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.

$270+ Cheap Flights from Port of Spain to New Windsor

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

Find cheap flights from Port of Spain to Stewart with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Port of Spain to Stewart

Most accurate provider	Expedia 2 stars
Most trusted provider	Expedia 3 stars
Round-trip from	$754 (Kiwi.com)
One-way from	$270 (Kiwi.com)
Popular in	July
Cheapest in	October
Average price	$414

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

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. 9% potential increase in price ($46 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in October 2025

Search Deals

Find 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 October 6, 2025.

Sun 12/1410:10 amPOS - SWF

1 stop26h 27mMultiple Airlines

Fri 1/211:57 amSWF - POS

1 stop31h 03mMultiple Airlines

Deal found 10/4

$754

Fri 12/1910:10 amPOS - SWF

1 stop8h 56mMultiple Airlines

Tue 12/2311:43 amSWF - POS

2 stops24h 48mMultiple Airlines

Deal found 10/5

$902

Fri 12/1910:10 amPOS - SWF

1 stop8h 56mMultiple Airlines

Fri 1/211:57 amSWF - POS

1 stop31h 03mMultiple Airlines

Deal found 10/4

$914

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 October 6, 2025.

Sun 12/1410:10 amPOS - SWF

1 stop26h 27mMultiple Airlines

Fri 1/211:57 amSWF - POS

1 stop31h 03mMultiple Airlines

Deal found 10/4

$754

Fri 12/1910:10 amPOS - SWF

1 stop8h 56mMultiple Airlines

Tue 12/2311:43 amSWF - POS

2 stops24h 48mMultiple Airlines

Deal found 10/5

$902

Fri 12/1910:10 amPOS - SWF

1 stop8h 56mMultiple Airlines

Fri 1/211:57 amSWF - POS

1 stop31h 03mMultiple Airlines

Deal found 10/4

$914

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 October 6, 2025.

Thu 10/3010:10 amPOS - SWF

1 stop24h 31mMultiple Airlines

Deal found 10/5

$270

Sun 10/2610:10 amPOS - SWF

1 stop28h 01mMultiple Airlines

Deal found 10/4

$274

Sat 10/189:10 amPOS - SWF

3 stops49h 01mMultiple Airlines

Deal found 10/5

$370

Tue 10/283:51 amPOS - SWF

3 stops31h 12mMultiple Airlines

Deal found 10/5

$374

Sat 11/19:10 amPOS - SWF

3 stops51h 01mMultiple Airlines

Deal found 10/5

$391

Fri 10/3110:10 amPOS - SWF

3 stops56h 16mMultiple Airlines

Deal found 10/5

$406

Thu 11/2710:10 amPOS - SWF

3 stops33h 28mMultiple Airlines

Deal found 10/5

$413

Fri 10/102:40 pmPOS - SWF

3 stops44h 23mMultiple Airlines

Deal found 10/5

$431

Fri 12/192:15 amPOS - SWF

3 stops33h 04mMultiple Airlines

Deal found 10/4

$463

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

Sun 12/14

10:10 am-11:37 am

1 stop26h 27m

New Windsor Stewart

Fri 1/2

11:57 am-8:00 pm

1 stop31h 03m

$754

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Fri 12/19

10:10 am-6:06 pm

1 stop8h 56m

New Windsor Stewart

Tue 12/23

11:43 am-1:31 pm

2 stops24h 48m

$902

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Fri 12/19

10:10 am-6:06 pm

1 stop8h 56m

New Windsor Stewart

Fri 1/2

11:57 am-8:00 pm

1 stop31h 03m

$914

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Thu 10/30

10:10 am-10:41 am

1 stop24h 31m

$270

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Sun 10/26

10:10 am-2:11 pm

1 stop28h 01m

$274

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Tue 1/27

9:10 am-11:08 am

3 stops50h 58m

$357

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Sat 10/18

9:10 am-10:11 am

3 stops49h 01m

$370

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Tue 10/28

3:51 am-11:03 am

3 stops31h 12m

$374

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Sat 11/1

9:10 am-12:11 pm

3 stops51h 01m

$391

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Fri 10/31

10:10 am-6:26 pm

3 stops56h 16m

$406

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/5

Showing 1-10 of 13 results

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 August is currently the most expensive (average of $257). 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 August is currently the most expensive (average of $257). 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

Kingston

Browse thousands of different options on Cheapflights for your next trip

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

$270+ 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 10/30. 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

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find 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 October 6, 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 October 6, 2025.

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?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Port of Spain to Stewart

See prices for flight routes from nearby airports that may be better suited for you.

100% Free

Book with Flexibility

Travel Smart

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 October 6, 2025.