HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Boston

$151+ 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 2/17. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — BOS
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 Simpson Bay to Boston 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.

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 February 2, 2026.

This American Airlines deal was found by Cheapflights users on 1/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/292:24 pm
SXM
-
BOS
1 stop8h 43m
American Airlines
Sun 5/39:15 pm
BOS
-
SXM
2 stops16h 06m
American Airlines
Deal found 1/30$274
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/153:20 pm
SXM
-
BOS
1 stop9h 24m
Spirit Airlines
Mon 2/234:22 pm
BOS
-
SXM
2 stops20h 53m
Spirit Airlines
Deal found 1/31$290
This Vliegwinkel 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/153:20 pm
SXM
-
BOS
1 stop9h 24m
Multiple Airlines
Sat 2/216:00 am
BOS
-
SXM
Nonstop4h 15m
Multiple Airlines
Deal found 1/31$294
This Delta deal was found by Cheapflights users on 1/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/293:30 pm
SXM
-
BOS
1 stop15h 59m
Delta
Sun 5/38:59 pm
BOS
-
SXM
1 stop15h 11m
Delta
Deal found 1/30$296
This Flysmarter 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/154:25 pm
SXM
-
BOS
Nonstop4h 40m
JetBlue
Sat 2/216:00 am
BOS
-
SXM
Nonstop4h 15m
JetBlue
Deal found 1/31$308
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.
Sun 2/154:15 pm
SXM
-
BOS
1 stop16h 15m
Delta
Mon 2/235:35 am
BOS
-
SXM
1 stop8h 15m
Delta
Deal found 1/31$317
This American Airlines deal was found by Cheapflights users on 1/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/51:29 pm
SXM
-
BOS
2 stops26h 48m
American Airlines
Wed 3/115:47 am
BOS
-
SXM
1 stop7h 29m
American Airlines
Deal found 1/30$318
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/162:11 pm
SXM
-
BOS
1 stop9h 48m
Spirit Airlines
Wed 4/225:40 am
BOS
-
SXM
1 stop7h 36m
Spirit Airlines
Deal found 1/31$319
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.
Sun 2/152:50 pm
SXM
-
BOS
1 stop17h 31m
Delta
Sat 2/217:00 pm
BOS
-
SXM
1 stop17h 25m
Delta
Deal found 1/31$326
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 4/1612:41 pm
SXM
-
BOS
2 stops10h 13m
American Airlines
Wed 4/226:00 am
BOS
-
SXM
2 stops9h 20m
American Airlines
Deal found 1/31$342

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 February 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$274
(American Airlines)

One-way from

$151
(Super.com)

Popular in

November

Cheapest in

May

Average price

$573

Good round-trip deal

$538 or less

Good one-way deal

$432 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. 11% potential increase in price ($63 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($32 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 Simpson Bay Princess Juliana to Boston Logan Intl.
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 February 2, 2026.
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

Wed 4/29

2:24 pm-11:07 pm

1 stop8h 43m

Boston Logan Intl

Sun 5/3

9:15 pm-1:21 pm

2 stops16h 06m

$274

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Wed 4/29

3:30 pm-7:29 am

1 stop15h 59m

Boston Logan Intl

Sun 5/3

8:59 pm-12:10 pm

1 stop15h 11m

$296

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sun 2/15

4:15 pm-7:30 am

1 stop16h 15m

Boston Logan Intl

Mon 2/23

5:35 am-2:50 pm

1 stop8h 15m

$317

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Thu 3/5

1:29 pm-3:17 pm

2 stops26h 48m

Boston Logan Intl

Wed 3/11

5:47 am-1:16 pm

1 stop7h 29m

$318

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sun 2/15

2:50 pm-7:21 am

1 stop17h 31m

Boston Logan Intl

Sat 2/21

7:00 pm-1:25 pm

1 stop17h 25m

$326

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sun 2/15

3:20 pm-11:44 pm

1 stop9h 24m

Boston Logan Intl

Mon 2/23

2:23 pm-2:15 pm

3 stops22h 52m

$327

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Thu 4/16

2:21 pm-11:07 pm

1 stop8h 46m

Boston Logan Intl

Wed 4/22

6:00 am-3:20 pm

2 stops9h 20m

$342

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sun 2/15

4:25 pm-8:05 pm

Nonstop4h 40m

Boston Logan Intl

Mon 2/23

7:43 pm-3:15 pm

1 stop18h 32m

$348

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Thu 3/5

4:35 pm-8:15 pm

Nonstop4h 40m

Boston Logan Intl

Wed 3/11

6:00 am-1:55 pm

1 stop7h 55m

$362

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sun 2/15

5:51 pm-7:13 am

1 stop14h 22m

Boston Logan Intl

Sat 2/21

7:50 pm-4:36 pm

2 stops19h 46m

$410

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/30

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 February.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 stars
BudgetAirPrice 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 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 $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 February 2, 2026.

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 February 2, 2026.
Read through reviews of airlines operating flights from Simpson Bay to Boston, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,212 reviews

Boarding

7.5

Overall

7.2

Food

6.4

Crew

8.0

Comfort

7.2

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,212 reviews
American Airlines
7.2
Good
11,212 reviews

Boarding

7.5

Overall

7.2

Food

6.4

Crew

8.0

Comfort

7.2

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

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.

  • What airports do I use to fly from Simpson Bay to Boston?

    Booking a flight from Simpson Bay Princess Juliana (SXM) to Boston Logan Intl (BOS) is your only option if you wish to fly from Simpson Bay to Boston. On a typical day, there is 1 flight from Princess Juliana to Logan Intl, all of which are around 4h 26m for a nonstop flight. You can also purchase a plane ticket from 1 airline when you book a flight from Princess Juliana to Boston.

  • How long is the flight from Simpson Bay to Boston?

    For as low as $274, American Airlines can have you in Boston from Simpson Bay in 8h 43m. 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 is the cheapest airline to fly from Simpson Bay to Boston round-trip?

    According to our current data, American Airlines ($423), offers the cheapest pricing from Simpson Bay to Boston. This flight start at 13% 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 $175. Spirit Airlines flights start at $200 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 $261. While the most popular route (Simpson Bay Princess Juliana - Boston Logan Intl) can be booked for $296 on average, our data indicates $630 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
Medford
Cambridge
Hampton Beach
Watertown
Seekonk
Brockton
Seabrook
Cranston
Lincoln
Warwick
Smithfield
Peabody
Quincy
York Beach
Londonderry
Swansea
Old Orchard Beach
Waltham
Lowell
Chelsea

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.

Other flights to Boston

Explore flights to Boston departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on February 2, 2026.
Miami to Boston flights
Atlanta to Boston flights
West Palm Beach to Boston flights
Savannah to Boston flights
Fort Myers to Boston flights
Fort Lauderdale to Boston flights
Boston to Atlanta flights
Boston to Syracuse flights
Boston to Myrtle Beach flights
Boston to Presque Isle, Maine flights
Boston to Knoxville flights
Boston to Orlando Airport flights
Boston to Miami flights
Boston to Fort Lauderdale flights
Boston to Buffalo flights
Boston to West Palm Beach flights
Boston to Philadelphia flights
Boston to Pittsburgh flights
Boston to Lebanon, New Hampshire flights
Boston to Sarasota flights
Boston to Chicago Midway Airport flights
Boston to Raleigh flights
Boston to Savannah flights
Boston to San Juan Luis Munoz Marin Intl Airport flights

Top airline flying from Simpson Bay to Boston

Discover the top airline 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 February 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$423Average$528FlexibilityNo 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