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Simpson Bay

$143+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SXM
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 July 29, 2025.

Round-trip from

$340
(American Airlines)

One-way from

$143
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$524
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 ($63 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 July 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 July 29, 2025.

This American Airlines deal was found by Cheapflights users on 7/27. 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.
Thu 12/47:42 pmHPN - SXM
2 stops17h 33mAmerican Airlines
Tue 12/93:15 pmSXM - HPN
2 stops20h 17mAmerican Airlines
Deal found 7/27$340
This Mytrip deal was found by Cheapflights users on 7/28. 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.
Thu 8/148:10 amHPN - SXM
3 stops29h 50mMultiple Airlines
Mon 8/183:05 pmSXM - HPN
3 stops29h 25mMultiple Airlines
Deal found 7/28$857
This Delta deal was found by Cheapflights users on 7/27. 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.
Fri 8/86:00 amHPN - SXM
1 stop7h 56mDelta
Wed 8/133:21 pmSXM - HPN
1 stop18h 28mDelta
Deal found 7/27$1,133
This WestJet deal was found by Cheapflights users on 7/27. 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.
Tue 11/2512:30 pmHPN - SXM
2 stops49h 51mWestJet
Wed 12/34:20 pmSXM - HPN
2 stops25h 14mWestJet
Deal found 7/27$3,246

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 July 29, 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

Thu 12/4

7:42 pm-2:15 pm

2 stops17h 33m

Simpson Bay Princess Juliana

Tue 12/9

3:15 pm-10:32 am

2 stops20h 17m

$340

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Mon 1/12

6:00 am-2:56 pm

1 stop7h 56m

Simpson Bay Princess Juliana

Thu 1/29

1:45 pm-9:36 pm

1 stop8h 51m

$537

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Thu 8/14

8:10 am-2:00 pm

3 stops29h 50m

Simpson Bay Princess Juliana

Mon 8/18

3:05 pm-8:30 pm

3 stops29h 25m

$857

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Thu 12/4

4:28 pm-1:55 pm

2 stops20h 27m

$143

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Mon 10/27

6:00 am-1:49 pm

1 stop7h 49m

$268

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Thu 12/4

12:09 pm-3:10 pm

3 stops26h 01m

$297

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Mon 10/27

5:20 pm-2:21 pm

2 stops21h 01m

$1,337

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

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 $655). 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.

Reviews of airlines servicing Simpson Bay

Get insights into the airlines that provide service to Simpson Bay. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Simpson Bay. Reviews last updated July 29, 2025.
Read through reviews of airlines operating flights from White Plains to Simpson Bay, such as Delta, American Airlines, and WestJet. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,977 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Delta
8.0
Very good
7,977 reviews
Delta
8.0
Very good
7,977 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,977 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
WestJet
7.2
Good
2,973 reviews
Delta
8.0
Very good
7,977 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

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.

  • What are the cheapest airlines flying from White Plains to Simpson Bay round-trip?

    According to our current data, American Airlines ($340), and Delta ($537) offers the cheapest pricing from White Plains to Simpson Bay.

  • What are the cheapest airlines to fly from White Plains to Simpson Bay one-way?

    $143 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on Delta and WestJet, with prices starting from $268 and $1,337, respectively.

  • 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 $655). 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

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from White Plains to Simpson Bay

Discover the top airline that operate flights from White Plains to Simpson Bay. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$413Average$625FlexibilityNo cancel feeOn-time71%

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