HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Massachusetts

$273+ 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 11/8. Fares are subject to change and may not be available on all flights or dates of travel.
POS — BOS
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Trinidad and Tobago to Massachusetts 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 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 July 31, 2025.

Round-trip from

$448
(Air Canada)

One-way from

$273
(Copa Airlines)

Popular in

March

Cheapest in

May

Average price

$663
From Trinidad and Tobago to Massachusetts
Search Deals
One-way flight from Trinidad and Tobago to Massachusetts
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($96 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

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 July 31, 2025.

This Air Canada deal was found by Cheapflights users on 7/30. 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 9/122:25 amPOS - BOS
1 stop20h 14mAir Canada
Sun 9/146:00 amBOS - POS
1 stop19h 20mAir Canada
Deal found 7/30$448
This Mytrip deal was found by Cheapflights users on 7/30. 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 9/510:10 amPOS - BOS
1 stop13h 47mMultiple Airlines
Sun 9/72:18 pmBOS - POS
1 stop13h 57mMultiple Airlines
Deal found 7/30$467
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 10/1610:10 amPOS - BDL
1 stop24h 25mMultiple Airlines
Mon 10/2711:30 amBDL - POS
2 stops14h 16mMultiple Airlines
Deal found 7/30$524
This United Airlines deal was found by Cheapflights users on 7/30. 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 10/1512:30 amPOS - BDL
2 stops41h 02mUnited Airlines
Mon 10/276:10 pmBDL - POS
2 stops29h 13mUnited Airlines
Deal found 7/30$555
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Thu 9/1112:30 amPOS - BOS
1 stop22h 58mUnited Airlines
Thu 9/187:10 amBOS - POS
2 stops16h 13mUnited Airlines
Deal found 7/30$555
This American Airlines deal was found by Cheapflights users on 7/30. 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 8/283:35 pmPOS - BOS
1 stop9h 13mAmerican Airlines
Tue 9/95:47 amBOS - POS
1 stop8h 29mAmerican Airlines
Deal found 7/30$574
This Expedia deal was found by Cheapflights users on 7/30. 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.
Thu 10/163:59 pmPOS - BDL
1 stop30h 02mJetBlue
Mon 10/277:00 amBDL - POS
1 stop7h 10mJetBlue
Deal found 7/30$587
This deal was found by Cheapflights users on 7/31. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/163:59 pmPOS - BOS
1 stop8h 15mJetBlue
Sat 9/207:08 amBOS - POS
1 stop7h 30mJetBlue
Deal found 7/31$620
This American Airlines deal was found by Cheapflights users on 7/30. 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 10/163:25 pmPOS - BDL
2 stops21h 39mAmerican Airlines
Mon 10/278:22 amBDL - POS
2 stops12h 58mAmerican Airlines
Deal found 7/30$639

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 July 31, 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

Fri 9/12

2:25 am-9:55 am

1 stop31h 30m

Boston Logan Intl

Sun 9/14

6:55 pm-1:20 am

1 stop30h 25m

$448

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Fri 9/5

10:10 am-11:57 pm

1 stop13h 47m

Boston Logan Intl

Sun 9/7

2:18 pm-4:15 am

1 stop13h 57m

$467

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Thu 9/11

12:30 am-11:28 pm

1 stop22h 58m

Boston Logan Intl

Mon 9/15

8:27 pm-11:23 pm

2 stops26h 56m

$482

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Thu 8/28

7:00 am-11:45 pm

1 stop16h 45m

Boston Logan Intl

Tue 9/9

5:47 am-2:16 pm

1 stop8h 29m

$484

Port of SpainHartford

POS - BDL

POSBDL

Port of Spain Piarco Intl

Thu 10/16

10:10 am-10:35 am

1 stop24h 25m

Hartford Bradley Intl

Mon 10/27

11:30 am-1:46 am

2 stops14h 16m

$524

Port of SpainHartford

POS - BDL

POSBDL

Port of Spain Piarco Intl

Wed 10/15

12:30 am-5:32 pm

2 stops41h 02m

Hartford Bradley Intl

Mon 10/27

6:10 pm-11:23 pm

2 stops29h 13m

$555

Port of SpainHartford

POS - BDL

POSBDL

Port of Spain Piarco Intl

Thu 10/16

3:59 pm-10:01 pm

1 stop30h 02m

Hartford Bradley Intl

Mon 10/27

7:00 am-2:10 pm

1 stop7h 10m

$587

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Tue 9/16

3:59 pm-12:14 am

1 stop8h 15m

Boston Logan Intl

Sat 9/20

7:08 am-2:38 pm

1 stop7h 30m

$620

Port of SpainHartford

POS - BDL

POSBDL

Port of Spain Piarco Intl

Thu 10/16

3:25 pm-1:04 pm

2 stops21h 39m

Hartford Bradley Intl

Mon 10/27

8:22 am-9:20 pm

2 stops12h 58m

$639

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Sat 11/8

3:48 am-10:03 pm

1 stop19h 15m

$273

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 13 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 July 31, 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.

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 July 31, 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. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.5
Good
1,493 reviews

Food

6.8

Overall

7.5

Crew

8.1

Boarding

7.8

Entertainment

6.8

Comfort

7.4

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
Copa Airlines
7.5
Good
1,493 reviews
Copa Airlines
7.5
Good
1,493 reviews

Food

6.8

Overall

7.5

Crew

8.1

Boarding

7.8

Entertainment

6.8

Comfort

7.4

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
United Airlines
7.4
Good
8,900 reviews
Copa Airlines
7.5
Good
1,493 reviews

Food

6.8

Overall

7.5

Crew

8.1

Boarding

7.8

Entertainment

6.8

Comfort

7.4

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
JetBlue
7.3
Good
2,914 reviews
Copa Airlines
7.5
Good
1,493 reviews

Food

6.8

Overall

7.5

Crew

8.1

Boarding

7.8

Entertainment

6.8

Comfort

7.4

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
American Airlines
7.2
Good
10,000 reviews
Copa Airlines
7.5
Good
1,493 reviews

Food

6.8

Overall

7.5

Crew

8.1

Boarding

7.8

Entertainment

6.8

Comfort

7.4

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
Air Canada
7.1
Good
9,851 reviews
Copa Airlines
7.5
Good
1,493 reviews

Food

6.8

Overall

7.5

Crew

8.1

Boarding

7.8

Entertainment

6.8

Comfort

7.4

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.

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 $273 on Copa Airlines. Other airlines that offer cheap prices include United Airlines from $314 and American Airlines from $319 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

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 Trinidad and Tobago to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
Luis Munoz Marin Intl to Orlando flights
Luis Munoz Marin Intl to John F Kennedy Intl flights
Luis Munoz Marin Intl to Newark flights
Santo Domingo to John F Kennedy Intl flights
Santo Domingo to Newark flights
Luis Munoz Marin Intl to LaGuardia flights
Santiago de los Caballeros to John F Kennedy Intl flights
Luis Munoz Marin Intl to O'Hare Intl flights
Luis Munoz Marin Intl to Fort Lauderdale flights
Luis Munoz Marin Intl to Tampa flights
Luis Munoz Marin Intl to Miami flights
Aguadilla to Orlando flights
Santiago de los Caballeros to Newark flights
Port of Spain to John F Kennedy Intl flights
Luis Munoz Marin Intl to Philadelphia flights
Luis Munoz Marin Intl to Midway flights
Santo Domingo to LaGuardia flights
Santo Domingo to Boston flights
Luis Munoz Marin Intl to Boston flights
Ponce to Orlando flights
Luis Munoz Marin Intl to Dallas/Fort Worth flights
Luis Munoz Marin Intl to Atlanta flights
Santo Domingo to Orlando flights
Nassau to Fort Lauderdale flights
Port of Spain to Miami flights
Luis Munoz Marin Intl to Hartford flights
Luis Munoz Marin Intl to Hobby flights
Santo Domingo to Miami flights
Kingston to John F Kennedy Intl flights
Luis Munoz Marin Intl to Reagan-National flights
Nassau to Orlando flights
Luis Munoz Marin Intl to Las Vegas flights
Montego Bay to John F Kennedy Intl flights
Luis Munoz Marin Intl to Denver flights
Luis Munoz Marin Intl to Baltimore flights
Kingston to Fort Lauderdale flights
Luis Munoz Marin Intl to George Bush Intcntl flights
Santo Domingo to Fort Lauderdale flights
Nassau to Miami flights
Bridgetown to John F Kennedy Intl flights
Luis Munoz Marin Intl to Dulles Intl flights
Punta Cana to John F Kennedy Intl flights
Luis Munoz Marin Intl to Austin flights
Luis Munoz Marin Intl to Charlotte flights
Luis Munoz Marin Intl to Seattle flights
Santiago de los Caballeros to LaGuardia flights
Luis Munoz Marin Intl to Los Angeles flights
Luis Munoz Marin Intl to Raleigh flights
Luis Munoz Marin Intl to Milwaukee flights
Port of Spain to Newark flights

Top 5 airlines flying from Trinidad and Tobago to Massachusetts

Discover the top 5 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$184Average$448FlexibilityNo cancel feeOn-time67%
Copa AirlinesCheapest$329Average$418FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$408Average$599FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$451Average$556FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$492Average$655FlexibilityNo 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.