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Stewart

$331+ Cheap flights from Port of Spain (POS) to New Windsor (SWF)

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 7/21. Fares are subject to change and may not be available on all flights or dates of travel.
POS — SWF
Mar 22 — Mar 291
Sun 3/22
Sun 3/29
1 adult, Economy
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Cheap flight deals from Port of Spain to Stewart

One-way flights from Port of Spain to Stewart
Search for one-way flight options from Port of Spain to Stewart. Find affordable one-way fares based on user searches. Data last updated February 20, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/18. 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.
Tue 7/219:10 am
POS
-
SWF
2 stops26h 15m
Multiple Airlines
Deal found 2/18$331
This Kiwi.com deal was found by Cheapflights users on 2/17. 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.
Tue 4/73:44 am
POS
-
SWF
3 stops31h 11m
Multiple Airlines
Deal found 2/17$335
This Kiwi.com deal was found by Cheapflights users on 2/18. 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.
Thu 3/510:10 am
POS
-
SWF
2 stops25h 02m
Multiple Airlines
Deal found 2/18$346
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 5/299:10 am
POS
-
SWF
2 stops26h 15m
Multiple Airlines
Deal found 2/19$348
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 5/309:10 am
POS
-
SWF
3 stops47h 41m
Multiple Airlines
Deal found 2/19$375
This Kiwi.com deal was found by Cheapflights users on 2/17. 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 5/29:10 am
POS
-
SWF
3 stops25h 45m
Multiple Airlines
Deal found 2/17$381
This Kiwi.com deal was found by Cheapflights users on 2/17. 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 7/319:10 am
POS
-
SWF
2 stops26h 15m
Multiple Airlines
Deal found 2/17$387
This Kiwi.com deal was found by Cheapflights users on 2/17. 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.
Mon 5/49:10 am
POS
-
SWF
3 stops50h 15m
Multiple Airlines
Deal found 2/17$391
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Thu 3/1910:10 am
POS
-
SWF
2 stops25h 21m
Multiple Airlines
Deal found 2/20$418
This Kiwi.com deal was found by Cheapflights users on 2/18. 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 7/229:10 am
POS
-
SWF
3 stops23h 48m
Multiple Airlines
Deal found 2/18$420
This Kiwi.com deal was found by Cheapflights users on 2/17. 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.
Tue 4/79:10 am
POS
-
SWF
3 stops49h 45m
Multiple Airlines
Deal found 2/17$427

Find flight deals from Port of Spain to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Port of Spain (POS) to Stewart (SWF). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 20, 2026.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Popular in

November

Cheapest in

February

Average price

$349
Provider with most accurate pricing for Port of Spain Piarco Intl-New Windsor Stewart flight deals.
Search Deals
Provider most trusted by Cheapflights users for Port of Spain Piarco Intl-New Windsor Stewart flights.
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($9 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 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 Port of Spain to Stewart 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 20, 2026.
Use the filters below to find and compare flights from Port of Spain to New Windsor that are best for you.

Fly from

Port of Spain

Fly to

Stewart

Route

Depart

Return

Price

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Thu 3/5

10:10 am-10:12 am

2 stops25h 02m

$346

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Fri 5/29

9:10 am-11:25 am

2 stops26h 15m

$348

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Sat 5/30

9:10 am-8:51 am

3 stops47h 41m

$375

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Sat 5/2

9:10 am-10:55 am

3 stops25h 45m

$381

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Fri 7/31

9:10 am-11:25 am

2 stops26h 15m

$387

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Wed 7/22

9:10 am-8:58 am

3 stops23h 48m

$420

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Tue 4/7

9:10 am-10:55 am

3 stops49h 45m

$427

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Tue 8/4

9:10 am-11:25 am

2 stops26h 15m

$440

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Tue 4/7

3:44 am-10:55 am

2 stops31h 11m

$441

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Mon 5/4

8:30 am-11:25 am

2 stops50h 55m

$443

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

Showing 1-10 of 11 results
1
2
  • Most accurate provider: When it comes to deals on Port of Spain-New Windsor flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Port of Spain-New Windsor flight deals on Cheapflights vs. Expedia <90% of the time. Price accuracy is based on data collected from Port of Spain-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Port of Spain-New Windsor flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Port of Spain-New Windsor flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Port of Spain to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Port of Spain 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 Port of Spain to New Windsor

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

Currently, September is the cheapest month in which you can book a flight from Port of Spain to New Windsor (average of $192). Flying from Port of Spain to New Windsor in October is currently the most expensive (average of $286). 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 Port of Spain to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Port of Spain to Stewart 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 Port of Spain to New Windsor?

    Currently, September is the cheapest month in which you can book a flight from Port of Spain to New Windsor (average of $192). Flying from Port of Spain to New Windsor in October is currently the most expensive (average of $286). 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

Traveling to a place near New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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Alternative routes for Port of Spain to Stewart

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