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Trinidad and Tobago

$142+ 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — POS
may. 8 — may. 151
vie. 5/8
vie. 5/15
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 abril 8, 2026.

This United Airlines deal was found by Cheapflights users on 4/6. 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.
mié. 4/297:15 am
BOS
-
POS
2 stops16h 08m
United Airlines
mar. 5/512:30 am
POS
-
BOS
1 stop11h 46m
United Airlines
Deal found 4/6$320
This American Airlines deal was found by Cheapflights users on 4/6. 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. 5/276:00 am
BOS
-
POS
1 stop16h 59m
American Airlines
mar. 6/23:12 pm
POS
-
BOS
1 stop9h 47m
American Airlines
Deal found 4/6$323
This American Airlines deal was found by Cheapflights users on 4/4. 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.
jue. 6/46:00 am
BOS
-
POS
1 stop17h 04m
American Airlines
lun. 6/87:00 am
POS
-
BOS
1 stop17h 59m
American Airlines
Deal found 4/4$326
This American Airlines deal was found by Cheapflights users on 4/4. 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. 5/275:00 am
BOS
-
POS
1 stop17h 59m
American Airlines
lun. 6/13:12 pm
POS
-
BOS
1 stop23h 09m
American Airlines
Deal found 4/4$331
This American Airlines deal was found by Cheapflights users on 4/5. 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.
dom. 5/316:00 pm
BOS
-
POS
1 stop20h 12m
American Airlines
jue. 6/43:12 pm
POS
-
BOS
1 stop9h 47m
American Airlines
Deal found 4/5$334
This American Airlines deal was found by Cheapflights users on 4/4. 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.
sáb. 5/96:53 pm
BOS
-
POS
2 stops19h 39m
American Airlines
dom. 5/173:47 pm
POS
-
BOS
2 stops19h 25m
American Airlines
Deal found 4/4$335
This JetBlue deal was found by Cheapflights users on 4/6. 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.
sáb. 5/96:00 am
BDL
-
POS
1 stop7h 37m
JetBlue
mié. 5/132:46 pm
POS
-
BDL
1 stop9h 03m
JetBlue
Deal found 4/6$338
This American Airlines deal was found by Cheapflights users on 4/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/96:22 pm
BOS
-
POS
1 stop20h 10m
American Airlines
vie. 5/153:47 pm
POS
-
BOS
2 stops19h 25m
American Airlines
Deal found 4/7$339
This United Airlines deal was found by Cheapflights users on 4/8. 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.
mié. 4/2910:05 am
BOS
-
POS
2 stops13h 18m
United Airlines
lun. 5/412:30 am
POS
-
BOS
1 stop16h 37m
United Airlines
Deal found 4/8$340
This American Airlines deal was found by Cheapflights users on 4/4. 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.
vie. 4/248:30 pm
BOS
-
POS
2 stops18h 02m
American Airlines
mar. 4/283:47 pm
POS
-
BOS
2 stops19h 25m
American Airlines
Deal found 4/4$341
This American Airlines deal was found by Cheapflights users on 4/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 4/248:42 pm
BDL
-
POS
2 stops17h 50m
American Airlines
mié. 4/293:47 pm
POS
-
BDL
2 stops18h 25m
American Airlines
Deal found 4/8$342
This United Airlines deal was found by Cheapflights users on 4/8. 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.
jue. 4/236:00 am
BDL
-
POS
2 stops17h 23m
United Airlines
lun. 4/2712:30 am
POS
-
BDL
2 stops13h 38m
United Airlines
Deal found 4/8$368

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 abril 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$320
(United Airlines)

One-way from

$142
(American Airlines)

Popular in

February

Cheapest in

May

Average price

$533
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 April 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 abril 8, 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
Quickest round-trip

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

sáb. 5/9

6:00 am-1:37 pm

1 stop7h 37m

Port of Spain Piarco Intl

mié. 5/13

2:46 pm-11:49 pm

1 stop9h 03m

$338

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

mié. 4/29

9:41 am-11:23 pm

1 stop13h 42m

Port of Spain Piarco Intl

lun. 5/4

12:30 am-5:07 pm

1 stop16h 37m

$340

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

jue. 5/28

4:00 pm-1:46 am

1 stop9h 46m

Port of Spain Piarco Intl

mar. 6/2

3:49 am-11:08 pm

1 stop19h 19m

$358

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

mié. 4/22

5:20 am-1:37 pm

1 stop8h 17m

Port of Spain Piarco Intl

lun. 4/27

5:38 pm-7:45 am

1 stop14h 07m

$404

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

jue. 4/30

9:45 am-11:23 pm

1 stop13h 38m

Port of Spain Piarco Intl

jue. 5/7

12:30 am-5:07 pm

1 stop16h 37m

$409

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

sáb. 8/22

3:20 pm-12:50 am

1 stop9h 30m

Port of Spain Piarco Intl

vie. 8/28

12:30 am-2:22 pm

2 stops13h 52m

$440

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

sáb. 5/2

10:00 am-11:23 pm

2 stops13h 23m

Port of Spain Piarco Intl

mar. 5/5

12:30 am-3:03 pm

2 stops14h 33m

$447

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

mar. 5/26

5:45 am-11:23 pm

2 stops17h 38m

Port of Spain Piarco Intl

vie. 6/5

12:30 am-9:47 pm

1 stop21h 17m

$447

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

mié. 5/27

7:27 pm-11:23 pm

2 stops27h 56m

Port of Spain Piarco Intl

vie. 6/5

12:30 am-11:59 pm

2 stops23h 29m

$447

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

dom. 5/3

6:00 am-11:23 pm

2 stops41h 23m

Port of Spain Piarco Intl

sáb. 5/9

12:30 am-11:44 pm

2 stops23h 14m

$449

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/7

Showing 1-10 of 26 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, December is the cheapest month in which you can book a flight from Massachusetts to Trinidad and Tobago (average of $164). Flying from Massachusetts to Trinidad and Tobago in November is currently the most expensive (average of $481). 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.

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 $338, JetBlue can have you in Trinidad and Tobago from Massachusetts in 7h 37m. 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, December is the cheapest month in which you can book a flight from Massachusetts to Trinidad and Tobago (average of $164). Flying from Massachusetts to Trinidad and Tobago in November is currently the most expensive (average of $481). 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 abril 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$164Average$447FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$242Average$433FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$255Average$561FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$276Average$567FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$490Average$590FlexibilityNo cancel feeOn-time71%

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