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Massachusetts

$161+ Cheap flights from Trinidad 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
POS — BOS
Feb 18 — Feb 251
Wed 2/18
Wed 2/25
1 adult, Economy
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Cheap flight deals from Trinidad to Massachusetts

Keep the following information in mind while searching for Trinidad to Massachusetts flight deals. Data was last updated January 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$271
(JetBlue)

One-way from

$161
(United Airlines)

Popular in

March

Cheapest in

December

Average price

$466
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 to Massachusetts
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One-way flight from Trinidad to Massachusetts
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Highest demand for flights based on searches. 5% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Trinidad to Massachusetts

Cheapest flights from Trinidad to Massachusetts
Explore the most affordable flight options available from Trinidad to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 19, 2026.

This JetBlue deal was found by Cheapflights users on 1/18. 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.
Fri 2/138:50 am
POS
-
BOS
1 stop9h 26m
JetBlue
Sat 2/216:15 pm
BOS
-
POS
1 stop12h 02m
JetBlue
Deal found 1/18$271
This United Airlines deal was found by Cheapflights users on 1/18. 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 2/121:30 am
POS
-
BOS
2 stops21h 31m
United Airlines
Sat 2/214:25 pm
BOS
-
POS
2 stops30h 58m
United Airlines
Deal found 1/18$276
This American Airlines deal was found by Cheapflights users on 1/17. 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.
Sat 5/23:47 pm
POS
-
BOS
2 stops18h 33m
American Airlines
Sun 5/104:59 pm
BOS
-
POS
2 stops21h 33m
American Airlines
Deal found 1/17$292
This JetBlue deal was found by Cheapflights users on 1/18. 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 2/78:20 am
POS
-
BOS
1 stop9h 53m
JetBlue
Sat 2/218:15 pm
BOS
-
POS
1 stop13h 42m
JetBlue
Deal found 1/18$304
This United Airlines deal was found by Cheapflights users on 1/18. 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 2/61:30 am
POS
-
BOS
2 stops13h 47m
United Airlines
Sat 2/214:15 pm
BOS
-
POS
1 stop7h 50m
United Airlines
Deal found 1/18$309
This JetBlue deal was found by Cheapflights users on 1/18. 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 7/211:57 pm
POS
-
BOS
1 stop10h 23m
JetBlue
Sun 7/129:25 am
BOS
-
POS
1 stop13h 06m
JetBlue
Deal found 1/18$427
This United Airlines deal was found by Cheapflights users on 1/17. 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 3/2612:30 am
POS
-
BOS
2 stops23h 27m
United Airlines
Wed 4/86:00 am
BOS
-
POS
2 stops17h 23m
United Airlines
Deal found 1/17$430
This JetBlue deal was found by Cheapflights users on 1/18. 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 7/2511:57 pm
POS
-
BOS
1 stop10h 23m
JetBlue
Sat 8/812:40 pm
BOS
-
POS
1 stop9h 51m
JetBlue
Deal found 1/18$436
This JetBlue deal was found by Cheapflights users on 1/18. 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.
Fri 3/273:29 pm
POS
-
BOS
1 stop8h 21m
JetBlue
Wed 4/85:15 am
BOS
-
POS
1 stop9h 00m
JetBlue
Deal found 1/18$477
This Expedia deal was found by Cheapflights users on 1/18. 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.
Fri 7/33:50 pm
POS
-
BDL
1 stop8h 04m
JetBlue
Sun 7/266:40 am
BDL
-
POS
1 stop7h 41m
JetBlue
Deal found 1/18$567
This United Airlines deal was found by Cheapflights users on 1/18. 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 7/212:30 am
POS
-
BDL
1 stop22h 27m
United Airlines
Sun 7/266:30 pm
BDL
-
POS
2 stops28h 53m
United Airlines
Deal found 1/18$580

Cheapflights Fare Finder

 
Customize your flight search to find flights from Trinidad 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 January 19, 2026.
Use the filters below to find and compare flights from Trinidad to Massachusetts that are best for you.

Fly from

Trinidad

Fly to

Massachusetts

Route

Depart

Return

Price

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Fri 5/1

12:30 am-12:16 pm

1 stop11h 46m

Boston Logan Intl

Tue 5/12

9:45 am-11:23 pm

1 stop13h 38m

$271

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Sat 2/7

8:20 am-8:18 pm

1 stop12h 58m

Boston Logan Intl

Sat 2/21

8:15 pm-7:17 am

1 stop10h 02m

$271

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Fri 2/13

8:50 am-8:03 pm

1 stop12h 13m

Boston Logan Intl

Sat 2/21

8:15 pm-10:57 am

1 stop13h 42m

$271

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Fri 5/1

12:30 am-12:16 pm

1 stop11h 46m

Boston Logan Intl

Sun 5/10

7:25 am-11:23 pm

1 stop15h 58m

$271

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Fri 2/6

1:30 am-3:09 pm

2 stops14h 39m

Boston Logan Intl

Sat 2/21

4:15 pm-1:05 am

1 stop7h 50m

$276

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Thu 2/12

1:30 am-11:57 pm

2 stops23h 27m

Boston Logan Intl

Sat 2/21

7:19 pm-12:23 am

2 stops28h 04m

$276

Port of SpainHartford

POS - BDL

POSBDL

Port of Spain Piarco Intl

Fri 7/3

3:50 pm-11:54 pm

1 stop8h 04m

Hartford Bradley Intl

Sun 7/26

6:40 am-2:21 pm

1 stop7h 41m

$567

Port of SpainHartford

POS - BDL

POSBDL

Port of Spain Piarco Intl

Thu 7/2

12:30 am-2:01 pm

2 stops13h 31m

Hartford Bradley Intl

Sun 7/26

6:30 pm-11:23 pm

2 stops28h 53m

$580

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Tue 3/3

1:30 am-11:30 pm

1 stop23h 00m

$161

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Fri 3/13

3:29 pm-11:50 pm

1 stop8h 21m

$161

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/18

Showing 1-10 of 15 results
1
2

Best time to book a flight from Trinidad to Massachusetts

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

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

Currently, May is the cheapest month in which you can book a flight from Trinidad to Massachusetts (average of $184). Flying from Trinidad to Massachusetts in July is currently the most expensive (average of $554). 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.

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 January 19, 2026.
Read reviews from past customers who have flown Copa Airlines, United Airlines, and American Airlines from Trinidad to Massachusetts. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.6
Good
1,560 reviews

Crew

8.1

Overall

7.6

Boarding

7.8

Entertainment

6.8

Food

6.8

Comfort

7.4

Reviews

1 / 20
2.0
Mediocre

Maria,Dec 2025

PTY - SLA

Old plain no entertainment , no outlet for cell or computer! And online they said you have all that! Almost 6 hrs looking to the floor..terrible expirencw and I pay a lot of money for it
Copa Airlines
7.6
Good
1,560 reviews
Copa Airlines
7.6
Good
1,560 reviews

Crew

8.1

Overall

7.6

Boarding

7.8

Entertainment

6.8

Food

6.8

Comfort

7.4

Reviews

1 / 20
2.0
Mediocre

Maria,Dec 2025

PTY - SLA

Old plain no entertainment , no outlet for cell or computer! And online they said you have all that! Almost 6 hrs looking to the floor..terrible expirencw and I pay a lot of money for it
United Airlines
7.4
Good
9,179 reviews
Copa Airlines
7.6
Good
1,560 reviews

Crew

8.1

Overall

7.6

Boarding

7.8

Entertainment

6.8

Food

6.8

Comfort

7.4

Reviews

1 / 20
2.0
Mediocre

Maria,Dec 2025

PTY - SLA

Old plain no entertainment , no outlet for cell or computer! And online they said you have all that! Almost 6 hrs looking to the floor..terrible expirencw and I pay a lot of money for it
American Airlines
7.2
Good
11,161 reviews
Copa Airlines
7.6
Good
1,560 reviews

Crew

8.1

Overall

7.6

Boarding

7.8

Entertainment

6.8

Food

6.8

Comfort

7.4

Reviews

1 / 20
2.0
Mediocre

Maria,Dec 2025

PTY - SLA

Old plain no entertainment , no outlet for cell or computer! And online they said you have all that! Almost 6 hrs looking to the floor..terrible expirencw and I pay a lot of money for it
JetBlue
7.2
Good
2,892 reviews
Copa Airlines
7.6
Good
1,560 reviews

Crew

8.1

Overall

7.6

Boarding

7.8

Entertainment

6.8

Food

6.8

Comfort

7.4

Reviews

1 / 20
2.0
Mediocre

Maria,Dec 2025

PTY - SLA

Old plain no entertainment , no outlet for cell or computer! And online they said you have all that! Almost 6 hrs looking to the floor..terrible expirencw and I pay a lot of money for it
Air Canada
7.1
Good
10,637 reviews
Copa Airlines
7.6
Good
1,560 reviews

Crew

8.1

Overall

7.6

Boarding

7.8

Entertainment

6.8

Food

6.8

Comfort

7.4

Reviews

1 / 20
2.0
Mediocre

Maria,Dec 2025

PTY - SLA

Old plain no entertainment , no outlet for cell or computer! And online they said you have all that! Almost 6 hrs looking to the floor..terrible expirencw and I pay a lot of money for it

Related info for your journey

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

    Departing from Trinidad to Massachusetts will take you 11h 46m. The distance from Trinidad to Massachusetts is about 2270 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    The cheapest airlines for a one-way flight from Trinidad to Massachusetts are JetBlue ($163), American Airlines ($202), and Air Canada ($209).

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Trinidad 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 to Massachusetts?

    Currently, May is the cheapest month in which you can book a flight from Trinidad to Massachusetts (average of $184). Flying from Trinidad to Massachusetts in July is currently the most expensive (average of $554). 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 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 to Massachusetts

Discover the top 5 airlines that operate flights from Trinidad 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 January 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$168Average$384FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$183Average$555FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$184Average$448FlexibilityNo cancel feeOn-time67%
JetBlueCheapest$241Average$573FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$515Average$635FlexibilityNo cancel feeOn-time71%

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