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$190+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — BOS
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$317
(Delta)

One-way from

$190
(Cheapflightsfares)

Popular in

February

Cheapest in

May

Average price

$513

Good one-way deal

$292 or less
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. 34% potential increase in price ($262 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($39 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 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 September 15, 2025.

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 12/65:25 pmSXM - BOS
1 stop8h 30mAmerican Airlines
Mon 12/158:40 pmBOS - SXM
2 stops16h 40mAmerican Airlines
Deal found 9/14$341
This Spirit 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/173:05 pmSXM - BOS
1 stop8h 54mSpirit Airlines
Fri 10/248:24 pmBOS - SXM
1 stop17h 36mSpirit Airlines
Deal found 9/14$342
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/62:40 pmSXM - BOS
1 stop21h 09mUnited Airlines
Mon 12/156:00 amBOS - SXM
1 stop6h 50mUnited Airlines
Deal found 9/15$377
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.
Sat 12/66:00 pmSXM - BOS
Nonstop4h 27mJetBlue
Mon 12/156:00 amBOS - SXM
1 stop8h 05mJetBlue
Deal found 9/15$391
This Kissandfly.com 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/63:05 pmSXM - BOS
1 stop20h 21mMultiple Airlines
Mon 10/134:54 pmBOS - SXM
2 stops39h 18mMultiple Airlines
Deal found 9/14$392
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.
Sat 12/61:16 pmSXM - BOS
Nonstop4h 33mJetBlue
Wed 12/108:05 amBOS - SXM
1 stop7h 33mJetBlue
Deal found 9/15$396
This American Airlines deal was found by Cheapflights users on 9/13. 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 12/64:00 pmSXM - BOS
1 stop19h 29mAmerican Airlines
Wed 12/105:34 amBOS - SXM
1 stop9h 51mAmerican Airlines
Deal found 9/13$397
This Spirit 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/63:05 pmSXM - BOS
1 stop8h 54mSpirit Airlines
Mon 10/136:16 amBOS - SXM
1 stop7h 44mSpirit Airlines
Deal found 9/14$413

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 September 15, 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

Thu 3/5

4:26 pm-7:24 am

1 stop15h 58m

Boston Logan Intl

Mon 3/9

8:45 pm-11:15 am

1 stop14h 30m

$317

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Thu 3/5

4:55 pm-10:39 am

2 stops18h 44m

Boston Logan Intl

Mon 3/9

6:33 pm-2:51 pm

2 stops20h 18m

$332

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sat 12/6

5:25 pm-12:55 am

1 stop8h 30m

Boston Logan Intl

Mon 12/15

8:40 pm-2:20 pm

2 stops16h 40m

$341

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sat 12/6

5:25 pm-9:35 am

2 stops17h 10m

Boston Logan Intl

Wed 12/10

8:40 pm-4:25 pm

2 stops18h 45m

$354

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Fri 11/14

4:28 pm-12:40 am

1 stop9h 12m

$199

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Thu 3/12

12:25 pm-8:50 pm

1 stop8h 25m

$214

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Tue 2/10

4:26 pm-7:24 am

1 stop15h 58m

$219

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sun 11/16

3:00 pm-9:30 am

1 stop19h 30m

$219

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Wed 12/17

4:17 pm-1:21 am

1 stop10h 04m

$219

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Thu 11/13

2:52 pm-10:48 pm

1 stop8h 56m

$219

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 13 results
1
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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, January is the cheapest month in which you can book a flight from Simpson Bay to Massachusetts (average of $218). Flying from Simpson Bay to Massachusetts in July is currently the most expensive (average of $311). 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.

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 September 15, 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
10,000 reviews

Overall

7.2

Food

6.4

Comfort

7.2

Boarding

7.5

Entertainment

6.9

Crew

8.0

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
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Overall

7.2

Food

6.4

Comfort

7.2

Boarding

7.5

Entertainment

6.9

Crew

8.0

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
2,912 reviews
American Airlines
7.2
Good
10,000 reviews

Overall

7.2

Food

6.4

Comfort

7.2

Boarding

7.5

Entertainment

6.9

Crew

8.0

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 $317, Delta can have you in Massachusetts from Simpson Bay in 15h 58m. 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 Spirit Airlines, which is currently one of the cheapest options available, starting at $199. Arajet flights start at $214 while deals on Delta start at $219 one-way.

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

    On average you can expect to pay $357 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 $317.

  • 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, January is the cheapest month in which you can book a flight from Simpson Bay to Massachusetts (average of $218). Flying from Simpson Bay to Massachusetts in July is currently the most expensive (average of $311). 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

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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$319Average$351FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$395Average$528FlexibilityNo cancel feeOn-time71%

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