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Simpson Bay

$115+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SXM
nov. 27 — dic. 41
jue. 11/27
jue. 12/4
1 adult, Economy
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Cheap 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 octubre 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$311
(Delta)

One-way from

$115
(Delta)

Popular in

December

Cheapest in

May

Average price

$428
Provider with most accurate pricing for White Plains Westchester County-Simpson Bay Princess Juliana flight deals.
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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
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One-way flight from White Plains Westchester County to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 7% potential increase in price ($38 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find 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 octubre 28, 2025.

This American Airlines deal was found by Cheapflights users on 10/26. 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.
mié. 12/105:19 pmHPN - SXM
2 stops22h 06mAmerican Airlines
mié. 12/173:20 pmSXM - HPN
2 stops20h 14mAmerican Airlines
Deal found 10/26$322
This American Airlines deal was found by Cheapflights users on 10/27. 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.
vie. 12/125:19 pmHPN - SXM
2 stops17h 51mAmerican Airlines
vie. 12/192:59 pmSXM - HPN
1 stop9h 01mAmerican Airlines
Deal found 10/27$366
This Priceline deal was found by Cheapflights users on 10/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/107:00 amHPN - SXM
1 stop7h 05mJetBlue
mié. 12/174:10 pmSXM - HPN
1 stop28h 45mJetBlue
Deal found 10/26$392
This American Airlines deal was found by Cheapflights users on 10/27. 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.
mar. 12/24:30 pmHPN - SXM
2 stops20h 22mAmerican Airlines
mar. 12/95:25 pmSXM - HPN
2 stops20h 35mAmerican Airlines
Deal found 10/27$494
This Delta deal was found by Cheapflights users on 10/27. 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.
mar. 12/26:10 amHPN - SXM
1 stop7h 18mDelta
mar. 12/93:53 pmSXM - HPN
2 stops21h 06mDelta
Deal found 10/27$957
This Delta deal was found by Cheapflights users on 10/27. 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.
dom. 12/216:03 amHPN - SXM
1 stop7h 47mDelta
dom. 12/281:45 pmSXM - HPN
1 stop9h 24mDelta
Deal found 10/27$1,606
This WestJet deal was found by Cheapflights users on 10/26. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/105:17 pmHPN - SXM
2 stops21h 04mWestJet
mié. 12/174:20 pmSXM - HPN
2 stops30h 49mWestJet
Deal found 10/26$3,142
This WestJet deal was found by Cheapflights users on 10/26. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/312:55 pmHPN - SXM
2 stops25h 26mWestJet
jue. 11/204:20 pmSXM - HPN
2 stops26h 41mWestJet
Deal found 10/26$3,189
This WestJet deal was found by Cheapflights users on 10/27. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/215:16 pmHPN - SXM
2 stops21h 05mWestJet
dom. 12/284:20 pmSXM - HPN
2 stops24h 29mWestJet
Deal found 10/27$3,398

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 octubre 28, 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

lun. 1/19

6:00 am-2:55 pm

1 stop7h 55m

Simpson Bay Princess Juliana

jue. 1/29

1:55 pm-10:02 pm

1 stop9h 07m

$311

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

lun. 1/19

6:00 am-2:55 pm

1 stop7h 55m

Simpson Bay Princess Juliana

sáb. 1/24

5:28 pm-9:49 am

1 stop17h 21m

$311

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

lun. 1/19

6:00 am-2:55 pm

1 stop7h 55m

Simpson Bay Princess Juliana

mié. 1/28

1:55 pm-10:02 pm

1 stop9h 07m

$311

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

lun. 1/19

6:00 am-2:55 pm

1 stop7h 55m

Simpson Bay Princess Juliana

mar. 1/27

1:55 pm-10:02 pm

1 stop9h 07m

$311

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

mié. 12/10

5:19 pm-4:25 pm

2 stops22h 06m

Simpson Bay Princess Juliana

mié. 12/17

3:20 pm-10:34 am

2 stops20h 14m

$322

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

vie. 12/12

5:19 pm-12:10 pm

2 stops17h 51m

Simpson Bay Princess Juliana

vie. 12/19

1:39 pm-9:29 am

2 stops20h 50m

$322

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

sáb. 1/24

5:30 pm-12:58 pm

1 stop18h 28m

Simpson Bay Princess Juliana

mié. 1/28

3:31 pm-10:59 pm

1 stop8h 28m

$373

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

jue. 1/22

7:00 am-4:28 pm

1 stop8h 28m

Simpson Bay Princess Juliana

jue. 1/29

3:31 pm-10:59 pm

1 stop8h 28m

$373

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

mar. 12/9

6:10 am-2:28 pm

1 stop7h 18m

$115

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

mié. 12/10

6:10 am-2:28 pm

1 stop7h 18m

$115

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 15 results
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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 October.
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 $311, Delta can have you in Simpson Bay from White Plains in 7h 55m. 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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