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$218+ 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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — POS
Nov 9 — Nov 161
Sun 11/9
Sun 11/16
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 October 10, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/9. 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.
Fri 10/1711:31 amSWF - POS
2 stops14h 15mMultiple Airlines
Sun 10/1910:10 amPOS - SWF
1 stop24h 01mMultiple Airlines
Deal found 10/9$566
This Kiwi.com deal was found by Cheapflights users on 10/9. 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.
Tue 12/2311:43 amSWF - POS
2 stops37h 05mMultiple Airlines
Thu 1/810:10 amPOS - SWF
1 stop25h 09mMultiple Airlines
Deal found 10/9$808
This Kiwi.com deal was found by Cheapflights users on 10/9. 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.
Fri 12/196:56 pmSWF - POS
1 stop24h 04mMultiple Airlines
Sun 1/410:10 amPOS - SWF
1 stop25h 37mMultiple Airlines
Deal found 10/9$1,240
This Kiwi.com deal was found by Cheapflights users on 10/9. 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.
Sat 12/209:45 amSWF - POS
1 stop31h 20mMultiple Airlines
Sun 1/410:10 amPOS - SWF
1 stop25h 37mMultiple Airlines
Deal found 10/9$1,337

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 October 10, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$1,037
(Kiwi.com)

One-way from

$218
(Kiwi.com)

Popular in

February

Cheapest in

January

Average price

$463
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.
Search Deals
From New Windsor Stewart to Trinidad
Search Deals
One-way flight from New Windsor Stewart to Trinidad
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
Search Deals

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 October 10, 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

Tue 12/23

11:43 am-1:48 am

2 stops37h 05m

Port of Spain Piarco Intl

Thu 1/8

10:10 am-10:19 am

1 stop25h 09m

$808

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Fri 12/19

6:56 pm-8:00 pm

1 stop24h 04m

Port of Spain Piarco Intl

Sun 1/4

10:10 am-10:47 am

1 stop25h 37m

$1,240

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Sat 12/20

9:45 am-6:05 pm

1 stop31h 20m

Port of Spain Piarco Intl

Sun 1/4

10:10 am-10:47 am

1 stop25h 37m

$1,337

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Fri 11/7

11:31 am-1:48 am

2 stops13h 17m

$255

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Mon 10/20

11:01 am-8:00 pm

1 stop8h 59m

$307

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Thu 12/25

11:43 am-1:48 am

2 stops13h 05m

$546

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Fri 12/19

6:56 pm-8:00 pm

1 stop24h 04m

$605

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/7

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 $160). Flying from New Windsor to Trinidad in August is currently the most expensive (average of $378). 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 $160). Flying from New Windsor to Trinidad in August is currently the most expensive (average of $378). 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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