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Simpson Bay

$198+ 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 10/10. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SXM
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Popular in

December

Cheapest in

May

Average price

$430
Highest demand for flights based on searches. 11% potential increase in price ($67 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Stewart to Simpson Bay

One-way flights from Stewart to Simpson Bay
Search for one-way flight options from Stewart to Simpson Bay. Find affordable one-way fares based on user searches. Data last updated September 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/1011:41 amSWF - SXM
1 stop26h 19mMultiple Airlines
Deal found 9/16$198
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 2/811:48 amSWF - SXM
2 stops26h 22mMultiple Airlines
Deal found 9/16$209
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/2611:43 amSWF - SXM
2 stops26h 17mMultiple Airlines
Deal found 9/17$232
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/3011:43 amSWF - SXM
2 stops26h 17mMultiple Airlines
Deal found 9/15$249
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 1/2911:48 amSWF - SXM
2 stops26h 22mMultiple Airlines
Deal found 9/16$261
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/2311:43 amSWF - SXM
2 stops26h 17mMultiple Airlines
Deal found 9/17$265
This Mytrip deal was found by Cheapflights users on 9/16. 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.
Mon 10/273:01 pmSWF - SXM
2 stops23h 20mMultiple Airlines
Deal found 9/16$297
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 9/2811:43 amSWF - SXM
2 stops26h 17mMultiple Airlines
Deal found 9/17$307
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 9/2612:24 pmSWF - SXM
3 stops25h 36mMultiple Airlines
Deal found 9/16$370
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Sat 12/207:50 pmSWF - SXM
3 stops42h 20mMultiple Airlines
Deal found 9/16$536

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 September 17, 2025.
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 2/8

11:48 am-3:10 pm

2 stops26h 22m

$209

New WindsorSimpson Bay

SWF - SXM

SWFSXM

New Windsor Stewart

Sun 10/26

11:43 am-2:00 pm

2 stops26h 17m

$232

New WindsorSimpson Bay

SWF - SXM

SWFSXM

New Windsor Stewart

Thu 10/30

11:43 am-2:00 pm

2 stops26h 17m

$249

New WindsorSimpson Bay

SWF - SXM

SWFSXM

New Windsor Stewart

Thu 1/29

11:48 am-3:10 pm

2 stops26h 22m

$261

New WindsorSimpson Bay

SWF - SXM

SWFSXM

New Windsor Stewart

Mon 10/27

3:01 pm-2:21 pm

2 stops23h 20m

$297

New WindsorSimpson Bay

SWF - SXM

SWFSXM

New Windsor Stewart

Sun 9/28

11:43 am-2:00 pm

2 stops26h 17m

$307

New WindsorSimpson Bay

SWF - SXM

SWFSXM

New Windsor Stewart

Fri 10/10

11:41 am-5:10 pm

2 stops29h 29m

$364

New WindsorSimpson Bay

SWF - SXM

SWFSXM

New Windsor Stewart

Fri 9/26

12:24 pm-2:00 pm

3 stops25h 36m

$370

New WindsorSimpson Bay

SWF - SXM

SWFSXM

New Windsor Stewart

Sat 12/20

7:50 pm-3:10 pm

3 stops42h 20m

$536

New WindsorSimpson Bay

SWF - SXM

SWFSXM

New Windsor Stewart

Fri 12/19

12:24 pm-3:10 pm

2 stops25h 46m

$586

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

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, September is the cheapest month in which you can book a flight from New Windsor to Simpson Bay (average of $459). Flying from New Windsor to Simpson Bay in March is currently the most expensive (average of $652). 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, September is the cheapest month in which you can book a flight from New Windsor to Simpson Bay (average of $459). Flying from New Windsor to Simpson Bay in March is currently the most expensive (average of $652). 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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