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Stewart

$258+ 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
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
1 adult, Economy
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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 November 4, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/3. 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 2/82:35 pmGCM - SWF
1 stop19h 44mMultiple Airlines
Deal found 11/3$258
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 2/72:35 pmGCM - SWF
2 stops27h 24mMultiple Airlines
Deal found 11/3$314
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.
Sat 2/212:35 pmGCM - SWF
2 stops44h 56mMultiple Airlines
Deal found 11/2$340
This Mytrip deal was found by Cheapflights users on 11/4. 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.
Thu 11/1312:40 pmGCM - SWF
2 stops21h 31mMultiple Airlines
Deal found 11/4$363
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 2/1011:30 amGCM - SWF
3 stops29h 26mMultiple Airlines
Deal found 11/3$366
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 1/611:30 amGCM - SWF
3 stops48h 03mMultiple Airlines
Deal found 11/2$367
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 2/1111:30 amGCM - SWF
3 stops46h 44mMultiple Airlines
Deal found 11/4$374
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 11/1211:30 amGCM - SWF
3 stops46h 41mMultiple Airlines
Deal found 11/4$383
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 2/122:40 pmGCM - SWF
3 stops19h 34mMultiple Airlines
Deal found 11/4$389

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 November 4, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Popular in

July

Cheapest in

March

Average price

$400
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 ($73 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 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 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 November 4, 2025.
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 2/8

2:35 pm-10:19 am

1 stop19h 44m

$258

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Sat 2/7

2:35 pm-5:59 pm

2 stops27h 24m

$314

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Tue 2/10

11:30 am-10:52 am

3 stops47h 22m

$363

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Tue 1/6

11:30 am-11:33 am

3 stops48h 03m

$367

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Sat 2/21

2:35 pm-11:02 am

1 stop20h 27m

$372

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Wed 11/12

11:30 am-10:11 am

3 stops46h 41m

$383

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Thu 2/12

2:40 pm-10:14 am

3 stops19h 34m

$389

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Thu 2/19

12:40 pm-11:31 am

2 stops22h 51m

$420

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Tue 11/11

11:30 am-5:24 pm

3 stops53h 54m

$422

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

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, January is the cheapest month in which you can book a flight from Cayman Islands to New Windsor (average of $133). Flying from Cayman Islands to New Windsor in February is currently the most expensive (average of $413). 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, January is the cheapest month in which you can book a flight from Cayman Islands to New Windsor (average of $133). Flying from Cayman Islands to New Windsor in February is currently the most expensive (average of $413). 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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