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Simpson Bay

$137+ 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 6/29. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SXM
May 6 — May 131
Tue 5/6
Tue 5/13
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 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 May 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$347
(Cheapflightsfares)

One-way from

$137
(Delta)

Popular in

December

Cheapest in

September

Average price

$575

Good round-trip deal

$568 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. 13% potential increase in price ($99 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($30 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 5/306:10 amBOS - SXM
1 stop7h 50mSpirit Airlines
Fri 6/63:05 pmSXM - BOS
1 stop8h 24mSpirit Airlines
Deal found 4/30$347
This Delta deal was found by Cheapflights users on 4/29. 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 8/26:05 amBOS - SXM
1 stop8h 07mDelta
Sat 8/233:10 pmSXM - BOS
1 stop9h 56mDelta
Deal found 4/29$379
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/53:55 pmBOS - SXM
1 stop19h 28mCopa Airlines
Sun 6/812:18 pmSXM - BOS
1 stop25h 56mCopa Airlines
Deal found 4/29$385
This United Airlines deal was found by Cheapflights users on 4/29. 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 5/315:30 amBOS - SXM
1 stop6h 59mUnited Airlines
Sat 6/71:35 pmSXM - BOS
1 stop9h 20mUnited Airlines
Deal found 4/29$387
This JetBlue deal was found by Cheapflights users on 4/29. 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 9/138:00 amBOS - SXM
Nonstop4h 04mJetBlue
Sat 9/201:25 pmSXM - BOS
Nonstop4h 29mJetBlue
Deal found 4/29$409
This Vliegwinkel deal was found by Cheapflights users on 4/29. 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 5/317:09 pmBOS - SXM
2 stops17h 20mAir Canada
Sat 6/73:55 pmSXM - BOS
2 stops17h 00mAir Canada
Deal found 4/29$411
This Vliegwinkel deal was found by Cheapflights users on 4/29. 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 5/315:30 amBOS - SXM
1 stop6h 59mBrussels Airlines
Sat 6/73:55 pmSXM - BOS
2 stops17h 00mBrussels Airlines
Deal found 4/29$417
This American Airlines deal was found by Cheapflights users on 4/29. 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 5/136:05 amBOS - SXM
1 stop8h 19mAmerican Airlines
Tue 5/204:40 pmSXM - BOS
1 stop17h 15mAmerican Airlines
Deal found 4/29$423
This CheapOair deal was found by Cheapflights users on 4/30. 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.
Fri 6/610:51 amBOS - SXM
1 stop24h 32mFrontier
Sat 6/146:26 pmSXM - BOS
2 stops13h 40mFrontier
Deal found 4/30$435
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/273:55 pmBOS - SXM
1 stop19h 28mMultiple Airlines
Mon 6/23:05 pmSXM - BOS
1 stop8h 24mMultiple Airlines
Deal found 4/30$455

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 May 1, 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 5/24

6:10 am-2:00 pm

1 stop7h 50m

Simpson Bay Princess Juliana

Sat 5/31

3:05 pm-11:29 pm

1 stop8h 24m

$347

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 5/31

5:40 am-1:54 pm

1 stop8h 14m

Simpson Bay Princess Juliana

Thu 6/5

3:19 pm-1:17 am

1 stop9h 58m

$379

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Thu 6/5

3:55 pm-11:23 am

1 stop19h 28m

Simpson Bay Princess Juliana

Sun 6/8

12:18 pm-2:14 pm

1 stop25h 56m

$385

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sun 5/25

6:00 am-2:43 pm

1 stop8h 43m

Simpson Bay Princess Juliana

Thu 6/5

1:35 pm-10:24 pm

1 stop8h 49m

$395

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 9/13

8:00 am-12:04 pm

Nonstop4h 04m

Simpson Bay Princess Juliana

Sat 9/20

1:25 pm-5:54 pm

Nonstop4h 29m

$409

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Tue 5/27

6:00 am-1:15 pm

1 stop7h 15m

Simpson Bay Princess Juliana

Tue 6/3

3:24 pm-9:55 am

1 stop18h 31m

$423

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Fri 6/6

10:51 am-11:23 am

1 stop24h 32m

Simpson Bay Princess Juliana

Sat 6/14

6:26 pm-8:06 am

2 stops13h 40m

$435

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Tue 5/27

3:55 pm-11:23 am

1 stop19h 28m

Simpson Bay Princess Juliana

Mon 6/2

3:05 pm-11:29 pm

1 stop8h 24m

$455

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sun 6/29

5:35 am-2:00 pm

1 stop8h 25m

$137

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Thu 5/29

3:49 pm-2:00 pm

1 stop22h 11m

$163

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 15 results
1
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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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 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 AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Boston-Simpson Bay flight deals on Cheapflights vs. AranGrant >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 AranGrant the most. AranGrant 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 April 25, 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 July is currently the most expensive (average of $669). 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 May 1, 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 57% 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 May 1, 2025.
Read reviews from past customers who have flown Delta, Copa Airlines and United 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
7,934 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Copa Airlines
7.5
Good
1,414 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,696 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
JetBlue
7.3
Good
2,924 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

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
7,934 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

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, Spirit Airlines ($347), Delta ($379), and Copa Airlines ($385) offers the cheapest pricing from Boston to Simpson Bay. Spirit Airlines is priced at 45% 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 $137 on Delta. Other airlines that offer cheap prices include Spirit Airlines from $163 and United Airlines from $182 one-way.

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

    On average you can expect to pay $477 for a flight from Boston to Simpson Bay. The cheapest flight overall is $151 while the most popular route, (Boston Logan Intl - Simpson Bay Princess Juliana) is currently priced at $362.

  • 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. New York 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 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. Travelers on a layover in Miami can visit Wynwood Art District, Bayfront Park, and Bayside Marketplace, by traveling 5.5 mi, 6.4 mi, and 6.4 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.

  • What are some popular points of interest to see during 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. Times Square, New York City Center, and Madison Square Garden are located about 13.6 mi, 13.6 mi, and 13.6 mi, respectively from New York John F Kennedy Intl. Travelers can book a car rental at New York John F Kennedy Intl for about $70 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 $669). 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 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$73Average$227FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$315Average$574FlexibilityNo cancel feeOn-time69%
DeltaCheapest$335Average$506FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$348Average$856FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$358Average$683FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$389Average$610FlexibilityNo cancel feeOn-time71%

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