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Simpson Bay

$149+ 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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SXM
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
1 adult, Economy
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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 June 16, 2025.

Round-trip from

$335
(Delta)

One-way from

$149
(Priceline)

Popular in

December

Cheapest in

September

Average price

$556

Good round-trip deal

$548 or less

Good one-way deal

$431 or less
From Massachusetts to Simpson Bay Princess Juliana
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One-way flight from Massachusetts to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 12% potential increase in price ($87 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Price to beat on a round-trip flight from Massachusetts to Simpson Bay Princess Juliana.
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Price to beat on a one-way flight from Massachusetts to Simpson Bay Princess Juliana.
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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 June 16, 2025.

This Priceline deal was found by Cheapflights users on 6/15. 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.
Fri 6/208:43 pmBDL - SXM
1 stop14h 43mFrontier
Fri 6/276:26 pmSXM - BDL
1 stop15h 56mFrontier
Deal found 6/15$326
This Delta deal was found by Cheapflights users on 6/14. 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.
Tue 7/85:35 amBOS - SXM
1 stop8h 21mDelta
Wed 7/163:21 pmSXM - BOS
1 stop10h 18mDelta
Deal found 6/14$335
This FlightHub deal was found by Cheapflights users on 6/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/49:40 amBOS - SXM
1 stop25h 48mMultiple Airlines
Wed 7/93:05 pmSXM - BOS
1 stop8h 43mMultiple Airlines
Deal found 6/13$365
This Cheapflightsfares deal was found by Cheapflights users on 6/15. 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 9/106:10 amBOS - SXM
1 stop8h 14mSpirit Airlines
Mon 9/223:27 pmSXM - BOS
1 stop9h 12mSpirit Airlines
Deal found 6/15$375
This FlightHub deal was found by Cheapflights users on 6/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/59:18 amBOS - SXM
1 stop27h 07mFrontier
Sat 9/131:58 pmSXM - BOS
1 stop18h 35mFrontier
Deal found 6/14$385
This United Airlines deal was found by Cheapflights users on 6/14. 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.
Mon 7/76:05 amBOS - SXM
1 stop6h 24mUnited Airlines
Wed 7/163:55 pmSXM - BOS
1 stop8h 04mUnited Airlines
Deal found 6/14$395
This JetBlue deal was found by Cheapflights users on 6/14. 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 8/167:50 amBOS - SXM
Nonstop4h 10mJetBlue
Sat 8/231:25 pmSXM - BOS
Nonstop4h 26mJetBlue
Deal found 6/14$409
This Air Canada deal was found by Cheapflights users on 6/14. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/195:40 pmBOS - SXM
1 stop19h 15mAir Canada
Thu 11/273:05 pmSXM - BOS
1 stop19h 33mAir Canada
Deal found 6/14$413
This American Airlines deal was found by Cheapflights users on 6/16. 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 9/62:16 pmBOS - SXM
2 stops23h 03mAmerican Airlines
Tue 9/92:45 pmSXM - BOS
2 stops17h 48mAmerican Airlines
Deal found 6/16$428
This FlightHub deal was found by Cheapflights users on 6/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/118:44 pmBDL - SXM
1 stop14h 44mMultiple Airlines
Mon 7/143:05 pmSXM - BDL
2 stops31h 52mMultiple Airlines
Deal found 6/14$431
This Mytrip deal was found by Cheapflights users on 6/14. 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.
Fri 8/84:08 pmBDL - SXM
1 stop21h 52mSpirit Airlines
Fri 8/153:32 pmSXM - BDL
2 stops22h 18mSpirit Airlines
Deal found 6/14$448
This JetBlue deal was found by Cheapflights users on 6/16. 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.
Sun 10/267:00 amBDL - SXM
1 stop7h 28mJetBlue
Fri 10/311:45 pmSXM - BDL
1 stop9h 06mJetBlue
Deal found 6/16$521

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 June 16, 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

Fri 6/20

8:43 pm-11:26 am

1 stop14h 43m

Simpson Bay Princess Juliana

Fri 6/27

6:26 pm-10:22 am

1 stop15h 56m

$326

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Tue 7/8

5:35 am-1:56 pm

1 stop8h 21m

Simpson Bay Princess Juliana

Wed 7/9

3:21 pm-1:39 am

1 stop10h 18m

$335

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Fri 7/4

9:40 am-11:28 am

1 stop25h 48m

Simpson Bay Princess Juliana

Wed 7/9

3:05 pm-11:48 pm

1 stop8h 43m

$365

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Wed 9/10

6:10 am-2:24 pm

1 stop8h 14m

Simpson Bay Princess Juliana

Mon 9/22

3:27 pm-12:39 am

1 stop9h 12m

$375

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Fri 9/5

9:18 am-12:25 pm

1 stop27h 07m

Simpson Bay Princess Juliana

Sat 9/13

1:58 pm-8:33 am

1 stop18h 35m

$385

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Mon 7/7

6:05 am-12:29 pm

1 stop6h 24m

Simpson Bay Princess Juliana

Wed 7/9

3:55 pm-11:59 pm

1 stop8h 04m

$395

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 8/16

7:50 am-12:00 pm

Nonstop4h 10m

Simpson Bay Princess Juliana

Sat 8/23

1:25 pm-5:51 pm

Nonstop4h 26m

$409

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Wed 11/19

5:40 pm-1:55 pm

1 stop19h 15m

Simpson Bay Princess Juliana

Thu 11/27

3:05 pm-9:38 am

1 stop19h 33m

$413

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 9/6

2:16 pm-1:19 pm

2 stops23h 03m

Simpson Bay Princess Juliana

Tue 9/9

2:45 pm-8:33 am

2 stops17h 48m

$428

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Fri 7/11

8:44 pm-11:28 am

1 stop14h 44m

Simpson Bay Princess Juliana

Mon 7/14

3:05 pm-10:57 pm

2 stops31h 52m

$431

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/14

Showing 1-10 of 32 results
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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 $459). Flying from Massachusetts to Simpson Bay in March is currently the most expensive (average of $657). 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 June 16, 2025.

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

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 June 16, 2025.
See what other customers who have flown with Delta, United Airlines and JetBlue from Massachusetts to Simpson Bay have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,963 reviews

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,963 reviews
Delta
8.0
Very good
7,963 reviews

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,801 reviews
Delta
8.0
Very good
7,963 reviews

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
JetBlue
7.3
Good
2,922 reviews
Delta
8.0
Very good
7,963 reviews

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,963 reviews

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Spirit Airlines
6.3
Okay
8,060 reviews
Delta
8.0
Very good
7,963 reviews

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • What are the cheapest airlines to fly from Massachusetts to Simpson Bay one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $149. Users have also found prices from $152 and $158 on Delta and Spirit Airlines, respectively.

  • 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 $467 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 $335.

  • 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 $459). Flying from Massachusetts to Simpson Bay in March is currently the most expensive (average of $657). 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

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Alternative routes for Massachusetts to Simpson Bay

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Massachusetts to Simpson Bay

Discover the top 6 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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$73Average$227FlexibilityNo cancel feeOn-time62%
DeltaCheapest$174Average$438FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$317Average$556FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$348Average$767FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$353Average$678FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$386Average$599FlexibilityNo cancel feeOn-time71%

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