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$189+ Cheap flights from Simpson Bay (SXM) to Boston (BOS)

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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — BOS
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheap flight deals from Simpson Bay to Boston

Discover tips and strategies to find the most affordable flight options for your journey from Simpson Bay (SXM) to Boston (BOS). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 18, 2025.

Round-trip from

$360
(Delta)

One-way from

$189
(Cheapflightsfares)

Popular in

February

Cheapest in

May

Average price

$556

Good one-way deal

$199 or less
From Simpson Bay Princess Juliana to Boston Logan Intl
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One-way flight from Simpson Bay Princess Juliana to Boston Logan Intl
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Highest demand for flights based on searches. 33% potential increase in price ($254 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($38 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a one-way flight from Simpson Bay Princess Juliana to Boston Logan Intl.
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Find flight deals from Simpson Bay to Boston

Cheapest flights from Simpson Bay to Boston
Explore the most affordable flight options available from Simpson Bay to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 18, 2025.

This Delta deal was found by Cheapflights users on 8/16. 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.
Sat 9/133:20 pmSXM - BOS
1 stop9h 58mDelta
Fri 9/195:35 amBOS - SXM
1 stop8h 15mDelta
Deal found 8/16$360
This Priceline deal was found by Cheapflights users on 8/16. 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 Priceline 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 35mSpirit Airlines
Deal found 8/16$382
This United Airlines deal was found by Cheapflights users on 8/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/264:55 pmSXM - BOS
1 stop7h 59mUnited Airlines
Sat 1/36:01 amBOS - SXM
2 stops30h 49mUnited Airlines
Deal found 8/17$389
This American Airlines deal was found by Cheapflights users on 8/16. 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.
Thu 9/112:20 pmSXM - BOS
1 stop10h 39mAmerican Airlines
Wed 9/175:47 amBOS - SXM
1 stop7h 32mAmerican Airlines
Deal found 8/16$404
This Trip.com deal was found by Cheapflights users on 8/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/131:35 pmSXM - BOS
1 stop27h 12mUnited Airlines
Fri 9/195:30 amBOS - SXM
2 stops30h 59mUnited Airlines
Deal found 8/16$419
This American Airlines deal was found by Cheapflights users on 8/16. 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.
Sat 9/132:40 pmSXM - BOS
2 stops17h 58mAmerican Airlines
Fri 9/197:30 pmBOS - SXM
2 stops17h 49mAmerican Airlines
Deal found 8/16$425
This Vliegwinkel deal was found by Cheapflights users on 8/16. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/41:00 pmSXM - BOS
Nonstop4h 20mJetBlue
Sat 10/117:30 amBOS - SXM
Nonstop4h 10mJetBlue
Deal found 8/16$428
This Mytrip deal was found by Cheapflights users on 8/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/133:05 pmSXM - BOS
2 stops22h 43mSpirit Airlines
Fri 9/1912:18 pmBOS - SXM
3 stops25h 42mSpirit Airlines
Deal found 8/16$440

Cheapflights Fare Finder

 
Customize your flight search to find flights from Simpson Bay to Boston 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 August 18, 2025.
Use the filters below to find and compare flights from Simpson Bay to Boston that are best for you.

Fly from

Simpson Bay

Fly to

Boston

Route

Depart

Return

Price

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sat 9/13

3:20 pm-1:18 am

1 stop9h 58m

Boston Logan Intl

Fri 9/19

5:35 am-1:50 pm

1 stop8h 15m

$360

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sat 1/10

5:16 pm-12:59 am

1 stop8h 43m

Boston Logan Intl

Sat 1/17

8:45 pm-12:15 pm

1 stop14h 30m

$368

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Fri 10/17

3:05 pm-11:59 pm

1 stop8h 54m

Boston Logan Intl

Fri 10/24

8:24 pm-1:59 pm

1 stop17h 35m

$382

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Fri 12/26

4:55 pm-11:54 pm

1 stop7h 59m

Boston Logan Intl

Sat 1/3

6:01 am-1:50 pm

2 stops30h 49m

$389

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Thu 9/11

2:20 pm-12:59 am

1 stop10h 39m

Boston Logan Intl

Wed 9/17

5:47 am-1:19 pm

1 stop7h 32m

$404

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sat 9/13

1:35 pm-4:47 pm

1 stop27h 12m

Boston Logan Intl

Fri 9/19

5:30 am-12:29 pm

2 stops30h 59m

$419

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sat 9/13

2:40 pm-8:38 am

2 stops17h 58m

Boston Logan Intl

Fri 9/19

7:30 pm-1:19 pm

2 stops17h 49m

$425

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sat 10/4

1:00 pm-5:20 pm

Nonstop4h 20m

Boston Logan Intl

Sat 10/11

7:30 am-11:40 am

Nonstop4h 10m

$428

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Fri 9/5

3:05 pm-11:57 pm

1 stop8h 52m

$189

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Wed 12/3

4:28 pm-12:40 am

1 stop9h 12m

$206

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/17

Showing 1-10 of 15 results
1
2

Best time to book a flight from Simpson Bay to Boston

Have a flexible travel schedule? Discover the best time to fly to Boston 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 Boston

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

Currently, January is the cheapest month in which you can book a flight from Simpson Bay to Boston (average of $218). Flying from Simpson Bay to Boston 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.

What is the cheapest time of day to fly from SXM to BOS?

Find hourly flight availability from Simpson Bay to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 18, 2025.

One of the essential ways to save on airfare from Simpson Bay to Boston is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 63% on airfare.

Reviews of airlines servicing Boston

Get insights into the airlines that provide service to Boston. 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 Boston. Reviews last updated August 18, 2025.
Read through reviews of airlines operating flights from Simpson Bay to Boston, such as American Airlines and JetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Food

6.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Boarding

7.5

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Food

6.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Boarding

7.5

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
JetBlue
7.2
Good
2,915 reviews
American Airlines
7.2
Good
10,000 reviews

Food

6.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Boarding

7.5

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

Related info for your journey

Find useful and relevant information for your journey from Simpson Bay to Boston. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    For as low as $389, Delta can have you in Boston from Simpson Bay in 7h 59m. Airlines will cover a distance of 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 flying from Simpson Bay to Boston round-trip?

    According to our current data, JetBlue ($326), and American Airlines ($395) offers the cheapest pricing from Simpson Bay to Boston. These flights start at 36% lower than the current average price 3 months from now.

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

    Looking at all options, your cheapest flight can be booked for $199. While the most popular route (Simpson Bay Princess Juliana - Boston Logan Intl) can be booked for $368 on average our data indicates $279 when flying from Simpson Bay to Boston.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Simpson Bay to Boston (average of $218). Flying from Simpson Bay to Boston 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

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Cambridge
Medford
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Lowell
Lincoln
Smithfield
Cranston
Chestnut Hill
Warwick
Peabody
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Top 2 airlines flying from Simpson Bay to Boston

Discover the top 2 airlines that operate flights from Simpson Bay to Boston. 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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$326Average$386FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$395Average$528FlexibilityNo cancel feeOn-time71%

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