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$150+ Cheap flights from Simpson Bay (SXM) to Massachusetts

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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — BOS
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap flight deals from Simpson Bay to Massachusetts

Cheapest flights from Simpson Bay to Massachusetts
Explore the most affordable flight options available from Simpson Bay to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 23, 2025.

This Flysmarter deal was found by Cheapflights users on 12/21. 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 12/281:59 pmSXM - BOS
Nonstop4h 35mJetBlue
Mon 1/57:35 amBOS - SXM
Nonstop4h 15mJetBlue
Deal found 12/21$313
This Delta deal was found by Cheapflights users on 12/21. 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 12/284:15 pmSXM - BOS
1 stop17h 05mDelta
Mon 1/55:35 amBOS - SXM
1 stop8h 20mDelta
Deal found 12/21$338
This Flysmarter deal was found by Cheapflights users on 12/21. 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 12/283:40 pmSXM - BOS
2 stops21h 32mAir Canada
Mon 1/54:35 pmBOS - SXM
2 stops21h 05mAir Canada
Deal found 12/21$636

Find flight deals from Simpson Bay to Massachusetts

Keep the following information in mind while searching for Simpson Bay to Massachusetts flight deals. Data was last updated December 23, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$344
(American Airlines)

One-way from

$150
(Super.com)

Popular in

November

Cheapest in

May

Average price

$407

Good round-trip deal

$435 or less

Good one-way deal

$282 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.
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From Simpson Bay Princess Juliana to Massachusetts
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One-way flight from Simpson Bay Princess Juliana to Massachusetts
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Highest demand for flights based on searches. 7% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($31 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Price to beat on a round-trip flight from Simpson Bay Princess Juliana to Massachusetts.
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Price to beat on a one-way flight from Simpson Bay Princess Juliana to Massachusetts.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Simpson Bay to Massachusetts 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 December 23, 2025.
Use the filters below to find and compare flights from Simpson Bay to Massachusetts that are best for you.

Fly from

Simpson Bay

Fly to

Massachusetts

Route

Depart

Return

Price

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Wed 2/4

3:09 pm-11:51 pm

1 stop9h 42m

Boston Logan Intl

Wed 2/11

5:20 pm-12:38 pm

2 stops18h 18m

$344

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Mon 3/16

4:28 pm-9:58 am

1 stop17h 30m

Boston Logan Intl

Fri 3/20

5:47 am-1:16 pm

1 stop7h 29m

$395

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sun 3/15

2:17 pm-10:02 am

1 stop19h 45m

Boston Logan Intl

Thu 3/19

8:00 am-3:00 pm

1 stop7h 00m

$401

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sun 3/15

2:17 pm-10:02 am

1 stop19h 45m

Boston Logan Intl

Fri 3/20

5:47 am-1:16 pm

1 stop7h 29m

$414

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Wed 2/4

3:43 pm-12:13 am

1 stop9h 30m

Boston Logan Intl

Wed 2/11

6:15 am-4:00 pm

1 stop8h 45m

$457

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sun 3/15

11:30 am-8:50 pm

1 stop9h 20m

Boston Logan Intl

Thu 3/19

7:15 am-11:29 am

Nonstop4h 14m

$461

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sun 3/15

11:30 am-8:50 pm

1 stop9h 20m

Boston Logan Intl

Fri 3/20

6:40 pm-3:00 pm

2 stops20h 20m

$471

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Mon 3/16

3:02 pm-9:12 am

1 stop18h 10m

Boston Logan Intl

Fri 3/20

7:15 am-11:29 am

Nonstop4h 14m

$496

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Sat 1/17

3:15 pm-11:57 pm

1 stop9h 42m

$150

Simpson BayBoston

SXM - BOS

SXMBOS

Simpson Bay Princess Juliana

Fri 1/23

3:15 pm-2:38 pm

2 stops24h 23m

$192

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 16 results
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Best time to book a flight from Simpson Bay to Massachusetts

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

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

Currently, October is the cheapest month in which you can book a flight from Simpson Bay to Massachusetts (average of $160). Flying from Simpson Bay to Massachusetts 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 MA?

Find hourly flight availability from Simpson Bay to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 23, 2025.

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

Weekly flight availability from Simpson Bay to Massachusetts

Explore weekly flight availability from Simpson Bay to Massachusetts. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated December 23, 2025.

The most flights from SXM to USMA are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated December 23, 2025.
See what other customers who have flown with American Airlines from Simpson Bay to Massachusetts have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,054 reviews

Entertainment

6.9

Crew

8.0

Overall

7.2

Food

6.4

Boarding

7.5

Comfort

7.2

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
American Airlines
7.2
Good
11,054 reviews
American Airlines
7.2
Good
11,054 reviews

Entertainment

6.9

Crew

8.0

Overall

7.2

Food

6.4

Boarding

7.5

Comfort

7.2

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

Related info for your journey

Find useful and relevant information for your journey from Simpson Bay to Massachusetts. 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 from for flights from Simpson Bay to Massachusetts?

    Simpson Bay Princess Juliana (SXM) is the airport you will fly out of if you book a flight from Simpson Bay to Massachusetts. It is only a 0.5 mi journey to Princess Juliana (SXM) from Simpson Bay’s city center.

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

    For as low as $344, American Airlines can have you in Massachusetts from Simpson Bay in 9h 42m. The distance from Simpson Bay to Massachusetts is about 1742 mi.

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $142. Spirit Airlines flights start at $205 while deals on Delta start at $214 one-way.

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

    On average you can expect to pay $413 for a flight from Simpson Bay to Massachusetts. The cheapest flight overall is $227 while the most popular route, (Simpson Bay Princess Juliana - Boston Logan Intl) is currently priced at $293.

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

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

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

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

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

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

    Currently, October is the cheapest month in which you can book a flight from Simpson Bay to Massachusetts (average of $160). Flying from Simpson Bay to Massachusetts 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.

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Alternative routes for Simpson Bay to Massachusetts

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Top airline flying from Simpson Bay to Massachusetts

Discover the top airline that operate flights from Simpson Bay to Massachusetts. 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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$423Average$528FlexibilityNo cancel feeOn-time71%

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