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Stewart

$373+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — SWF
Aug 22 — Aug 291
Fri 8/22
Fri 8/29
1 adult, Economy
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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 August 17, 2025.

Popular in

October

Cheapest in

March

Average price

$435
Highest demand for flights based on searches. 13% potential increase in price ($63 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Grand Cayman to Stewart

One-way flights from Grand Cayman to Stewart
Search for one-way flight options from Grand Cayman to Stewart. Find affordable one-way fares based on user searches. Data last updated August 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/15. 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.
Thu 12/117:00 amGCM - SWF
3 stops28h 37mMultiple Airlines
Deal found 8/15$373
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 12/311:30 amGCM - SWF
3 stops48h 07mMultiple Airlines
Deal found 8/16$378
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 10/111:45 pmGCM - SWF
2 stops43h 26mMultiple Airlines
Deal found 8/14$379
This Kiwi.com deal was found by Cheapflights users on 8/15. 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.
Tue 9/211:30 amGCM - SWF
3 stops48h 44mMultiple Airlines
Deal found 8/15$448
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 11/18:50 amGCM - SWF
3 stops27h 55mMultiple Airlines
Deal found 8/16$455
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 9/1311:25 amGCM - SWF
3 stops46h 38mMultiple Airlines
Deal found 8/16$479
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 12/2112:40 pmGCM - SWF
2 stops30h 55mMultiple Airlines
Deal found 8/16$493
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 9/124:45 pmGCM - SWF
3 stops41h 18mMultiple Airlines
Deal found 8/16$498
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 9/1711:30 amGCM - SWF
3 stops24h 44mMultiple Airlines
Deal found 8/16$565

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 August 17, 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

Thu 12/11

7:00 am-11:37 am

3 stops28h 37m

$373

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Wed 12/3

11:30 am-11:37 am

3 stops48h 07m

$378

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Wed 12/10

11:30 am-11:37 am

3 stops48h 07m

$378

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Sat 10/11

1:45 pm-10:11 am

2 stops43h 26m

$379

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Tue 9/2

11:30 am-1:14 pm

3 stops48h 44m

$448

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Sat 11/1

8:50 am-1:45 pm

3 stops27h 55m

$455

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Sat 9/13

11:25 am-11:03 am

3 stops46h 38m

$479

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Sun 12/21

12:40 pm-7:35 pm

2 stops30h 55m

$493

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Fri 9/12

4:45 pm-11:03 am

3 stops41h 18m

$498

George TownNew Windsor

GCM - SWF

GCMSWF

George Town Owen Roberts Intl

Wed 9/17

11:30 am-1:14 pm

3 stops24h 44m

$565

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/15

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, October is the cheapest month in which you can book a flight from Grand Cayman to New Windsor (average of $109). Flying from Grand Cayman to New Windsor in December is currently the most expensive (average of $202). 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, October is the cheapest month in which you can book a flight from Grand Cayman to New Windsor (average of $109). Flying from Grand Cayman to New Windsor in December is currently the most expensive (average of $202). 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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