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Simpson Bay

$211+ 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 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SXM
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$382
(American Airlines)

One-way from

$211
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$396
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. 11% potential increase in price ($64 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($21 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 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 September 11, 2025.

This American Airlines deal was found by Cheapflights users on 9/10. 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.
Tue 10/146:55 pmHPN - SXM
2 stops18h 42mAmerican Airlines
Sat 10/184:24 pmSXM - HPN
2 stops18h 10mAmerican Airlines
Deal found 9/10$454
This American Airlines deal was found by Cheapflights users on 9/10. 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 12/295:56 pmHPN - SXM
2 stops19h 21mAmerican Airlines
Thu 1/15:33 pmSXM - HPN
2 stops20h 32mAmerican Airlines
Deal found 9/10$696
This American Airlines deal was found by Cheapflights users on 9/10. 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 12/283:00 pmHPN - SXM
2 stops20h 32mAmerican Airlines
Thu 1/15:33 pmSXM - HPN
2 stops20h 32mAmerican Airlines
Deal found 9/10$846
This American Airlines deal was found by Cheapflights users on 9/10. 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 11/226:49 pmHPN - SXM
2 stops20h 33mAmerican Airlines
Sat 11/295:24 pmSXM - HPN
2 stops20h 36mAmerican Airlines
Deal found 9/10$1,207
This American Airlines deal was found by Cheapflights users on 9/10. 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 12/296:56 pmHPN - SXM
1 stop18h 03mAmerican Airlines
Fri 1/23:28 pmSXM - HPN
1 stop8h 14mAmerican Airlines
Deal found 9/10$1,308
This American Airlines deal was found by Cheapflights users on 9/10. 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 12/285:16 pmHPN - SXM
2 stops18h 16mAmerican Airlines
Fri 1/21:39 pmSXM - HPN
1 stop10h 03mAmerican Airlines
Deal found 9/10$1,377

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 September 11, 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 2/3

7:00 am-4:10 pm

1 stop8h 10m

Simpson Bay Princess Juliana

Fri 2/6

3:25 pm-10:32 am

2 stops20h 07m

$382

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Tue 10/14

6:55 pm-1:37 pm

2 stops18h 42m

Simpson Bay Princess Juliana

Sat 10/18

4:24 pm-10:34 am

2 stops18h 10m

$454

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Sun 2/8

7:00 am-4:10 pm

1 stop8h 10m

Simpson Bay Princess Juliana

Thu 2/12

4:15 pm-10:44 am

2 stops19h 29m

$465

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Mon 2/2

6:11 am-4:10 pm

2 stops8h 59m

Simpson Bay Princess Juliana

Thu 2/5

5:20 pm-9:19 am

2 stops16h 59m

$465

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Mon 2/2

6:11 am-4:10 pm

2 stops8h 59m

Simpson Bay Princess Juliana

Fri 2/6

3:25 pm-10:28 pm

1 stop8h 03m

$534

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Wed 2/4

6:11 am-4:10 pm

2 stops8h 59m

Simpson Bay Princess Juliana

Fri 2/6

3:25 pm-10:28 pm

1 stop8h 03m

$602

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Sun 2/15

3:07 pm-4:15 pm

2 stops24h 08m

Simpson Bay Princess Juliana

Sun 2/22

5:20 pm-1:06 pm

2 stops20h 46m

$637

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Mon 2/2

7:00 am-4:10 pm

1 stop8h 10m

Simpson Bay Princess Juliana

Sat 2/7

3:20 pm-10:49 pm

1 stop8h 29m

$699

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Tue 2/3

6:11 am-4:10 pm

2 stops8h 59m

Simpson Bay Princess Juliana

Sat 2/7

3:20 pm-10:49 pm

1 stop8h 29m

$704

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Sat 9/27

6:50 pm-1:19 pm

2 stops18h 29m

$211

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 21 results
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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, September is the cheapest month in which you can book a flight from White Plains to Simpson Bay (average of $459). Flying from White Plains 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 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 $382, American Airlines can have you in Simpson Bay from White Plains in 8h 10m. 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, September is the cheapest month in which you can book a flight from White Plains to Simpson Bay (average of $459). Flying from White Plains 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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