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Trinidad and Tobago

$238+ Cheap flights from New Windsor (SWF) to Trinidad and Tobago

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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — POS
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Stewart to Trinidad and Tobago

Keep the following information in mind while searching for Stewart to Trinidad and Tobago flight deals. Data was last updated September 15, 2025.

Round-trip from

$1,410
(Kiwi.com)

One-way from

$238
(Kiwi.com)

Popular in

February

Cheapest in

January

Average price

$422
From New Windsor Stewart to Trinidad and Tobago
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One-way flight from New Windsor Stewart to Trinidad and Tobago
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Highest demand for flights based on searches. 9% potential increase in price ($52 potential increase over avg. RT price).
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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 September 2025
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Find flight deals from Stewart to Trinidad and Tobago

Cheapest flights from Stewart to Trinidad and Tobago
Explore the most affordable flight options available from Stewart to Trinidad and Tobago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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 12/1811:43 amSWF - POS
2 stops13h 05mMultiple Airlines
Mon 12/2210:10 amPOS - SWF
1 stop10h 25mMultiple Airlines
Deal found 9/15$1,410

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Trinidad and Tobago 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 September 15, 2025.
Use the filters below to find and compare flights from New Windsor to Trinidad and Tobago that are best for you.

Fly from

Stewart

Fly to

Trinidad and Tobago

Route

Depart

Return

Price

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Thu 12/18

11:43 am-1:48 am

2 stops13h 05m

Port of Spain Piarco Intl

Mon 12/22

10:10 am-7:35 pm

1 stop10h 25m

$1,410

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Mon 10/13

11:01 am-1:46 am

2 stops14h 45m

$238

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Fri 11/21

11:12 am-7:50 pm

3 stops31h 38m

$272

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Fri 12/5

12:27 pm-7:50 pm

3 stops30h 23m

$274

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Thu 10/30

11:43 am-1:46 am

2 stops14h 03m

$306

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Fri 2/6

11:09 am-7:50 pm

3 stops31h 41m

$308

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Mon 10/20

11:01 am-8:00 pm

1 stop8h 59m

$313

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Fri 10/10

11:41 am-7:50 pm

3 stops32h 09m

$383

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Mon 11/24

10:57 am-1:48 am

2 stops13h 51m

$391

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Thu 12/25

11:43 am-1:17 pm

2 stops24h 34m

$469

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 13 results
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Best time to book a flight from Stewart to Trinidad and Tobago

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

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

Currently, October is the cheapest month in which you can book a flight from New Windsor to Trinidad and Tobago (average of $435). Flying from New Windsor to Trinidad and Tobago in December is currently the most expensive (average of $710). 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 and Tobago. 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 and Tobago?

    If you book a flight to Trinidad and Tobago from New Windsor, you will be flying from Stewart, which is the city’s only airport. New Windsor Stewart (SWF) is located 4.3 mi from the center of New Windsor.

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

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

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

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

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

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

    Currently, October is the cheapest month in which you can book a flight from New Windsor to Trinidad and Tobago (average of $435). Flying from New Windsor to Trinidad and Tobago in December is currently the most expensive (average of $710). 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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