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Simpson Bay

$140+ Cheap flights from New Windsor (SWF) to Simpson Bay (SXM)

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 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SXM
Feb 13 — Feb 201
Fri 2/13
Fri 2/20
1 adult, Economy
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Cheap flight deals from Stewart to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to Simpson Bay (SXM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 14, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$616
(Kiwi.com)

One-way from

$140
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$438
Provider with most accurate pricing for New York (NYC)-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Simpson Bay Princess Juliana flights.
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From New Windsor Stewart to Simpson Bay Princess Juliana
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One-way flight from New Windsor Stewart to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 1% potential increase in price ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Stewart to Simpson Bay

Cheapest flights from Stewart to Simpson Bay
Explore the most affordable flight options available from Stewart to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 14, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/12. 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 1/1611:09 am
SWF
-
SXM
1 stop26h 01m
Multiple Airlines
Sun 1/253:15 pm
SXM
-
SWF
1 stop20h 04m
Multiple Airlines
Deal found 1/12$532
This Kiwi.com deal was found by Cheapflights users on 1/12. 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 3/2210:29 am
SWF
-
SXM
2 stops24h 21m
Multiple Airlines
Sat 3/282:15 pm
SXM
-
SWF
1 stop19h 24m
Multiple Airlines
Deal found 1/12$616
This Kiwi.com deal was found by Cheapflights users on 1/12. 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 6/1810:28 am
SWF
-
SXM
1 stop26h 48m
Multiple Airlines
Sun 6/212:10 pm
SXM
-
SWF
2 stops44h 58m
Multiple Airlines
Deal found 1/12$823
This Kiwi.com deal was found by Cheapflights users on 1/12. 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 6/710:28 am
SWF
-
SXM
1 stop26h 48m
Multiple Airlines
Sun 6/212:11 pm
SXM
-
SWF
2 stops18h 38m
Multiple Airlines
Deal found 1/12$906

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Simpson Bay 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 January 14, 2026.
Use the filters below to find and compare flights from New Windsor to Simpson Bay that are best for you.

Fly from

Stewart

Fly to

Simpson Bay

Route

Depart

Return

Price

New WindsorSimpson Bay

SWF - SXM

SWFSXM

New Windsor Stewart

Sun 3/22

10:29 am-10:50 am

2 stops24h 21m

Simpson Bay Princess Juliana

Sat 3/28

2:15 pm-9:39 am

1 stop19h 24m

$616

New WindsorSimpson Bay

SWF - SXM

SWFSXM

New Windsor Stewart

Thu 6/18

10:28 am-1:16 pm

1 stop26h 48m

Simpson Bay Princess Juliana

Sun 6/21

2:10 pm-11:08 am

2 stops44h 58m

$823

New WindsorSimpson Bay

SWF - SXM

SWFSXM

New Windsor Stewart

Sun 6/7

10:28 am-1:16 pm

1 stop26h 48m

Simpson Bay Princess Juliana

Sun 6/21

2:11 pm-8:49 am

2 stops18h 38m

$906

New WindsorSimpson Bay

SWF - SXM

SWFSXM

New Windsor Stewart

Sun 2/22

11:52 am-2:15 pm

1 stop25h 23m

$140

New WindsorSimpson Bay

SWF - SXM

SWFSXM

New Windsor Stewart

Thu 2/26

11:52 am-2:15 pm

1 stop25h 23m

$140

New WindsorSimpson Bay

SWF - SXM

SWFSXM

New Windsor Stewart

Fri 1/23

11:09 am-2:10 pm

1 stop26h 01m

$145

New WindsorSimpson Bay

SWF - SXM

SWFSXM

New Windsor Stewart

Mon 3/9

11:02 am-1:15 pm

2 stops26h 13m

$148

New WindsorSimpson Bay

SWF - SXM

SWFSXM

New Windsor Stewart

Thu 4/16

11:45 am-1:16 pm

1 stop25h 31m

$149

New WindsorSimpson Bay

SWF - SXM

SWFSXM

New Windsor Stewart

Sun 3/22

10:29 am-1:08 pm

1 stop26h 39m

$149

New WindsorSimpson Bay

SWF - SXM

SWFSXM

New Windsor Stewart

Sun 2/1

12:13 pm-2:15 pm

2 stops25h 02m

$186

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/13

Showing 1-10 of 15 results
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Best time to book a flight from Stewart to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay 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 Simpson Bay

What is the cheapest month to book a flight from New Windsor to Simpson Bay?

Currently, November is the cheapest month in which you can book a flight from New Windsor to Simpson Bay (average of $121). Flying from New Windsor to Simpson Bay in September is currently the most expensive (average of $320). 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 Simpson Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find deals for flights from Stewart to Simpson Bay that include hotel bookings?

    Yes. In addition to deals on Stewart to Simpson Bay flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Stewart to Simpson Bay?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Stewart to Simpson Bay.

  • Can I find deals for business class flights from Stewart to Simpson Bay?

    Yes. Cheapflights offers flight deals from Stewart to Simpson Bay 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 Simpson Bay?

    Currently, November is the cheapest month in which you can book a flight from New Windsor to Simpson Bay (average of $121). Flying from New Windsor to Simpson Bay in September is currently the most expensive (average of $320). 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 Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Philipsburg

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