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Trinidad and Tobago

$91+ 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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — POS
Feb 1 — Feb 81
Sun 2/1
Sun 2/8
1 adult, Economy
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Cheap flight deals from Massachusetts to Trinidad and Tobago

Best flights from Massachusetts to Trinidad and Tobago
Discover carefully curated flight deals from Massachusetts to Trinidad and Tobago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 2, 2026.

This United Airlines deal was found by Cheapflights users on 1/1. 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 2/217:48 amBOS - POS
2 stops15h 35mUnited Airlines
Fri 2/271:30 amPOS - BOS
1 stop11h 47mUnited Airlines
Deal found 1/1$236
This American Airlines deal was found by Cheapflights users on 12/31. 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 3/185:30 pmBOS - POS
2 stops20h 40mAmerican Airlines
Wed 3/253:10 pmPOS - BOS
2 stops20h 26mAmerican Airlines
Deal found 12/31$273
This JetBlue deal was found by Cheapflights users on 12/31. 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.
Mon 1/127:08 amBOS - POS
1 stop11h 03mJetBlue
Mon 1/198:20 amPOS - BOS
1 stop9h 53mJetBlue
Deal found 12/31$313
This United Airlines deal was found by Cheapflights users on 12/31. 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 1/1511:42 amBOS - POS
1 stop11h 41mUnited Airlines
Sat 1/241:30 amPOS - BOS
1 stop11h 49mUnited Airlines
Deal found 12/31$264
This United Airlines deal was found by Cheapflights users on 12/31. 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 1/178:25 amBOS - POS
2 stops14h 58mUnited Airlines
Fri 1/231:30 amPOS - BOS
2 stops16h 54mUnited Airlines
Deal found 12/31$268
This JetBlue deal was found by Cheapflights users on 12/30. 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.
Tue 1/205:15 amBOS - POS
1 stop12h 26mJetBlue
Sat 1/248:45 amPOS - BOS
1 stop12h 33mJetBlue
Deal found 12/30$313
This JetBlue deal was found by Cheapflights users on 12/31. 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.
Wed 3/185:10 amBOS - POS
1 stop8h 26mJetBlue
Wed 3/253:26 pmPOS - BOS
1 stop8h 24mJetBlue
Deal found 12/31$333
This United Airlines deal was found by Cheapflights users on 12/30. 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 3/26:05 amBDL - POS
2 stops18h 00mUnited Airlines
Tue 3/31:30 amPOS - BDL
2 stops13h 24mUnited Airlines
Deal found 12/30$383
This Kiwi.com deal was found by Cheapflights users on 12/31. 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.
Fri 2/137:55 pmBDL - POS
2 stops29h 18mMultiple Airlines
Mon 2/238:30 amPOS - BDL
1 stop25h 23mMultiple Airlines
Deal found 12/31$1,158
This United Airlines deal was found by Cheapflights users on 12/31. 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 2/144:43 pmBDL - POS
2 stops30h 40mUnited Airlines
Fri 2/201:30 amPOS - BDL
2 stops20h 36mUnited Airlines
Deal found 12/31$732
This Gotogate deal was found by Cheapflights users on 12/30. 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.
Thu 1/2210:45 amBOS - TAB
2 stops20h 45mMultiple Airlines
Sun 1/2510:20 pmTAB - BOS
2 stops25h 17mMultiple Airlines
Deal found 12/30$1,285
This United Airlines deal was found by Cheapflights users on 12/31. 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.
Fri 2/134:43 pmBDL - POS
2 stops31h 22mUnited Airlines
Sun 2/221:30 amPOS - BDL
2 stops44h 36mUnited Airlines
Deal found 12/31$957
This Gotogate deal was found by Cheapflights users on 12/30. 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.
Fri 2/66:55 pmBOS - TAB
2 stops12h 35mMultiple Airlines
Sat 2/1412:30 amTAB - BOS
2 stops23h 07mMultiple Airlines
Deal found 12/30$1,466
This Expedia deal was found by Cheapflights users on 12/31. 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 2/146:00 amBDL - POS
2 stops30h 00mMultiple Airlines
Sat 2/2112:22 pmPOS - BDL
1 stop12h 35mMultiple Airlines
Deal found 12/31$1,960
This Expedia deal was found by Cheapflights users on 12/31. 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 2/146:00 amBDL - POS
1 stop24h 17mJetBlue
Sat 2/2112:22 pmPOS - BDL
1 stop12h 35mJetBlue
Deal found 12/31$2,296

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 January 2, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$235
(United Airlines)

One-way from

$91
(United Airlines)

Popular in

February

Cheapest in

September

Average price

$534
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
Highest demand for flights based on searches. 13% potential increase in price ($96 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 January 2, 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

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Sat 2/21

7:48 am-12:23 am

2 stops15h 35m

Port of Spain Piarco Intl

Fri 2/27

1:30 am-12:17 pm

1 stop11h 47m

$236

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Thu 1/15

11:42 am-12:23 am

1 stop11h 41m

Port of Spain Piarco Intl

Sat 1/24

1:30 am-12:19 pm

1 stop11h 49m

$264

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Sat 1/17

8:25 am-12:23 am

2 stops14h 58m

Port of Spain Piarco Intl

Fri 1/23

1:30 am-5:24 pm

2 stops16h 54m

$268

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Wed 3/18

5:30 pm-2:10 pm

2 stops20h 40m

Port of Spain Piarco Intl

Wed 3/25

3:10 pm-11:36 am

2 stops20h 26m

$273

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Mon 1/12

7:08 am-7:11 pm

1 stop11h 03m

Port of Spain Piarco Intl

Mon 1/19

8:20 am-5:13 pm

1 stop9h 53m

$313

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Tue 1/20

5:15 am-6:41 pm

1 stop12h 26m

Port of Spain Piarco Intl

Sat 1/24

8:45 am-8:18 pm

1 stop12h 33m

$313

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Wed 3/18

5:10 am-1:36 pm

1 stop8h 26m

Port of Spain Piarco Intl

Wed 3/25

3:26 pm-11:50 pm

1 stop8h 24m

$333

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

Mon 3/2

6:05 am-1:05 am

2 stops18h 00m

Port of Spain Piarco Intl

Tue 3/3

1:30 am-1:54 pm

2 stops13h 24m

$383

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

Sat 2/14

4:43 pm-12:23 am

2 stops30h 40m

Port of Spain Piarco Intl

Fri 2/20

1:30 am-9:06 pm

2 stops20h 36m

$732

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

Fri 2/13

4:43 pm-1:05 am

2 stops31h 22m

Port of Spain Piarco Intl

Sun 2/22

1:30 am-9:06 pm

2 stops44h 36m

$957

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/1

Showing 1-10 of 25 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, 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 August is currently the most expensive (average of $524). 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 $236, United Airlines can have you in Trinidad and Tobago from Massachusetts in 15h 35m. Airlines will cover a distance of 2270 mi.

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

    To fly one-way, consider booking your trip with Air Canada, which is currently one of the cheapest options available, starting at $144. United Airlines flights start at $146 while deals on JetBlue start at $202 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 August is currently the most expensive (average of $524). 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 January 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$164Average$496FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$242Average$433FlexibilityNo cancel feeOn-time67%
JetBlueCheapest$438Average$607FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$444Average$684FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$475Average$591FlexibilityNo cancel feeOn-time71%

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