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Find cheap flights from Massachusetts to Anguilla from $286

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Massachusetts to Anguilla departing on 5/10. 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
Sat 6/1
Sat 6/8

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Good to know

Low season

October

High season

May

Cheapest flight

$286
Best time to beat the crowds with an average 32% drop in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from Boston to The Valley

FAQs for booking flights from Massachusetts to Anguilla

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

    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 Anguilla.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Anguilla 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 Anguilla?

    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 Anguilla 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 Anguilla?

    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 Anguilla from Massachusetts up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top airline flying from Massachusetts to Anguilla

 
Need help choosing which airline to fly with from Massachusetts to Anguilla? 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.
6.1
Silver AirwaysOverall score based on 279 reviews
6.2Boarding
6.1Comfort
6.9Crew
5.0Food
5.0Entertainment
Airline reviews

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!

2.0 MediocreAnonymous, Mar 2024MCO - EYW
Read more about Silver Airways reviews

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

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

Thank you so much for initiating these much needle in state flights especially to Gainesville. Your service and personnel are ALL awesome.

Book cheap flights from Massachusetts to Anguilla

Recent round-trip flight deals

6/1Sat
2 stopsAmerican Airlines
20h 00mBOS-AXA
6/8Sat
1 stopAmerican Airlines
8h 48mAXA-BOS
$443
6/1Sat
1 stopAmerican Airlines
21h 18mBOS-AXA
6/8Sat
1 stopAmerican Airlines
8h 48mAXA-BOS
$451
6/21Fri
1 stopAmerican Airlines
26h 14mBOS-AXA
6/26Wed
1 stopAmerican Airlines
8h 48mAXA-BOS
$452
6/21Fri
1 stopAmerican Airlines
22h 54mBOS-AXA
6/26Wed
2 stopsAmerican Airlines
16h 20mAXA-BOS
$456
6/1Sat
2 stopsAmerican Airlines
20h 26mBOS-AXA
6/8Sat
2 stopsAmerican Airlines
19h 07mAXA-BOS
$492
6/11Tue
1 stopAmerican Airlines
10h 06mBOS-AXA
6/13Thu
1 stopAmerican Airlines
9h 35mAXA-BOS
$505
6/1Sat
3 stops
33h 00mBOS-AXA
6/8Sat
2 stops
12h 39mAXA-BOS
$711
6/1Sat
3 stops
26h 47mBOS-AXA
6/8Sat
3 stops
28h 25mAXA-BOS
$775
5/15Wed
1 stopJetBlue
10h 30mBOS-AXA
5/18Sat
1 stopJetBlue
12h 04mAXA-BOS
$1,075
5/15Wed
2 stopsUnited Airlines
11h 35mBOS-AXA
5/18Sat
2 stopsUnited Airlines
35h 33mAXA-BOS
$1,602

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Recent one-way flight deals

5/10Fri
1 stop
12h 31mBOS-AXA
$286
5/10Fri
2 stops
21h 37mBOS-AXA
$388
5/9Thu
3 stops
34h 55mBOS-AXA
$401
5/11Sat
3 stops
30h 02mBOS-AXA
$406
5/11Sat
2 stops
16h 11mBOS-AXA
$418
5/12Sun
3 stops
34h 40mBOS-AXA
$436
5/9Thu
2 stopsAmerican Airlines
9h 35mBOS-AXA
$440
5/9Thu
1 stopAmerican Airlines
9h 36mBOS-AXA
$441
5/7Tue
2 stopsAmerican Airlines
9h 35mBOS-AXA
$465
5/7Tue
1 stopAmerican Airlines
8h 35mBOS-AXA
$466

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Flights to Anguilla

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