$101+ Cheap flights from New Windsor (SWF) to Caribbean 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Stewart to Caribbean 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
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 Caribbean Islands
Keep the following information in mind while searching for Stewart to Caribbean Islands flight deals. Data was last updated February 23, 2025.
Round-trip from | $216 (Mytrip) |
|---|---|
One-way from | $101 (Mytrip) |
Popular in | December |
Cheapest in | September |
Average price | $327 |
Find flight deals from Stewart to Caribbean Islands
Cheapest flights from Stewart to Caribbean IslandsExplore the most affordable flight options available from Stewart to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 23, 2025.
Explore the most affordable flight options available from Stewart to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 23, 2025.
This Mytrip deal was found by Cheapflights users on 2/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 2/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 2/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 2/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 2/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Kiwi.com deal was found by Cheapflights users on 2/21. 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.
This Kiwi.com deal was found by Cheapflights users on 2/22. 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.
This Mytrip deal was found by Cheapflights users on 2/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Find flights from Stewart to Caribbean Islands within your budget
Customize your flight search to find flights from Stewart to Caribbean 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 February 23, 2025.
Fly from
Fly to
Route
Depart
Return
Price
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Fri 5/2
11:50 am-8:37 am
1 stop20h 47m
San Juan Luis Munoz Marin Intl
Sun 5/4
10:25 am-11:00 am
1 stop24h 35m
New WindsorOranjestad
SWF - AUA
SWFAUA
New Windsor Stewart
Fri 4/4
10:10 am-2:45 pm
1 stop28h 35m
Oranjestad Reina Beatrix
Sun 4/6
3:50 pm-9:20 am
1 stop17h 30m
New WindsorMontego Bay
SWF - MBJ
SWFMBJ
New Windsor Stewart
Mon 4/21
11:50 am-10:55 am
1 stop24h 05m
Montego Bay Sangster Intl
Thu 4/24
12:00 pm-11:00 am
1 stop22h 00m
New WindsorPunta Cana
SWF - PUJ
SWFPUJ
New Windsor Stewart
Mon 3/24
10:10 am-2:42 pm
1 stop28h 32m
Punta Cana
Sun 3/30
2:29 pm-8:06 pm
2 stops29h 37m
New WindsorNassau
SWF - NAS
SWFNAS
New Windsor Stewart
Fri 4/25
11:50 am-7:15 pm
1 stop7h 25m
Nassau Intl
Sun 4/27
4:00 pm-11:00 am
1 stop19h 00m
New WindsorKingston
SWF - KIN
SWFKIN
New Windsor Stewart
Fri 2/28
6:23 pm-12:21 pm
1 stop17h 58m
Kingston Norman Manley
Sun 3/9
1:36 pm-9:20 am
1 stop18h 44m
New WindsorSantiago de los Caballeros
SWF - STI
SWFSTI
New Windsor Stewart
Mon 3/24
10:10 am-2:35 pm
1 stop28h 25m
Santiago de los Caballeros
Thu 3/27
3:40 pm-9:20 am
1 stop17h 40m
New WindsorSanto Domingo
SWF - SDQ
SWFSDQ
New Windsor Stewart
Thu 3/6
7:54 pm-4:49 pm
2 stops19h 55m
Santo Domingo Las Americas
Thu 3/13
11:00 am-9:20 am
2 stops22h 20m
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Mon 5/5
11:50 am-4:37 pm
1 stop28h 47m
New WindsorMontego Bay
SWF - MBJ
SWFMBJ
New Windsor Stewart
Mon 3/24
10:10 am-11:02 am
1 stop25h 52m
Best time to book a flight from Stewart to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Stewart with our price prediction graph.
Travel insights for flights from Stewart to Caribbean Islands
Get recent, data-driven insights about flights from Stewart to Caribbean Islands including ideal travel times, pricing trends, and more.
What is the cheapest month to book a flight from New Windsor to Caribbean Islands?
Currently, September is the cheapest month in which you can book a flight from New Windsor to Caribbean Islands (average of $254). Flying from New Windsor to Caribbean Islands in March is currently the most expensive (average of $363). 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.
What is the cheapest time of day to fly from SWF to EPX?
Find hourly flight availability from Stewart to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 23, 2025.
When flying from New Windsor to Caribbean Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Rainfall in Caribbean Islands by month
Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.
Temperature in Caribbean Islands by month
Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).