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

According to our current data, American Airlines ($437), and Delta ($742) offers the cheapest pricing from White Plains to Simpson Bay.

What is the cheapest day to fly from White Plains to Simpson Bay?

Travelers seeking maximum savings on their White Plains to Simpson Bay flight should consider departing on Friday mornings when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

How far in advance should I book a flight from White Plains to Simpson Bay?

Travelers have found it’s best to book a flight 49 days in advance to save up to 37% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 49 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from White Plains to Simpson Bay 1-2 weeks in advance for as low as $522, or $669 for flights within the next 24 hours.

What is the cheapest month to fly from White Plains to Simpson Bay?

September is one of the best times of the year to fly to Simpson Bay from White Plains. Prices for September average $520 per person but you can even find prices for as low as $275. The most expensive prices can be found in the month of December. Opting for a September flight can save you 38% on your journey compared to booking in December

What is the cheapest time of day to fly from HPN to SXM?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from White Plains to Simpson Bay as you normally would.

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 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.

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.

$234+ Flights from White Plains to Simpson Bay

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

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

Most accurate provider	FlightHub 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$437 (American Airlines)
One-way from	$234 (American Airlines)
Popular in	December
Cheapest in	September
Average price	$562

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. 9% potential increase in price ($53 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 3% potential price decrease ($19 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in April 2025

Search Deals

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 April 29, 2025.

Wed 9/245:25 pmHPN - SXM

2 stops20h 00mAmerican Airlines

Mon 9/292:40 pmSXM - HPN

2 stops20h 37mAmerican Airlines

Deal found 4/29

$437

Wed 9/246:00 amHPN - SXM

1 stop7h 50mDelta

Wed 10/13:15 pmSXM - HPN

2 stops20h 31mDelta

Deal found 4/29

$742

Fri 12/265:14 pmHPN - SXM

2 stops45h 03mWestJet

Fri 1/24:10 pmSXM - HPN

2 stops25h 23mWestJet

Deal found 4/29

$5,762

Best flights from White Plains to Simpson Bay
Discover carefully curated flight deals from White Plains to Simpson Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 29, 2025.

Wed 9/245:25 pmHPN - SXM

2 stops20h 00mAmerican Airlines

Mon 9/292:40 pmSXM - HPN

2 stops20h 37mAmerican Airlines

Deal found 4/29

$437

Wed 9/246:00 amHPN - SXM

1 stop7h 50mDelta

Wed 10/13:15 pmSXM - HPN

2 stops20h 31mDelta

Deal found 4/29

$742

Last-minute flights from White Plains to Simpson Bay
Discover last-minute flight deals from White Plains to Simpson Bay. Data last updated April 29, 2025 and is based on user searches.

Fri 5/96:32 pmHPN - SXM

1 stop17h 03mAmerican Airlines

Tue 5/132:24 pmSXM - HPN

2 stops19h 05mAmerican Airlines

Deal found 4/29

$464

One-way flights from White Plains to Simpson Bay
Search for one-way flight options from White Plains to Simpson Bay. Find affordable one-way fares based on user searches. Data last updated April 29, 2025.

Fri 5/95:07 pmHPN - SXM

2 stops18h 28mAmerican Airlines

Deal found 4/29

$234

Fri 5/912:06 pmHPN - SXM

3 stops25h 54mMultiple Airlines

Deal found 4/29

$412

Thu 5/296:00 amHPN - SXM

1 stop7h 54mDelta

Deal found 4/29

$811

Cheapflights Fare Finder

Use the filters below to find and compare flights from White Plains to Simpson Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Wed 9/24

5:25 pm-1:25 pm

2 stops20h 00m

Simpson Bay Princess Juliana

Mon 9/29

2:40 pm-11:17 am

2 stops20h 37m

$437

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Wed 9/24

6:00 am-1:50 pm

1 stop7h 50m

Simpson Bay Princess Juliana

Wed 10/1

3:15 pm-11:46 am

2 stops20h 31m

$742

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Fri 5/9

6:32 pm-11:35 am

1 stop17h 03m

$234

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Fri 5/9

12:06 pm-2:00 pm

3 stops25h 54m

$412

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Thu 5/29

6:00 am-1:54 pm

1 stop7h 54m

$811

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Compare providers for flights from White Plains to Simpson Bay

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 April.

Provider	Price Accuracy	Trust Score*
FlightHub	Price Accuracy3 stars	Trust Score*2 stars
eDreams	Price Accuracy3 stars	Trust 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 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 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, 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 July is currently the most expensive (average of $675). 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

Delta

8.0

Very good

7,929 reviews

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

7,929 reviews

Delta

8.0

Very good

7,929 reviews

Reviews

1 / 20

10.0

Excellent

Kymberlee,Oct 2024

JFK - ATL

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

7,929 reviews

Reviews

1 / 20

10.0

Excellent

Kymberlee,Oct 2024

JFK - ATL

Related info for your journey

What are the cheapest airlines flying from White Plains to Simpson Bay round-trip?
According to our current data, American Airlines ($437), and Delta ($742) offers the cheapest pricing from White Plains to Simpson Bay.
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 July is currently the most expensive (average of $675). 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

Alternative routes for White Plains to Simpson Bay

Newark to Simpson Bay flights

John F Kennedy Intl to Simpson Bay flights

LaGuardia to Simpson Bay flights

Buffalo to Simpson Bay flights

Albany to Simpson Bay flights

Rochester to Simpson Bay flights

Syracuse to Simpson Bay flights

Stewart to Simpson Bay flights

Islip to Simpson Bay flights

Ithaca to Simpson Bay flights

Other flights to Simpson Bay

Minneapolis to Simpson Bay flights

John F Kennedy Intl to Simpson Bay flights

Fort Lauderdale to Simpson Bay flights

Miami to Simpson Bay flights

Newark to Simpson Bay flights

Orlando to Simpson Bay flights

Simpson Bay to Fort Lauderdale flights

Simpson Bay to Panama City flights

Simpson Bay to Santo Domingo flights

Simpson Bay to San Juan Luis Munoz Marin Intl Airport flights

Simpson Bay to Gustavia flights

Simpson Bay to Basseterre flights

Simpson Bay to Road Town flights

Simpson Bay to Washington, D.C. Dulles Intl Airport flights

Simpson Bay to St. John's, Saint John flights

Simpson Bay to New York John F Kennedy Intl Airport flights

Simpson Bay to Newark Airport flights

Simpson Bay to Willemstad flights

Simpson Bay to Road Town flights

Simpson Bay to Charlotte flights

Simpson Bay to Roseau flights

Top airline flying from White Plains to Simpson Bay

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$413	Average$625	FlexibilityNo cancel fee	On-time71%

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.

$234+ 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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from White Plains to Simpson Bay with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from White Plains to Simpson Bay

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from White Plains to Simpson Bay

Cheapest flights from White Plains to Simpson BayExplore 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 April 29, 2025.

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 April 29, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from White Plains to Simpson Bay that are best for you.

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 April.

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.

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?

Reviews of airlines servicing Simpson Bay

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?

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

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

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

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

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.

Alternative routes for White Plains to Simpson Bay

See prices for flight routes from nearby airports that may be better suited for you.

Top airline flying from White Plains to Simpson Bay

100% Free

Book with Flexibility

Travel Smart

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 April 29, 2025.