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Trinidad and Tobago

$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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — POS
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
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 julio 31, 2025.

Round-trip from

$437
(Air Canada)

One-way from

$236
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$579
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. 7% potential increase in price ($54 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in July 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 julio 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.
lun. 9/1510:40 amBOS - POS
1 stop14h 40mAir Canada
dom. 9/212:25 amPOS - BOS
1 stop15h 45mAir Canada
Deal found 7/30$437
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.
vie. 10/177:00 amBOS - POS
1 stop14h 20mAmerican Airlines
mié. 10/293:25 pmPOS - BOS
1 stop9h 09mAmerican Airlines
Deal found 7/30$454
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.
dom. 9/142:18 pmBOS - POS
1 stop13h 57mMultiple Airlines
sáb. 9/209:10 amPOS - BOS
1 stop28h 13mMultiple Airlines
Deal found 7/30$470
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/167:08 amBOS - POS
1 stop7h 26mJetBlue
jue. 9/253:59 pmPOS - BOS
1 stop8h 15mJetBlue
Deal found 7/30$524
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.
mié. 10/17:15 amBDL - POS
1 stop7h 19mJetBlue
mié. 10/83:59 pmPOS - BDL
1 stop30h 02mJetBlue
Deal found 7/30$536
This Mytrip deal was found by Cheapflights users on 7/29. 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.
lun. 10/2010:20 amBOS - TAB
3 stops19h 50mMultiple Airlines
dom. 10/2612:25 pmTAB - BOS
2 stops35h 30mMultiple Airlines
Deal found 7/29$574
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.
mié. 10/15:49 pmBDL - POS
2 stops20h 27mAmerican Airlines
mié. 10/87:00 amPOS - BDL
2 stops12h 18mAmerican Airlines
Deal found 7/30$583
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.
mié. 10/16:00 amBDL - POS
2 stops17h 23mUnited Airlines
mar. 10/712:30 amPOS - BDL
2 stops18h 22mUnited Airlines
Deal found 7/30$623
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.
dom. 8/37:00 amBDL - POS
2 stops13h 00mMultiple Airlines
mar. 8/511:10 amPOS - BDL
3 stops35h 47mMultiple Airlines
Deal found 7/30$863

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 julio 31, 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

lun. 9/15

10:40 am-1:20 am

1 stop14h 40m

Port of Spain Piarco Intl

dom. 9/21

2:25 am-6:10 pm

1 stop15h 45m

$437

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

vie. 10/17

7:00 am-9:20 pm

1 stop14h 20m

Port of Spain Piarco Intl

mié. 10/29

3:25 pm-12:34 am

1 stop9h 09m

$454

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

dom. 9/14

2:18 pm-4:15 am

1 stop13h 57m

Port of Spain Piarco Intl

sáb. 9/20

9:10 am-1:23 pm

1 stop28h 13m

$470

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

mar. 9/16

7:08 am-2:34 pm

1 stop7h 26m

Port of Spain Piarco Intl

jue. 9/25

3:59 pm-12:14 am

1 stop8h 15m

$524

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

mié. 10/1

7:15 am-2:34 pm

1 stop7h 19m

Port of Spain Piarco Intl

mié. 10/8

3:59 pm-10:01 pm

1 stop30h 02m

$536

BostonScarborough

BOS - TAB

BOSTAB

Boston Logan Intl

lun. 10/20

10:20 am-6:10 am

3 stops19h 50m

Scarborough ANR Robinson Intl

dom. 10/26

12:25 pm-11:55 pm

2 stops35h 30m

$574

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

mié. 10/1

5:49 pm-2:16 pm

2 stops20h 27m

Port of Spain Piarco Intl

mié. 10/8

7:00 am-7:18 pm

2 stops12h 18m

$583

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

mié. 10/1

6:00 am-11:23 pm

2 stops17h 23m

Port of Spain Piarco Intl

mar. 10/7

12:30 am-6:52 pm

2 stops18h 22m

$623

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

mié. 10/1

7:53 pm-1:25 am

3 stops29h 32m

Port of Spain Piarco Intl

mié. 10/8

4:20 pm-2:10 pm

2 stops21h 50m

$3,413

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

mié. 10/22

7:10 am-9:20 pm

2 stops14h 10m

$236

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 14 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 julio 31, 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.

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 julio 31, 2025.
Read reviews from past customers who have flown United Airlines, JetBlue, and American Airlines from Massachusetts to Trinidad and Tobago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,900 reviews

Overall

7.4

Crew

8.1

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Food

6.6

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
United Airlines
7.4
Good
8,900 reviews
United Airlines
7.4
Good
8,900 reviews

Overall

7.4

Crew

8.1

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Food

6.6

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
JetBlue
7.3
Good
2,914 reviews
United Airlines
7.4
Good
8,900 reviews

Overall

7.4

Crew

8.1

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Food

6.6

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,900 reviews

Overall

7.4

Crew

8.1

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Food

6.6

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
Air Canada
7.1
Good
9,851 reviews
United Airlines
7.4
Good
8,900 reviews

Overall

7.4

Crew

8.1

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Food

6.6

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

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. JetBlue flights start at $337 while deals on Air Canada start at $610 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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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.
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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 julio 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$152Average$181FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$400Average$452FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$433Average$649FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$433Average$622FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$459Average$623FlexibilityNo cancel feeOn-time62%

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