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Simpson Bay

$71+ 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SXM
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This JetBlue deal was found by Cheapflights users on 12/17. 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.
Tue 12/306:00 amBDL - SXM
1 stop6h 11mJetBlue
Mon 1/52:26 pmSXM - BDL
1 stop10h 33mJetBlue
Deal found 12/17$321
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/305:59 amBOS - SXM
1 stop6h 27mAmerican Airlines
Thu 1/82:42 pmSXM - BOS
1 stop9h 13mAmerican Airlines
Deal found 12/16$341
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Sun 12/216:00 amBDL - SXM
1 stop6h 50mUnited Airlines
Fri 12/264:55 pmSXM - BDL
1 stop8h 03mUnited Airlines
Deal found 12/16$366
This Expedia deal was found by Cheapflights users on 12/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/257:30 amBOS - SXM
Nonstop4h 14mJetBlue
Wed 12/311:59 pmSXM - BOS
Nonstop4h 35mJetBlue
Deal found 12/16$379
This Priceline deal was found by Cheapflights users on 12/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/227:30 amBOS - SXM
Nonstop4h 14mMultiple Airlines
Thu 12/253:40 pmSXM - BOS
2 stops21h 32mMultiple Airlines
Deal found 12/15$392
This Delta deal was found by Cheapflights users on 12/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/185:40 amBOS - SXM
1 stop8h 10mDelta
Tue 12/231:45 pmSXM - BOS
1 stop12h 22mDelta
Deal found 12/16$408
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Thu 12/185:20 amBOS - SXM
1 stop7h 30mUnited Airlines
Tue 12/234:55 pmSXM - BOS
2 stops20h 48mUnited Airlines
Deal found 12/16$417
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Sat 12/207:26 pmBOS - SXM
2 stops17h 24mUnited Airlines
Mon 12/222:52 pmSXM - BOS
1 stop8h 56mUnited Airlines
Deal found 12/16$424
This American Airlines deal was found by Cheapflights users on 12/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/165:05 amALB - SXM
2 stops10h 20mAmerican Airlines
Fri 12/192:59 pmSXM - ALB
1 stop8h 21mAmerican Airlines
Deal found 12/15$428
This JetBlue deal was found by Cheapflights users on 12/17. 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.
Tue 12/307:30 amBOS - SXM
Nonstop4h 14mJetBlue
Thu 1/85:36 pmSXM - BOS
1 stop7h 37mJetBlue
Deal found 12/17$431
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/217:47 pmBDL - SXM
2 stops17h 12mAmerican Airlines
Fri 12/263:28 pmSXM - BDL
2 stops18h 41mAmerican Airlines
Deal found 12/16$446
This American Airlines deal was found by Cheapflights users on 12/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/226:00 amBDL - SXM
2 stops9h 33mAmerican Airlines
Sat 12/273:28 pmSXM - BDL
2 stops18h 41mAmerican Airlines
Deal found 12/15$522

Find 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 December 18, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$257
(United Airlines)

One-way from

$71
(Cheapflightsfares)

Popular in

April

Cheapest in

September

Average price

$626

Good round-trip deal

$393 or less

Good one-way deal

$206 or less
Provider with most accurate pricing for Boston Logan Intl-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Simpson Bay Princess Juliana flights.
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From Massachusetts to Simpson Bay Princess Juliana
Search Deals
One-way flight from Massachusetts to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Massachusetts to Simpson Bay Princess Juliana.
Search Deals
Price to beat on a one-way flight from Massachusetts to Simpson Bay Princess Juliana.
Search Deals

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 December 18, 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

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Sun 1/11

6:00 am-1:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Sat 1/17

5:00 pm-11:44 pm

1 stop7h 44m

$257

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Thu 2/26

6:00 am-3:15 pm

1 stop8h 15m

Simpson Bay Princess Juliana

Thu 3/5

3:33 pm-12:24 am

1 stop9h 51m

$257

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Sun 1/25

6:00 am-2:28 pm

1 stop7h 28m

Simpson Bay Princess Juliana

Fri 1/30

5:36 pm-11:48 pm

1 stop7h 12m

$261

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Fri 1/30

6:00 am-2:28 pm

1 stop7h 28m

Simpson Bay Princess Juliana

Wed 2/4

3:43 pm-11:48 pm

1 stop9h 05m

$261

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Sun 1/25

7:40 pm-1:42 pm

2 stops17h 02m

Simpson Bay Princess Juliana

Mon 2/2

4:24 pm-11:40 am

2 stops20h 16m

$262

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Fri 1/23

5:03 pm-12:58 pm

2 stops18h 55m

Simpson Bay Princess Juliana

Fri 1/30

2:03 pm-11:44 pm

2 stops10h 41m

$262

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Mon 2/9

6:00 am-2:28 pm

1 stop7h 28m

Simpson Bay Princess Juliana

Sat 2/14

2:28 pm-11:57 pm

1 stop10h 29m

$273

AlbanySimpson Bay

ALB - SXM

ALBSXM

Albany Intl

Sun 3/8

6:10 am-2:57 pm

1 stop8h 47m

Simpson Bay Princess Juliana

Wed 3/11

3:55 pm-11:44 pm

1 stop7h 49m

$293

AlbanySimpson Bay

ALB - SXM

ALBSXM

Albany Intl

Sun 3/1

5:22 pm-2:20 pm

2 stops19h 58m

Simpson Bay Princess Juliana

Thu 3/12

12:29 pm-11:06 am

2 stops22h 37m

$298

AlbanySimpson Bay

ALB - SXM

ALBSXM

Albany Intl

Wed 3/18

4:28 pm-1:21 pm

2 stops20h 53m

Simpson Bay Princess Juliana

Mon 3/23

4:28 pm-11:38 am

2 stops19h 10m

$298

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 49 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 $143). Flying from Massachusetts to Simpson Bay in June is currently the most expensive (average of $372). 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 December 18, 2025.

It’s typically best to fly out from Massachusetts to Simpson Bay at noon. Doing so could potentially save you 38% on the flight price compared to flying in the morning, which is usually more expensive.

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 5 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 50m. Fly via United Airlines, American Airlines, 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 Frontier. According to our data, you can fly for as low as $44. Users have also found prices from $130 and $139 on Delta and Spirit Airlines, 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 $368 for a flight from Massachusetts to Simpson Bay. The cheapest flight overall is $151 while the most popular route, (Boston Logan Intl - Simpson Bay Princess Juliana) is currently priced at $223.

  • 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 $143). Flying from Massachusetts to Simpson Bay in June is currently the most expensive (average of $372). 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$81Average$248FlexibilityNo cancel feeOn-time62%
DeltaCheapest$174Average$377FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$180Average$641FlexibilityNo cancel feeOn-time67%
Spirit AirlinesCheapest$312Average$538FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$347Average$527FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$373Average$644FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$392Average$585FlexibilityNo cancel feeOn-time71%

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