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Stewart

$216+ Cheap flights from Grand Cayman 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — SWF
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
1 adult, Economy
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Find flight deals from Grand Cayman to Stewart

Best flights from Grand Cayman to Stewart
Discover carefully curated flight deals from Grand Cayman to Stewart that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 26, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/25. 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 1/93:00 pmGCM - SWF
2 stops44h 33mMultiple Airlines
Fri 1/1611:09 amSWF - GCM
1 stop26h 29mMultiple Airlines
Deal found 11/25$575

Cheap flight deals from Grand Cayman to Stewart

Keep the following information in mind while searching for Grand Cayman to Stewart flight deals. Data was last updated November 26, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$575
(Kiwi.com)

One-way from

$216
(Kiwi.com)

Popular in

July

Cheapest in

March

Average price

$329
Provider with most accurate pricing for George Town Owen Roberts Intl-New York (NYC) flight deals.
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Provider most trusted by Cheapflights users for George Town Owen Roberts Intl-New York (NYC) flights.
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From Grand Cayman to New Windsor Stewart
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One-way flight from Grand Cayman to New Windsor Stewart
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Highest demand for flights based on searches. 17% potential increase in price ($78 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Grand Cayman 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 26, 2025.
Use the filters below to find and compare flights from Grand Cayman to New Windsor that are best for you.

Fly from

Grand Cayman

Fly to

Stewart

Route

Depart

Return

Price

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Fri 1/9

3:00 pm-11:33 am

2 stops44h 33m

New Windsor Stewart

Fri 1/16

11:09 am-1:38 pm

1 stop26h 29m

$575

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Thu 1/29

2:49 pm-10:19 am

1 stop19h 30m

$216

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Sun 12/7

2:40 pm-11:37 am

1 stop20h 57m

$268

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Wed 12/10

11:30 am-11:37 am

3 stops48h 07m

$301

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Wed 12/24

7:00 am-11:07 am

3 stops52h 07m

$311

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Tue 12/9

11:30 am-11:03 am

3 stops47h 33m

$346

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Sat 12/6

5:56 pm-11:44 am

2 stops41h 48m

$350

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Sat 4/4

1:40 pm-9:39 am

1 stop18h 59m

$354

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Tue 3/3

11:30 am-9:24 am

3 stops45h 54m

$358

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Sat 4/11

1:40 pm-10:42 am

1 stop20h 02m

$397

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/25

Best time to book a flight from Grand Cayman to Stewart

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

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

Currently, January is the cheapest month in which you can book a flight from Grand Cayman to New Windsor (average of $133). Flying from Grand Cayman 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 Grand Cayman 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 Grand Cayman?

    Most people fly into New Windsor Stewart (SWF) if they book a flight to New Windsor from Grand Cayman. Stewart is conveniently located just 4.3 mi from New Windsor’s city center.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Grand Cayman to New Windsor (average of $133). Flying from Grand Cayman 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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