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Find cheap flights from Massachusetts to Anguilla from $385

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 6/29. 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 7/10
Wed 7/17

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Good to know

Low season

May

High season

February

Cheapest flight

$385
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly and prices are also 0% 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 274 reviews
6.9Crew
5.0Food
6.3Boarding
5.1Entertainment
6.2Comfort
Airline reviews

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

2.0 MediocreAnonymous, Jun 2024GNV - FLL
Read more about Silver Airways reviews

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.

Book cheap flights from Massachusetts to Anguilla

Recent round-trip flight deals

6/26Wed
1 stop
15h 14mBOS-AXA
7/3Wed
1 stop
20h 29mAXA-BOS
$396
6/26Wed
2 stops
28h 54mBOS-AXA
7/3Wed
1 stop
20h 29mAXA-BOS
$424
6/26Wed
2 stopsAmerican Airlines
18h 57mBOS-AXA
7/3Wed
2 stopsAmerican Airlines
20h 08mAXA-BOS
$605
6/23Sun
1 stopAmerican Airlines
8h 37mBOS-AXA
7/23Tue
1 stopAmerican Airlines
8h 38mAXA-BOS
$625
6/23Sun
1 stopAmerican Airlines
8h 37mBOS-AXA
7/23Tue
2 stopsAmerican Airlines
20h 06mAXA-BOS
$630
6/25Tue
2 stops
23h 01mBOS-AXA
6/29Sat
1 stop
23h 09mAXA-BOS
$639
7/20Sat
2 stopsAmerican Airlines
20h 10mBDL-AXA
7/24Wed
2 stopsAmerican Airlines
22h 00mAXA-BDL
$693
6/25Tue
1 stopAmerican Airlines
10h 06mBOS-AXA
6/29Sat
1 stopAmerican Airlines
8h 48mAXA-BOS
$700
7/20Sat
1 stopAmerican Airlines
9h 48mBDL-AXA
7/24Wed
2 stopsAmerican Airlines
10h 49mAXA-BDL
$718
6/25Tue
3 stopsUnited Airlines
53h 25mBOS-AXA
6/29Sat
2 stopsUnited Airlines
19h 47mAXA-BOS
$1,360

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Recent one-way flight deals

6/29Sat
2 stops
10h 30mBOS-AXA
$385
7/7Sun
2 stopsAmerican Airlines
20h 17mBDL-AXA
$390
11/27Wed
1 stopAmerican Airlines
7h 27mBOS-AXA
$411
6/29Sat
1 stopAmerican Airlines
10h 06mBOS-AXA
$436
6/29Sat
3 stops
25h 14mBOS-AXA
$465
11/27Wed
2 stopsAmerican Airlines
18h 35mBOS-AXA
$486
7/7Sun
3 stops
27h 12mBDL-AXA
$550
7/7Sun
1 stopAmerican Airlines
7h 53mBDL-AXA
$641

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Last minute flights from Massachusetts to Anguilla

Last minute flight, train and bus deals

6/11Tue
multi-stopAmerican Airlines
7h 20mBDL-AXA
6/17Mon
multi-stopAmerican Airlines
8h 41mAXA-BDL
$920
6/11Tue
multi-stopAmerican Airlines
22h 12mBDL-AXA
6/17Mon
multi-stopAmerican Airlines
19h 17mAXA-BDL
$925
6/11Tue
multi-stopAmerican Airlines
19h 59mBDL-AXA
6/16Sun
multi-stopAmerican Airlines
19h 17mAXA-BDL
$1,485
6/11Tue
multi-stop
10h 55mBDL-AXA
6/17Mon
multi-stop
27h 42mAXA-BDL
$2,455
6/12Wed
multi-stop
10h 55mBDL-AXA
6/17Mon
multi-stop
27h 42mAXA-BDL
$2,480
6/11Tue
multi-stop
10h 55mBDL-AXA
6/17Mon
multi-stop
27h 42mAXA-BDL
$2,570
6/11Tue
multi-stopAmerican Airlines
7h 20mBDL-AXA
6/16Sun
multi-stopAmerican Airlines
8h 41mAXA-BDL
$3,595
6/11Tue
multi-stopAmerican Airlines
22h 12mBDL-AXA
6/16Sun
multi-stopAmerican Airlines
8h 41mAXA-BDL
$3,600

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Flights to Anguilla

Cabin classes: