HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Trinidad

$101+ Cheap flights from Massachusetts to Trinidad

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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — POS
Feb 19 — Feb 261
Thu 2/19
Thu 2/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Massachusetts to Trinidad 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

Keep the following information in mind while searching for Massachusetts to Trinidad flight deals. Data was last updated January 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$256
(United Airlines)

One-way from

$101
(United Airlines)

Popular in

February

Cheapest in

January

Average price

$475
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
Search Deals
One-way flight from Massachusetts to Trinidad
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Find flight deals from Massachusetts to Trinidad

Cheapest flights from Massachusetts to Trinidad
Explore the most affordable flight options available from Massachusetts to Trinidad. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 20, 2026.

This United Airlines deal was found by Cheapflights users on 1/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:15 am
BOS
-
POS
1 stop16h 08m
United Airlines
Tue 3/1012:30 am
POS
-
BOS
1 stop11h 37m
United Airlines
Deal found 1/19$256
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/185:10 am
BOS
-
POS
1 stop8h 26m
JetBlue
Wed 3/253:26 pm
POS
-
BOS
1 stop8h 24m
JetBlue
Deal found 1/17$269
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/185:30 pm
BOS
-
POS
2 stops20h 40m
American Airlines
Fri 3/273:10 pm
POS
-
BOS
2 stops22h 12m
American Airlines
Deal found 1/18$274
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/37:44 am
BOS
-
POS
1 stop17h 02m
Copa Airlines
Mon 3/93:46 am
POS
-
BOS
1 stop19h 24m
Copa Airlines
Deal found 1/18$278
This United Airlines deal was found by Cheapflights users on 1/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/161:55 pm
BOS
-
POS
1 stop10h 10m
United Airlines
Fri 2/271:30 am
POS
-
BOS
1 stop11h 47m
United Airlines
Deal found 1/19$301
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/247:31 am
BOS
-
POS
1 stop17h 13m
Copa Airlines
Sun 1/253:40 am
POS
-
BOS
1 stop19h 23m
Copa Airlines
Deal found 1/17$322
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:53 pm
BOS
-
POS
2 stops19h 39m
American Airlines
Sat 4/183:47 pm
POS
-
BOS
2 stops18h 33m
American Airlines
Deal found 1/18$324
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:47 am
BOS
-
POS
1 stop17h 00m
Copa Airlines
Mon 10/193:50 am
POS
-
BOS
1 stop19h 12m
Copa Airlines
Deal found 1/17$325
This Expedia deal was found by Cheapflights users on 1/16. 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.
Sun 2/156:55 pm
BOS
-
POS
1 stop11h 22m
JetBlue
Wed 3/118:05 am
POS
-
BOS
1 stop9h 12m
JetBlue
Deal found 1/16$330
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/315:10 am
BOS
-
POS
1 stop13h 01m
JetBlue
Sun 2/18:20 am
POS
-
BOS
1 stop9h 53m
JetBlue
Deal found 1/17$334
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.
Mon 3/26:05 am
BDL
-
POS
2 stops18h 00m
United Airlines
Tue 3/31:30 am
POS
-
BDL
2 stops13h 24m
United Airlines
Deal found 1/17$404

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts to Trinidad 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 20, 2026.
Use the filters below to find and compare flights from Massachusetts to Trinidad that are best for you.

Fly from

Massachusetts

Fly to

Trinidad

Route

Depart

Return

Price

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Wed 3/11

9:32 am-11:23 pm

1 stop13h 51m

Port of Spain Piarco Intl

Mon 3/16

12:30 am-12:07 pm

1 stop11h 37m

$256

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Wed 3/4

7:15 am-12:23 am

1 stop16h 08m

Port of Spain Piarco Intl

Tue 3/10

12:30 am-12:07 pm

1 stop11h 37m

$256

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Wed 3/18

5:10 am-1:36 pm

1 stop8h 26m

Port of Spain Piarco Intl

Wed 3/25

3:26 pm-11:50 pm

1 stop8h 24m

$269

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Tue 3/3

6:54 pm-3:06 pm

2 stops19h 12m

Port of Spain Piarco Intl

Tue 3/10

3:10 pm-10:37 am

2 stops19h 27m

$274

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Tue 3/3

3:05 pm-1:46 am

1 stop9h 41m

Port of Spain Piarco Intl

Mon 3/9

3:46 am-11:10 pm

1 stop19h 24m

$278

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Mon 2/16

1:55 pm-1:05 am

1 stop10h 10m

Port of Spain Piarco Intl

Fri 2/27

1:30 am-12:17 pm

1 stop11h 47m

$301

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Sat 1/24

7:31 am-1:44 am

1 stop17h 13m

Port of Spain Piarco Intl

Sun 1/25

3:40 am-10:03 pm

1 stop19h 23m

$322

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Thu 3/19

5:10 am-1:36 pm

1 stop8h 26m

Port of Spain Piarco Intl

Fri 3/27

3:26 pm-11:50 pm

1 stop8h 24m

$343

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

Mon 3/2

6:05 am-1:05 am

2 stops18h 00m

Port of Spain Piarco Intl

Tue 3/3

1:30 am-1:54 pm

2 stops13h 24m

$404

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

Thu 3/5

6:00 am-12:23 am

2 stops41h 23m

Port of Spain Piarco Intl

Wed 3/11

12:30 am-2:15 pm

2 stops13h 45m

$419

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/17

Showing 1-10 of 18 results
1
2

Best time to book a flight from Massachusetts to Trinidad

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

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

Currently, December is the cheapest month in which you can book a flight from Massachusetts to Trinidad (average of $164). Flying from Massachusetts to Trinidad in August is currently the most expensive (average of $510). 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.

Related info for your journey

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

    Airlines like United Airlines fly from Massachusetts to Trinidad in about 13h 51m. The time it takes to get you to your destination can typically vary by up to . There are 2270 mi between Massachusetts and Trinidad.

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

    $120 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Air Canada and JetBlue, with prices starting from $144 and $202, respectively.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Massachusetts to Trinidad 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?

    Currently, December is the cheapest month in which you can book a flight from Massachusetts to Trinidad (average of $164). Flying from Massachusetts to Trinidad in August is currently the most expensive (average of $510). 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

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Port of Spain flights
Newark to Port of Spain flights
LaGuardia to Port of Spain flights
Miami to Port of Spain flights
Fort Lauderdale to Port of Spain flights
Atlanta to Port of Spain flights
Dulles Intl to Port of Spain flights
Reagan-National to Port of Spain flights
Orlando to Port of Spain flights
Baltimore to Port of Spain flights
Dallas/Fort Worth to Port of Spain flights
Boston to Port of Spain flights
Hobby to Port of Spain flights
George Bush Intcntl to Port of Spain flights
O'Hare Intl to Port of Spain flights
John F Kennedy Intl to Scarborough flights
Tampa to Port of Spain flights
Sky Harbor Intl to Port of Spain flights
Raleigh to Port of Spain flights
Los Angeles to Port of Spain flights
Detroit to Port of Spain flights
Miami to Scarborough flights
San Francisco to Port of Spain flights
Philadelphia to Port of Spain flights
West Palm Beach to Port of Spain flights
Denver to Port of Spain flights
Minneapolis to Port of Spain flights
Charlotte to Port of Spain flights
Las Vegas to Port of Spain flights
Norfolk to Port of Spain flights
Jacksonville to Port of Spain flights
Cleveland to Port of Spain flights
Fort Lauderdale to Scarborough flights
New Orleans to Port of Spain flights
Indianapolis to Port of Spain flights
Newark to Scarborough flights
Austin to Port of Spain flights
Charleston to Port of Spain flights
Pittsburgh to Port of Spain flights
Richmond to Port of Spain flights
Kansas City to Port of Spain flights
Providence to Port of Spain flights
Seattle to Port of Spain flights
Greenville to Port of Spain flights
Salt Lake City to Port of Spain flights
San Diego to Port of Spain flights
Roanoke to Port of Spain flights
Reagan-National to Scarborough flights
Santa Ana to Port of Spain flights

Top 5 airlines flying from Massachusetts to Trinidad

Discover the top 5 airlines that operate flights from Massachusetts to Trinidad. 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 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$164Average$492FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$195Average$432FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$260Average$617FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$280Average$601FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$459Average$591FlexibilityNo cancel feeOn-time71%

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.