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Simpson Bay

$129+ Cheap flights from Massachusetts 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SXM
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Massachusetts to Simpson Bay

Keep the following information in mind while searching for Massachusetts to Simpson Bay flight deals. Data was last updated September 16, 2025.

Round-trip from

$286
(Cheapflightsfares)

One-way from

$129
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$480

Good round-trip deal

$456 or less

Good one-way deal

$186 or less
From Massachusetts to Simpson Bay Princess Juliana
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One-way flight from Massachusetts to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 9% potential increase in price ($63 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Massachusetts to Simpson Bay Princess Juliana.
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Price to beat on a one-way flight from Massachusetts to Simpson Bay Princess Juliana.
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Find flight deals from Massachusetts to Simpson Bay

Cheapest flights from Massachusetts to Simpson Bay
Explore the most affordable flight options available from Massachusetts to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/46:10 amBOS - SXM
1 stop7h 50mSpirit Airlines
Sat 10/113:05 pmSXM - BOS
1 stop8h 54mSpirit Airlines
Deal found 9/14$286
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/125:45 amBOS - SXM
1 stop8h 25mSpirit Airlines
Wed 11/194:28 pmSXM - BOS
1 stop9h 12mSpirit Airlines
Deal found 9/14$318
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/36:10 amBOS - SXM
1 stop7h 50mSpirit Airlines
Sat 10/113:05 pmSXM - BOS
1 stop8h 54mSpirit Airlines
Deal found 9/14$327
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/256:16 amBOS - SXM
1 stop7h 44mSpirit Airlines
Sat 11/13:05 pmSXM - BOS
1 stop8h 54mSpirit Airlines
Deal found 9/14$328
This United Airlines deal was found by Cheapflights users on 9/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/276:00 amBOS - SXM
1 stop6h 50mUnited Airlines
Fri 10/311:52 pmSXM - BOS
1 stop7h 42mUnited Airlines
Deal found 9/16$335
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/145:45 amBOS - SXM
1 stop8h 25mSpirit Airlines
Mon 11/174:28 pmSXM - BOS
1 stop9h 12mSpirit Airlines
Deal found 9/14$337
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/28:24 pmBOS - SXM
1 stop17h 35mSpirit Airlines
Wed 11/124:28 pmSXM - BOS
1 stop9h 12mSpirit Airlines
Deal found 9/14$342
This Flightnetwork deal was found by Cheapflights users on 9/16. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/318:24 pmBOS - SXM
1 stop17h 36mSpirit Airlines
Fri 11/74:28 pmSXM - BOS
1 stop9h 12mSpirit Airlines
Deal found 9/16$343
This American Airlines deal was found by Cheapflights users on 9/14. 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 12/56:19 pmBOS - SXM
1 stop16h 51mAmerican Airlines
Fri 12/125:25 pmSXM - BOS
1 stop8h 30mAmerican Airlines
Deal found 9/14$349
This Priceline deal was found by Cheapflights users on 9/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/276:16 amBOS - SXM
1 stop7h 44mSpirit Airlines
Fri 10/313:05 pmSXM - BOS
1 stop8h 54mSpirit Airlines
Deal found 9/16$352
This American Airlines deal was found by Cheapflights users on 9/14. 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 12/135:20 pmBOS - SXM
2 stops19h 38mAmerican Airlines
Sat 12/205:33 pmSXM - BOS
2 stops15h 29mAmerican Airlines
Deal found 9/14$354
This JetBlue deal was found by Cheapflights users on 9/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/267:00 amBDL - SXM
1 stop6h 19mJetBlue
Fri 10/312:34 pmSXM - BDL
1 stop7h 55mJetBlue
Deal found 9/15$397

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts 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 16, 2025.
Use the filters below to find and compare flights from Massachusetts to Simpson Bay that are best for you.

Fly from

Massachusetts

Fly to

Simpson Bay

Route

Depart

Return

Price

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 11/15

6:00 am-3:57 pm

1 stop8h 57m

Simpson Bay Princess Juliana

Sun 11/23

3:00 pm-12:45 am

1 stop10h 45m

$335

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sun 1/11

8:45 pm-12:15 pm

1 stop14h 30m

Simpson Bay Princess Juliana

Sat 1/17

5:16 pm-12:59 am

1 stop8h 43m

$349

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 11/8

5:30 am-1:50 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sun 11/16

3:00 pm-9:30 am

1 stop19h 30m

$359

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Mon 11/10

5:40 am-2:55 pm

1 stop8h 15m

Simpson Bay Princess Juliana

Tue 11/18

4:20 pm-1:22 am

1 stop10h 02m

$363

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Mon 3/9

8:30 pm-1:53 pm

1 stop17h 23m

Simpson Bay Princess Juliana

Wed 3/11

3:45 pm-7:24 am

1 stop15h 39m

$363

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 1/17

8:45 pm-12:15 pm

1 stop14h 30m

Simpson Bay Princess Juliana

Sat 1/24

5:16 pm-12:59 am

1 stop8h 43m

$376

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Mon 11/10

6:00 am-1:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Tue 11/25

2:52 pm-10:47 pm

1 stop8h 55m

$385

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 11/15

6:00 am-3:57 pm

1 stop8h 57m

Simpson Bay Princess Juliana

Tue 11/25

2:52 pm-10:47 pm

1 stop8h 55m

$385

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sun 11/16

6:00 am-1:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Wed 11/19

2:52 pm-10:34 am

2 stops20h 42m

$387

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Sun 10/26

7:00 am-1:19 pm

1 stop6h 19m

Simpson Bay Princess Juliana

Fri 10/31

2:34 pm-10:29 pm

1 stop7h 55m

$397

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 46 results
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Best time to book a flight from Massachusetts to Simpson Bay

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

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

Currently, September is the cheapest month in which you can book a flight from Massachusetts to Simpson Bay (average of $459). Flying from Massachusetts 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.

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

Find hourly flight availability from Massachusetts to Simpson Bay. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

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

Related info for your journey

Find useful and relevant information for your journey from Massachusetts 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 airport do you fly into for flights to Simpson Bay from Massachusetts?

    Located just 0.5 mi from the city center, Simpson Bay Princess Juliana (SXM) is the airport most travelers will use when flying to Simpson Bay from Massachusetts.

  • How popular is this Massachusetts to Simpson Bay flight route?

    The Massachusetts to Simpson Bay Princess Juliana flight path was viewed by 1 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

  • How long is the flight from Massachusetts to Simpson Bay?

    There are many flights that can get you from Massachusetts to Simpson Bay in 6h 19m. Fly via United Airlines, Delta, or JetBlue to get the fastest option. Airlines will cover a distance of 1744 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $137. Users have also found prices from $142 and $142 on American Airlines and Delta, respectively.

  • What are the most popular routes from Massachusetts to Simpson Bay?

    The most popular route from Massachusetts to Simpson Bay is Boston Logan Intl - Simpson Bay Princess Juliana. You may also consider Hartford Bradley Intl - Simpson Bay Princess Juliana or Albany Intl - Simpson Bay Princess Juliana.

  • What are the cheapest flights from Massachusetts to Simpson Bay?

    On average you can expect to pay $463 for a flight from Massachusetts to Simpson Bay. The cheapest flight overall is $186 while the most popular route, (Boston Logan Intl - Simpson Bay Princess Juliana) is currently priced at $318.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Massachusetts 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 Massachusetts to Simpson Bay?

    Currently, September is the cheapest month in which you can book a flight from Massachusetts to Simpson Bay (average of $459). Flying from Massachusetts 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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Alternative routes for Massachusetts to Simpson Bay

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Massachusetts to Simpson Bay

Discover the top 7 airlines that operate flights from Massachusetts 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$73Average$215FlexibilityNo cancel feeOn-time62%
DeltaCheapest$174Average$393FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$180Average$641FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$335Average$560FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$348Average$802FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$354Average$680FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$390Average$592FlexibilityNo cancel feeOn-time71%

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