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$164+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — BOS
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
1 adult, Economy
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Cheap 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 November 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$246
(Delta)

One-way from

$164
(Delta)

Popular in

November

Cheapest in

May

Average price

$829

Good one-way deal

$272 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
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One-way flight from Simpson Bay Princess Juliana to Massachusetts
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Highest demand for flights based on searches. 4% potential increase in price ($22 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($28 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a one-way flight from Simpson Bay Princess Juliana to Massachusetts.
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Find 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 November 4, 2025.

This Delta deal was found by Cheapflights users on 11/4. 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.
Sat 11/84:14 pmSXM - BOS
1 stop10h 04mDelta
Sat 11/156:05 amBOS - SXM
1 stop7h 00mDelta
Deal found 11/4$246
This Delta deal was found by Cheapflights users on 11/2. 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 12/251:45 pmSXM - BOS
1 stop11h 09mDelta
Wed 12/317:15 pmBOS - SXM
1 stop18h 35mDelta
Deal found 11/2$260
This Delta deal was found by Cheapflights users on 11/3. 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.
Sat 12/63:25 pmSXM - BOS
1 stop8h 59mDelta
Wed 12/105:40 amBOS - SXM
1 stop7h 48mDelta
Deal found 11/3$298
This Cheapflightsfares deal was found by Cheapflights users on 11/3. 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 12/63:20 pmSXM - BOS
1 stop9h 36mSpirit Airlines
Sat 12/135:45 amBOS - SXM
1 stop7h 30mSpirit Airlines
Deal found 11/3$306
This American Airlines deal was found by Cheapflights users on 11/2. 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 12/201:15 pmSXM - BOS
1 stop8h 10mAmerican Airlines
Sun 1/45:53 amBOS - SXM
1 stop7h 06mAmerican Airlines
Deal found 11/2$317
This United Airlines deal was found by Cheapflights users on 11/2. 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 12/205:00 pmSXM - BOS
1 stop7h 54mUnited Airlines
Sun 1/47:32 pmBOS - SXM
2 stops17h 18mUnited Airlines
Deal found 11/2$321
This United Airlines deal was found by Cheapflights users on 11/3. 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 12/65:00 pmSXM - BOS
2 stops18h 49mUnited Airlines
Sat 12/136:00 amBOS - SXM
1 stop8h 57mUnited Airlines
Deal found 11/3$322
This Kissandfly.com deal was found by Cheapflights users on 11/3. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/254:55 pmSXM - BOS
1 stop7h 59mLufthansa
Wed 12/3110:25 amBOS - SXM
2 stops26h 25mLufthansa
Deal found 11/3$331
This Flysmarter deal was found by Cheapflights users on 11/3. 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.
Thu 12/251:59 pmSXM - BOS
Nonstop4h 35mJetBlue
Wed 12/315:30 amBOS - SXM
1 stop8h 00mJetBlue
Deal found 11/3$335
This American Airlines deal was found by Cheapflights users on 11/2. 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 12/255:33 pmSXM - BOS
1 stop19h 17mAmerican Airlines
Wed 12/315:20 amBOS - SXM
2 stops10h 13mAmerican Airlines
Deal found 11/2$360

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 November 4, 2025.
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

Sat 11/8

4:14 pm-1:18 am

1 stop10h 04m

Boston Logan Intl

Sat 11/15

6:05 am-2:05 pm

1 stop7h 00m

$246

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Thu 12/25

1:45 pm-11:54 pm

1 stop11h 09m

Boston Logan Intl

Wed 12/31

7:15 pm-2:50 pm

1 stop18h 35m

$260

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sat 12/6

3:25 pm-1:27 am

1 stop11h 02m

Boston Logan Intl

Mon 12/15

5:40 am-2:28 pm

1 stop7h 48m

$260

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sat 12/6

3:25 pm-11:24 pm

1 stop8h 59m

Boston Logan Intl

Wed 12/10

5:40 am-2:28 pm

1 stop7h 48m

$298

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sat 12/6

3:20 pm-11:56 pm

1 stop9h 36m

Boston Logan Intl

Sat 12/13

5:45 am-2:15 pm

1 stop7h 30m

$306

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sat 12/20

5:00 pm-11:54 pm

1 stop7h 54m

Boston Logan Intl

Sun 1/4

7:32 pm-1:50 pm

2 stops17h 18m

$321

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sat 12/6

5:00 pm-10:49 am

2 stops18h 49m

Boston Logan Intl

Sat 12/13

6:00 am-3:57 pm

1 stop8h 57m

$322

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Thu 12/4

3:53 pm-1:27 am

1 stop10h 34m

$164

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Wed 12/24

1:45 pm-11:54 pm

1 stop11h 09m

$164

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Wed 12/3

3:53 pm-1:27 am

1 stop10h 34m

$164

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 16 results
1
2

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 $167). 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 November 4, 2025.

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 November 4, 2025.
See what other customers who have flown with American Airlines and JetBlue 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
11,038 reviews

Crew

8.0

Boarding

7.5

Entertainment

6.9

Overall

7.2

Food

6.4

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.
American Airlines
7.2
Good
11,038 reviews
American Airlines
7.2
Good
11,038 reviews

Crew

8.0

Boarding

7.5

Entertainment

6.9

Overall

7.2

Food

6.4

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.
JetBlue
7.2
Good
2,907 reviews
American Airlines
7.2
Good
11,038 reviews

Crew

8.0

Boarding

7.5

Entertainment

6.9

Overall

7.2

Food

6.4

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.

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 $246, Delta can have you in Massachusetts from Simpson Bay in 10h 04m. The distance from Simpson Bay to Massachusetts is about 1742 mi.

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

    On average you can expect to pay $345 for a flight from Simpson Bay to Massachusetts. The cheapest flight overall is $242 while the most popular route, (Simpson Bay Princess Juliana - Boston Logan Intl) is currently priced at $255.

  • 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 $167). 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

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Top 2 airlines flying from Simpson Bay to Massachusetts

Discover the top 2 airlines 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 November 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$319Average$376FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$395Average$528FlexibilityNo cancel feeOn-time71%

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