What is the cheapest airline that flies from Massachusetts to Anguilla?

BermudAir and American Airlines are the most popular carriers operating from Massachusetts to Anguilla

How long is the flight from Massachusetts to Anguilla?

If you’re flying from a popular airport in Massachusetts, such as Boston or Provincetown, and flying into Anguilla, then you can expect flight times to average 4h 40m and 19h 05m, respectively.

When did momondo last update prices for flights from Massachusetts to Anguilla?

Prices for flights from Massachusetts to Anguilla were last updated today.

How many operators does momondo search for flights from Massachusetts to Anguilla?

As of September 2026, there are 2 operators available to choose from for flights from Massachusetts to Anguilla.

How old do you have to be to fly from Massachusetts to Anguilla?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Massachusetts to Anguilla.

What documentation or ID do you need to fly to Anguilla?

The travel and health documents required for your trip to Anguilla can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Anguilla. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$289 Cheap Flights from Massachusetts to Anguilla in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Massachusetts to Anguilla

Round-trip

One-way

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:30 am - 1:10 pmBOS Boston Logan Intl-AXA The Valley Wallblake Intl

4h 40mnonstop

1:25 pm - 5:10 pmAXA The Valley Wallblake Intl-BOS Boston Logan Intl

4h 45mnonstop

$645BermudAir

Fri, Jan 1 - Mon, Jan 11

5:00 am - 2:57 pmBOS Boston Logan Intl-AXA The Valley Wallblake Intl

8h 57m1 stop Miami

5:45 pm - 12:59 amAXA The Valley Wallblake Intl-BOS Boston Logan Intl

8h 14m1 stop Miami

$651American Airlines

Wed, Dec 9 - Wed, Dec 16

7:00 am - 4:46 pmBOS Boston Logan Intl-AXA The Valley Wallblake Intl

8h 46m1 stop Miami

5:18 pm - 12:59 amAXA The Valley Wallblake Intl-BOS Boston Logan Intl

8h 41m1 stop Miami

$651American Airlines

Wed, Mar 3 - Wed, Mar 10

7:00 am - 4:46 pmBOS Boston Logan Intl-AXA The Valley Wallblake Intl

8h 46m1 stop Miami

5:18 pm - 12:59 amAXA The Valley Wallblake Intl-BOS Boston Logan Intl

8h 41m1 stop Miami

$651American Airlines

Wed, Mar 3 - Wed, Mar 10

7:30 am - 1:10 pmBOS Boston Logan Intl-AXA The Valley Wallblake Intl

4h 40mnonstop

1:25 pm - 5:10 pmAXA The Valley Wallblake Intl-BOS Boston Logan Intl

4h 45mnonstop

$655BermudAir

Fri, Dec 25 - Mon, Dec 28

7:30 am - 1:10 pmBOS Boston Logan Intl-AXA The Valley Wallblake Intl

4h 40mnonstop

12:25 pm - 5:10 pmAXA The Valley Wallblake Intl-BOS Boston Logan Intl

4h 45mnonstop

$666BermudAir

Fri, Feb 26 - Mon, Mar 15

7:30 am - 1:10 pmBOS Boston Logan Intl-AXA The Valley Wallblake Intl

4h 40mnonstop

12:25 pm - 5:10 pmAXA The Valley Wallblake Intl-BOS Boston Logan Intl

4h 45mnonstop

$687BermudAir

Mon, Mar 8 - Mon, Mar 15

7:00 am - 10:15 amBOS Boston Logan Intl-AXA The Valley Wallblake Intl

26h 15m1 stop Simpson Bay Princess Juliana

1:25 pm - 5:10 pmAXA The Valley Wallblake Intl-BOS Boston Logan Intl

4h 45mnonstop

$791Multiple Airlines

Fri, Jan 1 - Mon, Jan 11

7:30 am - 1:10 pmBOS Boston Logan Intl-AXA The Valley Wallblake Intl

4h 40mnonstop

9:30 am - 7:50 pmAXA The Valley Wallblake Intl-BOS Boston Logan Intl

11h 20m2 stops Simpson Bay Princess Juliana Santo Domingo Las Americas

$839Multiple Airlines

Fri, Dec 25 - Thu, Dec 31

7:30 am - 1:10 pmBOS Boston Logan Intl-AXA The Valley Wallblake Intl

4h 40mnonstop

4:40 pm - 7:50 pmAXA The Valley Wallblake Intl-BOS Boston Logan Intl

28h 10m2 stops Simpson Bay Princess Juliana Santo Domingo Las Americas

$839Multiple Airlines

Fri, Dec 25 - Wed, Dec 30

Cheap direct flights

Enter your travel dates to find the best prices.

7:30 am - 1:10 pmBOS Boston Logan Intl-AXA The Valley Wallblake Intl

4h 40mnonstop

1:25 pm - 5:10 pmAXA The Valley Wallblake Intl-BOS Boston Logan Intl

4h 45mnonstop

$645BermudAir

Fri, Jan 1 - Mon, Jan 11

7:30 am - 1:10 pmBOS Boston Logan Intl-AXA The Valley Wallblake Intl

4h 40mnonstop

1:25 pm - 5:10 pmAXA The Valley Wallblake Intl-BOS Boston Logan Intl

4h 45mnonstop

$655BermudAir

Fri, Dec 25 - Mon, Dec 28

7:30 am - 1:10 pmBOS Boston Logan Intl-AXA The Valley Wallblake Intl

4h 40mnonstop

12:25 pm - 5:10 pmAXA The Valley Wallblake Intl-BOS Boston Logan Intl

4h 45mnonstop

$666BermudAir

Fri, Feb 26 - Mon, Mar 15

7:30 am - 1:10 pmBOS Boston Logan Intl-AXA The Valley Wallblake Intl

4h 40mnonstop

12:25 pm - 5:10 pmAXA The Valley Wallblake Intl-BOS Boston Logan Intl

4h 45mnonstop

$687BermudAir

Mon, Mar 8 - Mon, Mar 15

7:30 am - 1:10 pmBOS Boston Logan Intl-AXA The Valley Wallblake Intl

4h 40mnonstop

1:25 pm - 5:10 pmAXA The Valley Wallblake Intl-BOS Boston Logan Intl

4h 45mnonstop

$831BermudAir

Fri, Feb 19 - Fri, Feb 26

7:30 am - 1:10 pmBOS Boston Logan Intl-AXA The Valley Wallblake Intl

4h 40mnonstop

1:25 pm - 5:10 pmAXA The Valley Wallblake Intl-BOS Boston Logan Intl

4h 45mnonstop

$834BermudAir

Fri, Feb 19 - Fri, Feb 26

7:30 am - 12:10 pmBOS Boston Logan Intl-AXA The Valley Wallblake Intl

4h 40mnonstop

12:25 pm - 5:10 pmAXA The Valley Wallblake Intl-BOS Boston Logan Intl

4h 45mnonstop

$869BermudAir

Mon, Mar 15 - Mon, Mar 22

7:30 am - 1:10 pmBOS Boston Logan Intl-AXA The Valley Wallblake Intl

4h 40mnonstop

1:25 pm - 5:10 pmAXA The Valley Wallblake Intl-BOS Boston Logan Intl

4h 45mnonstop

$889BermudAir

Fri, Dec 25 - Mon, Jan 4

7:30 am - 1:10 pmBOS Boston Logan Intl-AXA The Valley Wallblake Intl

4h 40mnonstop

1:25 pm - 5:10 pmAXA The Valley Wallblake Intl-BOS Boston Logan Intl

4h 45mnonstop

$942BermudAir

Fri, Jan 29 - Fri, Feb 5

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BermudAir flights from Massachusetts to Anguilla

Our best BermudAir deals on Massachusetts to Anguilla flight tickets

BermudAir

Jan 1

BOS7:30 amBoston Logan Intl

4h 40m

AXA1:10 pmThe Valley Wallblake Intl

Jan 11

AXA1:25 pmThe Valley Wallblake Intl

4h 45m

BOS5:10 pmBoston Logan Intl

$645

BermudAir

Dec 25

BOS7:30 amBoston Logan Intl

4h 40m

AXA1:10 pmThe Valley Wallblake Intl

Dec 28

AXA1:25 pmThe Valley Wallblake Intl

4h 45m

BOS5:10 pmBoston Logan Intl

$655

BermudAir

Feb 8

BOS7:30 amBoston Logan Intl

4h 40m

AXA1:10 pmThe Valley Wallblake Intl

Feb 15

AXA1:25 pmThe Valley Wallblake Intl

4h 45m

BOS5:10 pmBoston Logan Intl

$661

American Airlines flights from Massachusetts to Anguilla

Our best American Airlines deals on Massachusetts to Anguilla flight tickets

American Airlines

Jan 6

BOS6:01 amBoston Logan Intl

9h 54m

1 stop

AXA4:55 pmThe Valley Wallblake Intl

Jan 13

AXA3:38 pmThe Valley Wallblake Intl

10h 21m

1 stop

BOS12:59 amBoston Logan Intl

$651

American Airlines

Jan 6

BOS6:00 amBoston Logan Intl

9h 55m

2 stops

AXA4:55 pmThe Valley Wallblake Intl

Jan 13

AXA5:35 pmThe Valley Wallblake Intl

15h 18m

2 stops

BOS7:53 amBoston Logan Intl

$656

American Airlines

Jan 13

BOS6:01 amBoston Logan Intl

7h 55m

1 stop

AXA2:56 pmThe Valley Wallblake Intl

Jan 20

AXA5:35 pmThe Valley Wallblake Intl

23h 26m

1 stop

BOS4:01 pmBoston Logan Intl

$666

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

BostonThe Valley

BOS Boston Logan Intl - AXA The Valley Wallblake Intl

BOSAXA

Boston Logan Intl

Fri 1/1

7:30 am-1:10 pm

Nonstop4h 40m

The Valley Wallblake Intl

Mon 1/11

1:25 pm-5:10 pm

Nonstop4h 45m

$645

BostonThe Valley

BOS Boston Logan Intl - AXA The Valley Wallblake Intl

BOSAXA

Boston Logan Intl

Wed 12/9

5:00 am-2:57 pm

1 stop8h 57m

The Valley Wallblake Intl

Wed 12/16

5:45 pm-12:59 am

1 stop8h 14m

$651

BostonThe Valley

BOS Boston Logan Intl - AXA The Valley Wallblake Intl

BOSAXA

Boston Logan Intl

Wed 3/3

7:00 am-4:46 pm

1 stop8h 46m

The Valley Wallblake Intl

Wed 3/10

5:18 pm-12:59 am

1 stop8h 41m

$651

BostonThe Valley

BOS Boston Logan Intl - AXA The Valley Wallblake Intl

BOSAXA

Boston Logan Intl

Wed 3/3

7:00 am-4:46 pm

1 stop8h 46m

The Valley Wallblake Intl

Wed 3/10

5:18 pm-12:59 am

1 stop8h 41m

$651

BostonThe Valley

BOS Boston Logan Intl - AXA The Valley Wallblake Intl

BOSAXA

Boston Logan Intl

Fri 12/25

7:30 am-1:10 pm

Nonstop4h 40m

The Valley Wallblake Intl

Mon 12/28

1:25 pm-5:10 pm

Nonstop4h 45m

$655

BostonThe Valley

BOS Boston Logan Intl - AXA The Valley Wallblake Intl

BOSAXA

Boston Logan Intl

Fri 2/26

7:30 am-1:10 pm

Nonstop4h 40m

The Valley Wallblake Intl

Mon 3/15

12:25 pm-5:10 pm

Nonstop4h 45m

$666

BostonThe Valley

BOS Boston Logan Intl - AXA The Valley Wallblake Intl

BOSAXA

Boston Logan Intl

Mon 3/8

7:30 am-1:10 pm

Nonstop4h 40m

The Valley Wallblake Intl

Mon 3/15

12:25 pm-5:10 pm

Nonstop4h 45m

$687

BostonThe Valley

BOS Boston Logan Intl - AXA The Valley Wallblake Intl

BOSAXA

Boston Logan Intl

Fri 1/1

7:00 am-10:15 am

1 stop26h 15m

The Valley Wallblake Intl

Mon 1/11

1:25 pm-5:10 pm

Nonstop4h 45m

$791

BostonThe Valley

BOS Boston Logan Intl - AXA The Valley Wallblake Intl

BOSAXA

Boston Logan Intl

Fri 12/25

7:30 am-1:10 pm

Nonstop4h 40m

The Valley Wallblake Intl

Thu 12/31

9:30 am-7:50 pm

2 stops11h 20m

$839

BostonThe Valley

BOS Boston Logan Intl - AXA The Valley Wallblake Intl

BOSAXA

Boston Logan Intl

Fri 12/25

7:30 am-1:10 pm

Nonstop4h 40m

The Valley Wallblake Intl

Wed 12/30

4:40 pm-7:50 pm

2 stops28h 10m

$839

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Massachusetts to Anguilla

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Anguilla?

If you aren’t able to travel to Anguilla during the month of August, then flying in December is also cheap. Prices for this month can be found on momondo for an average of $567.

What is the cheapest day to depart on your flight to Anguilla?

The cheapest day to depart from Massachusetts to Anguilla is on a Wednesday when prices can be found for as low as $587. The most expensive day to fly to Anguilla is Friday, with ticket prices averaging around $732.

What is the cheapest Massachusetts to Anguilla flight route?

Fly from Boston Logan Intl to The Valley Wallblake Intl for the best Massachusetts - Anguilla flight prices

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

You are more likely to see cheaper flights to Anguilla from Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Anguilla for around $779 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Anguilla from Massachusetts for as low as $506 on momondo.

What cabin class options are available on Massachusetts to Anguilla flights?

There are 3 cabin classes available to choose from on Massachusetts to Anguilla flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Massachusetts to Anguilla flights?

No. A direct flight is the cheapest option for a flight between Massachusetts to Anguilla.

Cheap Massachusetts to Anguilla flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Massachusetts to Anguilla

Best Price Found	$289
Fastest flight time	4h 40m
Direct flights	Tue and Sat
Airports in Anguilla	2 airports

The best one-way flight to Anguilla from Massachusetts in the past 72 hours is $289. The best round-trip flight deal from Massachusetts to Anguilla found on momondo in the last 72 hours is $645.

The fastest flight from Massachusetts to Anguilla takes 4h 40m

Direct flights go from Massachusetts to Anguilla on Tuesday and Saturday. There are no airlines offering direct flights.

There are 2 airports in Anguilla. From Massachusetts there are direct flights to The Valley Wallblake Intl (AXA).

Search flight deals

Frequently asked questions about flying from Massachusetts to Anguilla

When did momondo last update prices for flights from Massachusetts to Anguilla?
Prices for flights from Massachusetts to Anguilla were last updated today.
How many operators does momondo search for flights from Massachusetts to Anguilla?
As of September 2026, there are 2 operators available to choose from for flights from Massachusetts to Anguilla.
How old do you have to be to fly from Massachusetts to Anguilla?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Massachusetts to Anguilla.
What documentation or ID do you need to fly to Anguilla?
The travel and health documents required for your trip to Anguilla can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Anguilla. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Massachusetts to Anguilla?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Massachusetts to Anguilla is Embraer 170 / 175 / 190 / 195 (52.38% of total bookings). The next most popular plane models are Embraer 190 (38.10%), Airbus A321-100/200 (2.38%), and Airbus A318/A319/A320/A321 (2.38%).

Best airlines flying from Massachusetts to Anguilla

Compare and see reviews for airlines that fly from Massachusetts to Anguilla with momondo

Airline	Rating	Free Cancellation	Price
BermudAir	PriceFrom $457	Free Cancellation	Rating 0.0 0 reviews		Search BermudAir flights
American Airlines	PriceFrom $658	Free Cancellation	Rating 7.0 12,099 reviews		Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Massachusetts to Anguilla?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Massachusetts to Anguilla. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Massachusetts to Anguilla with flexible booking policies on momondo?

momondo does allow users to show only those flights to Anguilla from Massachusetts which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Massachusetts to Anguilla?

momondo helps you find the best flight between Massachusetts and Anguilla by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Massachusetts to Anguilla right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Massachusetts to Anguilla now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Anguilla and let you know when they change.

An easier way to manage your Anguilla trip

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Flights to The Valleyfrom $597

Cheap flights from Massachusetts to Anguilla from $289

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Massachusetts to Anguilla departing on 12/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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BermudAir flights from Massachusetts to Anguilla

Our best BermudAir deals on Massachusetts to Anguilla flight tickets

American Airlines flights from Massachusetts to Anguilla

Our best American Airlines deals on Massachusetts to Anguilla flight tickets

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Use the filters below to find and compare flights from Massachusetts to Anguilla that are best for you.

See travel insights to Anguilla from

How to get the cheapest flight ticket from Massachusetts to Anguilla

What is the cheapest month to fly to Anguilla?

What is the cheapest day to depart on your flight to Anguilla?

What is the cheapest Massachusetts to Anguilla flight route?

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

What cabin class options are available on Massachusetts to Anguilla flights?

Can stopping save me money on Massachusetts to Anguilla flights?

What is the cheapest airline that flies from Massachusetts to Anguilla?

How long is the flight from Massachusetts to Anguilla?

Cheap Massachusetts to Anguilla flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Airports in Anguilla

Frequently asked questions about flying from Massachusetts to Anguilla

Best airlines flying from Massachusetts to Anguilla

Compare and see reviews for airlines that fly from Massachusetts to Anguilla with momondo

Why use momondo?

An easier way to manage your Anguilla trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Anguilla

Popular cities in Anguilla

Popular flights according to clicks in the last 7 days on momondo

Massachusetts flight routes

According to popular flight searches on momondo this year

Anguilla flight routes

According to popular flight searches on momondo this year

Fly your favorite airline to Anguilla

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Anguilla

List of cabin classes available on flights landing in Anguilla. Availability may vary depending on flight origin and airline.

Complete your trip to Anguilla

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According to popular flight searches on momondo this year