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Port of Spain

$193+ 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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — POS
Nov 7 — Nov 141
Fri 11/7
Fri 11/14
1 adult, Economy
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Cheap 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 October 8, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$407
(Mytrip)

One-way from

$193
(Air Canada)

Popular in

December

Cheapest in

January

Average price

$583
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
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Highest demand for flights based on searches. 7% potential increase in price ($52 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 October 2025
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Find 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 October 8, 2025.

This Air Canada deal was found by Cheapflights users on 10/7. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/25:30 amBOS - POS
2 stops18h 40mAir Canada
Sun 12/72:15 amPOS - BOS
2 stops18h 27mAir Canada
Deal found 10/7$433
This Expedia deal was found by Cheapflights users on 10/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/265:30 amBOS - POS
2 stops42h 40mAir Canada
Sun 11/302:15 amPOS - BOS
2 stops20h 12mAir Canada
Deal found 10/6$443
This Priceline deal was found by Cheapflights users on 10/6. 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.
Wed 10/295:40 amBOS - POS
1 stop8h 27mJetBlue
Wed 11/55:12 pmPOS - BOS
1 stop15h 29mJetBlue
Deal found 10/6$455
This FlightHub deal was found by Cheapflights users on 10/6. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/246:00 amBOS - POS
2 stops19h 20mAir Canada
Sun 10/261:15 amPOS - BOS
2 stops13h 37mAir Canada
Deal found 10/6$463
This CheapOair deal was found by Cheapflights users on 10/8. 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.
Wed 11/195:40 amBOS - POS
1 stop8h 26mJetBlue
Fri 11/215:53 pmPOS - BOS
1 stop14h 49mJetBlue
Deal found 10/8$467
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/293:00 pmBOS - POS
1 stop29h 00mMultiple Airlines
Wed 11/59:10 amPOS - BOS
2 stops24h 50mMultiple Airlines
Deal found 10/6$475
This CheapOair deal was found by Cheapflights users on 10/8. 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.
Wed 11/195:40 amBOS - POS
1 stop8h 26mJetBlue
Thu 11/205:53 pmPOS - BOS
1 stop14h 49mJetBlue
Deal found 10/8$476
This Air Canada deal was found by Cheapflights users on 10/8. 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.
Tue 12/96:15 amBOS - POS
1 stop17h 55mAir Canada
Fri 12/262:15 amPOS - BOS
1 stop14h 42mAir Canada
Deal found 10/8$483
This Mytrip deal was found by Cheapflights users on 10/7. 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 11/176:16 amBOS - POS
1 stop12h 44mMultiple Airlines
Sun 11/302:15 amPOS - BOS
2 stops32h 17mMultiple Airlines
Deal found 10/7$487
This United Airlines deal was found by Cheapflights users on 10/6. 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 11/209:50 amBOS - POS
1 stop13h 33mUnited Airlines
Wed 11/261:30 amPOS - BOS
1 stop17h 13mUnited Airlines
Deal found 10/6$491
This Air Canada deal was found by Cheapflights users on 10/7. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/810:15 amBOS - POS
2 stops37h 55mAir Canada
Sun 12/282:15 amPOS - BOS
1 stop21h 22mAir Canada
Deal found 10/7$493
This United Airlines deal was found by Cheapflights users on 10/7. 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 10/106:00 amBDL - POS
2 stops17h 23mUnited Airlines
Mon 10/1312:30 amPOS - BDL
2 stops18h 22mUnited Airlines
Deal found 10/7$863

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 October 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

Wed 1/14

4:35 pm-1:10 am

1 stop31h 35m

Port of Spain Piarco Intl

Tue 1/27

2:15 am-9:32 am

2 stops32h 17m

$407

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Wed 1/14

7:30 am-7:15 pm

1 stop10h 45m

Port of Spain Piarco Intl

Wed 1/28

8:30 am-7:57 pm

1 stop12h 27m

$429

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Tue 12/9

6:15 am-1:10 am

1 stop17h 55m

Port of Spain Piarco Intl

Fri 12/26

2:15 am-6:02 pm

1 stop16h 47m

$483

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Mon 3/30

5:30 am-2:51 pm

1 stop9h 21m

Port of Spain Piarco Intl

Fri 4/3

4:16 pm-7:45 am

1 stop15h 29m

$485

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Sat 11/8

9:35 am-12:23 am

1 stop13h 48m

Port of Spain Piarco Intl

Sat 11/15

1:30 am-12:26 pm

1 stop11h 56m

$491

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Tue 1/13

9:30 am-12:23 am

2 stops13h 53m

Port of Spain Piarco Intl

Mon 1/19

1:30 am-2:29 pm

2 stops13h 59m

$495

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Thu 11/20

7:34 am-1:48 am

1 stop17h 14m

Port of Spain Piarco Intl

Thu 11/20

3:48 am-10:03 pm

1 stop19h 15m

$523

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Wed 11/19

9:40 am-12:23 am

2 stops13h 43m

Port of Spain Piarco Intl

Thu 11/20

1:30 am-5:43 pm

1 stop17h 13m

$542

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Tue 2/17

9:56 am-12:23 am

1 stop13h 27m

Port of Spain Piarco Intl

Wed 4/29

12:30 am-2:07 pm

2 stops13h 37m

$542

BostonPort of Spain

BOS - POS

BOSPOS

Boston Logan Intl

Sun 11/9

10:45 am-1:10 am

1 stop13h 25m

$193

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/7

Showing 1-10 of 18 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, January is the cheapest month in which you can book a flight from Massachusetts to Port of Spain (average of $188). 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 October 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.

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 45m. Fly via Air Canada, JetBlue, or United 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 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, January is the cheapest month in which you can book a flight from Massachusetts to Port of Spain (average of $188). 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 October 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$242Average$423FlexibilityNo cancel feeOn-time67%
Copa AirlinesCheapest$420Average$530FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$433Average$645FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$433Average$608FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$493Average$660FlexibilityNo cancel feeOn-time62%

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