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Simpson Bay

$56+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SXM
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:00 am
BDL
-
SXM
1 stop6h 33m
United Airlines
Tue 7/283:50 pm
SXM
-
BDL
1 stop8h 07m
United Airlines
Deal found 1/27$265
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/268:25 am
BDL
-
SXM
1 stop6h 35m
American Airlines
Mon 3/25:28 pm
SXM
-
BDL
2 stops18h 16m
American Airlines
Deal found 1/26$270
This American Airlines deal was found by Cheapflights users on 1/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/96:03 am
BDL
-
SXM
1 stop7h 13m
American Airlines
Mon 3/164:01 pm
SXM
-
BDL
1 stop27h 51m
American Airlines
Deal found 1/28$271
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/207:15 pm
BDL
-
SXM
2 stops19h 44m
American Airlines
Thu 2/265:01 pm
SXM
-
BDL
1 stop28h 12m
American Airlines
Deal found 1/27$275
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/225:24 pm
BDL
-
SXM
1 stop19h 52m
American Airlines
Tue 3/35:28 pm
SXM
-
BDL
2 stops19h 10m
American Airlines
Deal found 1/27$276
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/225:24 pm
BDL
-
SXM
1 stop19h 52m
American Airlines
Fri 3/274:01 pm
SXM
-
BDL
1 stop27h 51m
American Airlines
Deal found 1/27$277
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/226:00 am
BDL
-
SXM
1 stop9h 27m
JetBlue
Thu 3/263:07 pm
SXM
-
BDL
1 stop8h 39m
JetBlue
Deal found 1/27$281
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:00 am
BDL
-
SXM
1 stop6h 50m
United Airlines
Sun 3/81:20 pm
SXM
-
BDL
1 stop21h 33m
United Airlines
Deal found 1/27$293
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/246:00 am
BDL
-
SXM
1 stop9h 27m
JetBlue
Tue 3/312:50 pm
SXM
-
BDL
1 stop9h 07m
JetBlue
Deal found 1/27$295
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/256:00 am
BDL
-
SXM
1 stop11h 04m
JetBlue
Tue 3/312:50 pm
SXM
-
BDL
1 stop9h 07m
JetBlue
Deal found 1/27$309
This United Airlines deal was found by Cheapflights users on 1/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:00 am
BDL
-
SXM
1 stop6h 29m
United Airlines
Mon 7/203:50 pm
SXM
-
BDL
2 stops18h 35m
United Airlines
Deal found 1/28$312
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/96:00 am
BDL
-
SXM
1 stop8h 15m
JetBlue
Fri 3/133:07 pm
SXM
-
BDL
1 stop8h 39m
JetBlue
Deal found 1/27$315

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$265
(United Airlines)

One-way from

$56
(FlightHub)

Popular in

April

Cheapest in

September

Average price

$506

Good round-trip deal

$339 or less

Good one-way deal

$149 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.
Search Deals
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. 3% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
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 3/1

6:00 am-1:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Sun 3/8

1:20 pm-9:32 am

2 stops20h 12m

$270

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Thu 2/26

8:25 am-4:00 pm

1 stop6h 35m

Simpson Bay Princess Juliana

Wed 3/4

4:01 pm-11:08 am

2 stops20h 07m

$270

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Sun 3/15

5:24 pm-1:21 pm

2 stops19h 57m

Simpson Bay Princess Juliana

Thu 3/19

4:28 pm-11:08 am

2 stops18h 40m

$270

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Mon 3/9

5:33 pm-1:21 pm

2 stops19h 48m

Simpson Bay Princess Juliana

Mon 3/16

2:21 pm-11:08 am

2 stops20h 47m

$270

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Sun 3/22

6:00 am-3:27 pm

1 stop9h 27m

Simpson Bay Princess Juliana

Thu 3/26

3:07 pm-11:46 pm

1 stop8h 39m

$281

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Wed 3/4

6:00 am-3:15 pm

1 stop8h 15m

Simpson Bay Princess Juliana

Tue 3/10

1:25 pm-11:57 pm

1 stop10h 32m

$309

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Wed 3/25

6:00 am-5:04 pm

1 stop11h 04m

Simpson Bay Princess Juliana

Tue 3/31

2:50 pm-11:57 pm

1 stop9h 07m

$309

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Wed 7/15

6:00 am-12:29 pm

1 stop6h 29m

Simpson Bay Princess Juliana

Mon 7/20

3:50 pm-10:25 am

2 stops18h 35m

$312

AlbanySimpson Bay

ALB - SXM

ALBSXM

Albany Intl

Fri 2/27

6:16 pm-2:21 pm

2 stops19h 05m

Simpson Bay Princess Juliana

Tue 3/3

5:28 pm-11:38 am

2 stops19h 10m

$316

AlbanySimpson Bay

ALB - SXM

ALBSXM

Albany Intl

Wed 3/18

4:26 pm-1:21 pm

2 stops20h 55m

Simpson Bay Princess Juliana

Mon 3/23

4:28 pm-1:02 pm

2 stops20h 34m

$316

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 50 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 $140). Flying from Massachusetts to Simpson Bay in December is currently the most expensive (average of $345). 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 January 29, 2026.

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.

How much does it cost to fly round-trip from Massachusetts to Simpson Bay?

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 6 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 35m. Fly via United Airlines, American Airlines, or Delta 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 $84 and $136 on Delta and United 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 $319 for a flight from Massachusetts to Simpson Bay. The cheapest flight overall is $133 while the most popular route, (Boston Logan Intl - Simpson Bay Princess Juliana) is currently priced at $218.

  • 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 $140). Flying from Massachusetts to Simpson Bay in December is currently the most expensive (average of $345). 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$134Average$333FlexibilityNo cancel feeOn-time62%
DeltaCheapest$136Average$350FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$180Average$641FlexibilityNo cancel feeOn-time67%
Spirit AirlinesCheapest$205Average$438FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$297Average$476FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$331Average$579FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$373Average$568FlexibilityNo cancel feeOn-time71%

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