$178 Find Cheap Flights from Boston to Anguilla - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 25% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals
Booking Insights

Price, demand and travel trends for Boston to Anguilla flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What are the cheapest fares from Boston to Anguilla right now?

The cheapest fare from Boston to Anguilla in the last week was $411 round-trip, to The Valley Wallblake Intl (AXA).

What’s the cheapest month to fly from Boston to Anguilla?

December is the cheapest time of year to fly, with average fares of $591. Prices are highest in August, when average flight costs increase to around $1,213.

When is the best time to book flights from Boston to Anguilla?

Book your flights 6 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 34% compared to booking last-minute (within 2 weeks of departure).

Which airport in Anguilla is the cheapest to fly to from Boston?

All flights from Boston to Anguilla arrive at The Valley Wallblake Intl (AXA). On average, round-trip fares are around $668.

What’s the cheapest day to fly from Boston to Anguilla?

Saturday tends to be the cheapest day to fly from Boston to Anguilla, while Thursday is the most expensive. Fares run about 27% higher that day, based on the past 12 months of KAYAK data.

What's the cheapest time of day to fly from Boston to Anguilla?

Data from the past 12 months shows it's cheapest to fly to Anguilla during the morning with average prices of $668. The evening is the most expensive time to fly, with average prices of $904.

Key details for Boston to Anguilla flights

Low season

September

Cheapest flight

$178
Beat the crowds with an average 94% drop in travelers.
The most popular month to fly with an average 104% increase in travelers.
One-way flight from Boston to The Valley

Your Boston to Anguilla flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Boston to Anguilla?

    Yes. Fares from Boston to Anguilla are low right now. As a rule of thumb, a round-trip under $551 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Boston to Anguilla?

    Over the past 12 months, round-trip fares from Boston to Anguilla have ranged from $551 to $770.

  • What are the main airports serving Anguilla?

    Flights to Anguilla all arrive at The Valley Wallblake Intl (AXA).

  • What airlines fly nonstop from Boston to Anguilla?

    Based on the flight schedule for the next 3 months, just one airline regularly flies nonstop from Boston to Anguilla: BermudAir.

  • Where in Anguilla can I fly nonstop from Boston?

    Based on the flight schedule for the next 3 months, you can only fly nonstop from Boston to The Valley.

  • Is it cheaper to fly with a layover from Boston to Anguilla?

    No, nonstop flights from Boston to Anguilla are typically the cheaper option, averaging $627 over the past 12 months.

  • How long is a flight from Boston to Anguilla?

    Flights from Boston to Anguilla take 4h 40m on average.

  • Which cabin classes are available on flights from Boston to Anguilla?

    On flights from Boston to Anguilla you can book Economy Class or First Class.

  • What are the earliest and latest flights from Boston to Anguilla?

    The earliest nonstop flight from Boston to Anguilla departs at 7:30 am and the latest departs at 7:30 am. Nonstop flights take about 4h 40m.

Your guide to booking Boston to Anguilla flights

Get tips on when to book, when to fly and what to know before your trip.
  • If you can plan ahead, the sweet spot for booking your flight is 6 weeks before your trip. KAYAK data shows fares in this window are around 34% lower than last-minute bookings (made within 2 weeks of departure). Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • If your travel dates are flexible, book your trip for December when flights are typically cheapest and avoid August when prices are at their highest.
  • Flying on Saturday is usually the cheapest. Flights on Thursday cost about 27% more on average, so being flexible with your travel dates could help you save.
  • Start your trip in The Valley, which is the most popular destination in Anguilla. From there, it's easy to continue on to other popular destinations such as West End Village, Long Bay Village and Shoal Bay.
  • Whether you're trying to save time or money, the Boston to Anguilla nonstop route is usually your best option.

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.
9.4
BermudAirOverall score based on 7 reviews
9.7Crew
9.4Boarding
9.1Comfort
8.2Food
5.1Entertainment
Airline reviews

It was my first trip with BermudAir and a great experience. Organized boarding and the staff were polite and professional. The Bermuda shorts on the male attendants is a nice touch! I look forward to flying with BermudAir again in the near future!

10.0 ExcellentJaney, Aug 2026
Read more BermudAir reviews

It was my first trip with BermudAir and a great experience. Organized boarding and the staff were polite and professional. The Bermuda shorts on the male attendants is a nice touch! I look forward to flying with BermudAir again in the near future!

Excellent, as always. Friendly, free in-flight service of drinks and those delicious chocolate chip cookies. Arrived 17 minutes early. However, no in flight entertainment – 2 hours to read a book!

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

Boston sucks. Everything after 4p is delayed. AA switched planes on us so we ended up being 1.5 hours late (plus the delay at Logan). Not sure why the airline says it is on time until 1 h before the flight and then it becomes a rolling delay when they knew the incoming flight was arriving after our scheduled departure time. The crew was great as were the gate agent and ground crew. Just operations that sucked.

Flight was 2 hr late but at least I was upgraded to first class

I've flown American several times this summer and I have yet to get a flight that leaves on time. However, a delay is better than a cancel. So far I have had four canceled flights and two delayed flights

The flight was delayed in 30 minute increments for a total of 4 hours and 30 minute delay. All other flights to Chicago left on time except for this one flight. If there is an issue with the inbound flight, just let customers know so they can find another flight right away, Once we got on the plane there was another 30 minute delay taking off at 10:30 at night which is very unusual that a flight wouldn't be ready to take off

They have overselled the ticket and kicked me out from boarding, All my Plans were collapsed and important network meeting missed.also I booked direct flight i have to go through an 1 stop and it was frustrated.

Horrific. We were delayed due a flight attendant stuck in traffic en route to the airport. Over 100 people were then stuck in Charolette. Then I ran to make my layover only to find that my connection didn’t have a plane anymore. Waited 2.5 hours without any updates. On the flight we had to beg for even a pretzel option.

Because I bought my ticket from Underpricer, I could not check in online. I could only check in at the airport and that was deeply frustrating because I had to arrive very early. The flight also departed 45 min late and passengers were given no explanations about why we were delayed. I was worried I would miss my connecting flight. Once on board, however, the flight was fine.

Terrible boarding and first class experience. Nice staff but overall disorganized, dirty plane.

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

Early departure meant on time arrival. Only real problem was free internet had issues, although chatting with the internet help desk (you can do this via aainflight.com) got the issue resolved.

More options for your flight from Boston to Anguilla

Complete your trip to Anguilla with a hotel stay or car rental