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$54 Find cheap flights from Massachusetts to Simpson Bay

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Simpson Bay departing on 7/21. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Fri 7/12
Fri 7/19

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Good to know

Low season

September

High season

March

Cheapest flight

$54
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 13% increase in price.
Flight from Boston to Simpson Bay

FAQs for booking flights from Massachusetts to Simpson Bay

  • How does KAYAK find such low prices on flights from Massachusetts to Simpson Bay?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Massachusetts to Simpson Bay.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Massachusetts to Simpson Bay?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Simpson Bay from Massachusetts is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Massachusetts to Simpson Bay?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Simpson Bay with an airline and back to Massachusetts with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Massachusetts to Simpson Bay?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Simpson Bay from Massachusetts up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from Massachusetts to Simpson Bay?

Find which airlines fly direct from Massachusetts to Princess Juliana, which days they fly and book direct flights.

Nonstop departures

Massachusetts to Simpson Bay Princess Juliana

Monday

Air France, American Airlines, Anguilla Air Services, +10 more

Air France, American Airlines, +11 more

Tuesday

Air France, American Airlines, Anguilla Air Services, +12 more

Air France, American Airlines, +13 more

Wednesday

Air France, American Airlines, Anguilla Air Services, +11 more

Air France, American Airlines, +12 more

Thursday

Air Century, Air France, American Airlines, +12 more

Air Century, Air France, +13 more

Friday

Air France, American Airlines, Anguilla Air Services, +11 more

Air France, American Airlines, +12 more

Saturday

Air Canada, Air France, American Airlines, +13 more

Air Canada, Air France, +14 more

Sunday

Air Canada, Air Century, Air France, +15 more

Air Canada, Air Century, +16 more

See more direct flights

Nonstop returns

Simpson Bay Princess Juliana to Massachusetts

Monday

Air France, American Airlines, Anguilla Air Services, +10 more

Air France, American Airlines, +11 more

Tuesday

Air France, American Airlines, Anguilla Air Services, +12 more

Air France, American Airlines, +13 more

Wednesday

Air France, American Airlines, Anguilla Air Services, +11 more

Air France, American Airlines, +12 more

Thursday

Air Century, Air France, American Airlines, +12 more

Air Century, Air France, +13 more

Friday

Air France, American Airlines, Anguilla Air Services, +11 more

Air France, American Airlines, +12 more

Saturday

Air Canada, Air France, American Airlines, +13 more

Air Canada, Air France, +14 more

Sunday

Air Canada, Air Century, Air France, +15 more

Air Canada, Air Century, +16 more

See more direct flights
See more direct flights

Top 3 airlines serving from Massachusetts to Simpson Bay

Need help choosing which airline to fly with from Massachusetts to Simpson Bay? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
6.2
FrontierOverall score based on 3957 reviews
7.0Crew
4.9Entertainment
5.8Comfort
6.5Boarding
5.1Food
Airline reviews

Did not realize seats did not recline. Best to travel in an exit row... No question

10.0 ExcellentKeith, Jun 2024DEN - BUF
Read more about Frontier reviews

Did not realize seats did not recline. Best to travel in an exit row... No question

I strongly dislike Frontier. I find them barebones, the seats not particularly comfortable, the nickel and diming is maddening, the app is TERRIBLE - super confusing to navigate, and the last 4 frontier flights I have flown have been on AVERAGE 2 hours late, one ruining a fancy night out in Vegas with reservations made well in advance, which was nodded to with a measly 5000 miles, which translates to almost nothing. At least credit a free checked bag or something.

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

My flight was cancelled from Gainesville. I was able to get on another flight on Friday. Will see if this one cancels also?

the hospitality was excellent to me and I will return flying with them

I am very disappointed. I booked with kiwi when I got to the airport there was no reservation I had to purchase another ticket after my card was already charged for almost double the cost I payed through kiwi eight days after I went to their office in Tortola and they refuse to give me a receipt so that I can cancel the original payment. They said “ there is no record that you used silver to travel “ I know I did not swim to Puerto Rico . If someone can help me please so that I can cancel the payment the credit card company said I need it, I have less than 14 days or I will loose my money. This is terrible and there is no local number for them.

I booked because of time of the flights. I needed to be at my destination at a specific time, and missed my appointment because of your delays.Get rid of these junk planes. The ATR planes are dated old scary planes. And maybe you could actually be on time. This airlines on time record is horrible. The communications between the gate agents and this company dont exist.. They couldn't give any answers,. When trying to find out when the flight would leave, they get no response when they asked for details on flights, they receivedconflicting information. I felt bad for the gate agents having to deal with Silver's inability to communicate simple information. This is my last choice in air travel. On time flights are everywhere, and both flights I took were delayed. It's a sad company.

The flight itself was good and the flight attendant was very good.

It was awesome until we ran into some bad weather but the pilots did an amazing job getting us to safety and landed

If you take this airline, they WILL change the flight time, and make you miss your connection. It has happened every time I used it. It's so unreliable that I think it shouldn't be offered on Kayak. You will regret it!

In addition to the fact that Silver changed the flight time several days before the trip without offering any choices , I was sick with Covid and unable to go on the trip. I tried to ask Silver for a credit for a flight when I’d recooperated but they don’t do credits, even for illness. I will Never fly on Silver again

I canceled due to a 7 hour delay. Was forced to book another airline last minute , very expensive. Silver Aorways sucks

I spent hours with orbitz to get my tsa # on my ticket. They didn’t have a place to enter. I will never use orbitz again. No customer service. A number in which u press offered options and the message replays instead of getting customer to that area. Silver did not make the promised call back. Finally someone responded to my email and took care of it after I lost hours of my vacation arranging this. Staff on flight barked orders.

It was cancelled. And Kayak/Kiwi pocketed the money. Competence, ethics and customer service would be an idea.

There was nothing to like about this airline and everything needs improvement

Pros: "Nothing the flight was super late and there was no communication as to why or even and announcement to say it was late. I missed my flight to France lost a night in a hotel and missed an important event on my itinerary."
Cons: "My flight"
Cons: "it was too hot at the waiting gate in San Juan and the flight was delayed for about one hour and fifteen minutes. the terminal building smelled of mold."
Cons: "the arrival process in San Juan was horrible. passengers walk in the sun towards immigration and customs is way too long. Standing and waiting in line at immigration without any immigration officer took almost 25 minutes. that was horrible."

Book cheap flights from Massachusetts to Simpson Bay

Recent round-trip flight deals

7/24Wed
1 stop
8h 50mBOS-SXM
7/29Mon
1 stop
16h 10mSXM-BOS
$303
6/22Sat
2 stopsFrontier
45h 44mBDL-SXM
6/29Sat
1 stopFrontier
16h 30mSXM-BDL
$307
7/23Tue
1 stopSpirit Airlines
20h 13mBOS-SXM
7/31Wed
1 stopSpirit Airlines
8h 28mSXM-BOS
$377
9/17Tue
1 stopSpirit Airlines
26h 00mBOS-SXM
9/21Sat
1 stopSpirit Airlines
9h 32mSXM-BOS
$381
8/21Wed
1 stopDelta
7h 42mALB-SXM
9/11Wed
1 stopDelta
8h 20mSXM-ALB
$415
9/17Tue
2 stopsDelta
20h 40mALB-SXM
10/4Fri
1 stopDelta
8h 20mSXM-ALB
$419
8/3Sat
2 stopsAmerican Airlines
19h 39mBDL-SXM
8/20Tue
2 stopsAmerican Airlines
19h 15mSXM-BDL
$419
8/19Mon
2 stopsAmerican Airlines
19h 45mALB-SXM
8/27Tue
2 stopsAmerican Airlines
24h 43mSXM-ALB
$434
7/4Thu
nonstopJetBlue
4h 15mBOS-SXM
7/11Thu
nonstopJetBlue
4h 26mSXM-BOS
$444
8/10Sat
nonstopJetBlue
4h 12mBOS-SXM
8/17Sat
nonstopJetBlue
4h 23mSXM-BOS
$445

Search by stops

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Recent one-way flight deals

7/21Sun
1 stopFrontier
28h 57mBOS-SXM
$54
8/28Wed
1 stop
13h 45mBDL-SXM
$173
7/20Sat
1 stopSpirit Airlines
7h 55mBOS-SXM
$198
7/21Sun
2 stopsSpirit Airlines
20h 31mBOS-SXM
$221
8/28Wed
2 stopsAmerican Airlines
9h 38mBDL-SXM
$224
7/21Sun
3 stopsSpirit Airlines
27h 16mBOS-SXM
$244
7/20Sat
2 stopsSpirit Airlines
42h 25mBOS-SXM
$254
7/20Sat
3 stops
30h 14mBOS-SXM
$312
8/28Wed
3 stops
46h 13mBDL-SXM
$526

Search by stops

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Search by price

Last minute flights from Massachusetts to Simpson Bay

Last minute flight, train and bus deals

6/16Sun
multi-stopFrontier
28h 38mBOS-SXM
6/24Mon
multi-stopFrontier
16h 00mSXM-BOS
$404
6/15Sat
multi-stop
7h 38mBOS-SXM
6/17Mon
multi-stop
16h 00mSXM-BOS
$544
6/15Sat
multi-stop
12h 24mBOS-SXM
6/17Mon
multi-stop
22h 43mSXM-BOS
$591
6/15Sat
multi-stopSpirit Airlines
7h 38mBOS-SXM
6/19Wed
multi-stopSpirit Airlines
25h 59mSXM-BOS
$642
6/15Sat
multi-stopSpirit Airlines
7h 38mBOS-SXM
6/19Wed
multi-stopSpirit Airlines
24h 58mSXM-BOS
$650
6/15Sat
multi-stopSpirit Airlines
40h 31mBOS-SXM
6/19Wed
multi-stopSpirit Airlines
25h 59mSXM-BOS
$680
6/16Sun
multi-stopFrontier
28h 38mBOS-SXM
6/24Mon
multi-stopFrontier
37h 51mSXM-BOS
$718
6/15Sat
multi-stopSpirit Airlines
7h 38mBOS-SXM
6/17Mon
multi-stopSpirit Airlines
31h 18mSXM-BOS
$786
6/15Sat
nonstopJetBlue
4h 12mBOS-SXM
6/17Mon
multi-stopJetBlue
7h 49mSXM-BOS
$1,096
6/15Sat
nonstopJetBlue
4h 12mBOS-SXM
6/19Wed
multi-stopJetBlue
10h 48mSXM-BOS
$1,545

Search by stops

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Flights to Simpson Bay

Destination:

Simpson Bay (SXM)St. Maarten

Return flight deals:

Simpson Bay - Massachusetts

Cabin classes:

$1,140
$805
$445