HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Trinidad and Tobago

$185+ 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
May 5 — May 121
Mon 5/5
Mon 5/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Massachusetts to Trinidad and Tobago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 30, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$417
(Air Canada)

One-way from

$185
(Air Canada)

Popular in

December

Cheapest in

September

Average price

$749
Provider with most accurate pricing for Boston Logan Intl-Port of Spain Piarco Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Port of Spain Piarco Intl flights.
Search Deals
From Massachusetts to Trinidad and Tobago
Search Deals
One-way flight from Massachusetts to Trinidad and Tobago
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals

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 30, 2025.

This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/2710:20 amBOS - POS
2 stops15h 05mAir Canada
Fri 7/42:25 amPOS - BOS
1 stop9h 03mAir Canada
Deal found 4/29$417
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/43:20 pmBOS - POS
2 stops34h 05mMultiple Airlines
Sun 5/1110:10 amPOS - BOS
1 stop28h 34mMultiple Airlines
Deal found 4/29$496
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/137:12 amBDL - POS
1 stop10h 52mJetBlue
Fri 6/208:50 amPOS - BDL
1 stop14h 56mJetBlue
Deal found 4/29$507
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/45:12 amBOS - POS
1 stop8h 15mJetBlue
Thu 6/127:29 pmPOS - BOS
1 stop12h 15mJetBlue
Deal found 4/29$524
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/46:36 pmBOS - POS
2 stops19h 39mAmerican Airlines
Thu 6/127:09 amPOS - BOS
1 stop13h 42mAmerican Airlines
Deal found 4/29$529
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2911:38 amBDL - POS
1 stop30h 32mMultiple Airlines
Tue 6/33:44 amPOS - BDL
2 stops19h 47mMultiple Airlines
Deal found 4/29$592
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/157:45 amBOS - POS
1 stop15h 38mUnited Airlines
Sun 7/2712:30 amPOS - BOS
1 stop14h 03mUnited Airlines
Deal found 4/29$598
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2610:32 amBDL - POS
2 stops12h 51mUnited Airlines
Tue 9/212:30 amPOS - BDL
2 stops16h 53mUnited Airlines
Deal found 4/29$603
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/295:44 amBDL - POS
1 stop8h 31mAmerican Airlines
Tue 6/33:05 pmPOS - BDL
2 stops21h 54mAmerican Airlines
Deal found 4/29$653
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/48:47 amBOS - POS
1 stop17h 00mCopa Airlines
Fri 6/133:44 amPOS - BOS
1 stop15h 42mCopa Airlines
Deal found 4/29$683
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/316:00 amBDL - POS
2 stops19h 25mAir Canada
Fri 9/52:25 amPOS - BDL
2 stops35h 36mAir Canada
Deal found 4/29$1,050
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/37:00 pmBOS - TAB
2 stops16h 00mMultiple Airlines
Sat 7/1210:45 pmTAB - BOS
2 stops12h 43mMultiple Airlines
Deal found 4/28$3,903

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 30, 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

Fri 6/27

10:20 am-1:25 am

2 stops15h 05m

Port of Spain Piarco Intl

Fri 7/4

2:25 am-11:28 am

1 stop9h 03m

$417

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

Fri 6/13

7:12 am-6:04 pm

1 stop10h 52m

Port of Spain Piarco Intl

Fri 6/20

8:50 am-11:46 pm

1 stop14h 56m

$507

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Wed 6/4

5:12 am-1:27 pm

1 stop8h 15m

Port of Spain Piarco Intl

Thu 6/12

7:29 pm-7:44 am

1 stop12h 15m

$524

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Wed 6/4

6:36 pm-2:15 pm

2 stops19h 39m

Port of Spain Piarco Intl

Thu 6/12

7:09 am-8:51 pm

1 stop13h 42m

$529

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Wed 6/4

6:00 am-7:10 pm

2 stops13h 10m

Port of Spain Piarco Intl

Fri 6/13

2:25 am-2:32 pm

2 stops12h 07m

$588

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

Thu 5/29

11:38 am-6:10 pm

1 stop30h 32m

Port of Spain Piarco Intl

Tue 6/3

3:44 am-11:31 pm

2 stops19h 47m

$592

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Tue 7/15

7:45 am-11:23 pm

1 stop15h 38m

Port of Spain Piarco Intl

Sun 7/27

12:30 am-8:40 pm

2 stops20h 10m

$598

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

Tue 8/26

6:00 am-11:23 pm

2 stops17h 23m

Port of Spain Piarco Intl

Thu 9/4

12:30 am-2:01 pm

2 stops13h 31m

$603

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

Thu 5/29

5:44 am-2:15 pm

1 stop8h 31m

Port of Spain Piarco Intl

Tue 6/3

3:05 pm-12:59 pm

2 stops21h 54m

$653

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Wed 6/4

8:47 am-1:47 am

1 stop17h 00m

Port of Spain Piarco Intl

Fri 6/13

3:44 am-7:26 pm

1 stop15h 42m

$683

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 16 results
1
2

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 30, 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 30, 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
1,411 reviews

Entertainment

6.7

Boarding

7.8

Overall

7.5

Crew

8.1

Food

6.8

Comfort

7.4

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
1,411 reviews
Copa Airlines
7.5
Good
1,411 reviews

Entertainment

6.7

Boarding

7.8

Overall

7.5

Crew

8.1

Food

6.8

Comfort

7.4

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
8,696 reviews
Copa Airlines
7.5
Good
1,411 reviews

Entertainment

6.7

Boarding

7.8

Overall

7.5

Crew

8.1

Food

6.8

Comfort

7.4

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
2,922 reviews
Copa Airlines
7.5
Good
1,411 reviews

Entertainment

6.7

Boarding

7.8

Overall

7.5

Crew

8.1

Food

6.8

Comfort

7.4

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
1,411 reviews

Entertainment

6.7

Boarding

7.8

Overall

7.5

Crew

8.1

Food

6.8

Comfort

7.4

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.
Air Canada
7.0
Good
9,242 reviews
Copa Airlines
7.5
Good
1,411 reviews

Entertainment

6.7

Boarding

7.8

Overall

7.5

Crew

8.1

Food

6.8

Comfort

7.4

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 Air Canada, which is currently one of the cheapest options available, starting at $185. Copa Airlines flights start at $503 while deals on American Airlines start at $803 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Massachusetts to Trinidad and Tobago

See prices for flight routes from nearby airports that may be better suited for you.
Newark to Luis Munoz Marin Intl flights
John F Kennedy Intl to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santiago de los Caballeros flights
Orlando to Luis Munoz Marin Intl flights
Newark to Santiago de los Caballeros flights
LaGuardia to Luis Munoz Marin Intl flights
John F Kennedy Intl to Punta Cana flights
Newark to Punta Cana flights
John F Kennedy Intl to Montego Bay flights
John F Kennedy Intl to Santo Domingo flights
Newark to Santo Domingo flights
Newark to Montego Bay flights
Dallas/Fort Worth to Luis Munoz Marin Intl flights
Newark to Oranjestad flights
Dulles Intl to Luis Munoz Marin Intl flights
Philadelphia to Luis Munoz Marin Intl flights
Reagan-National to Luis Munoz Marin Intl flights
O'Hare Intl to Luis Munoz Marin Intl flights
Hartford to Luis Munoz Marin Intl flights
John F Kennedy Intl to Oranjestad flights
Fort Lauderdale to Luis Munoz Marin Intl flights
Miami to Luis Munoz Marin Intl flights
Boston to Luis Munoz Marin Intl flights
Atlanta to Luis Munoz Marin Intl flights
Baltimore to Luis Munoz Marin Intl flights
Atlanta to Montego Bay flights
Tampa to Luis Munoz Marin Intl flights
Newark to Nassau flights
LaGuardia to Punta Cana flights
John F Kennedy Intl to Nassau flights
Dulles Intl to Punta Cana flights
Hobby to Luis Munoz Marin Intl flights
LaGuardia to Montego Bay flights
Raleigh to Luis Munoz Marin Intl flights
John F Kennedy Intl to Saint Thomas Island flights
Boston to Oranjestad flights
John F Kennedy Intl to Kingston flights
Dulles Intl to Montego Bay flights
Atlanta to Punta Cana flights
Newark to Simpson Bay flights
John F Kennedy Intl to Simpson Bay flights
O'Hare Intl to Punta Cana flights
George Bush Intcntl to Luis Munoz Marin Intl flights
LaGuardia to Santo Domingo flights
LaGuardia to Oranjestad flights
John F Kennedy Intl to Bridgetown flights
Dallas/Fort Worth to Punta Cana flights
Boston to Punta Cana flights
Newark to Providenciales flights
John F Kennedy Intl to Willemstad flights

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 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$152Average$184FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$377Average$460FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$433Average$646FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$444Average$642FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$463Average$647FlexibilityNo cancel feeOn-time62%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.