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Stewart

$258+ Cheap flights from Trinidad and Tobago 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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
POS — SWF
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
1 adult, Economy
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Find flight deals from Trinidad and Tobago to Stewart

One-way flights from Trinidad and Tobago to Stewart
Search for one-way flight options from Trinidad and Tobago to Stewart. Find affordable one-way fares based on user searches. Data last updated November 2, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/2. 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 1/1810:10 amPOS - SWF
1 stop25h 09mMultiple Airlines
Deal found 11/2$258
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
Wed 11/53:48 amPOS - SWF
2 stops31h 53mMultiple Airlines
Deal found 10/31$272
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 12/1910:10 amPOS - SWF
1 stop8h 56mMultiple Airlines
Deal found 10/31$316
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 12/139:10 amPOS - SWF
3 stops51h 27mMultiple Airlines
Deal found 10/30$335
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 11/910:10 amPOS - SWF
1 stop26h 01mMultiple Airlines
Deal found 10/31$336
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/29:10 amPOS - SWF
3 stops50h 53mMultiple Airlines
Deal found 11/2$351
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 12/1810:10 amPOS - SWF
3 stops47h 45mMultiple Airlines
Deal found 10/31$358
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 11/119:10 amPOS - SWF
3 stops50h 53mMultiple Airlines
Deal found 10/31$422
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
Wed 1/79:10 amPOS - SWF
3 stops50h 09mMultiple Airlines
Deal found 10/31$448

Cheap flight deals from Trinidad and Tobago to Stewart

Keep the following information in mind while searching for Trinidad and Tobago to Stewart flight deals. Data was last updated November 2, 2025.

Most accurate provider

Gotogate
3 stars

Most trusted provider

Gotogate
3 stars

Popular in

July

Cheapest in

October

Average price

$489
Provider with most accurate pricing for Port of Spain Piarco Intl-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Port of Spain Piarco Intl-New York (NYC) flights.
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 ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Trinidad and Tobago 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 November 2, 2025.
Use the filters below to find and compare flights from Trinidad and Tobago to New Windsor that are best for you.

Fly from

Trinidad and Tobago

Fly to

Stewart

Route

Depart

Return

Price

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Sun 1/18

10:10 am-10:19 am

1 stop25h 09m

$258

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Fri 12/19

10:10 am-6:06 pm

1 stop8h 56m

$316

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Sat 12/13

9:10 am-11:37 am

3 stops51h 27m

$335

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Sun 11/9

10:10 am-11:11 am

1 stop26h 01m

$336

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Tue 12/2

9:10 am-11:03 am

3 stops50h 53m

$351

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Thu 12/18

10:10 am-8:55 am

3 stops47h 45m

$358

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Tue 11/11

9:10 am-11:03 am

3 stops50h 53m

$422

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Thu 11/6

7:40 am-10:41 am

3 stops28h 01m

$424

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Wed 1/7

9:10 am-10:19 am

3 stops50h 09m

$448

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Fri 11/21

2:26 pm-11:03 am

3 stops45h 37m

$450

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Best time to book a flight from Trinidad and Tobago to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Trinidad and Tobago 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 Trinidad and Tobago to New Windsor

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

Currently, January is the cheapest month in which you can book a flight from Trinidad and Tobago to New Windsor (average of $166). Flying from Trinidad and Tobago 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

Find useful and relevant information for your journey from Trinidad and Tobago to Stewart. 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 into for flights to New Windsor from Trinidad and Tobago?

    New Windsor Stewart (SWF) is the airport you will fly into if you book a flight from Trinidad and Tobago to New Windsor. It is only a 4.3 mi journey from Stewart (SWF) to New Windsor’s city center.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Trinidad and Tobago 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 Trinidad and Tobago to New Windsor?

    Currently, January is the cheapest month in which you can book a flight from Trinidad and Tobago to New Windsor (average of $166). Flying from Trinidad and Tobago 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

Traveling to a place near New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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