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Port of Spain

$91+ 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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — POS
Jan 7 — Jan 141
Wed 1/7
Wed 1/14
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 December 8, 2025.

This United Airlines deal was found by Cheapflights users on 12/6. 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 12/116:00 amBOS - POS
2 stops17h 23mUnited Airlines
Sat 12/131:30 amPOS - BOS
1 stop11h 51mUnited Airlines
Deal found 12/6$313
This JetBlue deal was found by Cheapflights users on 12/6. 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.
Tue 12/95:40 amBOS - POS
1 stop9h 24mJetBlue
Sat 12/273:32 pmPOS - BOS
1 stop9h 44mJetBlue
Deal found 12/6$358
This Copa Airlines deal was found by Cheapflights users on 12/7. 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 12/87:34 amBOS - POS
1 stop17h 14mCopa Airlines
Sun 12/283:47 amPOS - BOS
1 stop19h 53mCopa Airlines
Deal found 12/7$361
This Copa Airlines deal was found by Cheapflights users on 12/7. 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 12/87:34 amBOS - POS
1 stop17h 14mCopa Airlines
Sat 5/303:49 amPOS - BOS
1 stop10h 55mCopa Airlines
Deal found 12/7$391
This United Airlines deal was found by Cheapflights users on 12/5. 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 12/66:00 amBOS - POS
2 stops17h 23mUnited Airlines
Fri 12/121:30 amPOS - BOS
1 stop11h 52mUnited Airlines
Deal found 12/5$393
This JetBlue deal was found by Cheapflights users on 12/5. 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 12/127:50 pmBOS - POS
1 stop14h 04mJetBlue
Sat 12/203:35 pmPOS - BOS
1 stop9h 41mJetBlue
Deal found 12/5$453
This CheapOair deal was found by Cheapflights users on 12/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/95:30 amBOS - POS
2 stops18h 40mMultiple Airlines
Sat 12/273:32 pmPOS - BOS
1 stop9h 44mMultiple Airlines
Deal found 12/6$458
This JetBlue deal was found by Cheapflights users on 12/5. 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 12/278:07 pmBOS - POS
1 stop9h 11mJetBlue
Thu 1/88:20 amPOS - BOS
1 stop12h 34mJetBlue
Deal found 12/5$488
This Mytrip deal was found by Cheapflights users on 12/7. 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.
Mon 12/85:30 amBOS - POS
2 stops42h 40mAir Canada
Sat 5/302:35 amPOS - BOS
1 stop9h 08mAir Canada
Deal found 12/7$496
This Priceline deal was found by Cheapflights users on 12/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/185:30 amBOS - POS
1 stop8h 01mMultiple Airlines
Tue 3/171:20 amPOS - BOS
2 stops17h 52mMultiple Airlines
Deal found 12/6$503
This JetBlue deal was found by Cheapflights users on 12/7. 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 12/266:00 amBDL - POS
1 stop7h 30mJetBlue
Tue 12/303:56 pmPOS - BDL
1 stop9h 03mJetBlue
Deal found 12/7$548
This United Airlines deal was found by Cheapflights users on 12/7. 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 12/266:15 amBDL - POS
2 stops41h 08mUnited Airlines
Mon 12/291:30 amPOS - BDL
2 stops37h 46mUnited Airlines
Deal found 12/7$692

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 December 8, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$235
(United Airlines)

One-way from

$91
(United Airlines)

Popular in

March

Cheapest in

September

Average price

$646
Provider with most accurate pricing for Boston Logan Intl-Port of Spain Piarco Intl flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Port of Spain Piarco Intl flights.
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From Massachusetts to Port of Spain Piarco Intl
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One-way flight from Massachusetts to Port of Spain Piarco Intl
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($120 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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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 December 8, 2025.
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

Sat 1/31

6:00 am-12:23 am

2 stops17h 23m

Port of Spain Piarco Intl

Sat 2/7

2:20 am-11:11 am

1 stop9h 51m

$235

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Fri 1/9

10:41 am-7:11 pm

1 stop7h 30m

Port of Spain Piarco Intl

Wed 1/14

8:00 am-5:13 pm

1 stop10h 13m

$235

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Thu 1/22

6:00 am-12:23 am

2 stops17h 23m

Port of Spain Piarco Intl

Tue 3/3

2:20 am-10:55 am

1 stop9h 35m

$235

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Wed 1/21

10:41 am-7:11 pm

1 stop7h 30m

Port of Spain Piarco Intl

Wed 1/28

8:20 am-5:13 pm

1 stop9h 53m

$235

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Wed 1/28

9:42 am-7:11 pm

1 stop8h 29m

Port of Spain Piarco Intl

Fri 2/6

8:30 am-3:50 pm

1 stop8h 20m

$235

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Sun 3/8

9:32 am-11:23 pm

1 stop13h 51m

Port of Spain Piarco Intl

Tue 3/10

12:30 am-6:28 pm

1 stop17h 58m

$235

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Thu 1/8

7:08 am-7:11 pm

1 stop11h 03m

Port of Spain Piarco Intl

Wed 1/14

8:00 am-3:34 pm

1 stop8h 34m

$235

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Thu 1/22

5:45 am-12:23 am

2 stops17h 38m

Port of Spain Piarco Intl

Sun 1/25

1:30 am-12:19 pm

1 stop11h 49m

$239

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Wed 1/21

7:07 pm-12:23 am

2 stops28h 16m

Port of Spain Piarco Intl

Sun 1/25

1:30 am-12:19 pm

1 stop11h 49m

$239

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Tue 1/20

5:15 am-6:41 pm

1 stop12h 26m

Port of Spain Piarco Intl

Fri 1/23

8:20 am-6:48 pm

1 stop11h 28m

$264

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/7

Showing 1-10 of 25 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 August is currently the most expensive (average of $524). 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 POS?

Find hourly flight availability from Massachusetts to Port of Spain. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 8, 2025.

It’s optimal to fly from Massachusetts to Port of Spain in the morning. By choosing this option you can save up to 7% on the cost of your flight, compared to a flight in the evening.

What is the cheapest day to fly from Massachusetts to Port of Spain?

Use this chart to determine the cheapest time to fly round-trip from Massachusetts to Port of Spain. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Massachusetts to Port of Spain flight should consider departing on Monday afternoons when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Massachusetts to Port of Spain?

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 7h 30m. Fly via United Airlines or JetBlue 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?

    $144 is the cheapest one-way deal found within the past few days, from Air Canada. You may also be able to find cheap deals on United Airlines and American Airlines, with prices starting from $164 and $210, 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 August is currently the most expensive (average of $524). 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 December 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$242Average$433FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$444Average$653FlexibilityNo cancel feeOn-time69%
Copa AirlinesCheapest$447Average$530FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$459Average$590FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$489Average$614FlexibilityNo cancel feeOn-time62%

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