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$278+ Cheap flights from New Windsor (SWF) to Trinidad

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 3/15. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — POS
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
1 adult, Economy
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Find flight deals from Stewart to Trinidad

Cheapest flights from Stewart to Trinidad
Explore the most affordable flight options available from Stewart to Trinidad. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 26, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/23. 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.
Sun 11/3010:12 amSWF - POS
1 stop8h 48mMultiple Airlines
Sun 12/710:10 amPOS - SWF
1 stop26h 27mMultiple Airlines
Deal found 11/23$857

Cheap flight deals from Stewart to Trinidad

Keep the following information in mind while searching for Stewart to Trinidad flight deals. Data was last updated November 26, 2025.

Most accurate provider

Gotogate
3 stars

Most trusted provider

Gotogate
3 stars

Round-trip from

$857
(Kiwi.com)

One-way from

$278
(Kiwi.com)

Popular in

February

Cheapest in

November

Average price

$409
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 Trinidad
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One-way flight from New Windsor Stewart to Trinidad
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Highest demand for flights based on searches. 9% potential increase in price ($51 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Trinidad 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 November 26, 2025.
Use the filters below to find and compare flights from New Windsor to Trinidad that are best for you.

Fly from

Stewart

Fly to

Trinidad

Route

Depart

Return

Price

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Sun 11/30

10:12 am-8:00 pm

1 stop8h 48m

Port of Spain Piarco Intl

Sun 12/7

10:10 am-11:37 am

1 stop26h 27m

$857

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Sun 3/15

12:29 pm-8:00 pm

1 stop31h 31m

$278

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Fri 2/6

11:09 am-1:44 am

2 stops13h 35m

$429

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Tue 12/23

11:43 am-8:20 pm

3 stops31h 37m

$542

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Mon 12/22

8:25 pm-1:31 pm

2 stops40h 06m

$555

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Fri 12/26

11:57 am-1:48 am

2 stops12h 51m

$765

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/24

Best time to book a flight from Stewart to Trinidad

Have a flexible travel schedule? Discover the best time to fly to Trinidad 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 Trinidad

What is the cheapest month to book a flight from New Windsor to Trinidad?

Currently, January is the cheapest month in which you can book a flight from New Windsor to Trinidad (average of $164). Flying from New Windsor to Trinidad in August is currently the most expensive (average of $375). 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 Trinidad. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from New Windsor to Trinidad?

    Located just 4.3 mi from the city center, New Windsor Stewart (SWF) is the airport most travelers will use when flying to Trinidad from New Windsor.

  • Can I find deals for flights from Stewart to Trinidad that include hotel bookings?

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

  • How can I find direct flights from Stewart to Trinidad?

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

  • Can I find deals for business class flights from Stewart to Trinidad?

    Yes. Cheapflights offers flight deals from Stewart to Trinidad 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 Trinidad?

    Currently, January is the cheapest month in which you can book a flight from New Windsor to Trinidad (average of $164). Flying from New Windsor to Trinidad in August is currently the most expensive (average of $375). 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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