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$151+ Cheap flights from Simpson Bay (SXM) to Massachusetts

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 2/17. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — BOS
Mar 4 — Mar 111
Wed 3/4
Wed 3/11
1 adult, Economy
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Cheap flight deals from Simpson Bay to Massachusetts

Cheapest flights from Simpson Bay to Massachusetts
Explore the most affordable flight options available from Simpson Bay to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 2, 2026.

This American Airlines deal was found by Cheapflights users on 1/30. 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.
Wed 4/292:24 pm
SXM
-
BOS
1 stop8h 43m
American Airlines
Sun 5/39:15 pm
BOS
-
SXM
2 stops16h 06m
American Airlines
Deal found 1/30$274
This Mytrip deal was found by Cheapflights users on 1/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/153:20 pm
SXM
-
BOS
1 stop9h 24m
Spirit Airlines
Mon 2/234:22 pm
BOS
-
SXM
2 stops20h 53m
Spirit Airlines
Deal found 1/31$290
This Vliegwinkel deal was found by Cheapflights users on 1/31. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/153:20 pm
SXM
-
BOS
1 stop9h 24m
Multiple Airlines
Sat 2/216:00 am
BOS
-
SXM
Nonstop4h 15m
Multiple Airlines
Deal found 1/31$294
This Delta deal was found by Cheapflights users on 1/30. 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.
Wed 4/293:30 pm
SXM
-
BOS
1 stop15h 59m
Delta
Sun 5/38:59 pm
BOS
-
SXM
1 stop15h 11m
Delta
Deal found 1/30$296
This Flysmarter deal was found by Cheapflights users on 1/31. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/154:25 pm
SXM
-
BOS
Nonstop4h 40m
JetBlue
Sat 2/216:00 am
BOS
-
SXM
Nonstop4h 15m
JetBlue
Deal found 1/31$308
This Delta deal was found by Cheapflights users on 1/31. 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.
Sun 2/154:15 pm
SXM
-
BOS
1 stop16h 15m
Delta
Mon 2/235:35 am
BOS
-
SXM
1 stop8h 15m
Delta
Deal found 1/31$317
This American Airlines deal was found by Cheapflights users on 1/30. 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 3/51:29 pm
SXM
-
BOS
2 stops26h 48m
American Airlines
Wed 3/115:47 am
BOS
-
SXM
1 stop7h 29m
American Airlines
Deal found 1/30$318
This Flightnetwork deal was found by Cheapflights users on 1/31. 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.
Thu 4/162:11 pm
SXM
-
BOS
1 stop9h 48m
Spirit Airlines
Wed 4/225:40 am
BOS
-
SXM
1 stop7h 36m
Spirit Airlines
Deal found 1/31$319
This Delta deal was found by Cheapflights users on 1/31. 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.
Sun 2/152:50 pm
SXM
-
BOS
1 stop17h 31m
Delta
Sat 2/217:00 pm
BOS
-
SXM
1 stop17h 25m
Delta
Deal found 1/31$326
This American Airlines deal was found by Cheapflights users on 1/31. 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 4/1612:41 pm
SXM
-
BOS
2 stops10h 13m
American Airlines
Wed 4/226:00 am
BOS
-
SXM
2 stops9h 20m
American Airlines
Deal found 1/31$342

Find flight deals from Simpson Bay to Massachusetts

Keep the following information in mind while searching for Simpson Bay to Massachusetts flight deals. Data was last updated February 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$274
(American Airlines)

One-way from

$151
(Super.com)

Popular in

November

Cheapest in

May

Average price

$573

Good round-trip deal

$538 or less

Good one-way deal

$432 or less
Provider with most accurate pricing for Simpson Bay Princess Juliana-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Simpson Bay Princess Juliana-Boston Logan Intl flights.
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From Simpson Bay Princess Juliana to Massachusetts
Search Deals
One-way flight from Simpson Bay Princess Juliana to Massachusetts
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($63 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
Price to beat on a round-trip flight from Simpson Bay Princess Juliana to Massachusetts.
Search Deals
Price to beat on a one-way flight from Simpson Bay Princess Juliana to Massachusetts.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Simpson Bay to Massachusetts 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 February 2, 2026.
Use the filters below to find and compare flights from Simpson Bay to Massachusetts that are best for you.

Fly from

Simpson Bay

Fly to

Massachusetts

Route

Depart

Return

Price

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Wed 4/29

2:24 pm-11:07 pm

1 stop8h 43m

Boston Logan Intl

Sun 5/3

9:15 pm-1:21 pm

2 stops16h 06m

$274

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Wed 4/29

3:30 pm-7:29 am

1 stop15h 59m

Boston Logan Intl

Sun 5/3

8:59 pm-12:10 pm

1 stop15h 11m

$296

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sun 2/15

4:15 pm-7:30 am

1 stop16h 15m

Boston Logan Intl

Mon 2/23

5:35 am-2:50 pm

1 stop8h 15m

$317

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Thu 3/5

1:29 pm-3:17 pm

2 stops26h 48m

Boston Logan Intl

Wed 3/11

5:47 am-1:16 pm

1 stop7h 29m

$318

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sun 2/15

2:50 pm-7:21 am

1 stop17h 31m

Boston Logan Intl

Sat 2/21

7:00 pm-1:25 pm

1 stop17h 25m

$326

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sun 2/15

3:20 pm-11:44 pm

1 stop9h 24m

Boston Logan Intl

Mon 2/23

2:23 pm-2:15 pm

3 stops22h 52m

$327

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Thu 4/16

2:21 pm-11:07 pm

1 stop8h 46m

Boston Logan Intl

Wed 4/22

6:00 am-3:20 pm

2 stops9h 20m

$342

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sun 2/15

4:25 pm-8:05 pm

Nonstop4h 40m

Boston Logan Intl

Mon 2/23

7:43 pm-3:15 pm

1 stop18h 32m

$348

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Thu 3/5

4:35 pm-8:15 pm

Nonstop4h 40m

Boston Logan Intl

Wed 3/11

6:00 am-1:55 pm

1 stop7h 55m

$362

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sun 2/15

5:51 pm-7:13 am

1 stop14h 22m

Boston Logan Intl

Sat 2/21

7:50 pm-4:36 pm

2 stops19h 46m

$410

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/30

Showing 1-10 of 18 results
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Best time to book a flight from Simpson Bay to Massachusetts

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

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

Currently, October is the cheapest month in which you can book a flight from Simpson Bay to Massachusetts (average of $160). Flying from Simpson Bay to Massachusetts in November is currently the most expensive (average of $829). 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 SXM to MA?

Find hourly flight availability from Simpson Bay to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 2, 2026.

When flying from Simpson Bay to Massachusetts, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated February 2, 2026.
See what other customers who have flown with American Airlines from Simpson Bay to Massachusetts have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,212 reviews

Overall

7.2

Entertainment

6.9

Boarding

7.5

Crew

8.0

Comfort

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,212 reviews
American Airlines
7.2
Good
11,212 reviews

Overall

7.2

Entertainment

6.9

Boarding

7.5

Crew

8.0

Comfort

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

Related info for your journey

Find useful and relevant information for your journey from Simpson Bay to Massachusetts. 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 from for flights from Simpson Bay to Massachusetts?

    Simpson Bay Princess Juliana (SXM) is the airport you will fly out of if you book a flight from Simpson Bay to Massachusetts. It is only a 0.5 mi journey to Princess Juliana (SXM) from Simpson Bay’s city center.

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

    For as low as $274, American Airlines can have you in Massachusetts from Simpson Bay in 8h 43m. The distance from Simpson Bay to Massachusetts is about 1742 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $175. Spirit Airlines flights start at $200 while deals on Delta start at $214 one-way.

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

    On average you can expect to pay $630 for a flight from Simpson Bay to Massachusetts. The cheapest flight overall is $261 while the most popular route, (Simpson Bay Princess Juliana - Boston Logan Intl) is currently priced at $296.

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

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

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

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

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

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

    Currently, October is the cheapest month in which you can book a flight from Simpson Bay to Massachusetts (average of $160). Flying from Simpson Bay to Massachusetts in November is currently the most expensive (average of $829). 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.

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Alternative routes for Simpson Bay to Massachusetts

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

Discover the top airline that operate flights from Simpson Bay to Massachusetts. 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 February 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$423Average$528FlexibilityNo cancel feeOn-time71%

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