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Kailua

$310+ 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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — HNL
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Kailua are usually found in January or November, booked 58 days in advance, depart on a Tuesday or Monday and return on a Tuesday

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 June 12, 2025.

Round-trip from

$614
(Delta)

One-way from

$310
(Alaska Airlines)

Popular in

June

Cheapest in

January

Average price

$883
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. 15% potential increase in price ($124 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 June 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 June 12, 2025.

This Delta deal was found by Cheapflights users on 6/9. 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.
Mon 9/86:15 amBOS - HNL
1 stop16h 31mDelta
Tue 9/167:00 amHNL - BOS
1 stop16h 58mDelta
Deal found 6/9$614
This Alaska Airlines deal was found by Cheapflights users on 6/9. 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.
Mon 9/88:00 amBOS - HNL
Nonstop11h 10mAlaska Airlines
Mon 9/158:43 pmHNL - BOS
2 stops21h 40mAlaska Airlines
Deal found 6/9$615
This Hawaiian Airlines deal was found by Cheapflights users on 6/9. 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.
Sat 10/47:00 amBOS - HNL
1 stop16h 22mHawaiian Airlines
Sun 10/127:55 amHNL - BOS
1 stop15h 05mHawaiian Airlines
Deal found 6/9$617
This American Airlines deal was found by Cheapflights users on 6/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1312:15 pmBOS - HNL
1 stop15h 00mAmerican Airlines
Mon 11/247:50 pmHNL - BOS
1 stop14h 01mAmerican Airlines
Deal found 6/10$619
This JetBlue Airways deal was found by Cheapflights users on 6/10. 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 Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/128:00 amBOS - HNL
Nonstop11h 05mMultiple Airlines
Sat 8/231:30 pmHNL - BOS
1 stop34h 29mMultiple Airlines
Deal found 6/10$649
This United Airlines deal was found by Cheapflights users on 6/10. 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 8/55:25 amBOS - HNL
1 stop13h 34mUnited Airlines
Sun 8/107:55 pmHNL - BOS
1 stop12h 38mUnited Airlines
Deal found 6/10$706
This JetBlue deal was found by Cheapflights users on 6/10. 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.
Tue 8/128:00 amBOS - HNL
Nonstop11h 05mJetBlue
Mon 8/182:15 pmHNL - BOS
Nonstop9h 45mJetBlue
Deal found 6/10$744

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 June 12, 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

Mon 9/8

6:15 am-4:46 pm

1 stop16h 31m

Honolulu

Tue 9/16

7:00 am-5:58 am

1 stop16h 58m

$614

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Mon 9/8

9:20 am-9:48 am

2 stops30h 28m

Honolulu

Fri 9/12

6:30 am-5:40 pm

2 stops29h 10m

$615

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Thu 9/4

7:05 pm-5:00 am

1 stop15h 55m

Honolulu

Mon 9/8

8:00 am-5:00 am

1 stop15h 00m

$617

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Sat 8/23

8:01 am-4:18 pm

1 stop14h 17m

Honolulu

Wed 9/3

9:42 pm-5:17 pm

2 stops13h 35m

$622

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Tue 8/12

8:00 am-1:05 pm

Nonstop11h 05m

Honolulu

Sat 8/23

1:30 pm-5:59 am

1 stop34h 29m

$649

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Fri 7/4

10:40 am-7:44 pm

2 stops15h 04m

Honolulu

Tue 7/8

9:40 pm-3:45 pm

1 stop12h 05m

$660

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Tue 8/12

8:00 am-1:05 pm

Nonstop11h 05m

Honolulu

Mon 8/18

2:15 pm-6:00 am

Nonstop9h 45m

$744

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Wed 8/13

8:40 am-9:33 pm

2 stops18h 53m

$310

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Wed 8/13

11:14 am-9:34 pm

2 stops16h 20m

$314

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Fri 7/4

5:20 pm-11:10 am

1 stop23h 50m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 14 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 June 9, 2025.

The best time to book flights from Boston to Kailua is 58 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 June 12, 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 June 8, 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.

Rainfall in Kailua by month

Plan your trip to Kailua by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Kailua ranges from 0.3 - 3.2 inches per month. December is typically the wettest month, when rainfall can reach 3.2 in. June is typically the driest time to visit Kailua when rainfall is around 0.3 in.

Temperature in Kailua by month

Plan your trip to Kailua by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Kailua, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 73.4 F).

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 June 12, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest and Delta from Boston to Kailua to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,494 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 2 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 24 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

  • 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 $310 on Alaska Airlines. Other airlines that offer cheap prices include American Airlines from $314 and Hawaiian Airlines from $317 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 American Airlines (81%), Alaska Airlines (81%) and JetBlue (81%).

  • What are the cheapest flights from Boston to Kailua?

    While on average a flight from Boston to Kailua is generally $2,241, our data shows the cheapest flight currently is $251. When looking at the most popular route, (Boston Logan Intl - Honolulu), you can expect to pay $500 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$325Average$659FlexibilityNo cancel feeOn-time62%
Hawaiian AirlinesCheapest$339Average$692FlexibilityNo cancel feeOn-time85%
DeltaCheapest$379Average$646FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$439Average$742FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$445Average$682FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$487Average$755FlexibilityNo cancel feeOn-time75%

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