$387 Find Cheap Flights from Boston to Anguilla

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to Anguilla departing on 8/28. 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
1 adult, Economy

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Cheap Flights from Boston to Anguilla

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
The Valley
The Valley1 stop$573
The Valley
The Valley1 stop$573

Book Cheap Boston to Anguilla Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Boston to Anguilla that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Boston to Anguilla

Mon, Jan 12 - Thu, Jan 15
American Airlines Logo
5:24 am - 2:15 pmBOS-AXA
7h 51m1 stop
American Airlines Logo
5:25 pm - 12:55 amAXA-BOS
8h 30m1 stop
$573American Airlines
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Mon, Jan 12 - Thu, Jan 15
American Airlines Logo
6:30 am - 4:05 pmBOS-AXA
8h 35m1 stop
American Airlines Logo
5:25 pm - 9:19 amAXA-BOS
16h 54m2 stops
$577American Airlines
Find Deal
Fri, Dec 5 - Wed, Dec 10
American Airlines Logo
5:35 am - 4:15 pmBOS-AXA
9h 40m1 stop
American Airlines Logo
3:25 pm - 12:29 amAXA-BOS
10h 04m1 stop
$598American Airlines
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Fri, Dec 5 - Wed, Dec 10
American Airlines Logo
7:15 pm - 12:40 pmBOS-AXA
16h 25m2 stops
American Airlines Logo
3:25 pm - 11:01 pmAXA-BOS
8h 36m1 stop
$602American Airlines
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Sat, Dec 27 - Sat, Jan 3
BermudAir Logo
10:05 am - 4:05 pmBOS-AXA
5h 00mnonstop
BermudAir Logo
5:05 pm - 8:55 pmAXA-BOS
4h 50mnonstop
$946BermudAir
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Sat, Dec 27 - Sat, Jan 3
BermudAir Logo
10:05 am - 4:05 pmBOS-AXA
5h 00mnonstop
BermudAir Logo
5:05 pm - 8:55 pmAXA-BOS
4h 50mnonstop
$1,048BermudAir
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Wed, Aug 13 - Mon, Aug 18
 Logo
6:55 pm - 5:15 pmBOS-AXA
22h 20m3 stops
 Logo
9:35 am - 11:49 pmAXA-BOS
38h 14m3 stops
$1,451
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Fri, Nov 7 - Sat, Nov 15
 Logo
5:30 am - 5:15 pmBOS-AXA
10h 45m2 stops
 Logo
9:35 am - 10:48 pmAXA-BOS
14h 13m3 stops
$1,584
Find Deal
Fri, Dec 19 - Fri, Dec 26
United Airlines Logo
5:20 am - 5:35 pmBOS-AXA
11h 15m2 stops
United Airlines Logo
9:46 am - 10:59 pmAXA-BOS
14h 13m3 stops
$1,944United Airlines
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Wed, Aug 13 - Sun, Aug 17
United Airlines Logo
5:30 am - 5:15 pmBOS-AXA
11h 45m2 stops
United Airlines Logo
9:35 am - 11:59 pmAXA-BOS
14h 24m2 stops
$2,454United Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Boston to Anguilla flights

Get data-powered insights and trends into flights from Boston to Anguilla to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Boston to Anguilla?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $632, prices are generally cheapest when you fly direct.

How far in advance should I book a flight from Boston to Anguilla?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Boston to Anguilla, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Boston to Anguilla, you should book around 6 weeks before departure, which saves you about 67% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.


Good to know

Low seasonOctober
Cheapest flight$387
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from Boston to The Valley

FAQs - booking Anguilla flights

  • How does KAYAK find such low prices on flights from Boston 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 Boston to Anguilla.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Boston to Anguilla 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 Boston 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 from Boston to Anguilla with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Boston 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 from Boston to Anguilla up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Anguilla?

    The cheapest time of day to fly to Anguilla is generally in the morning, when round-trip flights cost $564 on average. The most expensive time of day to fly to Anguilla is generally at night, which is peak travel time and where the average cost of a ticket is $799.

Reviews of the top airlines flying from Boston to Anguilla

 
Need help choosing which airline to fly with from Boston 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.
7.2
JetBlueOverall score based on 2913 reviews
7.6Comfort
7.4Boarding
8.0Crew
7.3Entertainment
6.7Food
Airline reviews

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

2.0 MediocreAnthony, Jul 2025JFK - SAV
Read more JetBlue reviews

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

The captain gave good announcements and the flight attendants were friendly. The WiFi was pretty good. The plane itself looked very old inside and the seats were very uncomfortable. The screens in the seat backs were the smallest I’ve ever seen. There were so many loud and obnoxious kids on this flight and the parents didn’t do much to try to quiet them down. Some had videos and games on tablets with higher than necessary volume going the whole time.

Too many long delays with JetBlue. Worst major airline that serves JFK but unfortunately I keep going back because of the prices.

My JetBlue experience was nice. The flights ran on time, the aircraft was clean and comfortable, and the flight attendants were attentive. My only issue, which is isolated to the low-cost (budget) option at JetBlue, is that the check in process makes the user feel that they have to buy their seats. The seats offered for purchase are upgrades from the budget seats you get (which are essentially the last seats remaining). The interface should not make it feel like you must purchase a seat.

The plane was late to leave.. Internet was lousy. TV was not working. when we arrived, We stayed on the plane for a long time before we got to the gate. It took us a long time to retrieve our luggage because they didn’t know what carousel to send them to. It was a bad experience.

I especially liked the lead crew officer. His boarding and safety announcements were made with a bit of novelty and humor. The flight also left the gate 10 minutes early and we landed about 20 minutes early… It was a delightful flight…

There were mutliple delays. There was inconsistent, delayed, and poor communication regarding the delays.

flight was delayed for hours with no explanation. The plane was a very old aircraft.

Spend hours delayed with no food, water anything sitting on the aieplane with no ability to eat or use the restroom. My entire experience was the absolute worst. I will never fly jet Blue again.

It would have been nice if they had offered more than one set of snacks

Very poor delay in dfw was really bad n long

Our flight was 1.5 hours delayed. There was no weather for the inbound flight, so I don't understand why. This meant a VERY late arrival and only a quick nap before my morning flight.

Because of rescheduling, they had to put me on a flight that didn't go through Dallas

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Flight was cancelled 3 hrs AFTER etd. Thetefore Missed connection from JFK to New Zealand . No accommodation provided… This cost ne aporox 1000 USD in extra expenses and turned whst should have been a 24 hr trip ftom Boston - New Zealand into a VERY expensive , late 70+ hr nightmare … Complete nonsense!!!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

The plane was broken so we had to change planes.

The flight got delayed 2.5 hrs due to a maintenance issue that cause a domino effect. American should have spare planes for when something like this happens.

Everything you need to know for your flight from Boston to Anguilla

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