HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Stewart

$283+ 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 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
POS — SWF
ago. 4 — ago. 111
lun. 8/4
lun. 8/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Trinidad and Tobago to Stewart with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 julio 30, 2025.

Round-trip from

$938
(Mytrip)

One-way from

$283
(Kiwi.com)

Popular in

July

Cheapest in

September

Average price

$539
From Trinidad and Tobago to New Windsor Stewart
Search Deals
One-way flight from Trinidad and Tobago to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

Find flight deals from Trinidad and Tobago to Stewart

Cheapest flights from Trinidad and Tobago to Stewart
Explore the most affordable flight options available from Trinidad and Tobago to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on julio 30, 2025.

This Mytrip deal was found by Cheapflights users on 7/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/1110:10 amPOS - SWF
1 stop8h 56mMultiple Airlines
sáb. 8/237:29 pmSWF - POS
2 stops24h 31mMultiple Airlines
Deal found 7/30$938

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 julio 30, 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

lun. 8/11

10:10 am-7:06 pm

1 stop8h 56m

New Windsor Stewart

sáb. 8/23

7:29 pm-8:00 pm

2 stops24h 31m

$938

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

mié. 8/27

2:38 pm-1:05 pm

2 stops46h 27m

$283

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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, October is the cheapest month in which you can book a flight from Trinidad and Tobago to New Windsor (average of $109). Flying from Trinidad and Tobago to New Windsor in August is currently the most expensive (average of $206). 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, October is the cheapest month in which you can book a flight from Trinidad and Tobago to New Windsor (average of $109). Flying from Trinidad and Tobago to New Windsor in August is currently the most expensive (average of $206). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Trinidad and Tobago to Stewart

See prices for flight routes from nearby airports that may be better suited for you.
Luis Munoz Marin Intl to John F Kennedy Intl flights
Luis Munoz Marin Intl to Newark flights
Santo Domingo to John F Kennedy Intl flights
Luis Munoz Marin Intl to LaGuardia flights
Santo Domingo to Newark flights
Santiago de los Caballeros to John F Kennedy Intl flights
Santiago de los Caballeros to Newark flights
Santo Domingo to LaGuardia flights
Kingston to John F Kennedy Intl flights
Port of Spain to John F Kennedy Intl flights
Montego Bay to John F Kennedy Intl flights
Bridgetown to John F Kennedy Intl flights
Punta Cana to John F Kennedy Intl flights
Santiago de los Caballeros to LaGuardia flights
Luis Munoz Marin Intl to Rochester flights
Luis Munoz Marin Intl to White Plains flights
Luis Munoz Marin Intl to Islip flights
Aguadilla to John F Kennedy Intl flights
Punta Cana to Newark flights
Oranjestad to John F Kennedy Intl flights
Montego Bay to Newark flights
Nassau to John F Kennedy Intl flights
Kingston to Newark flights
Kingston to LaGuardia flights
Oranjestad to Newark flights
St. George's to John F Kennedy Intl flights
Luis Munoz Marin Intl to Buffalo flights
Port of Spain to Newark flights
Ponce to John F Kennedy Intl flights
Simpson Bay to Newark flights
Montego Bay to LaGuardia flights
Nassau to Newark flights
Simpson Bay to John F Kennedy Intl flights
Port of Spain to LaGuardia flights
Nassau to LaGuardia flights
Puerto Plata to John F Kennedy Intl flights
St. John's to John F Kennedy Intl flights
Oranjestad to LaGuardia flights
Punta Cana to LaGuardia flights
Willemstad to John F Kennedy Intl flights
Saint Thomas Island to John F Kennedy Intl flights
Basseterre to Newark flights
Pointe-à-Pitre to John F Kennedy Intl flights
Simpson Bay to LaGuardia flights
Aguadilla to Newark flights
Aguadilla to LaGuardia flights
Bridgetown to Newark flights
Basseterre to John F Kennedy Intl flights
Castries to John F Kennedy Intl flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.