HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Stewart

$232+ Cheap flights from the Cayman Islands 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 2/8. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — SWF
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Cayman Islands 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 Cayman Islands to Stewart

Keep the following information in mind while searching for Cayman Islands to Stewart flight deals. Data was last updated January 8, 2026.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Popular in

July

Cheapest in

March

Average price

$377
Provider with most accurate pricing for George Town Owen Roberts Intl-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for George Town Owen Roberts Intl-New York (NYC) flights.
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($72 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Find flight deals from Cayman Islands to Stewart

One-way flights from Cayman Islands to Stewart
Search for one-way flight options from Cayman Islands to Stewart. Find affordable one-way fares based on user searches. Data last updated January 8, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/7. 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 2/82:49 pmGCM - SWF
1 stop19h 30mMultiple Airlines
Deal found 1/7$232
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 3/12:49 pmGCM - SWF
2 stops19h 24mMultiple Airlines
Deal found 1/6$256
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 2/72:34 pmGCM - SWF
2 stops20h 34mMultiple Airlines
Deal found 1/7$269
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 1/312:34 pmGCM - SWF
2 stops19h 24mMultiple Airlines
Deal found 1/6$283
This Kiwi.com deal was found by Cheapflights users on 1/8. 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 5/301:40 pmGCM - SWF
1 stop18h 58mMultiple Airlines
Deal found 1/8$292
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 3/151:40 pmGCM - SWF
2 stops20h 51mMultiple Airlines
Deal found 1/6$313
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 2/411:30 amGCM - SWF
3 stops46h 49mMultiple Airlines
Deal found 1/7$317
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 4/41:15 pmGCM - SWF
1 stop19h 24mMultiple Airlines
Deal found 1/6$318
This Kiwi.com deal was found by Cheapflights users on 1/8. 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 2/311:30 amGCM - SWF
3 stops47h 38mMultiple Airlines
Deal found 1/8$322
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 2/64:45 pmGCM - SWF
3 stops42h 23mMultiple Airlines
Deal found 1/7$329
This Kiwi.com deal was found by Cheapflights users on 1/8. 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 3/221:40 pmGCM - SWF
2 stops20h 51mMultiple Airlines
Deal found 1/8$332

Cheapflights Fare Finder

 
Customize your flight search to find flights from Cayman Islands 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 January 8, 2026.
Use the filters below to find and compare flights from the Cayman Islands to New Windsor that are best for you.

Fly from

Cayman Islands

Fly to

Stewart

Route

Depart

Return

Price

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Sun 3/1

2:49 pm-10:13 am

2 stops19h 24m

$256

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Sat 2/7

2:34 pm-11:08 am

2 stops20h 34m

$269

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Sat 1/31

2:34 pm-9:58 am

2 stops19h 24m

$283

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Sun 3/15

1:40 pm-11:31 am

2 stops20h 51m

$313

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Wed 2/4

11:30 am-10:19 am

3 stops46h 49m

$317

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Sat 4/4

1:15 pm-9:39 am

1 stop19h 24m

$318

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Tue 2/3

11:30 am-11:08 am

3 stops47h 38m

$322

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Fri 2/6

4:45 pm-11:08 am

3 stops42h 23m

$329

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Sun 3/22

1:40 pm-11:31 am

2 stops20h 51m

$332

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Sat 4/25

1:40 pm-10:55 am

1 stop20h 15m

$341

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

Best time to book a flight from Cayman Islands to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Cayman Islands 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 the Cayman Islands to New Windsor

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

Currently, November is the cheapest month in which you can book a flight from Cayman Islands to New Windsor (average of $91). Flying from Cayman Islands to New Windsor in June is currently the most expensive (average of $493). 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 Cayman Islands 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 Cayman Islands?

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

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

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

  • How can I find direct flights from Cayman Islands to Stewart?

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

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

    Yes. Cheapflights offers flight deals from Cayman Islands 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 Cayman Islands to New Windsor?

    Currently, November is the cheapest month in which you can book a flight from Cayman Islands to New Windsor (average of $91). Flying from Cayman Islands to New Windsor in June is currently the most expensive (average of $493). 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 Cayman Islands 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
Santo Domingo to John F Kennedy Intl flights
Luis Munoz Marin Intl to Newark flights
Santo Domingo to Newark flights
Punta Cana to Newark flights
Punta Cana to John F Kennedy Intl flights
Luis Munoz Marin Intl to LaGuardia flights
Santo Domingo to LaGuardia flights
Punta Cana to LaGuardia flights
Santiago de los Caballeros to John F Kennedy Intl flights
Santiago de los Caballeros to Newark flights
Port of Spain to John F Kennedy Intl flights
Simpson Bay to John F Kennedy Intl flights
Kingston to John F Kennedy Intl flights
Simpson Bay to Newark flights
Aguadilla to John F Kennedy Intl flights
Montego Bay to John F Kennedy Intl flights
Santiago de los Caballeros to LaGuardia flights
Bridgetown to John F Kennedy Intl flights
Simpson Bay to LaGuardia flights
Oranjestad to Newark flights
Oranjestad to John F Kennedy Intl flights
Port of Spain to Newark flights
Port of Spain to LaGuardia flights
Luis Munoz Marin Intl to Buffalo flights
Nassau to John F Kennedy Intl flights
Willemstad to John F Kennedy Intl flights
Kingston to Newark flights
Montego Bay to Newark flights
Kingston to LaGuardia flights
Willemstad to Newark flights
Montego Bay to LaGuardia flights
Saint Thomas Island to John F Kennedy Intl flights
St. John's to John F Kennedy Intl flights
Oranjestad to LaGuardia flights
Nassau to LaGuardia flights
St. George's to John F Kennedy Intl flights
Aguadilla to Newark flights
Fort-de-France to John F Kennedy Intl flights
Luis Munoz Marin Intl to Islip flights
Nassau to Newark flights
Aguadilla to LaGuardia flights
Castries to John F Kennedy Intl flights
Puerto Plata to John F Kennedy Intl flights
George Town to Newark flights
Saint Thomas Island to Newark flights
Bridgetown to Newark flights
Luis Munoz Marin Intl to White Plains flights
George Town 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.