HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Stewart

$268+ 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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
POS — SWF
ago. 26 — sep. 21
mar. 8/26
mar. 9/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

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 agosto 21, 2025.

Round-trip from

$460
(Kiwi.com)

One-way from

$268
(Kiwi.com)

Popular in

July

Cheapest in

September

Average price

$492
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 ($48 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

Find 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 agosto 21, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/20. 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.
jue. 1/810:10 amPOS - SWF
1 stop25h 09mMultiple Airlines
Deal found 8/20$268
This Kiwi.com deal was found by Cheapflights users on 8/21. 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.
jue. 8/2810:10 amPOS - SWF
1 stop26h 55mMultiple Airlines
Deal found 8/21$387
This Kiwi.com deal was found by Cheapflights users on 8/21. 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.
vie. 9/1210:10 amPOS - SWF
3 stops56h 12mMultiple Airlines
Deal found 8/21$390
This Kiwi.com deal was found by Cheapflights users on 8/20. 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.
mar. 9/309:10 amPOS - SWF
3 stops57h 11mMultiple Airlines
Deal found 8/20$415
This Kiwi.com deal was found by Cheapflights users on 8/21. 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.
mar. 9/23:51 amPOS - SWF
3 stops33h 23mMultiple Airlines
Deal found 8/21$445
This Kiwi.com deal was found by Cheapflights users on 8/20. 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.
mié. 1/79:10 amPOS - SWF
3 stops50h 09mMultiple Airlines
Deal found 8/20$473
This Kiwi.com deal was found by Cheapflights users on 8/21. 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.
dom. 8/3110:10 amPOS - SWF
1 stop26h 55mMultiple Airlines
Deal found 8/21$482
This Kiwi.com deal was found by Cheapflights users on 8/21. 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.
vie. 8/2910:10 amPOS - SWF
2 stops27h 32mMultiple Airlines
Deal found 8/21$494
This Kiwi.com deal was found by Cheapflights users on 8/21. 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.
jue. 9/410:10 amPOS - SWF
3 stops25h 34mMultiple Airlines
Deal found 8/21$500
This Kiwi.com deal was found by Cheapflights users on 8/20. 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.
dom. 12/217:45 amPOS - SWF
3 stops36h 50mMultiple Airlines
Deal found 8/20$509
This Kiwi.com deal was found by Cheapflights users on 8/20. 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.
mié. 12/248:00 amPOS - SWF
2 stops52h 07mMultiple Airlines
Deal found 8/20$518

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 agosto 21, 2025.
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

jue. 1/8

10:10 am-10:19 am

1 stop25h 09m

$268

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

jue. 8/28

10:10 am-1:05 pm

1 stop26h 55m

$387

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

vie. 9/12

10:10 am-6:22 pm

3 stops56h 12m

$390

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

mar. 9/30

9:10 am-6:21 pm

3 stops57h 11m

$415

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

mar. 9/2

3:51 am-1:14 pm

3 stops33h 23m

$445

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

mié. 1/7

9:10 am-10:19 am

3 stops50h 09m

$473

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

dom. 8/31

10:10 am-1:05 pm

1 stop26h 55m

$482

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

vie. 8/29

10:10 am-1:42 pm

2 stops27h 32m

$494

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

jue. 9/4

10:10 am-11:44 am

3 stops25h 34m

$500

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

dom. 12/21

7:45 am-7:35 pm

3 stops36h 50m

$509

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/20

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, October is the cheapest month in which you can book a flight from Port of Spain to New Windsor (average of $109). Flying from Port of Spain to New Windsor in December is currently the most expensive (average of $202). 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, October is the cheapest month in which you can book a flight from Port of Spain to New Windsor (average of $109). Flying from Port of Spain to New Windsor in December is currently the most expensive (average of $202). 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

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.
Port of Spain to John F Kennedy Intl flights
Port of Spain to Newark flights
Port of Spain to LaGuardia flights
Scarborough to John F Kennedy Intl flights
Port of Spain to Islip flights

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.