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Grand Cayman

$107+ Cheap flights from New Windsor (SWF) to Grand Cayman

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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — GCM
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
1 adult, Economy
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Cheap flight deals from Stewart to Grand Cayman

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

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Popular in

April

Cheapest in

January

Average price

$373
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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Highest demand for flights based on searches. 3% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Stewart to Grand Cayman

One-way flights from Stewart to Grand Cayman
Search for one-way flight options from Stewart to Grand Cayman. 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 1/6. 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.
Fri 2/611:09 amSWF - GCM
1 stop26h 29mMultiple Airlines
Deal found 1/6$107
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 1/1611:09 amSWF - GCM
1 stop26h 29mMultiple Airlines
Deal found 1/7$217
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 5/107:47 pmSWF - GCM
1 stop22h 33mMultiple Airlines
Deal found 1/6$255

Cheapflights Fare Finder

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

Fly from

Stewart

Fly to

Grand Cayman

Route

Depart

Return

Price

New WindsorGeorge Town

SWF - GCM

SWFGCM

New Windsor Stewart

Fri 2/6

11:09 am-1:38 pm

1 stop26h 29m

$107

New WindsorGeorge Town

SWF - GCM

SWFGCM

New Windsor Stewart

Fri 1/16

11:09 am-1:38 pm

1 stop26h 29m

$217

New WindsorGeorge Town

SWF - GCM

SWFGCM

New Windsor Stewart

Sun 5/10

7:47 pm-5:20 pm

1 stop22h 33m

$255

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

Best time to book a flight from Stewart to Grand Cayman

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

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

Currently, October is the cheapest month in which you can book a flight from New Windsor to Grand Cayman (average of $119). Flying from New Windsor to Grand Cayman in June is currently the most expensive (average of $345). 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 Grand Cayman. 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 Grand Cayman?

    New Windsor Stewart (SWF), located 4.3 mi from the city center, is the airport you fly out of when you book flights from New Windsor to Grand Cayman.

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

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

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

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

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

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

    Currently, October is the cheapest month in which you can book a flight from New Windsor to Grand Cayman (average of $119). Flying from New Windsor to Grand Cayman in June is currently the most expensive (average of $345). 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.

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