$148+ 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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
POS — BOS
Jan 29 — Feb 51
1 adult, Economy
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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
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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
Best flights from Trinidad and Tobago to MassachusettsDiscover carefully curated flight deals from Trinidad and Tobago to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 30, 2025.
Discover carefully curated flight deals from Trinidad and Tobago to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 30, 2025.
This United Airlines deal was found by Cheapflights users on 12/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/131:30 amPOS - BOS
2 stops16h 56mUnited Airlines
Wed 2/181:55 pmBOS - POS
1 stop10h 10mUnited Airlines
Deal found 12/28![United Airlines logo]()
$242
This JetBlue deal was found by Cheapflights users on 12/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/138:50 amPOS - BOS
1 stop9h 26mJetBlue
Sat 2/216:15 pmBOS - POS
1 stop12h 02mJetBlue
Deal found 12/28![JetBlue logo]()
$248
This United Airlines deal was found by Cheapflights users on 12/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/121:30 amPOS - BOS
2 stops23h 27mUnited Airlines
Sat 2/217:48 amBOS - POS
2 stops15h 35mUnited Airlines
Deal found 12/28![United Airlines logo]()
$252
Find 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 December 30, 2025.
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $242 (United Airlines) |
One-way from | $148 (United Airlines) |
Popular in | March |
Cheapest in | December |
Average price | $370 |
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 December 30, 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 2/13
1:30 am-5:26 pm
2 stops16h 56m
Boston Logan Intl
Wed 2/18
1:55 pm-1:05 am
1 stop10h 10m
$242
Port of SpainBoston
POS - BOS
POSBOS
Port of Spain Piarco Intl
Fri 2/13
8:50 am-5:16 pm
1 stop9h 26m
Boston Logan Intl
Sat 2/21
6:15 pm-7:17 am
1 stop12h 02m
$248
Port of SpainBoston
POS - BOS
POSBOS
Port of Spain Piarco Intl
Thu 2/12
1:30 am-11:57 pm
2 stops23h 27m
Boston Logan Intl
Sat 2/21
7:48 am-12:23 am
2 stops15h 35m
$252
Port of SpainBoston
POS - BOS
POSBOS
Port of Spain Piarco Intl
Mon 2/9
1:30 am-5:19 pm
2 stops16h 49m
$148
Port of SpainBoston
POS - BOS
POSBOS
Port of Spain Piarco Intl
Mon 2/16
1:30 am-9:31 pm
1 stop21h 01m
$151
Port of SpainBoston
POS - BOS
POSBOS
Port of Spain Piarco Intl
Wed 1/28
6:30 am-10:19 pm
2 stops16h 49m
$174
Port of SpainBoston
POS - BOS
POSBOS
Port of Spain Piarco Intl
Tue 2/17
12:22 pm-11:59 pm
1 stop12h 37m
$183
Port of SpainBoston
POS - BOS
POSBOS
Port of Spain Piarco Intl
Wed 1/7
8:20 am-6:48 pm
1 stop11h 28m
$233
Port of SpainBoston
POS - BOS
POSBOS
Port of Spain Piarco Intl
Wed 1/7
6:30 am-10:19 pm
2 stops16h 49m
$267
Port of SpainBoston
POS - BOS
POSBOS
Port of Spain Piarco Intl
Mon 2/16
3:13 am-11:46 pm
3 stops45h 33m
$284
Showing 1-10 of 13 results
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, May is the cheapest month in which you can book a flight from Trinidad and Tobago to Massachusetts (average of $184). Flying from Trinidad and Tobago to Massachusetts in July is currently the most expensive (average of $554). 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.
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 December 30, 2025.
Get a feel of what it's like to fly with Copa Airlines, United Airlines, and American Airlines 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.
Comfort
7.4
Food
6.8
Boarding
7.8
Entertainment
6.8
Overall
7.6
Crew
8.1
Reviews
1 / 20
2.0
MediocreMaria,Dec 2025
PTY - SLA
Comfort
7.4
Food
6.8
Boarding
7.8
Entertainment
6.8
Overall
7.6
Crew
8.1
Reviews
1 / 20
2.0
MediocreMaria,Dec 2025
PTY - SLA
Comfort
7.4
Food
6.8
Boarding
7.8
Entertainment
6.8
Overall
7.6
Crew
8.1
Reviews
1 / 20
2.0
MediocreMaria,Dec 2025
PTY - SLA
Comfort
7.4
Food
6.8
Boarding
7.8
Entertainment
6.8
Overall
7.6
Crew
8.1
Reviews
1 / 20
2.0
MediocreMaria,Dec 2025
PTY - SLA
Comfort
7.4
Food
6.8
Boarding
7.8
Entertainment
6.8
Overall
7.6
Crew
8.1
Reviews
1 / 20
2.0
MediocreMaria,Dec 2025
PTY - SLA
Comfort
7.4
Food
6.8
Boarding
7.8
Entertainment
6.8
Overall
7.6
Crew
8.1
Reviews
1 / 20
2.0
MediocreMaria,Dec 2025
PTY - SLA
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.
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Alternative routes for Trinidad and Tobago to Massachusetts
See prices for flight routes from nearby airports that may be better suited for you.
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 December 30, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$168 | Average$384 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$184 | Average$448 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$241 | Average$584 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$242 | Average$555 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$459 | Average$613 | FlexibilityNo cancel fee | On-time71% |