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Kailua

$305+ 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 9/19. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — HNL
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$589
(Alaska Airlines)

One-way from

$305
(Alaska Airlines)

Popular in

June

Cheapest in

January

Average price

$829
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 ($120 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 31, 2025.

This Alaska Airlines deal was found by Cheapflights users on 7/31. 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 9/87:45 amBOS - HNL
1 stop19h 10mAlaska Airlines
Sun 9/1410:20 pmHNL - BOS
1 stop26h 05mAlaska Airlines
Deal found 7/31$589
This Hawaiian Airlines deal was found by Cheapflights users on 7/29. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/97:20 amBOS - HNL
1 stop18h 57mHawaiian Airlines
Tue 10/2110:20 pmHNL - BOS
1 stop13h 23mHawaiian Airlines
Deal found 7/29$593
This Delta deal was found by Cheapflights users on 7/31. 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.
Sat 8/306:50 amBOS - HNL
1 stop19h 38mDelta
Sun 9/74:09 pmHNL - BOS
1 stop12h 21mDelta
Deal found 7/31$595
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/27:00 amBOS - HNL
1 stop13h 15mAmerican Airlines
Wed 12/1011:00 pmHNL - BOS
1 stop12h 34mAmerican Airlines
Deal found 7/30$617
This United Airlines deal was found by Cheapflights users on 7/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/96:00 amBOS - HNL
2 stops15h 33mUnited Airlines
Sat 11/152:25 pmHNL - BOS
1 stop12h 41mUnited Airlines
Deal found 7/29$622

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 July 31, 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

7:45 am-8:55 pm

1 stop19h 10m

Honolulu

Sun 9/14

10:20 pm-6:25 am

1 stop26h 05m

$589

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Thu 10/9

7:20 am-8:17 pm

1 stop18h 57m

Honolulu

Tue 10/21

10:20 pm-5:43 pm

1 stop13h 23m

$593

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Sat 8/30

6:50 am-8:28 pm

1 stop19h 38m

Honolulu

Mon 9/8

4:09 pm-10:30 am

1 stop12h 21m

$595

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Sat 10/25

6:57 am-5:20 pm

2 stops16h 23m

Honolulu

Sat 11/1

11:00 pm-4:18 pm

1 stop12h 18m

$623

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Fri 9/19

8:23 pm-12:10 pm

1 stop21h 47m

$305

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Mon 8/25

5:15 am-2:20 pm

2 stops15h 05m

$312

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Thu 8/21

11:05 am-9:34 pm

2 stops16h 29m

$314

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Tue 8/19

6:15 am-4:40 pm

1 stop16h 25m

$317

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Mon 8/25

8:00 am-1:10 pm

Nonstop11h 10m

$319

BostonHonolulu

BOS - HNL

BOSHNL

Boston Logan Intl

Tue 9/30

8:00 am-1:10 pm

Nonstop11h 10m

$320

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 11 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 July 25, 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 July 31, 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 July 27, 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. 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 July 31, 2025.
See what other customers who have flown with Alaska Airlines, Southwest, and Delta 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

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,981 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Hawaiian Airlines
7.8
Good
2,611 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,900 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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 25 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 $305 on Alaska Airlines. Other airlines that offer cheap prices include Southwest from $312 and American Airlines from $314 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 (87%), Alaska Airlines (73%) and JetBlue (73%).

  • What are the cheapest flights from Boston to Kailua?

    While on average a flight from Boston to Kailua is generally $2,246, our data shows the cheapest flight currently is $241. When looking at the most popular route, (Boston Logan Intl - Honolulu), you can expect to pay $522 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$320Average$657FlexibilityNo cancel feeOn-time62%
DeltaCheapest$342Average$636FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$346Average$702FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$438Average$750FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$449Average$695FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$501Average$747FlexibilityNo cancel feeOn-time75%

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