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Trinidad and Tobago

$179+ 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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — POS
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap 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 September 15, 2025.

Round-trip from

$410
(American Airlines)

One-way from

$179
(United Airlines)

Popular in

December

Cheapest in

January

Average price

$531
From Massachusetts to Trinidad and Tobago
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One-way flight from Massachusetts to Trinidad and Tobago
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Highest demand for flights based on searches. 5% potential increase in price ($39 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($24 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 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 September 15, 2025.

This American Airlines deal was found by Cheapflights users on 9/15. 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 10/157:00 amBOS - POS
1 stop14h 20mAmerican Airlines
Wed 10/227:00 amPOS - BOS
1 stop17h 34mAmerican Airlines
Deal found 9/15$410
This Air Canada deal was found by Cheapflights users on 9/15. 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.
Sun 11/2310:45 amBOS - POS
1 stop13h 25mAir Canada
Fri 11/282:15 amPOS - BOS
1 stop16h 47mAir Canada
Deal found 9/15$423
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/145:23 amBOS - POS
1 stop9h 11mJetBlue
Tue 10/213:59 pmPOS - BOS
1 stop8h 15mJetBlue
Deal found 9/14$428
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/226:40 pmBOS - POS
2 stops29h 30mAir Canada
Tue 12/22:15 amPOS - BOS
2 stops32h 17mAir Canada
Deal found 9/14$433
This Air Canada deal was found by Cheapflights users on 9/15. 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.
Mon 9/156:00 amBOS - POS
1 stop19h 20mAir Canada
Fri 9/192:25 amPOS - BOS
2 stops15h 30mAir Canada
Deal found 9/15$435
This United Airlines deal was found by Cheapflights users on 9/15. 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 10/156:00 amBOS - POS
2 stops17h 23mUnited Airlines
Tue 10/2112:30 amPOS - BOS
1 stop11h 55mUnited Airlines
Deal found 9/15$440
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/118:15 pmBOS - POS
1 stop18h 19mJetBlue
Mon 10/204:12 pmPOS - BOS
1 stop17h 33mJetBlue
Deal found 9/14$453
This United Airlines deal was found by Cheapflights users on 9/15. 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 9/249:05 amBOS - POS
2 stops14h 18mUnited Airlines
Sun 9/2812:30 amPOS - BOS
2 stops14h 43mUnited Airlines
Deal found 9/15$455
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.
Fri 12/125:30 amBOS - POS
2 stops18h 40mAir Canada
Fri 12/192:15 amPOS - BOS
2 stops18h 27mAir Canada
Deal found 9/14$473
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/307:36 pmBDL - POS
1 stop8h 39mMultiple Airlines
Wed 11/53:48 amPOS - BDL
2 stops36h 32mMultiple Airlines
Deal found 9/14$480
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/307:00 amBDL - POS
1 stop7h 06mJetBlue
Thu 11/65:12 pmPOS - BDL
1 stop30h 17mJetBlue
Deal found 9/14$483
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/106:00 amBOS - POS
1 stop19h 20mAir Canada
Sun 10/122:25 amPOS - BOS
2 stops31h 05mAir Canada
Deal found 9/13$483

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 September 15, 2025.
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

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Sat 10/11

6:45 pm-1:20 am

1 stop30h 35m

Port of Spain Piarco Intl

Sun 10/19

2:25 am-6:10 pm

1 stop15h 45m

$433

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Sat 10/25

4:45 pm-12:10 am

1 stop31h 25m

Port of Spain Piarco Intl

Fri 10/31

1:15 am-12:12 pm

1 stop10h 57m

$433

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Sat 10/25

7:06 pm-2:06 pm

1 stop19h 00m

Port of Spain Piarco Intl

Sat 11/1

4:15 pm-8:41 am

1 stop16h 26m

$453

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Sat 10/11

8:15 pm-2:34 pm

1 stop18h 19m

Port of Spain Piarco Intl

Mon 10/20

4:12 pm-9:45 am

1 stop17h 33m

$453

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Fri 12/12

6:15 am-1:10 am

1 stop17h 55m

Port of Spain Piarco Intl

Fri 12/19

2:15 am-2:52 pm

2 stops13h 37m

$473

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

Thu 10/30

7:36 pm-4:15 am

1 stop8h 39m

Port of Spain Piarco Intl

Wed 11/5

3:48 am-3:20 pm

2 stops36h 32m

$480

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

Thu 10/30

7:00 am-2:06 pm

1 stop7h 06m

Port of Spain Piarco Intl

Thu 11/6

5:12 pm-10:29 pm

1 stop30h 17m

$483

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Sat 10/25

8:00 am-11:23 pm

2 stops15h 23m

Port of Spain Piarco Intl

Fri 10/31

12:30 am-2:08 pm

2 stops13h 38m

$490

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Sun 10/26

6:05 am-2:06 pm

1 stop8h 01m

Port of Spain Piarco Intl

Sun 11/2

5:12 pm-7:41 am

1 stop15h 29m

$493

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

Fri 2/20

5:26 pm-3:05 pm

2 stops20h 39m

Port of Spain Piarco Intl

Wed 2/25

4:40 pm-11:14 am

2 stops19h 34m

$495

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 35 results
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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, October is the cheapest month in which you can book a flight from Massachusetts to Trinidad and Tobago (average of $435). Flying from Massachusetts to Trinidad and Tobago in December is currently the most expensive (average of $710). 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 MA to TT?

Find hourly flight availability from Massachusetts to Trinidad and Tobago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

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

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 $453, Air Canada can have you in Trinidad and Tobago from Massachusetts in 19h. Airlines will cover a distance of 2270 mi. This flight may include one or multiple stops.

  • 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, October is the cheapest month in which you can book a flight from Massachusetts to Trinidad and Tobago (average of $435). Flying from Massachusetts to Trinidad and Tobago in December is currently the most expensive (average of $710). 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

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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$164Average$184FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$420Average$530FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$433Average$643FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$433Average$624FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$499Average$649FlexibilityNo cancel feeOn-time62%

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