5:46 am

Nonstop9h 42m

$567

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

mar. 10/28

8:00 am-1:18 pm

Nonstop11h 18m

Honolulu

jue. 11/6

11:07 pm-3:41 pm

1 stop11h 34m

$568

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

lun. 9/22

8:00 am-1:10 pm

Nonstop11h 10m

Honolulu

vie. 9/26

9:41 pm-4:37 pm

1 stop12h 56m

$568

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

jue. 11/13

6:15 am-9:49 pm

1 stop20h 34m

Honolulu

lun. 11/17

4:45 pm-11:55 am

1 stop14h 10m

$573

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

mar. 9/30

8:00 am-1:10 pm

Nonstop11h 10m

Honolulu

lun. 10/6

2:10 pm-6:00 am

Nonstop9h 50m

$578

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

lun. 10/6

9:00 am-2:17 pm

Nonstop11h 17m

Honolulu

lun. 10/20

3:10 pm-7:00 am

Nonstop9h 50m

$580

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 22 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 September 12, 2025.

The best time to book flights from Boston to Kailua is 18 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, November is the cheapest month in which you can book a flight from Boston to Kailua (average of $469). Flying from Boston to Kailua in June is currently the most expensive (average of $687). 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 septiembre 16, 2025.

When flying from Boston to Kailua, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 14, 2025.

Travelers seeking maximum savings on their Boston to Kailua flight should consider departing on Thursday afternoons when fares are most often at their lowest. Friday 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 septiembre 16, 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
10,000 reviews

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.1

Entertainment

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.1

Entertainment

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Delta
8.0
Very good
7,957 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.1

Entertainment

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Hawaiian Airlines
7.8
Good
2,724 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.1

Entertainment

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,924 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.1

Entertainment

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
JetBlue
7.2
Good
2,914 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.1

Entertainment

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

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 1 outbound flight 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 26 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 11h 18m. Delta provides one of the quickest options available for as low as $558. 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 Alaska Airlines (59%), JetBlue (59%) and Hawaiian Airlines (59%).

  • What are the cheapest flights from Boston to Kailua?

    While on average a flight from Boston to Kailua is generally $2,189, our data shows the cheapest flight currently is $247. When looking at the most popular route, (Boston Logan Intl - Honolulu), you can expect to pay $518 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, November is the cheapest month in which you can book a flight from Boston to Kailua (average of $469). Flying from Boston to Kailua in June is currently the most expensive (average of $687). 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 septiembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$309Average$624FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$316Average$654FlexibilityNo cancel feeOn-time62%
Hawaiian AirlinesCheapest$367Average$713FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$440Average$755FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$478Average$728FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$511Average$750FlexibilityNo cancel feeOn-time75%

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