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$165+ 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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — BOS
ene. 3 — ene. 101
sáb. 1/3
sáb. 1/10
1 adult, Economy
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Cheap 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 diciembre 4, 2025.

This Flysmarter deal was found by Cheapflights users on 12/2. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/261:59 pmSXM - BOS
Nonstop4h 35mJetBlue
dom. 1/47:35 amBOS - SXM
Nonstop4h 15mJetBlue
Deal found 12/2$332
This Flysmarter deal was found by Cheapflights users on 12/4. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/211:59 pmSXM - BOS
Nonstop4h 35mJetBlue
mar. 12/307:30 amBOS - SXM
Nonstop4h 14mJetBlue
Deal found 12/4$333
This Vliegwinkel deal was found by Cheapflights users on 12/2. 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.
vie. 12/263:20 pmSXM - BOS
1 stop9h 37mMultiple Airlines
dom. 1/47:35 amBOS - SXM
Nonstop4h 15mMultiple Airlines
Deal found 12/2$334
This Delta deal was found by Cheapflights users on 12/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/113:53 pmSXM - BOS
1 stop8h 31mDelta
lun. 12/155:40 amBOS - SXM
1 stop7h 48mDelta
Deal found 12/4$336
This American Airlines deal was found by Cheapflights users on 12/2. 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.
vie. 12/265:33 pmSXM - BOS
1 stop8h 26mAmerican Airlines
dom. 1/45:59 amBOS - SXM
1 stop6h 27mAmerican Airlines
Deal found 12/2$345
This American Airlines deal was found by Cheapflights users on 12/3. 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.
dom. 12/215:33 pmSXM - BOS
1 stop8h 26mAmerican Airlines
mar. 12/305:59 amBOS - SXM
1 stop6h 27mAmerican Airlines
Deal found 12/3$346
This American Airlines deal was found by Cheapflights users on 12/4. 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.
jue. 12/112:51 pmSXM - BOS
1 stop9h 01mAmerican Airlines
lun. 12/158:40 pmBOS - SXM
2 stops18h 45mAmerican Airlines
Deal found 12/4$350
This Kiwi.com deal was found by Cheapflights users on 12/2. 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.
vie. 12/263:20 pmSXM - BOS
1 stop20h 30mSpirit Airlines
dom. 1/412:29 pmBOS - SXM
2 stops24h 46mSpirit Airlines
Deal found 12/2$358
This United Airlines deal was found by Cheapflights users on 12/4. 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.
dom. 12/212:20 pmSXM - BOS
1 stop11h 25mUnited Airlines
mar. 12/3010:25 amBOS - SXM
1 stop28h 26mUnited Airlines
Deal found 12/4$359
This Kissandfly.com deal was found by Cheapflights users on 12/4. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/215:00 pmSXM - BOS
2 stops23h 35mLufthansa
mar. 12/3010:25 amBOS - SXM
2 stops26h 25mLufthansa
Deal found 12/4$363
This United Airlines deal was found by Cheapflights users on 12/2. 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.
sáb. 12/62:52 pmSXM - BOS
1 stop8h 53mUnited Airlines
sáb. 12/136:00 amBOS - SXM
1 stop8h 57mUnited Airlines
Deal found 12/2$373

Find 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 diciembre 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$275
(Expedia)

One-way from

$165
(Cheapflightsfares)

Popular in

November

Cheapest in

May

Average price

$338

Good one-way deal

$262 or less
Provider with most accurate pricing for Simpson Bay Princess Juliana-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Simpson Bay Princess Juliana-Boston Logan Intl flights.
Search Deals
From Simpson Bay Princess Juliana to Boston Logan Intl
Search Deals
One-way flight from Simpson Bay Princess Juliana to Boston Logan Intl
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($4 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($30 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a one-way flight from Simpson Bay Princess Juliana to Boston Logan Intl.
Search Deals

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 diciembre 4, 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

sáb. 1/17

3:15 pm-11:57 pm

1 stop9h 42m

Boston Logan Intl

sáb. 1/24

5:34 am-2:10 pm

1 stop7h 36m

$304

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

jue. 1/22

3:15 pm-11:57 pm

1 stop9h 42m

Boston Logan Intl

dom. 1/25

5:34 am-2:10 pm

1 stop7h 36m

$307

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

sáb. 1/17

5:00 pm-12:46 pm

2 stops20h 46m

Boston Logan Intl

sáb. 1/24

7:22 pm-1:50 pm

1 stop17h 28m

$316

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

vie. 12/26

1:59 pm-5:34 pm

Nonstop4h 35m

Boston Logan Intl

dom. 1/4

7:35 am-12:50 pm

Nonstop4h 15m

$332

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

dom. 12/21

1:59 pm-5:34 pm

Nonstop4h 35m

Boston Logan Intl

mar. 12/30

7:30 am-12:44 pm

Nonstop4h 14m

$333

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

vie. 12/26

3:20 pm-11:57 pm

1 stop9h 37m

Boston Logan Intl

dom. 1/4

7:35 am-12:50 pm

Nonstop4h 15m

$334

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

sáb. 1/17

3:15 pm-11:57 pm

1 stop9h 42m

Boston Logan Intl

sáb. 1/24

11:40 am-4:53 pm

Nonstop4h 13m

$340

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

vie. 12/26

5:33 pm-12:59 am

1 stop8h 26m

Boston Logan Intl

dom. 1/4

5:59 am-1:26 pm

1 stop6h 27m

$345

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

dom. 12/21

5:33 pm-12:59 am

1 stop8h 26m

Boston Logan Intl

mar. 12/30

5:59 am-1:26 pm

1 stop6h 27m

$346

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

sáb. 1/31

3:10 pm-1:13 am

1 stop11h 03m

$185

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/2

Showing 1-10 of 18 results
1
2

Compare providers for flights from Simpson Bay to Boston

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 Simpson Bay to Boston in December.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
ExpediaPrice Accuracy2 starsTrust Score*3 stars
AranGrantPrice 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 Simpson Bay-Boston flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Simpson Bay-Boston flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Simpson Bay-Boston flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Simpson Bay-Boston flights, Cheapflights users trust eDreams the most. eDreams 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 Simpson Bay-Boston 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 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, October is the cheapest month in which you can book a flight from Simpson Bay to Boston (average of $160). Flying from Simpson Bay to Boston in November is currently the most expensive (average of $829). 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 diciembre 4, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Simpson Bay to Boston as you normally would.

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 diciembre 4, 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
11,043 reviews

Food

6.5

Crew

8.0

Boarding

7.5

Overall

7.2

Entertainment

6.9

Comfort

7.2

Reviews

1 / 20
8.0
Excellent

Monica,Nov 2025

JAC - DFW

At least there was an option of entertainment on this flight.
American Airlines
7.2
Good
11,043 reviews
American Airlines
7.2
Good
11,043 reviews

Food

6.5

Crew

8.0

Boarding

7.5

Overall

7.2

Entertainment

6.9

Comfort

7.2

Reviews

1 / 20
8.0
Excellent

Monica,Nov 2025

JAC - DFW

At least there was an option of entertainment on this flight.
JetBlue
7.2
Good
2,899 reviews
American Airlines
7.2
Good
11,043 reviews

Food

6.5

Crew

8.0

Boarding

7.5

Overall

7.2

Entertainment

6.9

Comfort

7.2

Reviews

1 / 20
8.0
Excellent

Monica,Nov 2025

JAC - DFW

At least there was an option of entertainment on this flight.

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 $304, Spirit Airlines can have you in Boston from Simpson Bay in 9h 42m. 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 ($319), 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 airlines to fly from Simpson Bay to Boston one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $142. Spirit Airlines flights start at $205 while deals on Delta start at $214 one-way.

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

    Looking at all options, your cheapest flight can be booked for $227. While the most popular route (Simpson Bay Princess Juliana - Boston Logan Intl) can be booked for $304 on average, our data indicates $372 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, October is the cheapest month in which you can book a flight from Simpson Bay to Boston (average of $160). Flying from Simpson Bay to Boston in November is currently the most expensive (average of $829). 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
Hampton Beach
Watertown
Seabrook
Seekonk
Cranston
Lincoln
Lowell
Smithfield
Peabody
Brockton
Quincy
York Beach
Warwick
Londonderry
Swansea
Old Orchard Beach
Waltham
Chelsea

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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 diciembre 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$319Average$386FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$395Average$528FlexibilityNo cancel feeOn-time71%

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