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$240+ 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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
POS — BOS
may. 5 — may. 121
lun. 5/5
lun. 5/12
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 abril 30, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$438
(Air Canada)

One-way from

$240
(Copa Airlines)

Popular in

March

Cheapest in

October

Average price

$697
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. 11% potential increase in price ($74 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in April 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 abril 30, 2025.

This Air Canada deal was found by Cheapflights users on 4/27. 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.
lun. 6/22:25 amPOS - BOS
2 stops19h 32mAir Canada
dom. 6/810:40 amBOS - POS
1 stop14h 45mAir Canada
Deal found 4/27$438
This Mytrip deal was found by Cheapflights users on 4/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 6/1310:10 amPOS - BOS
1 stop12h 43mMultiple Airlines
vie. 6/2010:20 amBOS - POS
2 stops15h 05mMultiple Airlines
Deal found 4/28$464
This United Airlines deal was found by Cheapflights users on 4/28. 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.
mié. 8/2012:30 amPOS - BDL
2 stops13h 39mUnited Airlines
dom. 8/247:54 pmBDL - POS
2 stops27h 29mUnited Airlines
Deal found 4/28$554
This United Airlines deal was found by Cheapflights users on 4/28. 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.
jue. 6/1212:30 amPOS - BOS
1 stop21h 30mUnited Airlines
vie. 6/207:45 amBOS - POS
1 stop15h 38mUnited Airlines
Deal found 4/28$563
This American Airlines deal was found by Cheapflights users on 4/27. 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.
mar. 6/33:05 pmPOS - BOS
1 stop9h 14mAmerican Airlines
dom. 6/85:15 amBOS - POS
1 stop9h 00mAmerican Airlines
Deal found 4/27$574
This Copa Airlines deal was found by Cheapflights users on 4/29. 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.
lun. 5/53:44 amPOS - BOS
1 stop15h 42mCopa Airlines
mar. 5/138:47 amBOS - POS
1 stop17h 00mCopa Airlines
Deal found 4/29$611
This JetBlue deal was found by Cheapflights users on 4/28. 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.
vie. 8/221:40 pmPOS - BDL
1 stop8h 19mJetBlue
lun. 8/257:00 amBDL - POS
1 stop11h 24mJetBlue
Deal found 4/28$666
This JetBlue deal was found by Cheapflights users on 4/28. 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.
lun. 8/187:29 pmPOS - BOS
1 stop12h 15mJetBlue
sáb. 8/3010:00 amBOS - POS
1 stop8h 24mJetBlue
Deal found 4/28$666
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
mié. 5/288:30 amPOS - BDL
1 stop15h 55mMultiple Airlines
mié. 6/48:34 amBDL - POS
2 stops35h 26mMultiple Airlines
Deal found 4/28$683

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 abril 30, 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

lun. 6/2

2:25 am-9:57 pm

2 stops19h 32m

Boston Logan Intl

dom. 6/8

10:40 am-1:25 am

1 stop14h 45m

$438

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

vie. 6/13

10:10 am-10:53 pm

1 stop12h 43m

Boston Logan Intl

vie. 6/20

10:20 am-1:25 am

2 stops15h 05m

$464

Port of SpainHartford

POS - BDL

POSBDL

Port of Spain Piarco Intl

mié. 8/20

12:30 am-12:20 pm

2 stops35h 50m

Hartford Bradley Intl

lun. 8/25

6:00 am-11:23 pm

2 stops17h 23m

$554

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

jue. 6/12

12:30 am-5:56 pm

2 stops17h 26m

Boston Logan Intl

vie. 6/20

7:45 am-11:23 pm

1 stop15h 38m

$563

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

mar. 6/3

3:05 pm-12:19 am

1 stop9h 14m

Boston Logan Intl

dom. 6/8

5:15 am-2:15 pm

1 stop9h 00m

$574

Port of SpainHartford

POS - BDL

POSBDL

Port of Spain Piarco Intl

vie. 8/22

1:40 pm-9:59 pm

1 stop8h 19m

Hartford Bradley Intl

lun. 8/25

7:00 am-6:24 pm

1 stop11h 24m

$666

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

lun. 8/18

7:29 pm-7:44 am

1 stop12h 15m

Boston Logan Intl

sáb. 8/30

10:00 am-6:24 pm

1 stop8h 24m

$666

Port of SpainHartford

POS - BDL

POSBDL

Port of Spain Piarco Intl

mié. 5/28

8:30 am-12:25 am

1 stop15h 55m

Hartford Bradley Intl

mié. 6/4

8:34 am-8:00 pm

2 stops35h 26m

$683

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

lun. 6/2

3:44 am-7:26 pm

1 stop15h 42m

$240

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

vie. 5/16

2:25 am-10:38 pm

1 stop20h 13m

$243

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/27

Showing 1-10 of 14 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, January is the cheapest month in which you can book a flight from Trinidad and Tobago to Massachusetts (average of $218). Flying from Trinidad and Tobago to Massachusetts in July is currently the most expensive (average of $311). 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 abril 30, 2025.

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

Rainfall in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Massachusetts ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Massachusetts when rainfall is around 3.1 in.

Temperature in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Massachusetts, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

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 abril 30, 2025.
Get a feel of what it's like to fly with Copa Airlines, United Airlines and JetBlue from Trinidad and Tobago to Massachusetts by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.5
Good
1,411 reviews

Comfort

7.4

Food

6.8

Entertainment

6.7

Crew

8.1

Boarding

7.8

Overall

7.5

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

PTY - JFK

There was no chance for me to choose a seat even if I were willing to pay extra for it when I was doing the check-in on line. My seats were the last row on the plane and they didn't have enough food to give me. I had to eat what was left after everybody else had their choice of food. This is unacceptable. Everyone should have a choice. I paid money just like everybody else. Never had this happened on any other airlines even if my seats were last row on the plane.
Copa Airlines
7.5
Good
1,411 reviews
Copa Airlines
7.5
Good
1,411 reviews

Comfort

7.4

Food

6.8

Entertainment

6.7

Crew

8.1

Boarding

7.8

Overall

7.5

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

PTY - JFK

There was no chance for me to choose a seat even if I were willing to pay extra for it when I was doing the check-in on line. My seats were the last row on the plane and they didn't have enough food to give me. I had to eat what was left after everybody else had their choice of food. This is unacceptable. Everyone should have a choice. I paid money just like everybody else. Never had this happened on any other airlines even if my seats were last row on the plane.
United Airlines
7.4
Good
8,696 reviews
Copa Airlines
7.5
Good
1,411 reviews

Comfort

7.4

Food

6.8

Entertainment

6.7

Crew

8.1

Boarding

7.8

Overall

7.5

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

PTY - JFK

There was no chance for me to choose a seat even if I were willing to pay extra for it when I was doing the check-in on line. My seats were the last row on the plane and they didn't have enough food to give me. I had to eat what was left after everybody else had their choice of food. This is unacceptable. Everyone should have a choice. I paid money just like everybody else. Never had this happened on any other airlines even if my seats were last row on the plane.
JetBlue
7.3
Good
2,922 reviews
Copa Airlines
7.5
Good
1,411 reviews

Comfort

7.4

Food

6.8

Entertainment

6.7

Crew

8.1

Boarding

7.8

Overall

7.5

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

PTY - JFK

There was no chance for me to choose a seat even if I were willing to pay extra for it when I was doing the check-in on line. My seats were the last row on the plane and they didn't have enough food to give me. I had to eat what was left after everybody else had their choice of food. This is unacceptable. Everyone should have a choice. I paid money just like everybody else. Never had this happened on any other airlines even if my seats were last row on the plane.
American Airlines
7.2
Good
10,000 reviews
Copa Airlines
7.5
Good
1,411 reviews

Comfort

7.4

Food

6.8

Entertainment

6.7

Crew

8.1

Boarding

7.8

Overall

7.5

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

PTY - JFK

There was no chance for me to choose a seat even if I were willing to pay extra for it when I was doing the check-in on line. My seats were the last row on the plane and they didn't have enough food to give me. I had to eat what was left after everybody else had their choice of food. This is unacceptable. Everyone should have a choice. I paid money just like everybody else. Never had this happened on any other airlines even if my seats were last row on the plane.
Air Canada
7.0
Good
9,242 reviews
Copa Airlines
7.5
Good
1,411 reviews

Comfort

7.4

Food

6.8

Entertainment

6.7

Crew

8.1

Boarding

7.8

Overall

7.5

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

PTY - JFK

There was no chance for me to choose a seat even if I were willing to pay extra for it when I was doing the check-in on line. My seats were the last row on the plane and they didn't have enough food to give me. I had to eat what was left after everybody else had their choice of food. This is unacceptable. Everyone should have a choice. I paid money just like everybody else. Never had this happened on any other airlines even if my seats were last row on the plane.

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.

  • 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 $240 on Copa Airlines. Other airlines that offer cheap prices include Air Canada from $243 and American Airlines from $314 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, January is the cheapest month in which you can book a flight from Trinidad and Tobago to Massachusetts (average of $218). Flying from Trinidad and Tobago to Massachusetts in July is currently the most expensive (average of $311). 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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See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Trinidad and Tobago to Massachusetts

Discover the top 4 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 abril 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$384Average$418FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$408Average$602FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$431Average$521FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$492Average$662FlexibilityNo cancel feeOn-time62%

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