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Port of Spain

$360+ Cheap flights from New Windsor (SWF) 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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — POS
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheap flight deals from Stewart to Port of Spain

Best flights from Stewart to Port of Spain
Discover carefully curated flight deals from Stewart to Port of Spain that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/15. 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 2/1211:42 amSWF - POS
1 stop31h 18mMultiple Airlines
Sat 2/2110:10 amPOS - SWF
1 stop25h 52mMultiple Airlines
Deal found 12/15$1,187

Find flight deals from Stewart to Port of Spain

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to Port of Spain (POS). 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 December 15, 2025.

Most accurate provider

Gotogate
3 stars

Most trusted provider

Gotogate
3 stars

Round-trip from

$1,187
(Kiwi.com)

One-way from

$360
(Kiwi.com)

Popular in

February

Cheapest in

November

Average price

$682
Provider with most accurate pricing for New York (NYC)-Port of Spain Piarco Intl flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Port of Spain Piarco Intl flights.
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From New Windsor Stewart to Port of Spain Piarco Intl
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One-way flight from New Windsor Stewart to Port of Spain Piarco Intl
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($49 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($26 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart 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 December 15, 2025.
Use the filters below to find and compare flights from New Windsor to Port of Spain that are best for you.

Fly from

Stewart

Fly to

Port of Spain

Route

Depart

Return

Price

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Thu 2/12

11:42 am-8:00 pm

1 stop31h 18m

Port of Spain Piarco Intl

Sat 2/21

10:10 am-11:02 am

1 stop25h 52m

$1,187

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Fri 2/6

11:09 am-7:50 pm

2 stops31h 41m

$360

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Mon 12/22

12:24 pm-1:31 pm

3 stops48h 07m

$522

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Thu 2/12

11:42 am-8:00 pm

1 stop31h 18m

$524

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Fri 12/19

8:11 pm-1:48 am

2 stops28h 37m

$744

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Thu 12/18

11:43 am-1:48 am

2 stops13h 05m

$786

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

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

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

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

Currently, July is the cheapest month in which you can book a flight from New Windsor to Port of Spain (average of $71). Flying from New Windsor to Port of Spain in August is currently the most expensive (average of $371). 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 Stewart 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.

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

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

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

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

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

    Currently, July is the cheapest month in which you can book a flight from New Windsor to Port of Spain (average of $71). Flying from New Windsor to Port of Spain in August is currently the most expensive (average of $371). 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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