$243+ 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 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — GCM
Aug 4 — Aug 111
1 adult, Economy
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Find cheap flights from Stewart to Cayman Islands with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.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 July 30, 2025.
Popular in | December |
|---|---|
Cheapest in | March |
Average price | $468 |
Find flight deals from Stewart to Cayman Islands
One-way flights from Stewart to Cayman IslandsSearch for one-way flight options from Stewart to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated July 30, 2025.
Search for one-way flight options from Stewart to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated July 30, 2025.
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 9/147:12 pmSWF - GCM
1 stop23h 08mMultiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$243
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 July 30, 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
Sun 9/14
7:12 pm-5:20 pm
1 stop23h 08m
$243
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.