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Simpson Bay

$77+ Cheap flights from Boston (BOS) 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 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SXM
Dec 5 — Dec 121
Fri 12/5
Fri 12/12
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Simpson Bay Princess Juliana are usually found in September or August, booked 54 days in advance, depart on a Wednesday or Monday and return on a Monday

Cheap flight deals from Boston to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to Simpson Bay (SXM). 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 November 5, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$372
(United Airlines)

One-way from

$77
(Delta)

Popular in

February

Cheapest in

September

Average price

$563

Good round-trip deal

$408 or less

Good one-way deal

$186 or less
Provider with most accurate pricing for Boston Logan Intl-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Simpson Bay Princess Juliana flights.
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From Boston Logan Intl to Simpson Bay Princess Juliana
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One-way flight from Boston Logan Intl to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 6% potential increase in price ($38 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 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 round-trip flight from Boston Logan Intl to Simpson Bay Princess Juliana.
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Price to beat on a one-way flight from Boston Logan Intl to Simpson Bay Princess Juliana.
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Find flight deals from Boston to Simpson Bay

Cheapest flights from Boston to Simpson Bay
Explore the most affordable flight options available from Boston to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 5, 2025.

This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/176:19 pmBOS - SXM
2 stops17h 17mAmerican Airlines
Wed 12/243:28 pmSXM - BOS
2 stops19h 49mAmerican Airlines
Deal found 11/4$375
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/158:30 amBOS - SXM
1 stop7h 13mJetBlue
Mon 12/221:59 pmSXM - BOS
Nonstop4h 35mJetBlue
Deal found 11/4$376
This CheapOair deal was found by Cheapflights users on 11/5. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2211:38 amBOS - SXM
Nonstop4h 12mJetBlue
Thu 11/273:15 pmSXM - BOS
1 stop19h 07mJetBlue
Deal found 11/5$377
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/219:54 pmBOS - SXM
2 stops15h 21mSpirit Airlines
Mon 11/243:20 pmSXM - BOS
1 stop9h 33mSpirit Airlines
Deal found 11/4$378
This Orbitz deal was found by Cheapflights users on 11/5. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/156:16 amBOS - SXM
1 stop6h 59mSpirit Airlines
Sat 11/223:20 pmSXM - BOS
1 stop9h 33mSpirit Airlines
Deal found 11/5$379
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:02 amBOS - SXM
1 stop6h 48mUnited Airlines
Fri 11/212:52 pmSXM - BOS
1 stop8h 50mUnited Airlines
Deal found 11/4$380
This American Airlines deal was found by Cheapflights users on 11/5. 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 12/135:20 pmBOS - SXM
2 stops19h 38mAmerican Airlines
Sat 12/205:33 pmSXM - BOS
1 stop8h 26mAmerican Airlines
Deal found 11/5$383
This JetBlue deal was found by Cheapflights users on 11/5. 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 11/1510:00 amBOS - SXM
Nonstop4h 15mJetBlue
Sat 11/226:05 pmSXM - BOS
Nonstop4h 27mJetBlue
Deal found 11/5$384
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/107:17 pmBOS - SXM
2 stops18h 02mAmerican Airlines
Tue 11/255:24 pmSXM - BOS
2 stops17h 32mAmerican Airlines
Deal found 11/4$385
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/137:38 pmBOS - SXM
2 stops17h 12mUnited Airlines
Thu 11/202:52 pmSXM - BOS
1 stop8h 56mUnited Airlines
Deal found 11/4$386
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/611:54 amBOS - SXM
Nonstop4h 11mJetBlue
Sat 12/136:20 pmSXM - BOS
Nonstop4h 26mJetBlue
Deal found 11/4$389

Cheapflights Fare Finder

 
Customize your flight search to find flights from Boston 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 November 5, 2025.
Use the filters below to find and compare flights from Boston to Simpson Bay that are best for you.

Fly from

Boston

Fly to

Simpson Bay

Route

Depart

Return

Price

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Tue 4/28

8:45 pm-12:18 pm

1 stop15h 33m

Simpson Bay Princess Juliana

Sat 5/2

3:35 pm-7:22 am

1 stop15h 47m

$384

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Thu 3/5

5:30 am-2:40 pm

1 stop8h 10m

Simpson Bay Princess Juliana

Thu 3/12

11:30 am-8:50 pm

1 stop9h 20m

$387

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Fri 1/16

8:05 am-1:15 pm

Nonstop4h 10m

Simpson Bay Princess Juliana

Mon 1/19

2:30 pm-6:09 pm

Nonstop4h 39m

$389

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Fri 1/30

8:05 am-1:15 pm

Nonstop4h 10m

Simpson Bay Princess Juliana

Fri 2/6

2:30 pm-6:09 pm

Nonstop4h 39m

$389

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 12/6

11:54 am-5:05 pm

Nonstop4h 11m

Simpson Bay Princess Juliana

Sat 12/13

6:20 pm-9:46 pm

Nonstop4h 26m

$389

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sun 2/1

8:05 am-1:15 pm

Nonstop4h 10m

Simpson Bay Princess Juliana

Fri 2/13

4:25 pm-8:05 pm

Nonstop4h 40m

$399

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 1/31

8:10 pm-2:28 pm

1 stop17h 18m

Simpson Bay Princess Juliana

Fri 2/6

2:30 pm-6:09 pm

Nonstop4h 39m

$401

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 11/15

2:21 pm-3:57 pm

2 stops24h 36m

Simpson Bay Princess Juliana

Sat 11/22

5:00 pm-12:28 pm

2 stops20h 28m

$407

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Mon 11/17

6:02 am-1:50 pm

1 stop6h 48m

Simpson Bay Princess Juliana

Sun 11/23

3:00 pm-10:38 am

2 stops20h 38m

$407

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sun 5/3

8:45 pm-12:18 pm

1 stop15h 33m

$77

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

Showing 1-10 of 18 results
1
2

Compare providers for flights from Boston to Simpson Bay

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Boston to Simpson Bay in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
Trip.comPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Boston-Simpson Bay flights, users find the pricing of CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on Boston-Simpson Bay flight deals on Cheapflights vs. CheapOair >95% of the time. Price accuracy is based on data collected from Boston-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Boston-Simpson Bay flights, Cheapflights users trust CheapOair the most. CheapOair has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Boston-Simpson Bay flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Boston to Simpson Bay

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

How far ahead should I book a flight from Boston to Simpson Bay?

Use this chart to determine the optimal time to book a round-trip flight from Boston to Simpson Bay. Price data was last updated on October 31, 2025.

To ensure you get the cheapest price possible for a flight from Boston to Simpson Bay, you should look to book at least 54 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, September is the cheapest month in which you can book a flight from Boston to Simpson Bay (average of $143). Flying from Boston to Simpson Bay in June is currently the most expensive (average of $372). 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 BOS to SXM?

Find hourly flight availability from Boston 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 November 5, 2025.

When flying from Boston to Simpson Bay, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 54% versus a flight in the morning.

Reviews of airlines servicing Simpson Bay

Get insights into the airlines that provide service to Simpson Bay. 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 Simpson Bay. Reviews last updated November 5, 2025.
Read through reviews of airlines operating flights from Boston to Simpson Bay, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,004 reviews

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,004 reviews
Delta
7.9
Good
8,004 reviews

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,002 reviews
Delta
7.9
Good
8,004 reviews

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,042 reviews
Delta
7.9
Good
8,004 reviews

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
JetBlue
7.2
Good
2,907 reviews
Delta
7.9
Good
8,004 reviews

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,115 reviews
Delta
7.9
Good
8,004 reviews

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

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

  • How popular is this Boston to Simpson Bay flight route?

    Flights from Boston Logan Intl to Simpson Bay Princess Juliana have been viewed 5 times in the past calendar month.

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

    There are many flights that can get you from Boston to Simpson Bay in 4h 10m. Fly via Delta or JetBlue to get the fastest option. Airlines will cover a distance of 1742 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Boston to Simpson Bay round-trip?

    According to our current data, Frontier ($73), Delta ($174), and Air Canada ($180) offers the cheapest pricing from Boston to Simpson Bay. Frontier is priced at 87% lower than the current average price of a flight leaving 3 months from now.

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

    On average you can expect to pay $389 for a flight from Boston to Simpson Bay. The cheapest flight overall is $140 while the most popular route, (Boston Logan Intl - Simpson Bay Princess Juliana) is currently priced at $245.

  • Where are the most common layover locations when flying from Boston to Simpson Bay?

    Of the flights from Boston to Simpson Bay that have layovers, most of them stop in Miami.

  • What are some popular things to do or see while on a layover in Miami?

    Kaseya Center, Bayfront Park, and Wynwood Art District are the most popular attractions in Miami if you're in need of something to do during your layover. Travelers on a layover in Miami can visit Kaseya Center, Bayfront Park, and Wynwood Art District, by traveling 6.2 mi, 6.4 mi, and 5.5 mi, respectively after landing at Miami. Travelers can book a car rental at Miami for about $23 per day to make their sightseeing more efficient.

  • Where are the least popular layover locations for Boston to Simpson Bay flights?

    Boston to Simpson Bay flights have a layover in New York least often.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Boston to Simpson Bay (average of $143). Flying from Boston to Simpson Bay in June is currently the most expensive (average of $372). 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 Boston to Simpson Bay

See prices for flight routes from nearby airports that may be better suited for you.
Hartford to Simpson Bay flights
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Worcester to Simpson Bay flights

Top 7 airlines flying from Boston to Simpson Bay

Discover the top 7 airlines that operate flights from Boston 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 November 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$73Average$228FlexibilityNo cancel feeOn-time62%
DeltaCheapest$174Average$378FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$180Average$641FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$337Average$542FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$338Average$697FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$368Average$669FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$399Average$591FlexibilityNo cancel feeOn-time71%

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