$386 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 7/5. 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

Mon, Nov 9 - Wed, Nov 11
American Airlines Logo
6:44 am - 4:25 pm
BOS
-
AXA
8h 41m
1 stop
American Airlines Logo
5:05 pm - 12:46 am
AXA
-
BOS
8h 41m
1 stop
$664American Airlines
Mon, Nov 9 - Wed, Nov 11
American Airlines Logo
6:44 am - 4:25 pm
BOS
-
AXA
8h 41m
1 stop
American Airlines Logo
5:05 pm - 9:31 am
AXA
-
BOS
17h 26m
2 stops
$669American Airlines
Wed, Aug 12 - Wed, Aug 19
American Airlines Logo
5:35 am - 1:32 pm
BOS
-
AXA
7h 57m
1 stop
American Airlines Logo
2:12 pm - 9:37 am
AXA
-
BOS
19h 25m
2 stops
$704American Airlines
Sun, Nov 1 - Sun, Nov 8
American Airlines Logo
8:40 pm - 4:25 pm
BOS
-
AXA
18h 45m
2 stops
American Airlines Logo
5:05 pm - 12:46 am
AXA
-
BOS
8h 41m
1 stop
$709American Airlines
Sun, Nov 1 - Sun, Nov 8
American Airlines Logo
6:09 pm - 4:25 pm
BOS
-
AXA
21h 16m
1 stop
American Airlines Logo
5:05 pm - 12:46 am
AXA
-
BOS
8h 41m
1 stop
$720American Airlines
Tue, Nov 3 - Mon, Nov 9
American Airlines Logo
6:44 am - 4:25 pm
BOS
-
AXA
8h 41m
1 stop
American Airlines Logo
5:05 pm - 12:46 am
AXA
-
BOS
8h 41m
1 stop
$727American Airlines
Mon, Jul 27 - Fri, Jul 31
American Airlines Logo
5:10 am - 4:19 pm
BOS
-
AXA
11h 09m
1 stop
American Airlines Logo
1:51 pm - 12:59 am
AXA
-
BOS
11h 08m
1 stop
$729American Airlines
Tue, Nov 3 - Mon, Nov 9
American Airlines Logo
5:36 am - 2:18 pm
BOS
-
AXA
7h 42m
1 stop
American Airlines Logo
5:05 pm - 9:56 am
AXA
-
BOS
17h 51m
2 stops
$732American Airlines
Mon, Jul 27 - Fri, Jul 31
American Airlines Logo
7:37 pm - 1:11 pm
BOS
-
AXA
17h 34m
2 stops
American Airlines Logo
4:59 pm - 8:39 am
AXA
-
BOS
15h 40m
2 stops
$734American Airlines
Sat, Aug 15 - Sat, Aug 22
American Airlines Logo
5:00 am - 1:32 pm
BOS
-
AXA
8h 32m
1 stop
American Airlines Logo
2:12 pm - 9:37 am
AXA
-
BOS
19h 25m
2 stops
$739American 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 $590 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 $590.

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 $729, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Boston to Anguilla?

To calculate monthly average prices, KAYAK takes all prices for each month 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 median of all values for each month.

The cheapest month for flights from Boston to Anguilla is December, when tickets cost $348 (return) on average. On the other hand, the most expensive months are August and September, when the average cost of round-trip tickets is $1,437 and $1,185 respectively.

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 4 weeks before departure, which saves you about 24% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$386
Best time to beat the crowds but there is an average 41% increase in price.
Most popular time to fly and prices are also 24% 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.
9.2
BermudAirOverall score based on 5 reviews
9.2Boarding
5.6Entertainment
8.8Comfort
9.6Crew
7.6Food
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.

Leave on time. We waited on the plane for hour hours and it was hot and smelly

Two hours delay, probably one hour because they didn’t bring catering and they had to bring water in board. There a change of aircraft. But delays galore at CLT so it must be a CLT and/or AA operation issue. The 1 hr additional delays because nobody could bring 2 packs of water sooner is probably the best example of this airline operates

Flight was delayed 5 hours. Initial reason for delay was 'maintenance' - which makes sense. Then, the additional 2 hours continued to say it was maintenance - when I know EWR had a 2 hour delay. AA did not say that. Additionally, when boarding, there was only one agent at the counter for a long time - until another came to help. After boarding, we had to wait another 45 minutes due to 'no catering'. So while we waited for catering, AA continued to board additional passengers - which seemed odd - and raised questions about what really was going on. I sat in First Class. During the flight, the flight crew allowed a significant number of non-First Class passengers to use the front bathroom - which created a very crowded environment in First Class which was uncomfortable. This also delayed First Class passengers from using the bathroom. Overall, horrible experience.

The Charleston, WV airport was cute. Very good staff and small enough to feel comfortable. The plane had more leg room than bigger planes. Much more comfortable.

Another uncoordinated American experience. Always surprises me at DFW for them of all places. Have to take this flight as there are no other good time options. We knew from the start that something was wrong, but the pilot wouldn't tell us. I just watched my Kayak app grow the delay by 10 minutes as it went to 3.5 hours. They were uncoordinated with maintenance (as maintenance, when finally arriving, knew within 15 minutes the plane wasn't going. No 'sorry' or 'this is what is going on' comment. The pilot seemed unfazed / didn't care about the process we were going through.

The seats. The seat in front of me was awful and when the guy sat down, it flew back and hit my head when I was putting my backpack under the seat, It didn't make for a pleasant experience,

Luggage did not make it onto my plane. Business seats were economy with empty row seat. Just horrible experience. Why would the company allow for transfers that don’t give employees enough time to transfer luggages??

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

The gate experience at LAX was abysmal (same for the arrival experience two days prior). Despite the LAX -> SAT schedule of two flights daily, our departure gate was at a smaller hub that we had to be bussed to from Terminal 4. Fortunately, I arrived at LAX extra early and had time to spare, but if I had not known, I might have missed my flight. I looked at the LAX airport map in the AA app and there was no indication of the additional boarding process. Lastly the gate area we were bussed to was crowded with limited food and beverage options. On flight, the fight attendant was hospitable and attentive, the flight was smooth, and AA's free (and working) wifi for AA members were all on the positive side.

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

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

Information on your arrival and departure airports