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Massachusetts

$260+ Cheap flights from Trinidad and Tobago to Massachusetts

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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
POS — BOS
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
1 adult, Economy
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Cheap flight deals from Trinidad and Tobago to Massachusetts

Keep the following information in mind while searching for Trinidad and Tobago to Massachusetts flight deals. Data was last updated November 2, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$517
(Kiwi.com)

One-way from

$260
(Air Canada)

Popular in

March

Cheapest in

May

Average price

$610
Provider with most accurate pricing for Port of Spain Piarco Intl-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Port of Spain Piarco Intl-Boston Logan Intl flights.
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From Trinidad and Tobago to Massachusetts
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One-way flight from Trinidad and Tobago to Massachusetts
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Highest demand for flights based on searches. 10% potential increase in price ($64 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Trinidad and Tobago to Massachusetts

Cheapest flights from Trinidad and Tobago to Massachusetts
Explore the most affordable flight options available from Trinidad and Tobago to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 2, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
Tue 12/239:10 amPOS - BOS
2 stops49h 58mMultiple Airlines
Tue 1/1312:20 pmBOS - POS
1 stop29h 35mMultiple Airlines
Deal found 10/31$517
This United Airlines deal was found by Cheapflights users on 11/2. 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.
Sun 12/141:30 amPOS - BOS
2 stops14h 46mUnited Airlines
Wed 12/316:20 amBOS - POS
1 stop17h 03mUnited Airlines
Deal found 11/2$534
This American Airlines deal was found by Cheapflights users on 10/31. 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.
Tue 12/234:46 pmPOS - BOS
1 stop9h 13mAmerican Airlines
Tue 1/1312:55 pmBOS - POS
1 stop8h 53mAmerican Airlines
Deal found 10/31$536
This Air Canada deal was found by Cheapflights users on 11/2. 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 12/122:15 amPOS - BOS
2 stops13h 37mAir Canada
Thu 1/16:15 amBOS - POS
1 stop18h 05mAir Canada
Deal found 11/2$539
This Air Canada deal was found by Cheapflights users on 11/2. 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.
Thu 12/112:15 amPOS - BOS
2 stops42h 27mAir Canada
Thu 1/16:15 amBOS - POS
1 stop18h 05mAir Canada
Deal found 11/2$550
This United Airlines deal was found by Cheapflights users on 11/2. 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 12/121:30 amPOS - BOS
1 stop22h 45mUnited Airlines
Wed 12/311:40 pmBOS - POS
1 stop10h 25mUnited Airlines
Deal found 11/2$567
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
Mon 12/293:47 amPOS - BOS
2 stops31h 14mMultiple Airlines
Tue 1/1312:20 pmBOS - POS
1 stop29h 35mMultiple Airlines
Deal found 10/31$568
This JetBlue deal was found by Cheapflights users on 11/2. 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.
Thu 12/183:56 pmPOS - BOS
1 stop9h 20mJetBlue
Thu 1/15:30 amBOS - POS
1 stop8h 01mJetBlue
Deal found 11/2$571
This JetBlue deal was found by Cheapflights users on 11/2. 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 12/1312:19 pmPOS - BOS
1 stop8h 48mJetBlue
Thu 1/15:30 amBOS - POS
1 stop8h 01mJetBlue
Deal found 11/2$573
This United Airlines deal was found by Cheapflights users on 11/2. 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 12/111:30 amPOS - BOS
1 stop11h 51mUnited Airlines
Tue 12/309:30 amBOS - POS
2 stops37h 53mUnited Airlines
Deal found 11/2$577
This JetBlue deal was found by Cheapflights users on 11/2. 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.
Thu 12/183:56 pmPOS - BOS
1 stop9h 20mJetBlue
Tue 12/308:07 pmBOS - POS
1 stop9h 11mJetBlue
Deal found 11/2$592

Cheapflights Fare Finder

 
Customize your flight search to find flights from Trinidad and Tobago to Massachusetts 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 November 2, 2025.
Use the filters below to find and compare flights from Trinidad and Tobago to Massachusetts that are best for you.

Fly from

Trinidad and Tobago

Fly to

Massachusetts

Route

Depart

Return

Price

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Thu 12/11

1:30 am-2:59 pm

1 stop14h 29m

Boston Logan Intl

Wed 12/31

1:40 pm-1:05 am

1 stop10h 25m

$534

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Wed 12/17

1:30 am-12:06 pm

1 stop11h 36m

Boston Logan Intl

Wed 12/31

9:30 am-1:05 am

2 stops14h 35m

$534

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Mon 12/22

1:30 am-12:45 am

2 stops24h 15m

Boston Logan Intl

Tue 1/13

7:07 pm-12:23 am

2 stops52h 16m

$534

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Sun 12/14

1:30 am-5:16 pm

2 stops16h 46m

Boston Logan Intl

Wed 12/31

9:30 am-1:05 am

2 stops14h 35m

$534

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Sat 12/13

1:30 am-5:43 pm

1 stop17h 13m

Boston Logan Intl

Wed 12/31

7:25 am-12:23 am

1 stop15h 58m

$534

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Mon 12/15

1:30 am-12:21 pm

1 stop11h 51m

Boston Logan Intl

Wed 12/31

6:20 am-12:23 am

1 stop17h 03m

$534

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Tue 12/16

1:30 am-2:59 pm

1 stop14h 29m

Boston Logan Intl

Wed 12/31

1:40 pm-1:05 am

1 stop10h 25m

$534

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Fri 2/27

1:30 am-12:17 pm

1 stop11h 47m

Boston Logan Intl

Tue 3/3

11:48 am-12:23 am

1 stop11h 35m

$536

Port of SpainHartford

POS - BDL

POSBDL

Port of Spain Piarco Intl

Fri 2/6

6:30 am-11:47 pm

2 stops18h 17m

Hartford Bradley Intl

Mon 2/9

11:30 am-10:48 pm

2 stops34h 18m

$953

Port of SpainHartford

POS - BDL

POSBDL

Port of Spain Piarco Intl

Thu 2/5

1:30 am-2:03 pm

2 stops13h 33m

Hartford Bradley Intl

Mon 2/9

10:07 am-12:23 am

2 stops13h 16m

$1,261

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/31

Showing 1-10 of 18 results
1
2

Best time to book a flight from Trinidad and Tobago to Massachusetts

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

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

Currently, May is the cheapest month in which you can book a flight from Trinidad and Tobago to Massachusetts (average of $184). Flying from Trinidad and Tobago to Massachusetts in March is currently the most expensive (average of $564). 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 TT to MA?

Find hourly flight availability from Trinidad and Tobago to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 2, 2025.

When flying from Trinidad and Tobago to Massachusetts, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 36% versus a flight in the morning.

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated November 2, 2025.
Get a feel of what it's like to fly with Copa Airlines, United Airlines, and American Airlines from Trinidad and Tobago to Massachusetts by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.6
Good
1,561 reviews

Food

6.9

Overall

7.6

Entertainment

6.8

Boarding

7.8

Comfort

7.4

Crew

8.1

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
Copa Airlines
7.6
Good
1,561 reviews
Copa Airlines
7.6
Good
1,561 reviews

Food

6.9

Overall

7.6

Entertainment

6.8

Boarding

7.8

Comfort

7.4

Crew

8.1

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
United Airlines
7.4
Good
8,993 reviews
Copa Airlines
7.6
Good
1,561 reviews

Food

6.9

Overall

7.6

Entertainment

6.8

Boarding

7.8

Comfort

7.4

Crew

8.1

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
American Airlines
7.2
Good
11,032 reviews
Copa Airlines
7.6
Good
1,561 reviews

Food

6.9

Overall

7.6

Entertainment

6.8

Boarding

7.8

Comfort

7.4

Crew

8.1

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
JetBlue
7.2
Good
2,906 reviews
Copa Airlines
7.6
Good
1,561 reviews

Food

6.9

Overall

7.6

Entertainment

6.8

Boarding

7.8

Comfort

7.4

Crew

8.1

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
Air Canada
7.1
Good
10,390 reviews
Copa Airlines
7.6
Good
1,561 reviews

Food

6.9

Overall

7.6

Entertainment

6.8

Boarding

7.8

Comfort

7.4

Crew

8.1

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip

Related info for your journey

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

    Departing from Trinidad and Tobago to Massachusetts will take you 14h 29m. There are 2270 mi between Trinidad and Tobago and Massachusetts. Both multi-stop and nonstop flights can be found to your destination and back.

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

    One-way options have recently been found by users for as low as $260 on Air Canada. Other airlines that offer cheap prices include JetBlue from $269 and United Airlines from $300 one-way.

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

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

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

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

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

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

    Currently, May is the cheapest month in which you can book a flight from Trinidad and Tobago to Massachusetts (average of $184). Flying from Trinidad and Tobago to Massachusetts in March is currently the most expensive (average of $564). 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 Trinidad and Tobago to Massachusetts

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

Discover the top 5 airlines that operate flights from Trinidad and Tobago to Massachusetts. 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 November 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$184Average$448FlexibilityNo cancel feeOn-time67%
Copa AirlinesCheapest$256Average$387FlexibilityNo cancel feeOn-time70%
JetBlueCheapest$368Average$664FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$442Average$615FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$451Average$561FlexibilityNo cancel feeOn-time69%

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