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Simpson Bay

$45+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SXM
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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The best prices from Boston Logan Intl to Simpson Bay Princess Juliana are usually found in September or August, booked 2 days in advance, depart on a Thursday or Tuesday and return on a Thursday

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 January 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$353
(Gotogate)

One-way from

$58
(Frontier)

Popular in

December

Cheapest in

September

Average price

$583

Good round-trip deal

$509 or less

Good one-way deal

$235 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. 9% potential increase in price ($67 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in January 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 January 21, 2025.

This Gotogate deal was found by Cheapflights users on 1/20. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/211:18 amBOS - SXM
1 stop28h 51mFrontier
Fri 3/76:35 pmSXM - BOS
1 stop16h 32mFrontier
Deal found 1/20$353
This CheapOair deal was found by Cheapflights users on 1/21. 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.
Thu 3/2711:14 amBOS - SXM
1 stop26h 14mMultiple Airlines
Fri 4/46:15 pmSXM - BOS
1 stop16h 01mMultiple Airlines
Deal found 1/21$364
This CheapOair deal was found by Cheapflights users on 1/20. 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.
Sun 2/26:56 pmBOS - SXM
2 stops18h 34mSpirit Airlines
Fri 2/73:25 pmSXM - BOS
1 stop9h 07mSpirit Airlines
Deal found 1/20$365
This American Airlines deal was found by Cheapflights users on 1/20. 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.
Tue 3/45:00 amBOS - SXM
1 stop7h 55mAmerican Airlines
Tue 3/114:15 pmSXM - BOS
2 stops16h 08mAmerican Airlines
Deal found 1/20$367
This Delta deal was found by Cheapflights users on 1/20. 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.
Tue 3/115:40 amBOS - SXM
1 stop8h 21mDelta
Tue 3/181:40 pmSXM - BOS
1 stop11h 25mDelta
Deal found 1/20$374
This JetBlue deal was found by Cheapflights users on 1/19. 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.
Tue 4/87:00 amBOS - SXM
Nonstop4h 12mJetBlue
Thu 4/1012:35 pmSXM - BOS
Nonstop4h 32mJetBlue
Deal found 1/19$388
This United Airlines deal was found by Cheapflights users on 1/20. 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 2/227:39 pmBOS - SXM
1 stop17h 05mUnited Airlines
Thu 3/64:55 pmSXM - BOS
1 stop7h 55mUnited Airlines
Deal found 1/20$409
This Air Canada deal was found by Cheapflights users on 1/20. 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.
Wed 3/266:10 amBOS - SXM
1 stop9h 05mAir Canada
Sun 3/303:55 pmSXM - BOS
2 stops20h 16mAir Canada
Deal found 1/20$525

Find flights from Boston to Simpson Bay within your budget

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sun 3/2

11:18 am-5:09 pm

1 stop28h 51m

Simpson Bay Princess Juliana

Fri 3/7

6:35 pm-10:07 am

1 stop16h 32m

$353

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Thu 3/27

2:10 pm-1:28 pm

1 stop23h 18m

Simpson Bay Princess Juliana

Fri 4/4

6:15 pm-10:16 am

1 stop16h 01m

$364

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sun 2/2

6:56 pm-2:30 pm

2 stops18h 34m

Simpson Bay Princess Juliana

Fri 2/7

3:25 pm-11:32 pm

1 stop9h 07m

$365

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Tue 3/4

7:28 pm-2:15 pm

2 stops17h 47m

Simpson Bay Princess Juliana

Tue 3/11

3:20 pm-7:40 am

2 stops16h 20m

$367

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Tue 3/11

5:40 am-2:01 pm

1 stop8h 21m

Simpson Bay Princess Juliana

Tue 3/18

1:40 pm-1:05 am

1 stop11h 25m

$374

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Tue 4/8

7:00 am-11:12 am

Nonstop4h 12m

Simpson Bay Princess Juliana

Thu 4/10

12:35 pm-5:07 pm

Nonstop4h 32m

$388

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 2/22

7:39 pm-1:44 pm

1 stop17h 05m

Simpson Bay Princess Juliana

Thu 3/6

4:55 pm-11:50 pm

1 stop7h 55m

$409

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Wed 3/26

6:10 am-3:15 pm

1 stop9h 05m

Simpson Bay Princess Juliana

Sun 3/30

3:55 pm-12:11 pm

2 stops20h 16m

$525

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Mon 3/3

10:18 am-5:09 pm

1 stop5h 51m

$45

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Mon 3/10

10:43 am-5:15 pm

1 stop6h 32m

$97

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 16 results
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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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy2 starsTrust Score*2 stars
JustAirTicketPrice Accuracy-Trust 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Boston-Simpson Bay flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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.

Travel insights for flights from Boston to Simpson Bay

Get recent, data-driven insights about flights from Boston to Simpson Bay including ideal travel times, pricing trends, and more.

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 January 17, 2025.

To ensure you get the cheapest price possible for a flight from Boston to Simpson Bay, you should look to book at least 2 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 July is currently the most expensive (average of $684). 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 January 21, 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.

What is the cheapest day to fly from Boston to Simpson Bay?

Use this chart to determine the cheapest time to fly round-trip from Boston to Simpson Bay. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Boston to Simpson Bay flight should consider departing on Tuesday at noon when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 January 21, 2025.
Read reviews from past customers who have flown American Airlines, Delta and Spirit Airlines from Boston to Simpson Bay. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,521 reviews

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.6

Boarding

8.2

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta
8.0
Very good
8,521 reviews
Delta
8.0
Very good
8,521 reviews

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.6

Boarding

8.2

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

JetBlue
7.4
Good
3,201 reviews
Delta
8.0
Very good
8,521 reviews

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.6

Boarding

8.2

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

United Airlines
7.4
Good
8,985 reviews
Delta
8.0
Very good
8,521 reviews

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.6

Boarding

8.2

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
8,521 reviews

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.6

Boarding

8.2

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Air Canada
7.0
Good
8,635 reviews
Delta
8.0
Very good
8,521 reviews

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.6

Boarding

8.2

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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.

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

    According to our current data, Frontier ($353), Spirit Airlines ($365), and American Airlines ($367) offers the cheapest pricing from Boston to Simpson Bay. Frontier is priced at 46% 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 $58 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $120 and Delta from $144 one-way.

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

    On average you can expect to pay $511 for a flight from Boston to Simpson Bay. The cheapest flight overall is $149 while the most popular route, (Boston Logan Intl - Simpson Bay Princess Juliana) is currently priced at $269.

  • 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 New York. Miami sees the next most layovers on Boston to Simpson Bay flights.

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

    Times Square, New York City Center, and Madison Square Garden are the most popular attractions in New York if you're in need of something to do during your layover. Travelers on a layover in New York can visit Times Square, New York City Center, and Madison Square Garden, by traveling 13.6 mi, 13.6 mi, and 13.6 mi, respectively after landing at New York John F Kennedy Intl. Travelers can book a car rental at New York John F Kennedy Intl for about $63 per day to make their sightseeing more efficient.

  • What are some popular points of interest to see during a layover in Miami?

    Wynwood Art District, Bayfront Park, and Bayside Marketplace are the most popular attractions in Miami if you're in need of something to do during your layover. Wynwood Art District, Bayfront Park, and Bayside Marketplace are located about 5.5 mi, 6.4 mi, and 6.4 mi, respectively from Miami. Travelers can book a car rental at Miami for about $36 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 Fort Lauderdale least often. Charlotte follows Fort Lauderdale in terms of the least common layover location on Boston to Simpson Bay flights.

  • 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 July is currently the most expensive (average of $684). 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 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 6 airlines flying from Boston to Simpson Bay

Discover the top 6 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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$73Average$228FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$280Average$656FlexibilityNo cancel feeOn-time65%
DeltaCheapest$338Average$563FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$343Average$845FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$366Average$682FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$394Average$637FlexibilityNo cancel feeOn-time71%
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