What is the cheapest time of day to fly from POS to SWF?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Port of Spain to New Windsor as you normally would.

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 90-95% 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.

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.

$261+ Flights from Port of Spain to New Windsor

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1. Tell us where you want to go

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Cheap flight deals from Port of Spain to Stewart

Cheapest flights from Port of Spain to Stewart
Explore the most affordable flight options available from Port of Spain to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 9, 2025.

Mon 12/298:30 amPOS - SWF

1 stop27h 33mMultiple Airlines

Thu 1/111:43 amSWF - POS

2 stops13h 01mMultiple Airlines

Deal found 12/8

$1,394

Best flights from Port of Spain to Stewart
Discover carefully curated flight deals from Port of Spain to Stewart that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 9, 2025.

Mon 12/298:30 amPOS - SWF

1 stop27h 33mMultiple Airlines

Thu 1/111:43 amSWF - POS

2 stops13h 01mMultiple Airlines

Deal found 12/8

$1,394

Last-minute flights from Port of Spain to Stewart
Discover last-minute flight deals from Port of Spain to Stewart. Data last updated December 9, 2025 and is based on user searches.

Mon 12/298:30 amPOS - SWF

1 stop27h 33mMultiple Airlines

Thu 1/111:43 amSWF - POS

2 stops13h 01mMultiple Airlines

Deal found 12/8

$1,394

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 December 9, 2025.

Thu 1/1510:10 amPOS - SWF

1 stop25h 09mMultiple Airlines

Deal found 12/8

$261

Wed 1/142:16 pmPOS - SWF

3 stops45h 03mMultiple Airlines

Deal found 12/8

$283

Sun 12/1410:10 amPOS - SWF

1 stop26h 27mMultiple Airlines

Deal found 12/7

$291

Thu 1/810:10 amPOS - SWF

1 stop25h 09mMultiple Airlines

Deal found 12/7

$316

Wed 1/289:10 amPOS - SWF

3 stops27h 23mMultiple Airlines

Deal found 12/8

$329

Sat 1/179:10 amPOS - SWF

3 stops50h 09mMultiple Airlines

Deal found 12/7

$343

Mon 12/2210:10 amPOS - SWF

1 stop10h 25mMultiple Airlines

Deal found 12/9

$439

Wed 12/319:10 amPOS - SWF

3 stops26h 53mMultiple Airlines

Deal found 12/8

$457

Find flight deals from Port of Spain to Stewart

Most accurate provider	Expedia 2 stars
Most trusted provider	Expedia 3 stars
Round-trip from	$1,394 (Kiwi.com)
One-way from	$261 (Kiwi.com)
Popular in	July
Cheapest in	February
Average price	$465

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.

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From Port of Spain Piarco Intl to New Windsor Stewart

Search Deals

One-way flight from Port of Spain Piarco Intl to New Windsor Stewart

Search Deals

Highest demand for flights based on searches. 8% potential increase in price ($41 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in December 2025

Search Deals

Cheapflights Fare Finder

Use the filters below to find and compare flights from Port of Spain to New Windsor that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Mon 12/29

8:30 am-11:03 am

1 stop27h 33m

New Windsor Stewart

Thu 1/1

11:43 am-1:44 am

2 stops13h 01m

$1,394

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Thu 1/15

10:10 am-10:19 am

1 stop25h 09m

$261

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Wed 1/14

2:16 pm-10:19 am

3 stops45h 03m

$283

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Sun 12/14

10:10 am-11:37 am

1 stop26h 27m

$291

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Thu 1/8

10:10 am-10:19 am

1 stop25h 09m

$316

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Wed 1/28

9:10 am-11:33 am

3 stops27h 23m

$329

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Sat 1/17

9:10 am-10:19 am

3 stops50h 09m

$343

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Wed 12/31

9:10 am-11:03 am

3 stops26h 53m

$457

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/8

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 90-95% 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, January is the cheapest month in which you can book a flight from Port of Spain to New Windsor (average of $166). Flying from Port of Spain to New Windsor in October is currently the most expensive (average of $287). 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

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, January is the cheapest month in which you can book a flight from Port of Spain to New Windsor (average of $166). Flying from Port of Spain to New Windsor in October is currently the most expensive (average of $287). 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.

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$261+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Port of Spain to Stewart with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Port of Spain to Stewart

Cheapest flights from Port of Spain to StewartExplore the most affordable flight options available from Port of Spain to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 9, 2025.

Explore the most affordable flight options available from Port of Spain to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 9, 2025.

Find flight deals from Port of Spain to Stewart

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Cheapflights Fare Finder

Use the filters below to find and compare flights from Port of Spain to New Windsor that are best for you.

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.

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?

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?

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

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

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

Traveling to a place near New Windsor?

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Cheapest flights from Port of Spain to Stewart
Explore the most affordable flight options available from Port of Spain to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 9, 2025.