$355 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 3/28. 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, 0 bags

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Flight Deals

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

Sat, Apr 4 - Wed, Apr 8
BermudAir Logo
10:20 am - 3:00 pm
BOS
-
AXA
4h 40mnonstop
BermudAir Logo
4:05 pm - 8:50 pm
AXA
-
BOS
4h 45mnonstop
$644BermudAir
Wed, Apr 1 - Wed, Apr 8
BermudAir Logo
10:20 am - 3:00 pm
BOS
-
AXA
4h 40mnonstop
BermudAir Logo
4:05 pm - 8:50 pm
AXA
-
BOS
4h 45mnonstop
$664BermudAir
Sat, Jun 13 - Tue, Jun 16
American Airlines Logo
5:49 pm - 1:14 pm
BOS
-
AXA
19h 25m
2 stops
American Airlines Logo
4:55 pm - 12:59 am
AXA
-
BOS
8h 04m
1 stop
$669American Airlines
Sat, Mar 28 - Thu, Apr 2
Multiple Airlines Logo
10:15 am - 3:40 pm
BOS
-
AXA
29h 25m
2 stops
Multiple Airlines Logo
12:00 pm - 11:59 pm
AXA
-
BOS
11h 59m
2 stops
$671Multiple Airlines
Wed, May 6 - Wed, May 13
American Airlines Logo
6:00 am - 4:17 pm
BOS
-
AXA
10h 17m
2 stops
American Airlines Logo
4:57 pm - 8:26 am
AXA
-
BOS
15h 29m
2 stops
$674American Airlines
Sat, Mar 28 - Wed, Apr 1
Multiple Airlines Logo
10:15 am - 5:10 pm
BOS
-
AXA
30h 55m
2 stops
Multiple Airlines Logo
12:00 pm - 11:59 pm
AXA
-
BOS
11h 59m
2 stops
$676Multiple Airlines
Sat, Mar 28 - Thu, Apr 2
Multiple Airlines Logo
4:35 pm - 5:10 pm
BOS
-
AXA
24h 35m
3 stops
Multiple Airlines Logo
12:00 pm - 11:59 pm
AXA
-
BOS
11h 59m
2 stops
$680Multiple Airlines
Sat, Mar 28 - Wed, Apr 1
Multiple Airlines Logo
7:55 pm - 5:10 pm
BOS
-
AXA
21h 15m
3 stops
Multiple Airlines Logo
10:00 am - 11:59 pm
AXA
-
BOS
13h 59m
2 stops
$685Multiple Airlines
Sat, Apr 4 - Wed, Apr 8
Multiple Airlines Logo
5:30 am - 4:40 pm
BOS
-
AXA
11h 10m
2 stops
Multiple Airlines Logo
10:00 am - 11:59 pm
AXA
-
BOS
13h 59m
2 stops
$698Multiple Airlines
Sat, Apr 25 - Fri, May 1
American Airlines Logo
7:32 pm - 4:17 pm
BOS
-
AXA
20h 45m
2 stops
American Airlines Logo
4:57 pm - 10:39 am
AXA
-
BOS
17h 42m
2 stops
$699American Airlines
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.

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

The average price for all round-trip flights from Boston to Anguilla depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Anguilla is generally in the morning, when round-trip flights cost $589 on average. The most expensive time of day to fly to Anguilla is generally in the morning, which is peak travel time and where the average cost of a ticket is $589.

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $748 on average.

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 1 week before departure. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.

Find deals

Good to know

Low seasonDecember
Cheapest flight$355
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly and prices are also 16% lower on average.
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.

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.
9.5
BermudAirOverall score based on 4 reviews
9.5Boarding
9.0Comfort
6.5Entertainment
10.0Crew
8.5Food
Airline reviews

It was perfect! Will try to use BermudAir when it works.

10.0 ExcellentDonna, Feb 2026
BWI - BDA
Read more BermudAir reviews

It was perfect! Will try to use BermudAir when it works.

Not really sure I enjoyed the flight at all. The flight attendants seemed a little tired and rude at times. The snacks were lacking in taste and sustenance. The flight was incredibly turbulent for three plus hours and the pilot had to do a second pass to land at our final destination because he was coming in so fast. He must have taken a short cut and because of it we had to suffer the violent turbulence and the dropping down. It had to be one of if not the worse flights I have ever been on and have traveled vastly all over the world.

Delay after delay with little communication then AA lost my luggage and at airport would not assist just said scan this QR code to track your luggage and submit a claim. However QR code provided did not work so have to go back to airport

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

Easy boarding. Rows are smaller but that may be an older and bigger me now :)

It would have been nice if American tried to care.

American Airlines did everything they could with the high Spring Break crowd. I was frustrated to be changed from 1st class to a middle seat at the back of the plane. This has happened before, not sure booking 1st class and paying the extra actually works.

I booked 1st class, my flights were changed and I was sitting in the middle at the back of the plane. A far cry from the 1st class I purchased for my flights. I am grateful I arrived on time.

Aging planer and NO wifi on a 14 hour day flight. Unless you are retired or don't need to work or be in touch with the world... The lack of Wifif really ruined the flight. And the old plane - really showing it's age, wasn't great

There was no beverage service and the only time I saw a crew member walk through the cabin is when we were preparing to land.

Our flight was delayed 3 times and this is why I am giving such low reviews. Everything else was okay but being in the airport at 4:30pm for my initial flight at 7pm to not leave until after 9:30pm is insane,

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

Information on your arrival and departure airports

Boston (BOS)