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Cayman Islands

$337+ Cheap flights from New Windsor (SWF) to the Cayman Islands

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — GCM
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
1 adult, Economy
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Cheap flight deals from Stewart to Cayman Islands

Keep the following information in mind while searching for Stewart to Cayman Islands flight deals. Data was last updated November 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$333
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$448
Provider with most accurate pricing for New York (NYC)-George Town Owen Roberts Intl flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-George Town Owen Roberts Intl flights.
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From New Windsor Stewart to Cayman Islands
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Highest demand for flights based on searches. 3% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Stewart to Cayman Islands

Cheapest flights from Stewart to Cayman Islands
Explore the most affordable flight options available from Stewart to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 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.
Fri 12/196:56 pmSWF - GCM
1 stop21h 59mMultiple Airlines
Thu 12/252:40 pmGCM - SWF
1 stop20h 27mMultiple Airlines
Deal found 11/3$423

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Cayman Islands 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 New Windsor to the Cayman Islands that are best for you.

Fly from

Stewart

Fly to

Cayman Islands

Route

Depart

Return

Price

New WindsorGeorge Town

SWF - GCM

SWFGCM

New Windsor Stewart

Fri 1/30

11:09 am-1:40 pm

1 stop26h 31m

George Town Owen Roberts Intl

Thu 2/5

2:35 pm-10:19 am

1 stop19h 44m

$337

New WindsorGeorge Town

SWF - GCM

SWFGCM

New Windsor Stewart

Fri 12/19

6:56 pm-4:55 pm

1 stop21h 59m

George Town Owen Roberts Intl

Thu 12/25

2:40 pm-11:07 am

1 stop20h 27m

$423

New WindsorGeorge Town

SWF - GCM

SWFGCM

New Windsor Stewart

Sun 3/15

12:29 pm-12:44 pm

2 stops25h 15m

$339

New WindsorGeorge Town

SWF - GCM

SWFGCM

New Windsor Stewart

Mon 12/22

8:25 pm-11:35 am

3 stops39h 10m

$376

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Best time to book a flight from Stewart to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands 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 the Cayman Islands

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

Currently, October is the cheapest month in which you can book a flight from New Windsor to Cayman Islands (average of $119). Flying from New Windsor to Cayman Islands in June is currently the most expensive (average of $348). 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 Cayman Islands. 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 Cayman Islands?

    For a flight from New Windsor to Cayman Islands, you will be flying from Stewart. New Windsor Stewart (SWF) is just 4.3 mi from the center of the city.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Stewart to Cayman Islands 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 Cayman Islands?

    Currently, October is the cheapest month in which you can book a flight from New Windsor to Cayman Islands (average of $119). Flying from New Windsor to Cayman Islands in June is currently the most expensive (average of $348). 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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