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$236+ 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 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — POS
Apr 27 — May 41
Sun 4/27
Sun 5/4
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 April 22, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$417
(Air Canada)

One-way from

$236
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$741
Provider with most accurate pricing for Boston Logan Intl-Port of Spain Piarco Intl flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Port of Spain Piarco Intl flights.
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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. 4% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($22 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 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 April 22, 2025.

This Air Canada deal was found by Cheapflights users on 4/20. 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 5/1910:40 amBOS - POS
1 stop14h 45mAir Canada
Sun 5/252:25 amPOS - BOS
1 stop20h 13mAir Canada
Deal found 4/20$417
This Copa Airlines deal was found by Cheapflights users on 4/22. 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.
Tue 9/163:49 pmBOS - POS
1 stop9h 59mCopa Airlines
Mon 9/223:50 amPOS - BOS
1 stop15h 32mCopa Airlines
Deal found 4/22$452
This Mytrip deal was found by Cheapflights users on 4/21. 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.
Mon 5/126:10 amBOS - POS
1 stop13h 50mMultiple Airlines
Thu 5/2210:10 amPOS - BOS
1 stop13h 19mMultiple Airlines
Deal found 4/21$454
This United Airlines deal was found by Cheapflights users on 4/21. 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 8/227:30 amBOS - POS
1 stop15h 53mUnited Airlines
Mon 9/812:30 amPOS - BOS
1 stop12h 06mUnited Airlines
Deal found 4/21$517
This American Airlines deal was found by Cheapflights users on 4/22. 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 9/165:29 amBOS - POS
1 stop8h 46mAmerican Airlines
Tue 9/233:20 pmPOS - BOS
1 stop9h 07mAmerican Airlines
Deal found 4/22$524
This JetBlue deal was found by Cheapflights users on 4/21. 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 7/117:10 amBOS - POS
1 stop11h 14mJetBlue
Sat 7/197:29 pmPOS - BOS
1 stop13h 51mJetBlue
Deal found 4/21$566
This United Airlines deal was found by Cheapflights users on 4/22. 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 5/236:30 pmBDL - POS
2 stops28h 53mUnited Airlines
Sun 5/2512:30 amPOS - BDL
2 stops37h 47mUnited Airlines
Deal found 4/22$640
This Mytrip deal was found by Cheapflights users on 4/22. 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.
Sun 5/48:30 amBOS - TAB
3 stops37h 30mMultiple Airlines
Fri 5/97:35 amTAB - BOS
3 stops40h 12mMultiple Airlines
Deal found 4/22$658
This American Airlines deal was found by Cheapflights users on 4/22. 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.
Fri 5/231:49 pmBDL - POS
2 stops24h 16mAmerican Airlines
Mon 5/263:05 pmPOS - BDL
2 stops21h 54mAmerican Airlines
Deal found 4/22$753
This Mytrip deal was found by Cheapflights users on 4/22. 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.
Fri 5/2312:27 pmBDL - POS
3 stops31h 23mMultiple Airlines
Mon 5/2610:10 amPOS - BDL
2 stops21h 29mMultiple Airlines
Deal found 4/22$796

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 April 22, 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

Mon 5/19

10:40 am-1:25 am

1 stop14h 45m

Port of Spain Piarco Intl

Sun 5/25

2:25 am-10:38 pm

1 stop20h 13m

$417

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Tue 9/16

3:49 pm-1:48 am

1 stop9h 59m

Port of Spain Piarco Intl

Mon 9/22

3:50 am-7:22 pm

1 stop15h 32m

$452

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Mon 5/12

6:10 am-8:00 pm

1 stop13h 50m

Port of Spain Piarco Intl

Thu 5/22

10:10 am-11:29 pm

1 stop13h 19m

$454

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Fri 8/22

7:30 am-11:23 pm

1 stop15h 53m

Port of Spain Piarco Intl

Mon 9/8

12:30 am-12:36 pm

1 stop12h 06m

$517

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Tue 9/16

5:29 am-2:15 pm

1 stop8h 46m

Port of Spain Piarco Intl

Tue 9/23

3:20 pm-12:27 am

1 stop9h 07m

$524

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Fri 7/11

7:10 am-6:24 pm

1 stop11h 14m

Port of Spain Piarco Intl

Sat 7/19

7:29 pm-9:20 am

1 stop13h 51m

$566

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

Fri 5/23

6:30 pm-11:23 pm

2 stops28h 53m

Port of Spain Piarco Intl

Sun 5/25

12:30 am-2:17 pm

2 stops37h 47m

$640

BostonScarborough

BOS - TAB

BOSTAB

Boston Logan Intl

Sun 5/4

8:30 am-10:00 pm

3 stops37h 30m

Scarborough ANR Robinson Intl

Fri 5/9

7:35 am-11:47 pm

3 stops40h 12m

$658

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

Fri 5/23

1:49 pm-2:05 pm

2 stops24h 16m

Port of Spain Piarco Intl

Mon 5/26

3:05 pm-12:59 pm

2 stops21h 54m

$753

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

Fri 5/23

12:27 pm-7:50 pm

3 stops31h 23m

Port of Spain Piarco Intl

Mon 5/26

10:10 am-7:39 am

2 stops21h 29m

$796

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 17 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 April 22, 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.

Rainfall in Trinidad and Tobago by month

Plan your trip to Trinidad and Tobago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Trinidad and Tobago ranges from 1.2 - 9.8 inches per month. June is typically the wettest month, when rainfall can reach 9.8 in. March is typically the driest time to visit Trinidad and Tobago when rainfall is around 1.2 in.

Temperature in Trinidad and Tobago by month

Plan your trip to Trinidad and Tobago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Trinidad and Tobago, use this chart to help with planning. For those seeking warmer temperatures, April is the ideal time of year to visit, when temperatures reach an average of 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Trinidad and Tobago

Get insights into the airlines that provide service to Trinidad and Tobago. 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 Trinidad and Tobago. Reviews last updated April 22, 2025.
To help decide which airline to fly from Massachusetts to Trinidad and Tobago, see what other customers have to say about Copa Airlines, United Airlines and JetBlue. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.5
Good
1,408 reviews

Comfort

7.4

Food

6.8

Boarding

7.8

Overall

7.5

Crew

8.1

Entertainment

6.8

Reviews

1 / 20
4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.
Copa Airlines
7.5
Good
1,408 reviews
Copa Airlines
7.5
Good
1,408 reviews

Comfort

7.4

Food

6.8

Boarding

7.8

Overall

7.5

Crew

8.1

Entertainment

6.8

Reviews

1 / 20
4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.
United Airlines
7.4
Good
8,683 reviews
Copa Airlines
7.5
Good
1,408 reviews

Comfort

7.4

Food

6.8

Boarding

7.8

Overall

7.5

Crew

8.1

Entertainment

6.8

Reviews

1 / 20
4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.
JetBlue
7.3
Good
2,923 reviews
Copa Airlines
7.5
Good
1,408 reviews

Comfort

7.4

Food

6.8

Boarding

7.8

Overall

7.5

Crew

8.1

Entertainment

6.8

Reviews

1 / 20
4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.
Turkish Airlines
7.3
Good
3,773 reviews
Copa Airlines
7.5
Good
1,408 reviews

Comfort

7.4

Food

6.8

Boarding

7.8

Overall

7.5

Crew

8.1

Entertainment

6.8

Reviews

1 / 20
4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.
American Airlines
7.2
Good
10,000 reviews
Copa Airlines
7.5
Good
1,408 reviews

Comfort

7.4

Food

6.8

Boarding

7.8

Overall

7.5

Crew

8.1

Entertainment

6.8

Reviews

1 / 20
4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.

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.

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

    To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $236. Air Canada flights start at $308 while deals on JetBlue start at $357 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, 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

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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 April 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$152Average$184FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$400Average$530FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$433Average$640FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$444Average$642FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$463Average$647FlexibilityNo cancel feeOn-time62%

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