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Cayman Islands

$237+ Cheap flights from New Windsor (SWF) to the Cayman Islands

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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — GCM
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
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 September 16, 2025.

Round-trip from

$1,054
(Kiwi.com)

One-way from

$237
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$389
From New Windsor Stewart to Cayman Islands
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One-way flight from New Windsor Stewart to Cayman Islands
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Highest demand for flights based on searches. 7% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 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 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 September 16, 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.
Fri 12/1912:24 pmSWF - GCM
2 stops27h 41mMultiple Airlines
Sun 1/411:55 amGCM - SWF
1 stop22h 52mMultiple Airlines
Deal found 9/15$1,054
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.
Mon 12/2911:37 amSWF - GCM
2 stops22h 48mMultiple Airlines
Sun 1/411:55 amGCM - SWF
1 stop22h 52mMultiple Airlines
Deal found 9/15$1,266
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.
Wed 11/2612:17 pmSWF - GCM
2 stops22h 08mMultiple Airlines
Sun 11/3012:40 pmGCM - SWF
1 stop20h 26mMultiple Airlines
Deal found 9/15$1,342
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.
Mon 12/2911:37 amSWF - GCM
2 stops22h 48mMultiple Airlines
Sat 1/311:25 amGCM - SWF
1 stop22h 34mMultiple Airlines
Deal found 9/15$1,386

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 September 16, 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

Wed 11/26

12:17 pm-10:25 am

2 stops22h 08m

George Town Owen Roberts Intl

Sun 11/30

12:40 pm-9:06 am

1 stop20h 26m

$1,342

New WindsorGeorge Town

SWF - GCM

SWFGCM

New Windsor Stewart

Thu 12/11

11:09 am-4:05 pm

1 stop28h 56m

$237

New WindsorGeorge Town

SWF - GCM

SWFGCM

New Windsor Stewart

Thu 10/2

7:11 pm-4:00 pm

1 stop21h 49m

$237

New WindsorGeorge Town

SWF - GCM

SWFGCM

New Windsor Stewart

Fri 10/3

12:11 pm-12:42 pm

2 stops25h 31m

$292

New WindsorGeorge Town

SWF - GCM

SWFGCM

New Windsor Stewart

Mon 10/13

11:01 am-3:45 pm

2 stops29h 44m

$495

New WindsorGeorge Town

SWF - GCM

SWFGCM

New Windsor Stewart

Mon 11/24

10:57 am-3:45 pm

2 stops28h 48m

$503

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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, January is the cheapest month in which you can book a flight from New Windsor to Cayman Islands (average of $467). Flying from New Windsor to Cayman Islands in March is currently the most expensive (average of $594). 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, January is the cheapest month in which you can book a flight from New Windsor to Cayman Islands (average of $467). Flying from New Windsor to Cayman Islands in March is currently the most expensive (average of $594). 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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