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Trinidad and Tobago

$151+ Cheap flights from Massachusetts to Trinidad and Tobago

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 7/26. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — POS
Jul 12 — Jul 191
Sun 7/12
Sun 7/19
1 adult, Economy
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Cheap flight deals from Massachusetts to Trinidad and Tobago

Cheapest flights from Massachusetts to Trinidad and Tobago
Explore the most affordable flight options available from Massachusetts to Trinidad and Tobago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2026.

This Orbitz deal was found by Cheapflights users on 6/8. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/145:10 am
BOS
-
POS
1 stop19h 05m
Air Canada
Mon 6/221:25 am
POS
-
BOS
1 stop14h 43m
Air Canada
Deal found 6/8$349
This JetBlue deal was found by Cheapflights users on 6/7. 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.
Sat 8/296:45 am
BDL
-
POS
1 stop11h 46m
JetBlue
Tue 9/13:15 pm
POS
-
BDL
1 stop8h 44m
JetBlue
Deal found 6/7$350
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Thu 7/1610:58 am
BOS
-
POS
1 stop13h 52m
United Airlines
Wed 7/222:00 am
POS
-
BOS
1 stop9h 16m
United Airlines
Deal found 6/8$356
This American Airlines deal was found by Cheapflights users on 6/12. 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.
Fri 9/115:56 pm
BOS
-
POS
2 stops20h 05m
American Airlines
Tue 9/153:06 pm
POS
-
BOS
2 stops17h 39m
American Airlines
Deal found 6/12$360
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.
Sun 9/136:25 am
BDL
-
POS
1 stop7h 35m
JetBlue
Thu 9/173:50 pm
POS
-
BDL
1 stop7h 54m
JetBlue
Deal found 6/10$363
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.
Tue 7/288:00 am
BOS
-
POS
1 stop14h 33m
American Airlines
Tue 8/113:15 pm
POS
-
BOS
1 stop23h 15m
American Airlines
Deal found 6/10$365
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/278:00 am
BOS
-
POS
1 stop16h 50m
United Airlines
Mon 6/292:00 am
POS
-
BOS
1 stop9h 16m
United Airlines
Deal found 6/9$368
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.
Tue 8/183:21 pm
BOS
-
POS
1 stop22h 53m
American Airlines
Tue 8/257:00 am
POS
-
BOS
2 stops15h 50m
American Airlines
Deal found 6/10$369
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Thu 7/210:58 am
BOS
-
POS
1 stop13h 52m
United Airlines
Sat 7/412:30 am
POS
-
BOS
1 stop11h 58m
United Airlines
Deal found 6/8$371
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/255:00 am
BDL
-
POS
2 stops18h 00m
American Airlines
Thu 7/23:16 pm
POS
-
BDL
2 stops19h 06m
American Airlines
Deal found 6/9$372
This United Airlines deal was found by Cheapflights users on 6/7. 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.
Mon 6/225:47 am
BOS
-
POS
1 stop17h 36m
United Airlines
Sun 6/282:00 am
POS
-
BOS
1 stop9h 16m
United Airlines
Deal found 6/7$375
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/256:45 am
BDL
-
POS
1 stop11h 50m
JetBlue
Thu 7/23:15 pm
POS
-
BDL
1 stop8h 44m
JetBlue
Deal found 6/10$379

Find flight deals from Massachusetts to Trinidad and Tobago

Keep the following information in mind while searching for Massachusetts to Trinidad and Tobago flight deals. Data was last updated June 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$350
(JetBlue)

One-way from

$151
(United Airlines)

Popular in

February

Cheapest in

May

Average price

$588
Provider with most accurate pricing for Boston Logan Intl-Port of Spain Piarco Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Port of Spain Piarco Intl flights.
Search Deals
From Massachusetts to Trinidad and Tobago
Search Deals
One-way flight from Massachusetts to Trinidad and Tobago
Search Deals
High demand for flights, 2% potential price rise
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts to Trinidad and Tobago 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, 2026.
Use the filters below to find and compare flights from Massachusetts to Trinidad and Tobago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

Sat 8/29

6:45 am-6:31 pm

1 stop11h 46m

Port of Spain Piarco Intl

Tue 9/1

3:15 pm-11:59 pm

1 stop8h 44m

$350

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Tue 8/18

12:41 pm-12:50 am

1 stop12h 09m

Port of Spain Piarco Intl

Mon 8/24

12:30 am-12:24 pm

1 stop11h 54m

$356

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Sat 9/19

4:29 pm-2:01 pm

2 stops21h 32m

Port of Spain Piarco Intl

Sat 9/26

3:06 pm-9:39 am

2 stops18h 33m

$360
Quickest round-trip

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

Sun 9/13

6:25 am-2:00 pm

1 stop7h 35m

Port of Spain Piarco Intl

Thu 9/17

3:50 pm-11:44 pm

1 stop7h 54m

$363

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Sat 6/27

8:00 am-12:50 am

1 stop16h 50m

Port of Spain Piarco Intl

Mon 6/29

2:00 am-11:16 am

1 stop9h 16m

$368

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Tue 8/18

3:21 pm-2:14 pm

1 stop22h 53m

Port of Spain Piarco Intl

Tue 8/25

7:00 am-11:59 pm

2 stops16h 59m

$369

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Fri 7/10

9:30 am-12:50 am

1 stop15h 20m

Port of Spain Piarco Intl

Sun 7/12

2:00 am-11:16 am

1 stop9h 16m

$371

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

Thu 6/25

5:00 am-11:00 pm

2 stops18h 00m

Port of Spain Piarco Intl

Thu 7/2

3:16 pm-10:22 am

2 stops19h 06m

$372

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

Thu 6/25

6:45 am-6:35 pm

1 stop11h 50m

Port of Spain Piarco Intl

Thu 7/2

3:15 pm-11:59 pm

1 stop8h 44m

$379

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

Mon 7/27

6:28 am-6:35 pm

1 stop12h 07m

Port of Spain Piarco Intl

Tue 8/4

3:14 pm-11:59 pm

1 stop8h 45m

$388

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 31 resultsSorted by cheapest first
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Best time to book a flight from Massachusetts to Trinidad and Tobago

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

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

Currently, July is the cheapest month in which you can book a flight from Massachusetts to Trinidad and Tobago (average of $47). Flying from Massachusetts to Trinidad and Tobago in November is currently the most expensive (average of $477). 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 far ahead should I book a flight from Massachusetts to Trinidad and Tobago?

To ensure you get the cheapest price possible for a flight from Massachusetts to Trinidad and Tobago, you should look to book at least 50 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Trinidad and Tobago. 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 Massachusetts to Trinidad and Tobago?

    For as low as $350, JetBlue can have you in Trinidad and Tobago from Massachusetts in 11h 46m. Airlines will cover a distance of 2270 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Massachusetts to Trinidad and Tobago one-way?

    To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at $120. JetBlue flights start at $130 while deals on Air Canada start at $144 one-way.

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

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

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

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

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

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

    Currently, July is the cheapest month in which you can book a flight from Massachusetts to Trinidad and Tobago (average of $47). Flying from Massachusetts to Trinidad and Tobago in November is currently the most expensive (average of $477). 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 Massachusetts to Trinidad and Tobago

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

Discover the top 5 airlines that operate flights from Massachusetts to Trinidad and Tobago. 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, 2026.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$164Average$420FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$255Average$561FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$276Average$568FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$329Average$443FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$370Average$592FlexibilityNo cancel feeOn-time71%

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