HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Simpson Bay

$94+ Cheap flights from Massachusetts 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SXM
Nov 30 — Dec 71
Sun 11/30
Sun 12/7
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Massachusetts 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.

Find flight deals from Massachusetts to Simpson Bay

Cheapest flights from Massachusetts to Simpson Bay
Explore the most affordable flight options available from Massachusetts to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 31, 2025.

This United Airlines deal was found by Cheapflights users on 10/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/157:45 pmBDL - SXM
2 stops17h 10mUnited Airlines
Sat 11/225:00 pmSXM - BDL
1 stop17h 38mUnited Airlines
Deal found 10/30$311
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Sun 12/145:25 pmBDL - SXM
2 stops19h 55mAmerican Airlines
Thu 12/182:59 pmSXM - BDL
1 stop8h 59mAmerican Airlines
Deal found 10/28$316
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Mon 11/175:00 amBDL - SXM
1 stop7h 50mAmerican Airlines
Mon 11/245:24 pmSXM - BDL
2 stops22h 46mAmerican Airlines
Deal found 10/29$329
This American Airlines deal was found by Cheapflights users on 10/31. 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.
Mon 11/245:00 amBDL - SXM
1 stop7h 50mAmerican Airlines
Thu 12/43:20 pmSXM - BDL
1 stop9h 38mAmerican Airlines
Deal found 10/31$361
This JetBlue deal was found by Cheapflights users on 10/29. 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.
Wed 11/267:10 amBDL - SXM
1 stop6h 54mJetBlue
Mon 12/84:25 pmSXM - BDL
1 stop8h 34mJetBlue
Deal found 10/29$364
This United Airlines deal was found by Cheapflights users on 10/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/153:42 pmBOS - SXM
2 stops23h 15mUnited Airlines
Sat 11/225:00 pmSXM - BOS
2 stops18h 43mUnited Airlines
Deal found 10/30$372
This JetBlue deal was found by Cheapflights users on 10/29. 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 12/136:45 amBOS - SXM
Nonstop4h 10mJetBlue
Sun 12/211:59 pmSXM - BOS
Nonstop4h 35mJetBlue
Deal found 10/29$373
This Delta deal was found by Cheapflights users on 10/31. 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.
Mon 11/105:40 amBOS - SXM
1 stop8h 15mDelta
Tue 11/254:20 pmSXM - BOS
1 stop10h 06mDelta
Deal found 10/31$374
This United Airlines deal was found by Cheapflights users on 10/29. 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 12/136:23 pmBOS - SXM
1 stop20h 34mUnited Airlines
Mon 12/222:52 pmSXM - BOS
1 stop8h 56mUnited Airlines
Deal found 10/29$375
This American Airlines deal was found by Cheapflights users on 10/30. 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 11/195:36 amBOS - SXM
1 stop9h 46mAmerican Airlines
Tue 11/252:51 pmSXM - BOS
1 stop9h 05mAmerican Airlines
Deal found 10/30$378
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Mon 11/105:36 amBOS - SXM
1 stop9h 46mAmerican Airlines
Tue 11/255:24 pmSXM - BOS
1 stop8h 27mAmerican Airlines
Deal found 10/29$380
This Priceline deal was found by Cheapflights users on 10/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/131:40 pmBOS - SXM
1 stop26h 03mJetBlue
Fri 12/191:59 pmSXM - BOS
Nonstop4h 35mJetBlue
Deal found 10/29$384

Cheap flight deals from Massachusetts to Simpson Bay

Keep the following information in mind while searching for Massachusetts to Simpson Bay flight deals. Data was last updated October 31, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$311
(United Airlines)

One-way from

$94
(Delta)

Popular in

February

Cheapest in

September

Average price

$558

Good round-trip deal

$408 or less

Good one-way deal

$186 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 Massachusetts to Simpson Bay Princess Juliana
Search Deals
One-way flight from Massachusetts to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($39 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Massachusetts to Simpson Bay Princess Juliana.
Search Deals
Price to beat on a one-way flight from Massachusetts to Simpson Bay Princess Juliana.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts 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 October 31, 2025.
Use the filters below to find and compare flights from Massachusetts to Simpson Bay that are best for you.

Fly from

Massachusetts

Fly to

Simpson Bay

Route

Depart

Return

Price

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Sat 11/15

6:00 am-1:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Sat 11/22

5:00 pm-9:38 am

1 stop17h 38m

$311

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Sat 1/17

4:15 pm-1:45 pm

2 stops20h 30m

Simpson Bay Princess Juliana

Sat 1/24

5:33 pm-12:32 pm

2 stops19h 59m

$341

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Mon 11/24

5:00 am-1:50 pm

1 stop7h 50m

Simpson Bay Princess Juliana

Thu 12/4

3:20 pm-11:58 pm

1 stop9h 38m

$361

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Mon 2/9

5:30 am-4:28 pm

1 stop9h 58m

Simpson Bay Princess Juliana

Fri 2/13

3:19 pm-9:05 am

2 stops18h 46m

$362

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 12/13

6:45 am-11:55 am

Nonstop4h 10m

Simpson Bay Princess Juliana

Sun 12/21

1:59 pm-5:34 pm

Nonstop4h 35m

$373

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Thu 1/22

8:50 pm-12:30 pm

1 stop14h 40m

Simpson Bay Princess Juliana

Tue 1/27

4:20 pm-8:27 am

1 stop17h 07m

$374

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Thu 12/11

9:15 pm-2:28 pm

1 stop16h 13m

Simpson Bay Princess Juliana

Mon 12/22

1:45 pm-1:07 am

1 stop12h 22m

$374

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 12/13

6:23 pm-3:57 pm

1 stop20h 34m

Simpson Bay Princess Juliana

Sun 12/21

2:20 pm-12:45 am

1 stop11h 25m

$375

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Mon 12/15

6:00 am-1:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Fri 12/19

4:55 pm-5:17 pm

2 stops25h 22m

$376

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sun 12/14

6:00 am-3:57 pm

1 stop8h 57m

Simpson Bay Princess Juliana

Fri 12/19

4:55 pm-5:17 pm

2 stops25h 22m

$376

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 37 results
1
2
3
4

Best time to book a flight from Massachusetts to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Massachusetts 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 Massachusetts to Simpson Bay

What is the cheapest month to book a flight from Massachusetts to Simpson Bay?

Currently, September is the cheapest month in which you can book a flight from Massachusetts to Simpson Bay (average of $143). Flying from Massachusetts to Simpson Bay in June is currently the most expensive (average of $372). 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 MA to SXM?

Find hourly flight availability from Massachusetts 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 October 31, 2025.

It’s typically best to fly out from Massachusetts to Simpson Bay at noon. Doing so could potentially save you 43% on the flight price compared to flying in the morning, which is usually more expensive.

Related info for your journey

Find useful and relevant information for your journey from Massachusetts 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 airport do you fly into for flights to Simpson Bay from Massachusetts?

    Located just 0.5 mi from the city center, Simpson Bay Princess Juliana (SXM) is the airport most travelers will use when flying to Simpson Bay from Massachusetts.

  • How popular is this Massachusetts to Simpson Bay flight route?

    The Massachusetts to Simpson Bay Princess Juliana flight path was viewed by 5 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

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

    There are many flights that can get you from Massachusetts to Simpson Bay in 4h 10m. Fly via United Airlines, American Airlines, or JetBlue to get the fastest option. Airlines will cover a distance of 1742 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Massachusetts to Simpson Bay?

    The most popular route from Massachusetts to Simpson Bay is Boston Logan Intl - Simpson Bay Princess Juliana. You may also consider Hartford Bradley Intl - Simpson Bay Princess Juliana or Albany Intl - Simpson Bay Princess Juliana.

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

    On average you can expect to pay $343 for a flight from Massachusetts to Simpson Bay. The cheapest flight overall is $186 while the most popular route, (Boston Logan Intl - Simpson Bay Princess Juliana) is currently priced at $269.

  • Can I find deals for flights from Massachusetts to Simpson Bay that include hotel bookings?

    Yes. In addition to deals on Massachusetts to Simpson Bay flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Massachusetts to Simpson Bay?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Massachusetts to Simpson Bay.

  • Can I find deals for business class flights from Massachusetts to Simpson Bay?

    Yes. Cheapflights offers flight deals from Massachusetts 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 Massachusetts to Simpson Bay?

    Currently, September is the cheapest month in which you can book a flight from Massachusetts to Simpson Bay (average of $143). Flying from Massachusetts to Simpson Bay in June is currently the most expensive (average of $372). 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 Massachusetts to Simpson Bay

See prices for flight routes from nearby airports that may be better suited for you.
Newark to Simpson Bay flights
John F Kennedy Intl to Simpson Bay flights
LaGuardia to Simpson Bay flights
Boston to Simpson Bay flights
Dulles Intl to Simpson Bay flights
Atlanta to Simpson Bay flights
O'Hare Intl to Simpson Bay flights
Miami to Simpson Bay flights
Reagan-National to Simpson Bay flights
Baltimore to Simpson Bay flights
Philadelphia to Simpson Bay flights
Charlotte to Simpson Bay flights
Tampa to Simpson Bay flights
Orlando to Simpson Bay flights
Fort Lauderdale to Simpson Bay flights
Los Angeles to Simpson Bay flights
Dallas/Fort Worth to Simpson Bay flights
Denver to Simpson Bay flights
Midway to Simpson Bay flights
Hobby to Simpson Bay flights
Minneapolis to Simpson Bay flights
Detroit to Simpson Bay flights
George Bush Intcntl to Simpson Bay flights
New Orleans to Simpson Bay flights
Des Moines to Simpson Bay flights
Raleigh to Simpson Bay flights
Richmond to Simpson Bay flights
Cleveland to Simpson Bay flights
Cincinnati to Simpson Bay flights
Columbus to Simpson Bay flights
St. Louis to Simpson Bay flights
Sky Harbor Intl to Simpson Bay flights
Austin to Simpson Bay flights
Omaha to Simpson Bay flights
San Francisco to Simpson Bay flights
Seattle to Simpson Bay flights
Hartford to Simpson Bay flights
Indianapolis to Simpson Bay flights
Rochester to Simpson Bay flights
Charleston to Simpson Bay flights
Milwaukee to Simpson Bay flights
West Palm Beach to Simpson Bay flights
Sarasota to Simpson Bay flights
Syracuse to Simpson Bay flights
Wilmington to Simpson Bay flights
Kansas City to Simpson Bay flights
Buffalo to Simpson Bay flights
Love Field to Simpson Bay flights
Providence to Simpson Bay flights
Norfolk to Simpson Bay flights

Top 7 airlines flying from Massachusetts to Simpson Bay

Discover the top 7 airlines that operate flights from Massachusetts 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 October 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$73Average$228FlexibilityNo cancel feeOn-time62%
DeltaCheapest$174Average$377FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$180Average$641FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$337Average$547FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$338Average$704FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$364Average$669FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$401Average$592FlexibilityNo 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©2025 Cheapflights