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Simpson Bay

$363+ Cheap flights from Islip, NY (ISP) 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 7/22. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — SXM
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
1 adult, Economy
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Cheap flight deals from Islip to Simpson Bay

Cheapest flights from Islip to Simpson Bay
Explore the most affordable flight options available from Islip to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 28, 2026.

This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:25 am
ISP
-
SXM
1 stop7h 35m
Southwest
Sun 7/262:15 pm
SXM
-
ISP
2 stops18h 05m
Southwest
Deal found 1/26$820
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/221:51 pm
ISP
-
SXM
2 stops20h 48m
JetBlue
Sun 7/262:34 pm
SXM
-
ISP
2 stops22h 22m
JetBlue
Deal found 1/26$1,109
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/138:25 pm
ISP
-
SXM
1 stop17h 27m
JetBlue
Fri 3/203:02 pm
SXM
-
ISP
1 stop28h 28m
JetBlue
Deal found 1/27$1,158

Find flight deals from Islip to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Islip (ISP) 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 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$820
(Southwest)

One-way from

$363
(Southwest)

Popular in

December

Cheapest in

October

Average price

$443
Provider with most accurate pricing for Islip Long Island-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Islip Long Island-Simpson Bay Princess Juliana flights.
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From Islip Long Island to Simpson Bay Princess Juliana
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One-way flight from Islip Long Island to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 2% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Islip 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 28, 2026.
Use the filters below to find and compare flights from Islip to Simpson Bay that are best for you.

Fly from

Islip

Fly to

Simpson Bay

Route

Depart

Return

Price

IslipSimpson Bay

ISP - SXM

ISPSXM

Islip Long Island

Wed 7/22

6:25 am-2:00 pm

1 stop7h 35m

Simpson Bay Princess Juliana

Sun 7/26

2:15 pm-8:20 am

2 stops18h 05m

$820

IslipSimpson Bay

ISP - SXM

ISPSXM

Islip Long Island

Wed 7/22

1:51 pm-10:39 am

2 stops20h 48m

Simpson Bay Princess Juliana

Sun 7/26

2:34 pm-12:56 pm

2 stops22h 22m

$1,109

IslipSimpson Bay

ISP - SXM

ISPSXM

Islip Long Island

Fri 3/13

8:25 pm-1:52 pm

1 stop17h 27m

Simpson Bay Princess Juliana

Fri 3/20

3:02 pm-7:30 pm

1 stop28h 28m

$1,158

IslipSimpson Bay

ISP - SXM

ISPSXM

Islip Long Island

Wed 7/22

6:25 am-2:00 pm

1 stop7h 35m

$363

IslipSimpson Bay

ISP - SXM

ISPSXM

Islip Long Island

Wed 7/22

1:51 pm-10:39 am

2 stops20h 48m

$363

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

  • Most accurate provider: When it comes to deals on Islip, New York-Simpson Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Islip, New York-Simpson Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Islip, New York-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Islip, New York-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 Islip, New York-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 Islip to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Islip 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 Islip to Simpson Bay

What is the cheapest month to book a flight from Islip, New York to Simpson Bay?

Currently, November is the cheapest month in which you can book a flight from Islip, New York to Simpson Bay (average of $121). Flying from Islip, New York 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 Islip 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 Islip, New York to Simpson Bay?

    For as low as $820, Southwest can have you in Simpson Bay from Islip, New York in 7h 35m. The distance between Islip, New York and Simpson Bay is about 1679 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from Islip to Simpson Bay that include hotel bookings?

    Yes. In addition to deals on Islip to Simpson Bay flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Islip to Simpson Bay?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Islip to Simpson Bay.

  • Can I find deals for business class flights from Islip to Simpson Bay?

    Yes. Cheapflights offers flight deals from Islip 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 Islip, New York to Simpson Bay?

    Currently, November is the cheapest month in which you can book a flight from Islip, New York to Simpson Bay (average of $121). Flying from Islip, New York 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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