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$200+ 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 3/20. Fares are subject to change and may not be available on all flights or dates of travel.
POS — BOS
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$345
(Kiwi.com)

One-way from

$200
(Kiwi.com)

Popular in

July

Cheapest in

October

Average price

$562
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. 12% potential increase in price ($83 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/276:01 pmPOS - BOS
1 stop16h 21mMultiple Airlines
Tue 4/111:45 amBOS - POS
1 stop31h 10mMultiple Airlines
Deal found 2/18$345
This Copa Airlines deal was found by Cheapflights users on 2/19. 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.
Mon 4/73:39 amPOS - BOS
1 stop15h 41mCopa Airlines
Mon 5/123:55 pmBOS - POS
1 stop9h 52mCopa Airlines
Deal found 2/19$431
This United Airlines deal was found by Cheapflights users on 2/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/3112:30 amPOS - BOS
1 stop19h 21mUnited Airlines
Sun 4/67:15 amBOS - POS
1 stop16h 08mUnited Airlines
Deal found 2/20$441
This American Airlines deal was found by Cheapflights users on 2/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/83:10 pmPOS - BOS
1 stop19h 13mAmerican Airlines
Mon 5/125:15 amBOS - POS
1 stop8h 50mAmerican Airlines
Deal found 2/18$443

Find flights from Trinidad and Tobago to Massachusetts within your budget

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 February 20, 2025.

Fly from

Trinidad and Tobago

Fly to

Massachusetts

Route

Depart

Return

Price

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Thu 3/27

6:01 pm-10:22 am

1 stop16h 21m

Boston Logan Intl

Tue 4/1

11:45 am-6:55 pm

1 stop31h 10m

$345

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Mon 4/7

3:39 am-7:20 pm

1 stop15h 41m

Boston Logan Intl

Mon 5/12

3:55 pm-1:47 am

1 stop9h 52m

$431

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Mon 3/31

12:30 am-9:49 pm

2 stops21h 19m

Boston Logan Intl

Sun 4/6

5:30 am-11:23 pm

2 stops17h 53m

$441

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Tue 4/8

3:10 pm-10:23 am

1 stop19h 13m

Boston Logan Intl

Mon 5/12

5:15 am-2:05 pm

1 stop8h 50m

$443

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Thu 3/20

6:01 pm-5:14 pm

3 stops23h 13m

$200

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Thu 3/20

6:01 pm-10:32 am

1 stop16h 31m

$252

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Mon 3/24

3:15 pm-11:02 am

2 stops19h 47m

$253

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Sun 3/23

12:30 am-5:37 pm

2 stops41h 07m

$254

Port of SpainHartford

POS - BDL

POSBDL

Port of Spain Piarco Intl

Fri 3/14

11:10 am-10:41 am

2 stops23h 31m

$307

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Sat 5/10

3:44 am-7:26 pm

1 stop15h 42m

$353

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 11 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.

Travel insights for flights from Trinidad and Tobago to Massachusetts

Get recent, data-driven insights about flights from Trinidad and Tobago to Massachusetts including ideal travel times, pricing trends, and more.

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 February 20, 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 February 20, 2025.
Copa Airlines
7.6
Good
1,510 reviews

Crew

8.1

Boarding

7.8

Comfort

7.4

Food

6.9

Overall

7.6

Entertainment

6.9

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
7.6
Good
1,510 reviews
Copa Airlines
7.6
Good
1,510 reviews

Crew

8.1

Boarding

7.8

Comfort

7.4

Food

6.9

Overall

7.6

Entertainment

6.9

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
7.4
Good
3,070 reviews
Copa Airlines
7.6
Good
1,510 reviews

Crew

8.1

Boarding

7.8

Comfort

7.4

Food

6.9

Overall

7.6

Entertainment

6.9

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
8,766 reviews
Copa Airlines
7.6
Good
1,510 reviews

Crew

8.1

Boarding

7.8

Comfort

7.4

Food

6.9

Overall

7.6

Entertainment

6.9

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
7.6
Good
1,510 reviews

Crew

8.1

Boarding

7.8

Comfort

7.4

Food

6.9

Overall

7.6

Entertainment

6.9

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.

Frontier
6.0
Okay
3,355 reviews
Copa Airlines
7.6
Good
1,510 reviews

Crew

8.1

Boarding

7.8

Comfort

7.4

Food

6.9

Overall

7.6

Entertainment

6.9

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 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 $252 on Frontier. Other airlines that offer cheap prices include American Airlines from $253 and United Airlines from $254 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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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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$384Average$438FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$408Average$606FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$412Average$502FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$492Average$638FlexibilityNo cancel feeOn-time62%
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