$114+ 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 3/14. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — POS
Mar 16 — Mar 231
1 adult, Economy
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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
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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 Massachusetts to Trinidad and Tobago
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Cheapest flights from Massachusetts to Trinidad and TobagoExplore 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 February 14, 2026.
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 February 14, 2026.
This American Airlines deal was found by Cheapflights users on 2/12. 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.
Sun 3/156:05 pm
BDL
- POS
2 stops20h 05m
American Airlines
Wed 3/183:10 pm
POS
- BDL
2 stops19h 00m
American Airlines
Deal found 2/12![American Airlines logo]()
$274
This American Airlines deal was found by Cheapflights users on 2/11. 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.
Fri 4/105:40 pm
BOS
- POS
2 stops20h 52m
American Airlines
Fri 5/13:47 pm
POS
- BOS
2 stops19h 25m
American Airlines
Deal found 2/11![American Airlines logo]()
$274
This American Airlines deal was found by Cheapflights users on 2/13. 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 5/75:30 pm
BOS
- POS
2 stops21h 02m
American Airlines
Sun 5/103:47 pm
POS
- BOS
2 stops21h 31m
American Airlines
Deal found 2/13![American Airlines logo]()
$279
This Copa Airlines deal was found by Cheapflights users on 2/13. 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.
Wed 4/153:51 pm
BOS
- POS
1 stop9h 49m
Copa Airlines
Mon 4/203:44 am
POS
- BOS
1 stop10h 47m
Copa Airlines
Deal found 2/13![Copa Airlines logo]()
$280
This American Airlines deal was found by Cheapflights users on 2/13. 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.
Sun 5/33:06 pm
BDL
- POS
1 stop23h 26m
American Airlines
Thu 5/73:47 pm
POS
- BDL
2 stops22h 10m
American Airlines
Deal found 2/13![American Airlines logo]()
$282
This United Airlines deal was found by Cheapflights users on 2/12. 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 7/15:45 am
BOS
- POS
1 stop17h 38m
United Airlines
Sat 7/42:00 am
POS
- BOS
1 stop9h 46m
United Airlines
Deal found 2/12![United Airlines logo]()
$282
This United Airlines deal was found by Cheapflights users on 2/11. 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 4/157:25 am
BOS
- POS
1 stop15h 58m
United Airlines
Mon 4/2012:30 am
POS
- BOS
2 stops14h 18m
United Airlines
Deal found 2/11![United Airlines logo]()
$283
This American Airlines deal was found by Cheapflights users on 2/12. 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.
Fri 2/277:50 pm
BOS
- POS
2 stops18h 16m
American Airlines
Thu 3/54:06 pm
POS
- BOS
2 stops20h 19m
American Airlines
Deal found 2/12![American Airlines logo]()
$286
This American Airlines deal was found by Cheapflights users on 2/10. 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 4/155:25 pm
BDL
- POS
2 stops21h 07m
American Airlines
Wed 4/223:47 pm
POS
- BDL
2 stops22h 10m
American Airlines
Deal found 2/10![American Airlines logo]()
$294
This American Airlines deal was found by Cheapflights users on 2/10. 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 4/155:40 pm
BOS
- POS
2 stops20h 52m
American Airlines
Tue 4/213:47 pm
POS
- BOS
1 stop18h 15m
American Airlines
Deal found 2/10![American Airlines logo]()
$294
This United Airlines deal was found by Cheapflights users on 2/12. 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.
Sat 5/169:45 am
BOS
- POS
1 stop13h 38m
United Airlines
Mon 5/1812:30 am
POS
- BOS
1 stop11h 46m
United Airlines
Deal found 2/12![United Airlines logo]()
$295
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 2/247:15 pm
BDL
- POS
2 stops18h 51m
American Airlines
Fri 2/274:06 pm
POS
- BDL
2 stops21h 59m
American Airlines
Deal found 2/10![American Airlines logo]()
$298
Best flights from Massachusetts to Trinidad and TobagoDiscover carefully curated flight deals from Massachusetts to Trinidad and Tobago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 14, 2026.
Discover carefully curated flight deals from Massachusetts to Trinidad and Tobago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 14, 2026.
This American Airlines deal was found by Cheapflights users on 2/12. 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.
Sun 3/156:05 pm
BDL
- POS
2 stops20h 05m
American Airlines
Wed 3/183:10 pm
POS
- BDL
2 stops19h 00m
American Airlines
Deal found 2/12![American Airlines logo]()
$274
This Copa Airlines deal was found by Cheapflights users on 2/10. 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.
Wed 4/153:51 pm
BOS
- POS
1 stop9h 49m
Copa Airlines
Mon 4/203:44 am
POS
- BOS
1 stop19h 25m
Copa Airlines
Deal found 2/10![Copa Airlines logo]()
$280
This United Airlines deal was found by Cheapflights users on 2/12. 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 7/15:45 am
BOS
- POS
1 stop17h 38m
United Airlines
Sat 7/42:00 am
POS
- BOS
1 stop9h 46m
United Airlines
Deal found 2/12![United Airlines logo]()
$282
This American Airlines deal was found by Cheapflights users on 2/12. 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 4/155:25 pm
BDL
- POS
2 stops21h 07m
American Airlines
Wed 4/223:47 pm
POS
- BDL
2 stops18h 25m
American Airlines
Deal found 2/12![American Airlines logo]()
$274
This Copa Airlines deal was found by Cheapflights users on 2/11. 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.
Wed 4/153:51 pm
BOS
- POS
1 stop9h 49m
Copa Airlines
Tue 4/213:44 am
POS
- BOS
1 stop19h 25m
Copa Airlines
Deal found 2/11![Copa Airlines logo]()
$280
This United Airlines deal was found by Cheapflights users on 2/10. 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 3/109:20 am
BOS
- POS
2 stops14h 03m
United Airlines
Mon 3/1612:30 am
POS
- BOS
2 stops16h 49m
United Airlines
Deal found 2/10![United Airlines logo]()
$283
This American Airlines deal was found by Cheapflights users on 2/11. 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.
Sat 5/95:40 pm
BOS
- POS
2 stops20h 52m
American Airlines
Tue 5/193:47 pm
POS
- BOS
2 stops21h 10m
American Airlines
Deal found 2/11![American Airlines logo]()
$274
This Copa Airlines deal was found by Cheapflights users on 2/10. 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.
Thu 4/23:51 pm
BOS
- POS
1 stop9h 49m
Copa Airlines
Wed 4/83:44 am
POS
- BOS
1 stop10h 50m
Copa Airlines
Deal found 2/10![Copa Airlines logo]()
$280
This American Airlines deal was found by Cheapflights users on 2/12. 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
Tue 4/213:47 pm
POS
- BOS
2 stops19h 17m
American Airlines
Deal found 2/12![American Airlines logo]()
$274
This American Airlines deal was found by Cheapflights users on 2/13. 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.
Sun 5/33:06 pm
BDL
- POS
1 stop23h 26m
American Airlines
Thu 5/73:47 pm
POS
- BDL
2 stops22h 10m
American Airlines
Deal found 2/13![American Airlines logo]()
$282
This United Airlines deal was found by Cheapflights users on 2/10. 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 40m
United Airlines
Deal found 2/10![United Airlines logo]()
$396
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 2/247:15 pm
BDL
- POS
2 stops18h 51m
American Airlines
Fri 2/274:06 pm
POS
- BDL
2 stops21h 59m
American Airlines
Deal found 2/10![American Airlines logo]()
$298
This Mytrip deal was found by Cheapflights users on 2/11. 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.
Sat 3/284:35 pm
BOS
- TAB
2 stops27h 30m
Multiple Airlines
Sat 4/410:20 pm
TAB
- BOS
2 stops25h 39m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$1,042
Last-minute flights from Massachusetts to Trinidad and TobagoDiscover last-minute flight deals from Massachusetts to Trinidad and Tobago. Data last updated February 14, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Trinidad and Tobago. Data last updated February 14, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 2/13. 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.
Mon 2/236:25 pm
BOS
- POS
1 stop19h 41m
American Airlines
Fri 2/274:06 pm
POS
- BOS
2 stops23h 08m
American Airlines
Deal found 2/13![American Airlines logo]()
$318
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 2/247:15 pm
BDL
- POS
2 stops18h 51m
American Airlines
Fri 2/274:06 pm
POS
- BDL
2 stops21h 59m
American Airlines
Deal found 2/10![American Airlines logo]()
$298
This American Airlines deal was found by Cheapflights users on 2/12. 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.
Fri 2/277:50 pm
BOS
- POS
2 stops18h 16m
American Airlines
Thu 3/54:06 pm
POS
- BOS
2 stops20h 19m
American Airlines
Deal found 2/12![American Airlines logo]()
$286
This Cheapflightsfares deal was found by Cheapflights users on 2/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/278:05 pm
BOS
- POS
1 stop10h 12m
JetBlue
Thu 3/59:05 am
POS
- BOS
1 stop11h 53m
JetBlue
Deal found 2/12![JetBlue logo]()
$323
This United Airlines deal was found by Cheapflights users on 2/12. 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 2/271:55 pm
BOS
- POS
1 stop10h 10m
United Airlines
Wed 3/42:20 am
POS
- BOS
1 stop9h 50m
United Airlines
Deal found 2/12![United Airlines logo]()
$331
This JetBlue deal was found by Cheapflights users on 2/9. 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.
Sat 2/287:39 pm
BOS
- POS
1 stop10h 38m
JetBlue
Wed 3/49:05 am
POS
- BOS
1 stop9h 10m
JetBlue
Deal found 2/9![JetBlue logo]()
$308
This American Airlines deal was found by Cheapflights users on 2/11. 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.
Sat 2/285:30 pm
BOS
- POS
2 stops20h 36m
American Airlines
Sun 3/83:10 pm
POS
- BOS
2 stops20h 26m
American Airlines
Deal found 2/11![American Airlines logo]()
$311
This United Airlines deal was found by Cheapflights users on 2/10. 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 3/109:20 am
BOS
- POS
2 stops14h 03m
United Airlines
Mon 3/1612:30 am
POS
- BOS
2 stops16h 49m
United Airlines
Deal found 2/10![United Airlines logo]()
$283
This American Airlines deal was found by Cheapflights users on 2/9. 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 3/115:30 pm
BOS
- POS
2 stops20h 40m
American Airlines
Wed 3/183:10 pm
POS
- BOS
2 stops18h 55m
American Airlines
Deal found 2/9![American Airlines logo]()
$294
This Copa Airlines deal was found by Cheapflights users on 2/9. 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.
Wed 3/114:05 pm
BOS
- POS
1 stop9h 41m
Copa Airlines
Tue 3/173:46 am
POS
- BOS
1 stop19h 24m
Copa Airlines
Deal found 2/9![Copa Airlines logo]()
$301
This American Airlines deal was found by Cheapflights users on 2/12. 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.
Sun 3/156:05 pm
BDL
- POS
2 stops20h 05m
American Airlines
Wed 3/183:10 pm
POS
- BDL
2 stops19h 00m
American Airlines
Deal found 2/12![American Airlines logo]()
$274
This FlightHub deal was found by Cheapflights users on 2/10. 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.
Wed 3/184:40 pm
BOS
- POS
1 stop31h 40m
Multiple Airlines
Fri 3/273:29 pm
POS
- BOS
1 stop8h 21m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$317
One-way flights from Massachusetts to Trinidad and TobagoSearch for one-way flight options from Massachusetts to Trinidad and Tobago. Find affordable one-way fares based on user searches. Data last updated February 14, 2026.
Search for one-way flight options from Massachusetts to Trinidad and Tobago. Find affordable one-way fares based on user searches. Data last updated February 14, 2026.
This American Airlines deal was found by Cheapflights users on 2/12. 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.
Sat 3/149:58 am
BDL
- POS
2 stops28h 12m
American Airlines
Deal found 2/12![American Airlines logo]()
$114
This FlightHub deal was found by Cheapflights users on 2/10. 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.
Wed 2/184:35 pm
BOS
- POS
1 stop31h 45m
Air Canada
Deal found 2/10![Air Canada logo]()
$149
This Air Canada deal was found by Cheapflights users on 2/13. 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 4/31:00 pm
BOS
- POS
1 stop11h 20m
Air Canada
Deal found 2/13![Air Canada logo]()
$169
This Booking.com deal was found by Cheapflights users on 2/9. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/185:45 am
BOS
- POS
2 stops42h 30m
Air Canada
Deal found 2/9![Air Canada logo]()
$195
This United Airlines deal was found by Cheapflights users on 2/9. 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 6/185:45 am
BOS
- POS
1 stop17h 38m
United Airlines
Deal found 2/9![United Airlines logo]()
$212
This Cheapflightsfares deal was found by Cheapflights users on 2/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/146:00 am
BDL
- POS
1 stop7h 36m
JetBlue
Deal found 2/12![JetBlue logo]()
$269
This Mytrip deal was found by Cheapflights users on 2/11. 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.
Wed 2/189:57 am
BOS
- POS
3 stops38h 23m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
Sat 3/148:08 pm
BDL
- POS
3 stops22h 47m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 2/13. 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.
Fri 4/34:23 pm
BOS
- POS
3 stops20h 47m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$429
This Booking.com deal was found by Cheapflights users on 2/9. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/185:45 am
BOS
- POS
3 stops19h 40m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$689
Find 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 February 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $274 (American Airlines) |
One-way from | $114 (American Airlines) |
Popular in | February |
Cheapest in | January |
Average price | $769 |
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 February 14, 2026.
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
HartfordPort of Spain
BDL - POS
BDLPOS
Hartford Bradley Intl
Sun 3/15
6:05 pm-2:10 pm
2 stops20h 05m
Port of Spain Piarco Intl
Wed 3/18
3:10 pm-10:10 am
2 stops19h 00m
$274
HartfordPort of Spain
BDL - POS
BDLPOS
Hartford Bradley Intl
Wed 4/15
5:25 pm-2:32 pm
2 stops21h 07m
Port of Spain Piarco Intl
Wed 4/22
3:47 pm-10:12 am
2 stops18h 25m
$274
BostonPort of Spain
BOS - POS
BOSPOS
Boston Logan Intl
Sat 5/9
5:40 pm-2:32 pm
2 stops20h 52m
Port of Spain Piarco Intl
Tue 5/19
3:47 pm-12:57 pm
2 stops21h 10m
$274
BostonPort of Spain
BOS - POS
BOSPOS
Boston Logan Intl
Wed 4/15
6:53 pm-2:32 pm
2 stops19h 39m
Port of Spain Piarco Intl
Tue 4/21
3:47 pm-11:04 am
2 stops19h 17m
$274
BostonPort of Spain
BOS - POS
BOSPOS
Boston Logan Intl
Wed 4/15
3:51 pm-1:40 am
1 stop9h 49m
Port of Spain Piarco Intl
Mon 4/20
3:44 am-11:09 pm
1 stop19h 25m
$280
BostonPort of Spain
BOS - POS
BOSPOS
Boston Logan Intl
Wed 4/15
3:51 pm-1:40 am
1 stop9h 49m
Port of Spain Piarco Intl
Tue 4/21
3:44 am-11:09 pm
1 stop19h 25m
$280
BostonPort of Spain
BOS - POS
BOSPOS
Boston Logan Intl
Thu 4/2
3:51 pm-1:40 am
1 stop9h 49m
Port of Spain Piarco Intl
Wed 4/8
3:44 am-2:34 pm
1 stop10h 50m
$280
BostonPort of Spain
BOS - POS
BOSPOS
Boston Logan Intl
Wed 7/1
5:45 am-11:23 pm
1 stop17h 38m
Port of Spain Piarco Intl
Sat 7/4
2:00 am-11:46 am
1 stop9h 46m
$282
HartfordPort of Spain
BDL - POS
BDLPOS
Hartford Bradley Intl
Sun 5/3
3:06 pm-2:32 pm
1 stop23h 26m
Port of Spain Piarco Intl
Thu 5/7
3:47 pm-1:57 pm
2 stops22h 10m
$282
BostonPort of Spain
BOS - POS
BOSPOS
Boston Logan Intl
Tue 3/10
9:20 am-11:23 pm
2 stops14h 03m
Port of Spain Piarco Intl
Mon 3/16
12:30 am-5:19 pm
2 stops16h 49m
$283
Showing 1-10 of 21 results
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.
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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
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What is the cheapest month to book a flight from Massachusetts to Trinidad and Tobago?
Currently, December is the cheapest month in which you can book a flight from Massachusetts to Trinidad and Tobago (average of $164). Flying from Massachusetts to Trinidad and Tobago in June is currently the most expensive (average of $506). 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 and Tobago. 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 Massachusetts to Trinidad and Tobago
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Trinidad and Tobago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Massachusetts to Trinidad and Tobago by cabin class
Find flights from Massachusetts to Trinidad and Tobago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Massachusetts and Trinidad and Tobago flights
Browse other Massachusetts and Trinidad and Tobago flight options. Last updated on February 14, 2026.
Popular flight searches
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Find a return flight route from Trinidad and Tobago
Find the right flight back to Massachusetts after your stay in Trinidad and Tobago
Massachusetts to Trinidad and Tobago flights
Consider these flights traveling from Massachusetts to Trinidad and Tobago.
Fly to Trinidad and Tobago regions
Consider these flights traveling to Trinidad and Tobago regions.
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 February 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$164 | Average$492 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$195 | Average$432 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$260 | Average$617 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$280 | Average$570 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$490 | Average$597 | FlexibilityNo cancel fee | On-time71% |