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$191+ 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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — BOS
Nov 19 — Nov 261
Wed 11/19
Wed 11/26
1 adult, Economy
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Find 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 October 20, 2025.

This Mytrip deal was found by Cheapflights users on 10/17. 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.
Sat 11/83:20 pmSXM - BOS
1 stop9h 39mSpirit Airlines
Sat 11/156:16 amBOS - SXM
1 stop6h 59mSpirit Airlines
Deal found 10/17$291
This American Airlines deal was found by Cheapflights users on 10/17. 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 11/81:13 pmSXM - BOS
2 stops10h 36mAmerican Airlines
Sat 11/156:00 amBOS - SXM
1 stop7h 41mAmerican Airlines
Deal found 10/17$301
This American Airlines deal was found by Cheapflights users on 10/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/65:25 pmSXM - BOS
2 stops16h 23mAmerican Airlines
Sat 12/136:36 pmBOS - SXM
2 stops18h 44mAmerican Airlines
Deal found 10/19$314
This United Airlines deal was found by Cheapflights users on 10/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/82:40 pmSXM - BOS
1 stop19h 50mUnited Airlines
Sat 11/155:30 amBOS - SXM
1 stop7h 20mUnited Airlines
Deal found 10/19$317
This Cheapflightsfares deal was found by Cheapflights users on 10/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/63:15 pmSXM - BOS
1 stop9h 42mSpirit Airlines
Sat 12/135:50 amBOS - SXM
1 stop7h 20mSpirit Airlines
Deal found 10/19$359
This American Airlines deal was found by Cheapflights users on 10/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/65:25 pmSXM - BOS
1 stop8h 34mAmerican Airlines
Mon 12/157:00 amBOS - SXM
2 stops32h 25mAmerican Airlines
Deal found 10/19$360
This American Airlines deal was found by Cheapflights users on 10/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/65:25 pmSXM - BOS
1 stop8h 34mAmerican Airlines
Wed 12/105:34 amBOS - SXM
1 stop9h 51mAmerican Airlines
Deal found 10/19$365
This Flysmarter deal was found by Cheapflights users on 10/18. 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.
Sat 11/14:00 pmSXM - BOS
1 stop7h 42mLufthansa
Sat 11/83:42 pmBOS - SXM
2 stops23h 15mLufthansa
Deal found 10/18$371

Cheap 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 October 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$291
(Mytrip)

One-way from

$191
(Copa Airlines)

Popular in

November

Cheapest in

May

Average price

$427

Good one-way deal

$292 or less
Provider with most accurate pricing for Simpson Bay Princess Juliana-Boston Logan Intl flight deals.
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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. 4% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 20, 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

Sat 11/8

1:13 pm-10:49 pm

2 stops10h 36m

Boston Logan Intl

Sat 11/15

6:00 am-2:41 pm

1 stop7h 41m

$301

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sat 12/6

5:25 pm-8:48 am

2 stops16h 23m

Boston Logan Intl

Sat 12/13

6:36 pm-2:20 pm

2 stops18h 44m

$314

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sat 11/8

2:40 pm-9:30 am

1 stop19h 50m

Boston Logan Intl

Sat 11/15

5:30 am-1:50 pm

1 stop7h 20m

$317

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Thu 3/5

4:26 pm-7:24 am

1 stop15h 58m

Boston Logan Intl

Mon 3/9

8:30 pm-1:53 pm

1 stop17h 23m

$317

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sat 11/1

4:00 pm-11:42 pm

1 stop7h 42m

Boston Logan Intl

Sat 11/8

6:23 pm-3:57 pm

1 stop20h 34m

$359

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Mon 1/26

12:25 pm-10:03 pm

1 stop10h 38m

$191

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Wed 12/24

12:24 pm-10:40 pm

1 stop11h 16m

$191

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Mon 1/26

5:33 pm-10:27 am

2 stops17h 54m

$206

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sun 1/25

5:33 pm-10:29 am

2 stops17h 56m

$211

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sat 11/22

5:00 pm-12:28 pm

2 stops20h 28m

$220

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/19

Showing 1-10 of 14 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 October.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy2 starsTrust Score*3 stars
AranGrantPrice Accuracy3 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Simpson Bay-Boston flight deals on Cheapflights vs. FlightHub >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 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 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 $167). 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 October 20, 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 October 20, 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
11,026 reviews

Boarding

7.5

Crew

8.0

Overall

7.2

Food

6.4

Entertainment

6.9

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.
American Airlines
7.2
Good
11,026 reviews
American Airlines
7.2
Good
11,026 reviews

Boarding

7.5

Crew

8.0

Overall

7.2

Food

6.4

Entertainment

6.9

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.
JetBlue
7.2
Good
2,907 reviews
American Airlines
7.2
Good
11,026 reviews

Boarding

7.5

Crew

8.0

Overall

7.2

Food

6.4

Entertainment

6.9

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.

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 $301, American Airlines can have you in Boston from Simpson Bay in 10h 36m. 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 39% lower than the current average price 3 months from now.

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

    Looking at all options, your cheapest flight can be booked for $262. While the most popular route (Simpson Bay Princess Juliana - Boston Logan Intl) can be booked for $279 on average, our data indicates $437 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 $167). 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
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Seekonk
Lincoln
Lowell
Smithfield
Cranston
Chestnut Hill
Peabody
Quincy
York Beach
Warwick
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Old Orchard Beach
Brockton
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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 October 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$319Average$376FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$395Average$528FlexibilityNo cancel feeOn-time71%

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