Trinidad and Tobago

$114+ 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 3/14. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — POS
Mar 16 — Mar 231
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Massachusetts to Trinidad and Tobago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 February 14, 2026.

This American Airlines deal was found by Cheapflights users on 2/12. 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.
Sun 3/156:05 pm
BDL
-
POS
2 stops20h 05m
American Airlines
Wed 3/183:10 pm
POS
-
BDL
2 stops19h 00m
American Airlines
Deal found 2/12$274
This American Airlines deal was found by Cheapflights users on 2/11. 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 4/105:40 pm
BOS
-
POS
2 stops20h 52m
American Airlines
Fri 5/13:47 pm
POS
-
BOS
2 stops19h 25m
American Airlines
Deal found 2/11$274
This American Airlines deal was found by Cheapflights users on 2/13. 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.
Thu 5/75:30 pm
BOS
-
POS
2 stops21h 02m
American Airlines
Sun 5/103:47 pm
POS
-
BOS
2 stops21h 31m
American Airlines
Deal found 2/13$279
This Copa Airlines deal was found by Cheapflights users on 2/13. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/153:51 pm
BOS
-
POS
1 stop9h 49m
Copa Airlines
Mon 4/203:44 am
POS
-
BOS
1 stop10h 47m
Copa Airlines
Deal found 2/13$280
This American Airlines deal was found by Cheapflights users on 2/13. 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.
Sun 5/33:06 pm
BDL
-
POS
1 stop23h 26m
American Airlines
Thu 5/73:47 pm
POS
-
BDL
2 stops22h 10m
American Airlines
Deal found 2/13$282
This United Airlines deal was found by Cheapflights users on 2/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/15:45 am
BOS
-
POS
1 stop17h 38m
United Airlines
Sat 7/42:00 am
POS
-
BOS
1 stop9h 46m
United Airlines
Deal found 2/12$282
This United Airlines deal was found by Cheapflights users on 2/11. 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.
Wed 4/157:25 am
BOS
-
POS
1 stop15h 58m
United Airlines
Mon 4/2012:30 am
POS
-
BOS
2 stops14h 18m
United Airlines
Deal found 2/11$283
This American Airlines deal was found by Cheapflights users on 2/12. 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 2/277:50 pm
BOS
-
POS
2 stops18h 16m
American Airlines
Thu 3/54:06 pm
POS
-
BOS
2 stops20h 19m
American Airlines
Deal found 2/12$286
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Wed 4/155:25 pm
BDL
-
POS
2 stops21h 07m
American Airlines
Wed 4/223:47 pm
POS
-
BDL
2 stops22h 10m
American Airlines
Deal found 2/10$294
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Wed 4/155:40 pm
BOS
-
POS
2 stops20h 52m
American Airlines
Tue 4/213:47 pm
POS
-
BOS
1 stop18h 15m
American Airlines
Deal found 2/10$294
This United Airlines deal was found by Cheapflights users on 2/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/169:45 am
BOS
-
POS
1 stop13h 38m
United Airlines
Mon 5/1812:30 am
POS
-
BOS
1 stop11h 46m
United Airlines
Deal found 2/12$295
This American Airlines deal was found by Cheapflights users on 2/10. 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 2/247:15 pm
BDL
-
POS
2 stops18h 51m
American Airlines
Fri 2/274:06 pm
POS
-
BDL
2 stops21h 59m
American Airlines
Deal found 2/10$298

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 February 14, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$274
(American Airlines)

One-way from

$114
(American Airlines)

Popular in

February

Cheapest in

January

Average price

$769
Provider with most accurate pricing for Boston Logan Intl-Port of Spain Piarco Intl flight deals.
Provider most trusted by Cheapflights users for Boston Logan Intl-Port of Spain Piarco Intl flights.
From Massachusetts to Trinidad and Tobago
One-way flight from Massachusetts to Trinidad and Tobago
Highest demand for flights based on searches. 3% potential increase in price ($23 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
Average for round-trip flights in February 2026

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 February 14, 2026.
Use the filters below to find and compare flights from Massachusetts to Trinidad and Tobago that are best for you.

Fly from

Massachusetts

Fly to

Trinidad and Tobago

Route

Depart

Return

Price

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

Sun 3/15

6:05 pm-2:10 pm

2 stops20h 05m

Port of Spain Piarco Intl

Wed 3/18

3:10 pm-10:10 am

2 stops19h 00m

$274

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

Wed 4/15

5:25 pm-2:32 pm

2 stops21h 07m

Port of Spain Piarco Intl

Wed 4/22

3:47 pm-10:12 am

2 stops18h 25m

$274

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Sat 5/9

5:40 pm-2:32 pm

2 stops20h 52m

Port of Spain Piarco Intl

Tue 5/19

3:47 pm-12:57 pm

2 stops21h 10m

$274

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Wed 4/15

6:53 pm-2:32 pm

2 stops19h 39m

Port of Spain Piarco Intl

Tue 4/21

3:47 pm-11:04 am

2 stops19h 17m

$274

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Wed 4/15

3:51 pm-1:40 am

1 stop9h 49m

Port of Spain Piarco Intl

Mon 4/20

3:44 am-11:09 pm

1 stop19h 25m

$280

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Wed 4/15

3:51 pm-1:40 am

1 stop9h 49m

Port of Spain Piarco Intl

Tue 4/21

3:44 am-11:09 pm

1 stop19h 25m

$280

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Thu 4/2

3:51 pm-1:40 am

1 stop9h 49m

Port of Spain Piarco Intl

Wed 4/8

3:44 am-2:34 pm

1 stop10h 50m

$280

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Wed 7/1

5:45 am-11:23 pm

1 stop17h 38m

Port of Spain Piarco Intl

Sat 7/4

2:00 am-11:46 am

1 stop9h 46m

$282

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

Sun 5/3

3:06 pm-2:32 pm

1 stop23h 26m

Port of Spain Piarco Intl

Thu 5/7

3:47 pm-1:57 pm

2 stops22h 10m

$282

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Tue 3/10

9:20 am-11:23 pm

2 stops14h 03m

Port of Spain Piarco Intl

Mon 3/16

12:30 am-5:19 pm

2 stops16h 49m

$283

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/12

Showing 1-10 of 21 results
1
2
3

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 June is currently the most expensive (average of $506). 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 $280, American Airlines can have you in Trinidad and Tobago from Massachusetts in 9h 49m. 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. Air Canada flights start at $144 while deals on American Airlines start at $182 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 June is currently the most expensive (average of $506). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Massachusetts to Trinidad and Tobago

See prices for flight routes from nearby airports that may be better suited for you.

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 February 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$164Average$492FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$195Average$432FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$260Average$617FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$280Average$570FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$490Average$597FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.