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Simpson Bay

$256+ Cheap flights from White Plains (HPN) 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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SXM
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from White Plains to Simpson Bay

Cheapest flights from White Plains to Simpson Bay
Explore the most affordable flight options available from White Plains to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This Delta deal was found by Cheapflights users on 12/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:03 amHPN - SXM
1 stop7h 47mDelta
Thu 1/81:55 pmSXM - HPN
1 stop9h 05mDelta
Deal found 12/11$309
This Delta deal was found by Cheapflights users on 12/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3012:55 pmHPN - SXM
2 stops24h 55mDelta
Thu 1/81:55 pmSXM - HPN
1 stop9h 05mDelta
Deal found 12/11$314
This American Airlines deal was found by Cheapflights users on 12/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/295:16 pmHPN - SXM
2 stops19h 43mAmerican Airlines
Thu 1/82:03 pmSXM - HPN
2 stops21h 27mAmerican Airlines
Deal found 12/11$424
This Delta deal was found by Cheapflights users on 12/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:03 amHPN - SXM
1 stop7h 47mDelta
Wed 1/71:55 pmSXM - HPN
1 stop9h 05mDelta
Deal found 12/11$452
This Delta deal was found by Cheapflights users on 12/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3012:55 pmHPN - SXM
2 stops24h 55mDelta
Wed 1/71:55 pmSXM - HPN
2 stops23h 01mDelta
Deal found 12/11$457
This Delta deal was found by Cheapflights users on 12/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:03 amHPN - SXM
1 stop7h 47mDelta
Tue 1/61:55 pmSXM - HPN
1 stop9h 05mDelta
Deal found 12/11$571
This American Airlines deal was found by Cheapflights users on 12/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/215:56 pmHPN - SXM
2 stops19h 03mAmerican Airlines
Sun 12/281:39 pmSXM - HPN
1 stop10h 05mAmerican Airlines
Deal found 12/11$673
This American Airlines deal was found by Cheapflights users on 12/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/286:30 amHPN - SXM
2 stops30h 29mAmerican Airlines
Thu 1/83:31 pmSXM - HPN
1 stop8h 28mAmerican Airlines
Deal found 12/11$703
This Delta deal was found by Cheapflights users on 12/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/146:10 amHPN - SXM
1 stop7h 18mDelta
Sun 12/211:45 pmSXM - HPN
1 stop9h 24mDelta
Deal found 12/11$727
This Delta deal was found by Cheapflights users on 12/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:03 amHPN - SXM
1 stop7h 47mDelta
Wed 1/71:55 pmSXM - HPN
1 stop9h 05mDelta
Deal found 12/11$737

Find flight deals from White Plains to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from White Plains (HPN) 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 December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$297
(American Airlines)

One-way from

$256
(Delta)

Popular in

December

Cheapest in

May

Average price

$620
Provider with most accurate pricing for White Plains Westchester County-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for White Plains Westchester County-Simpson Bay Princess Juliana flights.
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From White Plains Westchester County to Simpson Bay Princess Juliana
Search Deals
One-way flight from White Plains Westchester County to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($21 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from White Plains 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 December 12, 2025.
Use the filters below to find and compare flights from White Plains to Simpson Bay that are best for you.

Fly from

White Plains

Fly to

Simpson Bay

Route

Depart

Return

Price

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Tue 1/13

6:40 pm-4:28 pm

2 stops20h 48m

Simpson Bay Princess Juliana

Thu 1/22

4:24 pm-9:29 am

2 stops18h 05m

$302

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Fri 1/9

6:40 pm-12:58 pm

2 stops17h 18m

Simpson Bay Princess Juliana

Fri 1/16

5:33 pm-10:30 am

2 stops17h 57m

$302

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Mon 1/19

5:15 pm-2:31 pm

2 stops20h 16m

Simpson Bay Princess Juliana

Mon 1/26

3:31 pm-9:29 am

2 stops18h 58m

$302

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Sat 1/31

6:00 am-2:55 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Thu 2/5

1:55 pm-10:00 pm

1 stop9h 05m

$307

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Tue 2/3

6:00 am-2:55 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Sat 2/7

5:28 pm-9:44 am

1 stop17h 16m

$307

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Tue 2/3

6:00 am-2:55 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Fri 2/6

1:55 pm-10:00 pm

1 stop9h 05m

$307

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Sat 1/31

6:00 am-2:55 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Fri 2/6

1:55 pm-10:00 pm

1 stop9h 05m

$307

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Sat 1/31

6:00 am-2:55 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Sat 2/7

5:28 pm-9:44 am

1 stop17h 16m

$307

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Fri 1/9

6:00 am-2:55 pm

1 stop7h 55m

$256

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Fri 1/9

10:29 am-3:21 pm

2 stops51h 52m

$1,360

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Compare providers for flights from White Plains to Simpson Bay

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from White Plains to Simpson Bay in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on White Plains-Simpson Bay flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on White Plains-Simpson Bay flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from White Plains-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on White Plains-Simpson Bay flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for White Plains-Simpson Bay flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from White Plains to Simpson Bay

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

What is the cheapest month to book a flight from White Plains to Simpson Bay?

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

  • How long is the flight from White Plains to Simpson Bay?

    For as low as $302, American Airlines can have you in Simpson Bay from White Plains in 20h 48m. White Plains and Simpson Bay are separated by a distance of 1709 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from White Plains 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 White Plains to Simpson Bay?

    Currently, November is the cheapest month in which you can book a flight from White Plains to Simpson Bay (average of $121). Flying from White Plains 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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