HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Simpson Bay

$113+ 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 2/16. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SXM
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from White Plains to Simpson Bay 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 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 January 27, 2026.

This Delta deal was found by Cheapflights users on 1/27. 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.
Mon 2/166:00 am
HPN
-
SXM
1 stop7h 50m
Delta
Sat 2/213:40 pm
SXM
-
HPN
2 stops21h 16m
Delta
Deal found 1/27$320
This American Airlines deal was found by Cheapflights users on 1/25. 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.
Thu 4/25:29 pm
HPN
-
SXM
2 stops19h 52m
American Airlines
Mon 4/64:28 pm
SXM
-
HPN
2 stops20h 32m
American Airlines
Deal found 1/25$346
This American Airlines deal was found by Cheapflights users on 1/26. 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.
Thu 3/125:29 pm
HPN
-
SXM
2 stops19h 47m
American Airlines
Sun 3/152:17 pm
SXM
-
HPN
2 stops21h 12m
American Airlines
Deal found 1/26$369
This American Airlines deal was found by Cheapflights users on 1/24. 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.
Sat 2/211:37 pm
HPN
-
SXM
2 stops23h 42m
American Airlines
Sat 2/285:01 pm
SXM
-
HPN
2 stops19h 28m
American Airlines
Deal found 1/24$374
This American Airlines deal was found by Cheapflights users on 1/26. 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.
Mon 2/164:30 pm
HPN
-
SXM
2 stops18h 59m
American Airlines
Sat 2/215:01 pm
SXM
-
HPN
2 stops19h 28m
American Airlines
Deal found 1/26$389
This American Airlines deal was found by Cheapflights users on 1/26. 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.
Fri 5/86:57 pm
HPN
-
SXM
2 stops18h 19m
American Airlines
Sun 5/102:24 pm
SXM
-
HPN
2 stops21h 05m
American Airlines
Deal found 1/26$403
This American Airlines deal was found by Cheapflights users on 1/26. 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.
Wed 7/15:37 pm
HPN
-
SXM
2 stops20h 08m
American Airlines
Sat 7/112:45 pm
SXM
-
HPN
2 stops20h 44m
American Airlines
Deal found 1/26$420
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Sun 2/154:30 pm
HPN
-
SXM
2 stops20h 49m
American Airlines
Mon 2/233:17 pm
SXM
-
HPN
2 stops21h 12m
American Airlines
Deal found 1/27$428
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Mon 2/166:54 pm
HPN
-
SXM
1 stop18h 22m
American Airlines
Mon 2/233:17 pm
SXM
-
HPN
2 stops21h 12m
American Airlines
Deal found 1/27$435
This Delta deal was found by Cheapflights users on 1/27. 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.
Sun 2/156:00 am
HPN
-
SXM
1 stop7h 50m
Delta
Mon 2/231:38 pm
SXM
-
HPN
1 stop9h 22m
Delta
Deal found 1/27$458

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 January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$346
(American Airlines)

One-way from

$113
(Delta)

Popular in

December

Cheapest in

October

Average price

$443
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.
Search Deals
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. 2% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 27, 2026.
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

Mon 2/16

6:00 am-2:50 pm

1 stop7h 50m

Simpson Bay Princess Juliana

Sat 2/21

3:40 pm-11:56 am

2 stops21h 16m

$320

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Thu 4/2

5:29 pm-1:21 pm

2 stops19h 52m

Simpson Bay Princess Juliana

Mon 4/6

4:28 pm-1:00 pm

2 stops20h 32m

$346

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Sat 2/21

1:37 pm-2:19 pm

2 stops23h 42m

Simpson Bay Princess Juliana

Sat 2/28

5:01 pm-11:29 am

2 stops19h 28m

$374

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Mon 2/16

4:30 pm-12:29 pm

2 stops18h 59m

Simpson Bay Princess Juliana

Sat 2/21

5:01 pm-11:29 am

2 stops19h 28m

$389

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Mon 2/16

6:54 pm-2:16 pm

1 stop18h 22m

Simpson Bay Princess Juliana

Mon 2/23

3:17 pm-11:29 am

2 stops21h 12m

$435

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Sat 2/21

6:00 am-4:00 pm

1 stop9h 00m

Simpson Bay Princess Juliana

Sat 2/28

5:25 pm-9:43 am

1 stop17h 18m

$458

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Sun 2/15

6:00 am-2:50 pm

1 stop7h 50m

Simpson Bay Princess Juliana

Mon 2/23

1:38 pm-10:00 pm

1 stop9h 22m

$458

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Sun 2/15

6:00 am-2:50 pm

1 stop7h 50m

Simpson Bay Princess Juliana

Sat 2/21

3:40 pm-11:56 am

2 stops21h 16m

$463

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Fri 2/13

5:30 pm-2:21 pm

2 stops19h 51m

Simpson Bay Princess Juliana

Tue 2/17

4:01 pm-1:07 pm

1 stop22h 06m

$472

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Sun 2/22

6:00 am-2:50 pm

1 stop7h 50m

$113

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 18 results
1
2

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 January.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on White Plains-Simpson Bay flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 $320, Delta can have you in Simpson Bay from White Plains in 7h 50m. White Plains and Simpson Bay are separated by a distance of 1709 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.