HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Simpson Bay

$56+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SXM
Mar 4 — Mar 111
Wed 3/4
Wed 3/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Boston to Simpson Bay with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.
Cheapflights Tip: The best prices from Boston Logan Intl to Simpson Bay Princess Juliana are usually found in September or March, booked 28 days in advance, depart on a Sunday or Wednesday and return on a Monday

Cheap 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 February 2, 2026.

This Delta deal was found by Cheapflights users on 1/31. 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.
Thu 2/198:59 pm
BOS
-
SXM
1 stop14h 14m
Delta
Wed 2/251:38 pm
SXM
-
BOS
1 stop12h 31m
Delta
Deal found 1/31$316
This Delta deal was found by Cheapflights users on 1/31. 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.
Fri 2/2712:00 pm
BOS
-
SXM
2 stops25h 15m
Delta
Wed 3/41:38 pm
SXM
-
BOS
1 stop8h 58m
Delta
Deal found 1/31$317
This Priceline deal was found by Cheapflights users on 2/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/237:49 am
BOS
-
SXM
Nonstop4h 16m
Multiple Airlines
Fri 2/273:20 pm
SXM
-
BOS
1 stop9h 24m
Multiple Airlines
Deal found 2/1$318
This Cheapflightsfares deal was found by Cheapflights users on 2/1. 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 3/47:54 am
BOS
-
SXM
Nonstop4h 16m
JetBlue
Tue 3/103:35 pm
SXM
-
BOS
Nonstop4h 37m
JetBlue
Deal found 2/1$319
This KAYAK deal was found by Cheapflights users on 1/31. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:54 am
BOS
-
SXM
Nonstop4h 16m
JetBlue
Wed 3/44:35 pm
SXM
-
BOS
Nonstop4h 40m
JetBlue
Deal found 1/31$320
This American Airlines deal was found by Cheapflights users on 1/31. 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.
Thu 12/38:40 pm
BOS
-
SXM
2 stops16h 18m
American Airlines
Mon 12/75:25 pm
SXM
-
BOS
2 stops18h 44m
American Airlines
Deal found 1/31$324
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Thu 2/265:49 am
BOS
-
SXM
1 stop9h 11m
American Airlines
Mon 3/25:01 pm
SXM
-
BOS
1 stop21h 44m
American Airlines
Deal found 2/1$325
This Expedia deal was found by Cheapflights users on 2/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/177:49 am
BOS
-
SXM
Nonstop4h 16m
Multiple Airlines
Tue 2/243:20 pm
SXM
-
BOS
1 stop9h 24m
Multiple Airlines
Deal found 2/1$327
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Wed 2/256:10 pm
BOS
-
SXM
1 stop19h 05m
Spirit Airlines
Wed 3/43:20 pm
SXM
-
BOS
1 stop9h 24m
Spirit Airlines
Deal found 1/31$328
This Expedia deal was found by Cheapflights users on 1/31. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/55:34 am
BOS
-
SXM
1 stop7h 41m
Multiple Airlines
Sun 2/811:30 am
SXM
-
BOS
1 stop7h 30m
Multiple Airlines
Deal found 1/31$329

Find 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 February 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$316
(Delta)

One-way from

$56
(Cheapflightsfares)

Popular in

April

Cheapest in

September

Average price

$597

Good round-trip deal

$337 or less

Good one-way deal

$149 or less
Provider with most accurate pricing for Boston Logan Intl-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Simpson Bay Princess Juliana flights.
Search Deals
From Boston Logan Intl to Simpson Bay Princess Juliana
Search Deals
One-way flight from Boston Logan Intl to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
Price to beat on a round-trip flight from Boston Logan Intl to Simpson Bay Princess Juliana.
Search Deals
Price to beat on a one-way flight from Boston Logan Intl to Simpson Bay Princess Juliana.
Search Deals

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 February 2, 2026.
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

Thu 2/19

8:59 pm-12:13 pm

1 stop14h 14m

Simpson Bay Princess Juliana

Wed 2/25

1:38 pm-1:09 am

1 stop12h 31m

$316

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Fri 3/20

5:45 am-12:50 pm

1 stop7h 05m

Simpson Bay Princess Juliana

Tue 3/24

3:55 pm-12:56 pm

2 stops21h 01m

$317

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Fri 2/27

12:00 pm-2:15 pm

2 stops25h 15m

Simpson Bay Princess Juliana

Tue 3/3

1:38 pm-1:09 am

1 stop12h 31m

$317

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 3/7

6:10 pm-1:15 pm

1 stop18h 05m

Simpson Bay Princess Juliana

Fri 3/13

4:00 pm-9:32 am

2 stops17h 32m

$318

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Fri 4/10

6:15 am-2:50 pm

1 stop8h 35m

Simpson Bay Princess Juliana

Tue 4/14

2:35 pm-11:59 pm

1 stop9h 24m

$341

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 4/18

8:00 pm-12:10 pm

1 stop16h 10m

Simpson Bay Princess Juliana

Thu 4/23

3:30 pm-7:25 am

1 stop15h 55m

$360

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Wed 4/22

6:00 am-2:43 pm

1 stop8h 43m

Simpson Bay Princess Juliana

Mon 4/27

1:35 pm-10:04 am

2 stops20h 29m

$362

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Fri 4/10

4:23 pm-1:30 pm

2 stops21h 07m

Simpson Bay Princess Juliana

Tue 4/14

2:35 pm-11:59 pm

1 stop9h 24m

$374

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Thu 3/26

3:35 pm-3:00 pm

2 stops23h 25m

Simpson Bay Princess Juliana

Tue 3/31

2:35 pm-11:59 pm

1 stop9h 24m

$375

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Mon 3/30

5:45 am-12:33 pm

1 stop6h 48m

Simpson Bay Princess Juliana

Wed 4/1

3:50 pm-11:59 pm

1 stop8h 09m

$391

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/30

Showing 1-10 of 21 results
1
2
3

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
Trip.comPrice Accuracy1 starTrust 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.

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 January 30, 2026.

To ensure you get the cheapest price possible for a flight from Boston to Simpson Bay, you should look to book at least 28 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 $140). Flying from Boston to Simpson Bay in June is currently the most expensive (average of $342). 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 February 2, 2026.

When flying from Boston to Simpson Bay, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 February 2, 2026.
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
7.9
Good
8,131 reviews

Comfort

7.9

Overall

7.9

Boarding

8.1

Crew

8.5

Food

7.2

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,131 reviews
Delta
7.9
Good
8,131 reviews

Comfort

7.9

Overall

7.9

Boarding

8.1

Crew

8.5

Food

7.2

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,229 reviews
Delta
7.9
Good
8,131 reviews

Comfort

7.9

Overall

7.9

Boarding

8.1

Crew

8.5

Food

7.2

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,212 reviews
Delta
7.9
Good
8,131 reviews

Comfort

7.9

Overall

7.9

Boarding

8.1

Crew

8.5

Food

7.2

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
JetBlue
7.2
Good
2,892 reviews
Delta
7.9
Good
8,131 reviews

Comfort

7.9

Overall

7.9

Boarding

8.1

Crew

8.5

Food

7.2

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,396 reviews
Delta
7.9
Good
8,131 reviews

Comfort

7.9

Overall

7.9

Boarding

8.1

Crew

8.5

Food

7.2

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 6 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 7h 05m. Fly via Delta or United Airlines 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 ($134), Delta ($136), and Air Canada ($180) offers the cheapest pricing from Boston to Simpson Bay. Frontier is priced at 75% 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 $44 on Frontier. Other airlines that offer cheap prices include Delta from $84 and United Airlines from $136 one-way.

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

    On average you can expect to pay $312 for a flight from Boston to Simpson Bay. The cheapest flight overall is $138 while the most popular route, (Boston Logan Intl - Simpson Bay Princess Juliana) is currently priced at $217.

  • 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?

    Kaseya Center, 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 Kaseya Center, Bayfront Park, and Bayside Marketplace, by traveling 6.2 mi, 6.4 mi, and 6.4 mi, respectively after landing at Miami. Travelers can book a car rental at Miami for about $28 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 $140). Flying from Boston to Simpson Bay in June is currently the most expensive (average of $342). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 February 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$134Average$333FlexibilityNo cancel feeOn-time62%
DeltaCheapest$136Average$350FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$180Average$641FlexibilityNo cancel feeOn-time67%
Spirit AirlinesCheapest$205Average$438FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$297Average$476FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$331Average$579FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$373Average$568FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
Cookie settings©2026 Cheapflights