HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Grand Cayman

$234+ 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 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — GCM
Sep 2 — Sep 91
Tue 9/2
Tue 9/9
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Stewart to Grand Cayman 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

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

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 Grand Cayman

Keep the following information in mind while searching for Stewart to Grand Cayman flight deals. Data was last updated August 28, 2025.

Popular in

December

Cheapest in

March

Average price

$521
Highest demand for flights based on searches. 5% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

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 August 28, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/26. 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 9/47:12 pmSWF - GCM
1 stop21h 48mMultiple Airlines
Deal found 8/26$234
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 10/27:11 pmSWF - GCM
1 stop21h 49mMultiple Airlines
Deal found 8/27$262
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 9/117:12 pmSWF - GCM
1 stop21h 48mMultiple Airlines
Deal found 8/26$353
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 stops29h 03mMultiple Airlines
Deal found 8/27$355
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 11/2410:57 amSWF - GCM
2 stops28h 48mMultiple Airlines
Deal found 8/27$490
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 11/2111:12 amSWF - GCM
2 stops23h 13mMultiple Airlines
Deal found 8/26$545
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 12/2611:57 amSWF - GCM
2 stops22h 28mMultiple Airlines
Deal found 8/26$892
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 2/1312:22 pmSWF - GCM
2 stops22h 03mMultiple Airlines
Deal found 8/27$1,006

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 August 28, 2025.
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

Thu 9/4

7:12 pm-4:00 pm

1 stop21h 48m

$234

New WindsorGeorge Town

SWF - GCM

SWFGCM

New Windsor Stewart

Thu 10/2

7:11 pm-4:00 pm

1 stop21h 49m

$262

New WindsorGeorge Town

SWF - GCM

SWFGCM

New Windsor Stewart

Thu 9/11

7:12 pm-4:00 pm

1 stop21h 48m

$353

New WindsorGeorge Town

SWF - GCM

SWFGCM

New Windsor Stewart

Wed 11/26

12:17 pm-5:20 pm

2 stops29h 03m

$355

New WindsorGeorge Town

SWF - GCM

SWFGCM

New Windsor Stewart

Mon 11/24

10:57 am-3:45 pm

2 stops28h 48m

$490

New WindsorGeorge Town

SWF - GCM

SWFGCM

New Windsor Stewart

Fri 11/21

11:12 am-10:25 am

2 stops23h 13m

$545

New WindsorGeorge Town

SWF - GCM

SWFGCM

New Windsor Stewart

Fri 12/26

11:57 am-10:25 am

2 stops22h 28m

$892

New WindsorGeorge Town

SWF - GCM

SWFGCM

New Windsor Stewart

Fri 2/13

12:22 pm-10:25 am

2 stops22h 03m

$1,006

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/26

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, January is the cheapest month in which you can book a flight from New Windsor to Grand Cayman (average of $467). Flying from New Windsor to Grand Cayman 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 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, January is the cheapest month in which you can book a flight from New Windsor to Grand Cayman (average of $467). Flying from New Windsor to Grand Cayman 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.