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Port of Spain

$100+ Cheap flights from Massachusetts to Port of Spain (POS)

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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — POS
Mar 7 — Mar 141
Sat 3/7
Sat 3/14
1 adult, Economy
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Cheap flight deals from Massachusetts to Port of Spain

Cheapest flights from Massachusetts to Port of Spain
Explore the most affordable flight options available from Massachusetts to Port of Spain. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 5, 2026.

This United Airlines deal was found by Cheapflights users on 2/1. 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 3/119:32 am
BOS
-
POS
1 stop13h 51m
United Airlines
Mon 3/1612:30 am
POS
-
BOS
1 stop11h 37m
United Airlines
Deal found 2/1$256
This Cheapflightsfares deal was found by Cheapflights users on 2/2. 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 3/68:04 pm
BOS
-
POS
1 stop10h 13m
JetBlue
Mon 3/98:05 am
POS
-
BOS
1 stop11h 53m
JetBlue
Deal found 2/2$268
This JetBlue deal was found by Cheapflights users on 2/1. 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 stop11h 53m
JetBlue
Deal found 2/1$269
This American Airlines deal was found by Cheapflights users on 2/3. 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 3/165:24 pm
BDL
-
POS
2 stops20h 46m
American Airlines
Thu 3/193:10 pm
POS
-
BDL
2 stops19h 58m
American Airlines
Deal found 2/3$274
This American Airlines deal was found by Cheapflights users on 2/2. 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 3/24:20 pm
BOS
-
POS
2 stops21h 46m
American Airlines
Mon 3/93:10 pm
POS
-
BOS
2 stops19h 36m
American Airlines
Deal found 2/2$274
This United Airlines deal was found by Cheapflights users on 2/4. 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 10/286:00 am
BOS
-
POS
2 stops17h 23m
United Airlines
Tue 11/31:30 am
POS
-
BOS
1 stop12h 05m
United Airlines
Deal found 2/4$275
This Copa Airlines deal was found by Cheapflights users on 2/4. 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 10/284:07 pm
BOS
-
POS
1 stop9h 37m
Copa Airlines
Tue 11/33:40 am
POS
-
BOS
1 stop10h 59m
Copa Airlines
Deal found 2/4$278
This Cheapflightsfares deal was found by Cheapflights users on 2/2. 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.
Thu 3/55:32 pm
BOS
-
POS
1 stop12h 45m
JetBlue
Sun 3/88:45 am
POS
-
BOS
1 stop9h 02m
JetBlue
Deal found 2/2$284
This American Airlines deal was found by Cheapflights users on 2/2. 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 3/191:50 pm
BDL
-
POS
2 stops24h 20m
American Airlines
Tue 3/243:10 pm
POS
-
BDL
2 stops19h 58m
American Airlines
Deal found 2/2$287
This United Airlines deal was found by Cheapflights users on 2/2. 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 10/299:50 am
BOS
-
POS
1 stop13h 33m
United Airlines
Tue 11/31:30 am
POS
-
BOS
2 stops16h 58m
United Airlines
Deal found 2/2$289
This Copa Airlines deal was found by Cheapflights users on 2/3. 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.
Mon 3/164:05 pm
BOS
-
POS
1 stop9h 41m
Copa Airlines
Wed 3/183:46 am
POS
-
BOS
1 stop19h 24m
Copa Airlines
Deal found 2/3$300
This United Airlines deal was found by Cheapflights users on 2/2. 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 2/214:15 pm
BOS
-
POS
1 stop7h 50m
United Airlines
Thu 2/262:20 am
POS
-
BOS
1 stop9h 35m
United Airlines
Deal found 2/2$302

Find flight deals from Massachusetts to Port of Spain

Keep the following information in mind while searching for Massachusetts to Port of Spain flight deals. Data was last updated February 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$256
(United Airlines)

One-way from

$100
(Cheapflightsfares)

Popular in

February

Cheapest in

January

Average price

$769
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 Port of Spain Piarco Intl
Search Deals
One-way flight from Massachusetts to Port of Spain Piarco Intl
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($44 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 February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts to Port of Spain 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 5, 2026.
Use the filters below to find and compare flights from Massachusetts to Port of Spain that are best for you.

Fly from

Massachusetts

Fly to

Port of Spain

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

Fri 3/6

8:04 pm-7:17 am

1 stop10h 13m

Port of Spain Piarco Intl

Mon 3/9

8:05 am-7:58 pm

1 stop11h 53m

$268

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Sat 2/28

7:39 pm-7:17 am

1 stop10h 38m

Port of Spain Piarco Intl

Wed 3/4

9:05 am-7:58 pm

1 stop11h 53m

$269

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

Mon 3/16

5:24 pm-2:10 pm

2 stops20h 46m

Port of Spain Piarco Intl

Thu 3/19

3:10 pm-11:08 am

2 stops19h 58m

$274

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

$274

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Wed 3/11

5:30 pm-2:10 pm

2 stops20h 40m

Port of Spain Piarco Intl

Tue 3/17

3:10 pm-10:05 am

2 stops18h 55m

$274

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Thu 3/5

3:05 pm-1:46 am

1 stop9h 41m

Port of Spain Piarco Intl

Wed 3/11

3:46 am-11:10 pm

1 stop19h 24m

$278

HartfordPort of Spain

BDL - POS

BDLPOS

Hartford Bradley Intl

Thu 3/19

1:50 pm-2:10 pm

2 stops24h 20m

Port of Spain Piarco Intl

Tue 3/24

3:10 pm-11:08 am

2 stops19h 58m

$287

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Mon 3/16

4:05 pm-1:46 am

1 stop9h 41m

Port of Spain Piarco Intl

Wed 3/18

3:46 am-11:10 pm

1 stop19h 24m

$300

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Sat 2/21

4:15 pm-1:05 am

1 stop7h 50m

Port of Spain Piarco Intl

Thu 2/26

2:20 am-10:55 am

1 stop9h 35m

$302

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/3

Showing 1-10 of 28 results
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Best time to book a flight from Massachusetts to Port of Spain

Have a flexible travel schedule? Discover the best time to fly to Port of Spain 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 Port of Spain

What is the cheapest month to book a flight from Massachusetts to Port of Spain?

Currently, December is the cheapest month in which you can book a flight from Massachusetts to Port of Spain (average of $164). Flying from Massachusetts to Port of Spain in June is currently the most expensive (average of $496). 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 Port of Spain. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Port of Spain from Massachusetts?

    Located just 12.6 mi from the city center, Port of Spain Piarco Intl (POS) is the airport most travelers will use when flying to Port of Spain from Massachusetts.

  • How long is the flight from Massachusetts to Port of Spain?

    There are many flights that can get you from Massachusetts to Port of Spain in 10h 13m. Fly via JetBlue, United Airlines, or American Airlines to get the fastest option. There are 2270 mi between Massachusetts and Port of Spain. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Massachusetts to Port of Spain 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 American Airlines, with prices starting from $144 and $182, respectively.

  • What are the most popular routes from Massachusetts to Port of Spain?

    When deciding which route to take from Massachusetts to Port of Spain consider Boston Logan Intl - Port of Spain Piarco Intl, Hartford Bradley Intl - Port of Spain Piarco Intl or Hyannis Barnstable - Port of Spain Piarco Intl as they are the most popular.

  • Can I find deals for flights from Massachusetts to Port of Spain that include hotel bookings?

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

  • How can I find direct flights from Massachusetts to Port of Spain?

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

  • Can I find deals for business class flights from Massachusetts to Port of Spain?

    Yes. Cheapflights offers flight deals from Massachusetts to Port of Spain 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 Port of Spain?

    Currently, December is the cheapest month in which you can book a flight from Massachusetts to Port of Spain (average of $164). Flying from Massachusetts to Port of Spain in June is currently the most expensive (average of $496). 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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Alternative routes for Massachusetts to Port of Spain

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 Port of Spain

Discover the top 5 airlines that operate flights from Massachusetts to Port of Spain. 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 5, 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$276Average$572FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$490Average$596FlexibilityNo cancel feeOn-time71%

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