$114+ Cheap flights from New Windsor (SWF) to Caribbean
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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Stewart to Caribbean 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
Keep the following information in mind while searching for Stewart to Caribbean flight deals. Data was last updated June 12, 2025.
Round-trip from | $246 (Mytrip) |
|---|---|
One-way from | $114 (Mytrip) |
Popular in | December |
Cheapest in | March |
Average price | $255 |
Find flight deals from Stewart to Caribbean
Cheapest flights from Stewart to CaribbeanExplore the most affordable flight options available from Stewart to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.
Explore the most affordable flight options available from Stewart to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.
This Mytrip deal was found by Cheapflights users on 6/9. 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 6/11. 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 6/11. 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 6/10. 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 6/10. 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 6/11. 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 6/10. 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 Booking.com deal was found by Cheapflights users on 6/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Booking.com deal was found by Cheapflights users on 6/10. 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 Booking.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 6/10. 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.
Cheapflights Fare Finder
Customize your flight search to find flights from Stewart to Caribbean 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 June 12, 2025.
Use the filters below to find and compare flights from New Windsor to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Fri 6/20
8:01 pm-7:19 pm
1 stop23h 18m
San Juan Luis Munoz Marin Intl
Thu 6/26
8:24 pm-7:11 pm
1 stop22h 47m
New WindsorPunta Cana
SWF - PUJ
SWFPUJ
New Windsor Stewart
Mon 7/28
7:56 pm-2:30 pm
1 stop18h 34m
Punta Cana
Thu 7/31
3:25 pm-7:06 pm
1 stop27h 41m
New WindsorMontego Bay
SWF - MBJ
SWFMBJ
New Windsor Stewart
Mon 7/28
7:56 pm-11:05 am
1 stop16h 09m
Montego Bay Sangster Intl
Thu 7/31
1:40 pm-7:06 pm
1 stop28h 26m
New WindsorSantiago de los Caballeros
SWF - STI
SWFSTI
New Windsor Stewart
Fri 7/18
7:56 pm-9:50 am
1 stop13h 54m
Santiago de los Caballeros
Mon 7/21
10:55 am-7:06 pm
1 stop8h 11m
New WindsorSanto Domingo
SWF - SDQ
SWFSDQ
New Windsor Stewart
Mon 8/4
7:56 pm-9:50 am
1 stop13h 54m
Santo Domingo Las Americas
Fri 8/8
12:46 pm-10:13 am
1 stop21h 27m
New WindsorOranjestad
SWF - AUA
SWFAUA
New Windsor Stewart
Fri 7/18
7:56 pm-2:40 pm
1 stop18h 44m
Oranjestad Reina Beatrix
Sun 7/20
3:45 pm-7:06 pm
1 stop27h 21m
New WindsorKingston
SWF - KIN
SWFKIN
New Windsor Stewart
Fri 7/25
7:56 pm-7:47 am
1 stop12h 51m
Kingston Norman Manley
Fri 8/8
7:05 am-7:06 pm
1 stop11h 01m
New WindsorNassau
SWF - NAS
SWFNAS
New Windsor Stewart
Fri 9/5
7:04 pm-10:30 am
1 stop15h 26m
Nassau Intl
Mon 9/8
11:30 am-6:14 pm
1 stop6h 44m
New WindsorFreeport
SWF - FPO
SWFFPO
New Windsor Stewart
Fri 9/5
7:04 pm-1:45 pm
1 stop18h 41m
Freeport Grand Bahama Intl
Mon 9/8
11:00 am-6:14 pm
1 stop7h 14m
New WindsorProvidenciales
SWF - PLS
SWFPLS
New Windsor Stewart
Wed 7/2
11:50 am-11:30 am
2 stops23h 40m
Providenciales
Sun 7/6
12:30 pm-7:06 pm
2 stops30h 36m
Best time to book a flight from Stewart to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Stewart with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from New Windsor to Caribbean
What is the cheapest month to book a flight from New Windsor to Caribbean?
Currently, September is the cheapest month in which you can book a flight from New Windsor to Caribbean (average of $254). Flying from New Windsor to Caribbean in June is currently the most expensive (average of $339). 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 CB?
Find hourly flight availability from Stewart to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 12, 2025.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from New Windsor to Caribbean as you normally would.
Rainfall in Caribbean by month
Plan your trip to Caribbean by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Caribbean 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 when rainfall is around 2.2 in.
Temperature in Caribbean by month
Plan your trip to Caribbean by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Caribbean, 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).
Related info for your journey
Find useful and relevant information for your journey from Stewart to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Stewart to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Top 2 airlines flying from Stewart to Caribbean
Discover the top 2 airlines that operate flights from Stewart to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$90 | Average$186 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$175 | Average$338 | FlexibilityNo cancel fee | On-time62% |