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Find cheap flights from Massachusetts to Simpson Bay from $60

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 6/2. 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
Wed 5/29
Wed 6/5

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In the last 7 days travelers have searched 43,219,010 times on KAYAK, and here is why:

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Good to know

Low season

September

High season

February

Cheapest flight

$60
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly and prices are also 1% lower on average.
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, +13 more

Air France, American Airlines, +14 more

Tuesday

Air France, American Airlines, Anguilla Air Services, +13 more

Air France, American Airlines, +14 more

Wednesday

Air Canada, Air France, American Airlines, +14 more

Air Canada, Air France, +15 more

Thursday

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

Air Century, Air France, +13 more

Friday

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

Air France, American Airlines, +13 more

Saturday

Air Canada, Air France, American Airlines, +15 more

Air Canada, Air France, +16 more

Sunday

Air Canada, Air Century, Air France, +16 more

Air Canada, Air Century, +17 more

See more direct flights

Nonstop returns

Simpson Bay Princess Juliana to Massachusetts

Monday

Air France, American Airlines, Anguilla Air Services, +13 more

Air France, American Airlines, +14 more

Tuesday

Air France, American Airlines, Anguilla Air Services, +13 more

Air France, American Airlines, +14 more

Wednesday

Air Canada, Air France, American Airlines, +14 more

Air Canada, Air France, +15 more

Thursday

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

Air Century, Air France, +13 more

Friday

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

Air France, American Airlines, +13 more

Saturday

Air Canada, Air France, American Airlines, +15 more

Air Canada, Air France, +16 more

Sunday

Air Canada, Air Century, Air France, +16 more

Air Canada, Air Century, +17 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
FlexFlightOverall score based on 4 reviews
6.5boarding
6.5comfort
6.5crew
5.3food
5.3entertainment
Airline reviews
Pros: "Ok crew and good enough planes. I was on a short flight, so I didn’t mind. Just know what you are getting, budget airlines with little or no service."
Cons: "too many to list"
7.0 GoodTigran, Jun 2020TBS - IEV
Read more about FlexFlight reviews
Pros: "Ok crew and good enough planes. I was on a short flight, so I didn’t mind. Just know what you are getting, budget airlines with little or no service."
Cons: "too many to list"

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.

Our pilot and flight attendant, Desiree, were great. I always fly this route and this crew was better than most.

The worst flight ever; 1st and last flying to this airlines

Easy boarding and deplaning. Short flight. Water was given but that was it.

Flight was delayed a bit since booking but otherwise everything was very good.

While this is a VERY SMALL plane; take-off to landing was fine. It's the constant departure time changes that wore me out and I'll try to never use this inconsistent airway again. Four delays in one day. Done!!!!!!

This has been, by far, my worst experience with an airline company. I had a reservation for a Tuesday at 8:30 pm departure from Gainesville, FL (1.5 hours - direct flight) I received an email on Monday that my flight had been changed to Monday at night to depart from Jacksonville, FL (and it was an 11 .5 hours flight ). There was no way I would have had the time to gather my things, drive 1.5 hours to the Jacksonville airport, and make it on time to board the plane. Besides, I had a full day of work on Tuesday. The only good thing I xan say about Silver airlines is that they did give me a refund, but I had to wait about 4 hours for a call back

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

5/31Fri
1 stopFrontier
29h 13mBOS-SXM
6/2Sun
1 stopFrontier
16h 42mSXM-BOS
$220
5/29Wed
1 stop
7h 34mBOS-SXM
6/2Sun
1 stop
16h 42mSXM-BOS
$225
5/17Fri
1 stopFrontier
29h 00mBOS-SXM
5/19Sun
1 stopFrontier
16h 47mSXM-BOS
$230
5/14Tue
2 stops
18h 08mBOS-SXM
5/19Sun
1 stop
16h 47mSXM-BOS
$241
5/22Wed
1 stopSpirit Airlines
7h 34mBOS-SXM
5/29Wed
2 stopsSpirit Airlines
33h 38mSXM-BOS
$337
5/22Wed
1 stopSpirit Airlines
7h 34mBOS-SXM
5/29Wed
3 stopsSpirit Airlines
33h 11mSXM-BOS
$338
5/19Sun
1 stopUnited Airlines
6h 50mBOS-SXM
5/26Sun
1 stopUnited Airlines
8h 04mSXM-BOS
$400
8/20Tue
2 stopsAmerican Airlines
18h 01mBOS-SXM
8/27Tue
2 stopsAmerican Airlines
18h 13mSXM-BOS
$416
9/28Sat
2 stopsAmerican Airlines
20h 07mBOS-SXM
10/4Fri
2 stopsAmerican Airlines
19h 59mSXM-BOS
$418
5/11Sat
1 stopUnited Airlines
6h 50mBOS-SXM
5/18Sat
1 stopUnited Airlines
7h 43mSXM-BOS
$424

Search by stops

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Recent one-way flight deals

6/2Sun
1 stopFrontier
27h 28mBOS-SXM
$60
6/28Fri
1 stopFrontier
29h 54mBOS-SXM
$73
5/14Tue
2 stopsSpirit Airlines
18h 08mBOS-SXM
$100
6/3Mon
1 stopSpirit Airlines
7h 34mBOS-SXM
$108
5/14Tue
3 stopsSpirit Airlines
31h 44mBOS-SXM
$120
10/1Tue
1 stopCopa Airlines
19h 55mBOS-SXM
$196
6/2Sun
nonstopJetBlue
4h 01mBOS-SXM
$206
7/9Tue
1 stopAmerican Airlines
7h 48mBOS-SXM
$209
8/6Tue
2 stopsAmerican Airlines
18h 01mBOS-SXM
$214
6/8Sat
nonstopJetBlue
4h 21mBOS-SXM
$236

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Last minute flights from Massachusetts to Simpson Bay

Last minute flight, train and bus deals

5/1Wed
multi-stopSpirit Airlines
8h 42mBOS-SXM
5/8Wed
multi-stopSpirit Airlines
33h 38mSXM-BOS
$525
5/1Wed
multi-stopSpirit Airlines
8h 42mBOS-SXM
5/4Sat
multi-stopSpirit Airlines
9h 15mSXM-BOS
$534
5/3Fri
multi-stop
20h 08mBOS-SXM
5/7Tue
multi-stop
21h 14mSXM-BOS
$622
5/3Fri
multi-stop
15h 35mBOS-SXM
5/7Tue
multi-stop
21h 14mSXM-BOS
$624
5/1Wed
multi-stopUnited Airlines
6h 43mBOS-SXM
5/4Sat
multi-stopUnited Airlines
18h 49mSXM-BOS
$631
5/1Wed
multi-stopUnited Airlines
8h 58mBOS-SXM
5/4Sat
multi-stopUnited Airlines
20h 51mSXM-BOS
$689
5/1Wed
multi-stopJetBlue
7h 06mBOS-SXM
5/5Sun
nonstopJetBlue
4h 36mSXM-BOS
$712
5/1Wed
multi-stopAmerican Airlines
8h 31mBOS-SXM
5/5Sun
multi-stopAmerican Airlines
17h 18mSXM-BOS
$769
5/3Fri
multi-stopAmerican Airlines
16h 32mBOS-SXM
5/7Tue
multi-stopAmerican Airlines
12h 26mSXM-BOS
$772
5/1Wed
multi-stopJetBlue
7h 06mBOS-SXM
5/4Sat
nonstopJetBlue
4h 28mSXM-BOS
$802

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Flights to Simpson Bay

Destination:

Simpson Bay (SXM)St. Maarten

Return flight deals:

Simpson Bay - Massachusetts

Cabin classes:

$1,340
$1,333
$445