Hawaii

$244+ Cheap flights from Massachusetts to Hawaii

BOS — HNL
Nov 18 — Nov 251
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Cheap flight deals from Massachusetts to Hawaii

Cheapest flights from Massachusetts to Hawaii

Tue 11/176:36 am -
1 stop15h 43m
Tue 11/2410:35 pm -
1 stop13h 30m
Deal found 10/15$558
Tue 11/1710:40 am -
1 stop14h 27m
Tue 11/2410:59 pm -
2 stops16h 57m
Deal found 10/15$562
Sat 11/1410:40 am -
1 stop14h 27m
Thu 11/199:45 pm -
1 stop13h 15m
Deal found 10/15$566
Tue 11/179:03 am -
2 stops29h 23m
Tue 11/242:17 pm -
2 stops21h 25m
Deal found 10/15$567
Sat 11/146:36 am -
1 stop14h 34m
Thu 11/192:53 pm -
2 stops14h 29m
Deal found 10/15$572
Mon 12/76:13 pm -
1 stop32h 10m
Tue 12/2211:59 pm -
1 stop24h 29m
Deal found 10/14$592
Tue 12/86:13 pm -
1 stop32h 10m
Wed 12/911:43 pm -
1 stop12h 25m
Deal found 10/14$594
Wed 11/117:03 am -
1 stop19h 46m
Wed 11/1811:37 pm -
1 stop12h 04m
Deal found 10/15$596
Sun 11/87:03 am -
1 stop35h 44m
Mon 11/161:24 pm -
1 stop22h 17m
Deal found 10/16$602
Wed 11/116:36 am -
1 stop14h 34m
Wed 11/2510:35 pm -
1 stop13h 30m
Deal found 10/19$603
Wed 11/117:03 am -
1 stop19h 46m
Wed 11/182:08 pm -
2 stops21h 33m
Deal found 10/15$617
Fri 11/136:09 pm -
1 stop32h 40m
Wed 11/1811:37 pm -
1 stop12h 04m
Deal found 10/15$624

Find flight deals from Massachusetts to Hawaii

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$556
(Alaska Airlines)

One-way from

$244
(Southwest)

Popular in

December

Cheapest in

January

Average price

$769

Good round-trip deal

$1,180 or less

Good one-way deal

$592 or less
Provider with most accurate pricing for Boston Logan Intl-Honolulu flight deals.
Provider most trusted by Cheapflights users for Boston Logan Intl-Honolulu flights.
From Massachusetts to Hawaii
One-way flight from Massachusetts to Hawaii
Highest demand for flights based on searches. 5% potential increase in price ($42 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($29 potential savings vs. average RT price).
Average for round-trip flights in October 2026
Price to beat on a round-trip flight from Massachusetts to Hawaii.
Price to beat on a one-way flight from Massachusetts to Hawaii.

Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Massachusetts to Hawaii that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonLihue

BOS Boston Logan Intl - LIH Lihue

BOSLIH

Boston Logan Intl

Thu 1/28

7:05 am-8:22 pm

1 stop18h 17m

Lihue

Wed 12/31

12:00 am-5:00 am

Nonstop0h 00m

$278

BostonLihue

BOS Boston Logan Intl - LIH Lihue

BOSLIH

Boston Logan Intl

Tue 11/17

6:00 am-4:55 pm

2 stops15h 55m

Lihue

Wed 12/31

12:00 am-5:00 am

Nonstop0h 00m

$284

BostonLihue

BOS Boston Logan Intl - LIH Lihue

BOSLIH

Boston Logan Intl

Tue 12/8

6:00 am-4:55 pm

2 stops15h 55m

Lihue

Wed 12/31

12:00 am-5:00 am

Nonstop0h 00m

$284

BostonLihue

BOS Boston Logan Intl - LIH Lihue

BOSLIH

Boston Logan Intl

Tue 11/17

5:30 am-6:41 pm

2 stops18h 11m

Lihue

Wed 12/31

12:00 am-5:00 am

Nonstop0h 00m

$284

BostonKahului

BOS Boston Logan Intl - OGG Kahului

BOSOGG

Boston Logan Intl

Wed 11/25

5:45 am-4:29 pm

1 stop15h 44m

Kahului

Wed 12/31

12:00 am-5:00 am

Nonstop0h 00m

$313

BostonKahului

BOS Boston Logan Intl - OGG Kahului

BOSOGG

Boston Logan Intl

Wed 11/11

7:03 am-9:49 pm

1 stop19h 46m

Kahului

Wed 12/31

12:00 am-5:00 am

Nonstop0h 00m

$318

BostonKahului

BOS Boston Logan Intl - OGG Kahului

BOSOGG

Boston Logan Intl

Sat 12/5

7:30 am-5:43 pm

1 stop15h 13m

Kahului

Wed 12/31

12:00 am-5:00 am

Nonstop0h 00m

$323

BostonLihue

BOS Boston Logan Intl - LIH Lihue

BOSLIH

Boston Logan Intl

Wed 11/11

10:40 am-8:07 pm

1 stop14h 27m

Lihue

Wed 12/31

12:00 am-5:00 am

Nonstop0h 00m

$325

BostonLihue

BOS Boston Logan Intl - LIH Lihue

BOSLIH

Boston Logan Intl

Thu 11/5

7:15 am-4:55 pm

1 stop14h 40m

Lihue

Wed 12/31

12:00 am-5:00 am

Nonstop0h 00m

$325

BostonKahului

BOS Boston Logan Intl - OGG Kahului

BOSOGG

Boston Logan Intl

Mon 11/2

8:05 am-5:42 pm

1 stop14h 37m

Kahului

Wed 12/31

12:00 am-5:00 am

Nonstop0h 00m

$325

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/18

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Massachusetts to Hawaii

Have a flexible travel schedule? Discover the best time to fly to Hawaii from Massachusetts with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Massachusetts to Hawaii

What is the cheapest month to book a flight from Massachusetts to Hawaii?

Currently, January is the cheapest month in which you can book a flight from Massachusetts to Hawaii (average of $661). Flying from Massachusetts to Hawaii in December is currently the most expensive (average of $1,038). 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.

How much does it cost to fly round-trip from Massachusetts to Hawaii?

Airfare is below average for this route at the moment.
Massachusetts to Hawaii flights typically cost between $662 and $886 in January.
The cheapest round-trip price found within the last 5 days was $644 on Multiple Airlines (Jan 19-Jan 26).

How far ahead should I book a flight from Massachusetts to Hawaii?

The price you pay for your flight from Massachusetts to Hawaii may vary depending on when you book. For the best chance of a lower fare, look to book 57 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

Reviews of airlines servicing Hawaii

Get a feel of what it's like to fly with Alaska Airlines,Delta, andUnited Airlines from Massachusetts to Hawaii by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Overall

7.9

Entertainment

7.0

Comfort

7.8

Boarding

8.1

Crew

8.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Chris,Aug 2026

GEG - SFO

Our flight was delayed multiple times over the course of the day for a total of almost ten hours. It was supposed to be a two-hour flight from San Francisco to Spokane. It turned into a nightmare of waiting all day in the airport, not knowing whether we would fly or not, whether we would miss my son's wedding and lose the expenses already incurred for car rental and accommodations. The Alaska staff seemed clueless and never gave us any convincing or definitive information. The airline offered food vouchers and discounts on future flights to make up for the trouble. However, the information about these concessions was not timely, nor were the vouchers themselves very useful. We were a family group of four people. The airline decided to give us one food voucher for $96, which is barely enough for four to get a sandwich and a drink each. Only by persistently addressing the airport food retailers were we able to get anything at all. Then, taking the exact opposite approach, the airline sent me, the original purchaser of all four tickets and the only email account they had, four vouchers for $150 each in the names of each of the four passengers. So, any one of us could get a discount on a future flight with Alaska in that amount. But I originally paid for all the tickets. It makes no sense, except to suggest that Alaska chooses the way to distribute vouchers that seems most likely to minimize the probability that they will be utilized. In my opinion, I should be offered a total refund for the ordeal we were forced to endure or at least a discount voucher for the entire $600.

Overall

7.9

Entertainment

7.0

Comfort

7.8

Boarding

8.1

Crew

8.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Chris,Aug 2026

GEG - SFO

Our flight was delayed multiple times over the course of the day for a total of almost ten hours. It was supposed to be a two-hour flight from San Francisco to Spokane. It turned into a nightmare of waiting all day in the airport, not knowing whether we would fly or not, whether we would miss my son's wedding and lose the expenses already incurred for car rental and accommodations. The Alaska staff seemed clueless and never gave us any convincing or definitive information. The airline offered food vouchers and discounts on future flights to make up for the trouble. However, the information about these concessions was not timely, nor were the vouchers themselves very useful. We were a family group of four people. The airline decided to give us one food voucher for $96, which is barely enough for four to get a sandwich and a drink each. Only by persistently addressing the airport food retailers were we able to get anything at all. Then, taking the exact opposite approach, the airline sent me, the original purchaser of all four tickets and the only email account they had, four vouchers for $150 each in the names of each of the four passengers. So, any one of us could get a discount on a future flight with Alaska in that amount. But I originally paid for all the tickets. It makes no sense, except to suggest that Alaska chooses the way to distribute vouchers that seems most likely to minimize the probability that they will be utilized. In my opinion, I should be offered a total refund for the ordeal we were forced to endure or at least a discount voucher for the entire $600.

Overall

7.9

Entertainment

7.0

Comfort

7.8

Boarding

8.1

Crew

8.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Chris,Aug 2026

GEG - SFO

Our flight was delayed multiple times over the course of the day for a total of almost ten hours. It was supposed to be a two-hour flight from San Francisco to Spokane. It turned into a nightmare of waiting all day in the airport, not knowing whether we would fly or not, whether we would miss my son's wedding and lose the expenses already incurred for car rental and accommodations. The Alaska staff seemed clueless and never gave us any convincing or definitive information. The airline offered food vouchers and discounts on future flights to make up for the trouble. However, the information about these concessions was not timely, nor were the vouchers themselves very useful. We were a family group of four people. The airline decided to give us one food voucher for $96, which is barely enough for four to get a sandwich and a drink each. Only by persistently addressing the airport food retailers were we able to get anything at all. Then, taking the exact opposite approach, the airline sent me, the original purchaser of all four tickets and the only email account they had, four vouchers for $150 each in the names of each of the four passengers. So, any one of us could get a discount on a future flight with Alaska in that amount. But I originally paid for all the tickets. It makes no sense, except to suggest that Alaska chooses the way to distribute vouchers that seems most likely to minimize the probability that they will be utilized. In my opinion, I should be offered a total refund for the ordeal we were forced to endure or at least a discount voucher for the entire $600.

Overall

7.9

Entertainment

7.0

Comfort

7.8

Boarding

8.1

Crew

8.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Chris,Aug 2026

GEG - SFO

Our flight was delayed multiple times over the course of the day for a total of almost ten hours. It was supposed to be a two-hour flight from San Francisco to Spokane. It turned into a nightmare of waiting all day in the airport, not knowing whether we would fly or not, whether we would miss my son's wedding and lose the expenses already incurred for car rental and accommodations. The Alaska staff seemed clueless and never gave us any convincing or definitive information. The airline offered food vouchers and discounts on future flights to make up for the trouble. However, the information about these concessions was not timely, nor were the vouchers themselves very useful. We were a family group of four people. The airline decided to give us one food voucher for $96, which is barely enough for four to get a sandwich and a drink each. Only by persistently addressing the airport food retailers were we able to get anything at all. Then, taking the exact opposite approach, the airline sent me, the original purchaser of all four tickets and the only email account they had, four vouchers for $150 each in the names of each of the four passengers. So, any one of us could get a discount on a future flight with Alaska in that amount. But I originally paid for all the tickets. It makes no sense, except to suggest that Alaska chooses the way to distribute vouchers that seems most likely to minimize the probability that they will be utilized. In my opinion, I should be offered a total refund for the ordeal we were forced to endure or at least a discount voucher for the entire $600.

Overall

7.9

Entertainment

7.0

Comfort

7.8

Boarding

8.1

Crew

8.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Chris,Aug 2026

GEG - SFO

Our flight was delayed multiple times over the course of the day for a total of almost ten hours. It was supposed to be a two-hour flight from San Francisco to Spokane. It turned into a nightmare of waiting all day in the airport, not knowing whether we would fly or not, whether we would miss my son's wedding and lose the expenses already incurred for car rental and accommodations. The Alaska staff seemed clueless and never gave us any convincing or definitive information. The airline offered food vouchers and discounts on future flights to make up for the trouble. However, the information about these concessions was not timely, nor were the vouchers themselves very useful. We were a family group of four people. The airline decided to give us one food voucher for $96, which is barely enough for four to get a sandwich and a drink each. Only by persistently addressing the airport food retailers were we able to get anything at all. Then, taking the exact opposite approach, the airline sent me, the original purchaser of all four tickets and the only email account they had, four vouchers for $150 each in the names of each of the four passengers. So, any one of us could get a discount on a future flight with Alaska in that amount. But I originally paid for all the tickets. It makes no sense, except to suggest that Alaska chooses the way to distribute vouchers that seems most likely to minimize the probability that they will be utilized. In my opinion, I should be offered a total refund for the ordeal we were forced to endure or at least a discount voucher for the entire $600.

Overall

7.9

Entertainment

7.0

Comfort

7.8

Boarding

8.1

Crew

8.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Chris,Aug 2026

GEG - SFO

Our flight was delayed multiple times over the course of the day for a total of almost ten hours. It was supposed to be a two-hour flight from San Francisco to Spokane. It turned into a nightmare of waiting all day in the airport, not knowing whether we would fly or not, whether we would miss my son's wedding and lose the expenses already incurred for car rental and accommodations. The Alaska staff seemed clueless and never gave us any convincing or definitive information. The airline offered food vouchers and discounts on future flights to make up for the trouble. However, the information about these concessions was not timely, nor were the vouchers themselves very useful. We were a family group of four people. The airline decided to give us one food voucher for $96, which is barely enough for four to get a sandwich and a drink each. Only by persistently addressing the airport food retailers were we able to get anything at all. Then, taking the exact opposite approach, the airline sent me, the original purchaser of all four tickets and the only email account they had, four vouchers for $150 each in the names of each of the four passengers. So, any one of us could get a discount on a future flight with Alaska in that amount. But I originally paid for all the tickets. It makes no sense, except to suggest that Alaska chooses the way to distribute vouchers that seems most likely to minimize the probability that they will be utilized. In my opinion, I should be offered a total refund for the ordeal we were forced to endure or at least a discount voucher for the entire $600.

Related info for your journey

  • How popular is this Massachusetts to Hawaii flight route?

  • How long is the flight from Massachusetts to Hawaii?

    Airlines like Delta, American Airlines, and United Airlines fly from Massachusetts to Hawaii in about 14h 27m. The time it takes to get you to your destination can typically vary by up to 2h 24m. Massachusetts and Hawaii are separated by a distance of 5124 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Massachusetts to Hawaii one-way?

    The cheapest airline one-way is Alaska Airlines, with whom users have recently found tickets for as low as $227. However, be on the lookout for offers from Delta and American Airlines, as they are both options that can get you from Massachusetts to Hawaii for a low price.

  • Can I find deals for flights from Massachusetts to Hawaii that include hotel bookings?

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

  • How can I find direct flights from Massachusetts to Hawaii?

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

  • Can I find deals for business class flights from Massachusetts to Hawaii?

    Yes. Cheapflights offers flight deals from Massachusetts to Hawaii 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 Massachusetts to Hawaii?

    Currently, January is the cheapest month in which you can book a flight from Massachusetts to Hawaii (average of $661). Flying from Massachusetts to Hawaii in December is currently the most expensive (average of $1,038). 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

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Massachusetts to Hawaii

Top 5 airlines flying from Massachusetts to Hawaii

AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$274Average$713FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$310Average$827FlexibilityNo cancel feeOn-time75%
JetBlueCheapest$331Average$719FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$415Average$802FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$417Average$722FlexibilityNo cancel feeOn-time69%

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