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Simpson Bay

$129+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SXM
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$286
(Cheapflightsfares)

One-way from

$129
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$480

Good round-trip deal

$456 or less

Good one-way deal

$186 or less
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. 9% potential increase in price ($63 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($19 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 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 September 17, 2025.

This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/46:10 amBOS - SXM
1 stop7h 50mSpirit Airlines
Sat 10/113:05 pmSXM - BOS
1 stop8h 54mSpirit Airlines
Deal found 9/15$286
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/125:45 amBOS - SXM
1 stop8h 25mSpirit Airlines
Wed 11/194:28 pmSXM - BOS
1 stop9h 12mSpirit Airlines
Deal found 9/14$318
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/36:10 amBOS - SXM
1 stop7h 50mSpirit Airlines
Sat 10/113:05 pmSXM - BOS
1 stop8h 54mSpirit Airlines
Deal found 9/15$327
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/256:16 amBOS - SXM
1 stop7h 44mSpirit Airlines
Sat 11/13:05 pmSXM - BOS
1 stop8h 54mSpirit Airlines
Deal found 9/15$328
This United Airlines deal was found by Cheapflights users on 9/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/276:00 amBOS - SXM
1 stop6h 50mUnited Airlines
Fri 10/311:52 pmSXM - BOS
1 stop7h 42mUnited Airlines
Deal found 9/16$335
This Flightnetwork deal was found by Cheapflights users on 9/16. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/318:24 pmBOS - SXM
1 stop17h 36mSpirit Airlines
Fri 11/74:28 pmSXM - BOS
1 stop9h 12mSpirit Airlines
Deal found 9/16$343
This FlightHub deal was found by Cheapflights users on 9/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/45:30 amBOS - SXM
1 stop8h 10mMultiple Airlines
Wed 12/104:28 pmSXM - BOS
1 stop9h 12mMultiple Airlines
Deal found 9/16$344
This Air Canada deal was found by Cheapflights users on 9/16. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/45:30 amBOS - SXM
1 stop8h 10mAir Canada
Thu 12/113:40 pmSXM - BOS
1 stop29h 02mAir Canada
Deal found 9/16$345
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/145:45 amBOS - SXM
1 stop8h 25mSpirit Airlines
Mon 11/174:28 pmSXM - BOS
1 stop9h 12mSpirit Airlines
Deal found 9/16$347

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 September 17, 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

Sat 11/15

6:00 am-3:57 pm

1 stop8h 57m

Simpson Bay Princess Juliana

Sun 11/23

3:00 pm-12:45 am

1 stop10h 45m

$335

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 11/8

5:30 am-1:50 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sun 11/16

3:00 pm-9:30 am

1 stop19h 30m

$359

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sun 1/11

8:45 pm-12:15 pm

1 stop14h 30m

Simpson Bay Princess Juliana

Sat 1/17

5:16 pm-12:59 am

1 stop8h 43m

$363

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Mon 3/9

8:30 pm-1:53 pm

1 stop17h 23m

Simpson Bay Princess Juliana

Wed 3/11

3:45 pm-7:24 am

1 stop15h 39m

$363

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 1/17

8:45 pm-12:15 pm

1 stop14h 30m

Simpson Bay Princess Juliana

Sat 1/24

5:16 pm-12:59 am

1 stop8h 43m

$376

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Mon 11/10

6:00 am-1:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Tue 11/25

2:52 pm-10:47 pm

1 stop8h 55m

$385

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 11/15

5:30 am-1:50 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Tue 11/25

2:52 pm-10:47 pm

1 stop8h 55m

$385

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sun 11/16

6:00 am-1:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Wed 11/19

2:52 pm-10:34 am

2 stops20h 42m

$387

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Tue 11/11

6:00 am-1:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Wed 11/19

2:52 pm-9:30 am

2 stops19h 38m

$387

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Thu 11/27

5:30 am-2:40 pm

1 stop8h 10m

$129

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 17 results
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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 September 12, 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 $459). Flying from Boston to Simpson Bay in March is currently the most expensive (average of $652). 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 September 17, 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 56% 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 September 17, 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
8.0
Very good
7,961 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,961 reviews
Delta
8.0
Very good
7,961 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,926 reviews
Delta
8.0
Very good
7,961 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,961 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
JetBlue
7.2
Good
2,914 reviews
Delta
8.0
Very good
7,961 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Spirit Airlines
6.3
Okay
8,023 reviews
Delta
8.0
Very good
7,961 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 1 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 8h 57m. Fly via United Airlines or Delta 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 airlines to fly from Boston to Simpson Bay one-way?

    One-way options have recently been found by users for as low as $129 on Air Canada. Other airlines that offer cheap prices include United Airlines from $137 and American Airlines from $142 one-way.

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

    On average you can expect to pay $463 for a flight from Boston to Simpson Bay. The cheapest flight overall is $186 while the most popular route, (Boston Logan Intl - Simpson Bay Princess Juliana) is currently priced at $337.

  • 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?

    Wynwood Art District, Bayfront Park, and Kaseya Center 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 Wynwood Art District, Bayfront Park, and Kaseya Center, by traveling 5.5 mi, 6.4 mi, and 6.2 mi, respectively after landing at Miami. Travelers can book a car rental at Miami for about $24 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 $459). Flying from Boston to Simpson Bay in March is currently the most expensive (average of $652). 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
Albany to Simpson Bay flights
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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$73Average$215FlexibilityNo cancel feeOn-time62%
DeltaCheapest$174Average$393FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$180Average$641FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$335Average$560FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$348Average$802FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$354Average$680FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$390Average$592FlexibilityNo cancel feeOn-time71%

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