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Massachusetts

$249+ Cheap flights from Trinidad and Tobago to Massachusetts

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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
POS — BOS
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
1 adult, Economy
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Cheap flight deals from Trinidad and Tobago to Massachusetts

Keep the following information in mind while searching for Trinidad and Tobago to Massachusetts flight deals. Data was last updated septiembre 16, 2025.

Round-trip from

$438
(Kiwi.com)

One-way from

$249
(United Airlines)

Popular in

March

Cheapest in

May

Average price

$702
From Trinidad and Tobago to Massachusetts
Search Deals
One-way flight from Trinidad and Tobago to Massachusetts
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($85 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($17 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 Trinidad and Tobago to Massachusetts

Cheapest flights from Trinidad and Tobago to Massachusetts
Explore the most affordable flight options available from Trinidad and Tobago to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/2410:10 amPOS - BOS
1 stop25h 16mMultiple Airlines
lun. 10/274:54 pmBOS - POS
1 stop26h 01mMultiple Airlines
Deal found 9/13$438
This United Airlines deal was found by Cheapflights users on 9/13. 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.
sáb. 10/1812:30 amPOS - BOS
1 stop14h 09mUnited Airlines
mar. 10/285:30 amBOS - POS
2 stops17h 53mUnited Airlines
Deal found 9/13$443
This Trip.com deal was found by Cheapflights users on 9/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/222:40 pmPOS - BOS
1 stop23h 31mMultiple Airlines
lun. 10/277:55 pmBOS - POS
1 stop28h 15mMultiple Airlines
Deal found 9/13$447
This American Airlines deal was found by Cheapflights users on 9/13. 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.
mié. 10/223:25 pmPOS - BOS
1 stop23h 28mAmerican Airlines
lun. 10/278:29 amBOS - POS
2 stops12h 51mAmerican Airlines
Deal found 9/13$451
This JetBlue deal was found by Cheapflights users on 9/13. 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.
dom. 10/193:59 pmPOS - BOS
1 stop8h 15mJetBlue
mar. 10/285:40 amBOS - POS
1 stop8h 27mJetBlue
Deal found 9/13$459
This JetBlue deal was found by Cheapflights users on 9/13. 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.
vie. 10/243:59 pmPOS - BOS
1 stop8h 15mJetBlue
dom. 10/265:10 amBOS - POS
1 stop8h 56mJetBlue
Deal found 9/13$464
This Air Canada deal was found by Cheapflights users on 9/13. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/242:25 amPOS - BOS
2 stops15h 30mAir Canada
dom. 10/266:15 amBOS - POS
1 stop17h 55mAir Canada
Deal found 9/13$469
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/152:25 amPOS - BOS
1 stop9h 04mAir Canada
dom. 9/214:45 pmBOS - POS
1 stop8h 35mAir Canada
Deal found 9/14$473
This Air Canada deal was found by Cheapflights users on 9/13. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/242:25 amPOS - BOS
1 stop9h 04mAir Canada
sáb. 10/256:30 pmBOS - POS
2 stops29h 40mAir Canada
Deal found 9/13$476
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/152:25 amPOS - BOS
2 stops19h 00mAir Canada
jue. 9/256:30 pmBOS - POS
2 stops30h 50mAir Canada
Deal found 9/14$484
This JetBlue deal was found by Cheapflights users on 9/13. 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.
mié. 10/223:59 pmPOS - BOS
1 stop8h 15mJetBlue
mié. 10/295:40 amBOS - POS
1 stop8h 27mJetBlue
Deal found 9/13$487
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/2312:30 amPOS - BDL
2 stops23h 27mUnited Airlines
mié. 10/294:35 pmBDL - POS
2 stops30h 48mUnited Airlines
Deal found 9/14$535

Cheapflights Fare Finder

 
Customize your flight search to find flights from Trinidad and Tobago to Massachusetts 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 Trinidad and Tobago to Massachusetts that are best for you.

Fly from

Trinidad and Tobago

Fly to

Massachusetts

Route

Depart

Return

Price

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

mié. 10/22

12:30 am-4:22 pm

2 stops15h 52m

Boston Logan Intl

mié. 10/29

7:00 am-11:23 pm

1 stop16h 23m

$443

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

mié. 10/22

12:30 am-4:22 pm

2 stops15h 52m

Boston Logan Intl

jue. 10/30

9:50 am-11:23 pm

1 stop13h 33m

$443

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

lun. 10/20

12:30 am-2:39 pm

1 stop14h 09m

Boston Logan Intl

mié. 10/29

5:30 am-11:23 pm

2 stops17h 53m

$443

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

lun. 10/20

12:30 am-3:13 pm

2 stops14h 43m

Boston Logan Intl

sáb. 10/25

10:00 am-11:23 pm

1 stop13h 23m

$443

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

vie. 10/24

12:30 am-4:22 pm

2 stops15h 52m

Boston Logan Intl

mar. 10/28

5:30 am-11:23 pm

2 stops17h 53m

$443

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

sáb. 10/18

12:30 am-5:55 pm

1 stop17h 25m

Boston Logan Intl

mié. 10/29

9:45 am-11:23 pm

1 stop13h 38m

$443

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

mar. 10/21

12:30 am-5:55 pm

1 stop17h 25m

Boston Logan Intl

jue. 10/30

9:50 am-11:23 pm

1 stop13h 33m

$443

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

jue. 10/23

12:30 am-10:57 pm

2 stops22h 27m

Boston Logan Intl

jue. 10/30

9:50 am-11:23 pm

1 stop13h 33m

$443

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

sáb. 10/18

12:30 am-4:22 pm

2 stops15h 52m

Boston Logan Intl

mar. 10/28

5:30 am-11:23 pm

2 stops17h 53m

$443

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

mar. 10/21

12:30 am-2:39 pm

1 stop14h 09m

Boston Logan Intl

mié. 10/29

9:45 am-11:23 pm

1 stop13h 38m

$443

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 33 results
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Best time to book a flight from Trinidad and Tobago to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Trinidad and Tobago 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 Trinidad and Tobago to Massachusetts

What is the cheapest month to book a flight from Trinidad and Tobago to Massachusetts?

Currently, January is the cheapest month in which you can book a flight from Trinidad and Tobago to Massachusetts (average of $218). Flying from Trinidad and Tobago to Massachusetts in July is currently the most expensive (average of $311). 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 TT to MA?

Find hourly flight availability from Trinidad and Tobago to Massachusetts. 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 Trinidad and Tobago to Massachusetts, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated septiembre 16, 2025.
Get a feel of what it's like to fly with Copa Airlines, United Airlines, and American Airlines from Trinidad and Tobago to Massachusetts by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.6
Good
1,531 reviews

Crew

8.1

Comfort

7.4

Overall

7.6

Entertainment

6.8

Boarding

7.8

Food

6.8

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
Copa Airlines
7.6
Good
1,531 reviews
Copa Airlines
7.6
Good
1,531 reviews

Crew

8.1

Comfort

7.4

Overall

7.6

Entertainment

6.8

Boarding

7.8

Food

6.8

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
United Airlines
7.4
Good
8,929 reviews
Copa Airlines
7.6
Good
1,531 reviews

Crew

8.1

Comfort

7.4

Overall

7.6

Entertainment

6.8

Boarding

7.8

Food

6.8

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
American Airlines
7.2
Good
10,000 reviews
Copa Airlines
7.6
Good
1,531 reviews

Crew

8.1

Comfort

7.4

Overall

7.6

Entertainment

6.8

Boarding

7.8

Food

6.8

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
JetBlue
7.2
Good
2,912 reviews
Copa Airlines
7.6
Good
1,531 reviews

Crew

8.1

Comfort

7.4

Overall

7.6

Entertainment

6.8

Boarding

7.8

Food

6.8

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
Air Canada
7.1
Good
10,000 reviews
Copa Airlines
7.6
Good
1,531 reviews

Crew

8.1

Comfort

7.4

Overall

7.6

Entertainment

6.8

Boarding

7.8

Food

6.8

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip

Related info for your journey

Find useful and relevant information for your journey from Trinidad and Tobago to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Trinidad and Tobago to Massachusetts?

    Departing from Trinidad and Tobago to Massachusetts will take you 15h 52m. There are 2270 mi between Trinidad and Tobago and Massachusetts.

  • Can I find deals for flights from Trinidad and Tobago to Massachusetts that include hotel bookings?

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

  • How can I find direct flights from Trinidad and Tobago to Massachusetts?

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

  • Can I find deals for business class flights from Trinidad and Tobago to Massachusetts?

    Yes. Cheapflights offers flight deals from Trinidad and Tobago to Massachusetts 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 Trinidad and Tobago to Massachusetts?

    Currently, January is the cheapest month in which you can book a flight from Trinidad and Tobago to Massachusetts (average of $218). Flying from Trinidad and Tobago to Massachusetts in July is currently the most expensive (average of $311). 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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Alternative routes for Trinidad and Tobago to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Trinidad and Tobago to Massachusetts

Discover the top 5 airlines that operate flights from Trinidad and Tobago to Massachusetts. 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
Air CanadaCheapest$184Average$448FlexibilityNo cancel feeOn-time67%
Copa AirlinesCheapest$270Average$418FlexibilityNo cancel feeOn-time70%
JetBlueCheapest$368Average$665FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$430Average$609FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$451Average$555FlexibilityNo cancel feeOn-time69%

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