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Cheap flights from Massachusetts to Anguilla from $307

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 1/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from Massachusetts to Anguilla

Cheap round-trip flights

Enter your travel dates to find the best prices.
BermudAir Logo
7:30 am - 1:10 pmBOS  Boston Logan Intl-AXA The Valley Wallblake Intl
4h 40mnonstop
BermudAir Logo
1:25 pm - 5:10 pmAXA  The Valley Wallblake Intl-BOS Boston Logan Intl
4h 45mnonstop
$649BermudAir
Fri, Jan 1 - Fri, Jan 8
BermudAir Logo
7:30 am - 1:10 pmBOS  Boston Logan Intl-AXA The Valley Wallblake Intl
4h 40mnonstop
BermudAir Logo
1:25 pm - 5:10 pmAXA  The Valley Wallblake Intl-BOS Boston Logan Intl
4h 45mnonstop
$662BermudAir
Mon, Jan 25 - Fri, Jan 29
BermudAir Logo
7:30 am - 1:10 pmBOS  Boston Logan Intl-AXA The Valley Wallblake Intl
4h 40mnonstop
BermudAir Logo
1:25 pm - 5:10 pmAXA  The Valley Wallblake Intl-BOS Boston Logan Intl
4h 45mnonstop
$666BermudAir
Fri, Dec 25 - Mon, Dec 28
BermudAir Logo
7:30 am - 1:10 pmBOS  Boston Logan Intl-AXA The Valley Wallblake Intl
4h 40mnonstop
BermudAir Logo
1:25 pm - 5:10 pmAXA  The Valley Wallblake Intl-BOS Boston Logan Intl
4h 45mnonstop
$701BermudAir
Mon, Dec 21 - Mon, Dec 28
American Airlines Logo
5:15 am - 2:23 pmBOS  Boston Logan Intl-AXA The Valley Wallblake Intl
8h 08m1 stop Miami
American Airlines Logo
5:06 pm - 10:01 amAXA  The Valley Wallblake Intl-BOS Boston Logan Intl
17h 55m1 stop Miami
$709American Airlines
Wed, Jan 13 - Wed, Jan 20
American Airlines Logo
5:00 am - 4:48 pmBOS  Boston Logan Intl-AXA The Valley Wallblake Intl
10h 48m1 stop Miami
American Airlines Logo
3:03 pm - 11:05 pmAXA  The Valley Wallblake Intl-BOS Boston Logan Intl
9h 02m1 stop Miami
$712American Airlines
Tue, Jan 5 - Tue, Jan 12
American Airlines Logo
6:17 pm - 2:23 pmBOS  Boston Logan Intl-AXA The Valley Wallblake Intl
19h 06m1 stop Miami
American Airlines Logo
5:06 pm - 10:01 amAXA  The Valley Wallblake Intl-BOS Boston Logan Intl
17h 55m1 stop Miami
$712American Airlines
Sun, Jan 24 - Thu, Jan 28
Multiple Airlines Logo
7:30 am - 1:10 pmBOS  Boston Logan Intl-AXA The Valley Wallblake Intl
4h 40mnonstop
Multiple Airlines Logo
3:30 pm - 7:50 pmAXA  The Valley Wallblake Intl-BOS Boston Logan Intl
29h 20m2 stops Simpson Bay Princess Juliana Santo Domingo Las Americas
$822Multiple Airlines
Fri, Dec 25 - Wed, Dec 30
Multiple Airlines Logo
7:30 am - 1:10 pmBOS  Boston Logan Intl-AXA The Valley Wallblake Intl
4h 40mnonstop
Multiple Airlines Logo
3:30 pm - 7:50 pmAXA  The Valley Wallblake Intl-BOS Boston Logan Intl
29h 20m2 stops Simpson Bay Princess Juliana Santo Domingo Las Americas
$830Multiple Airlines
Fri, Dec 25 - Wed, Dec 30
Multiple Airlines Logo
7:30 am - 1:10 pmBOS  Boston Logan Intl-AXA The Valley Wallblake Intl
4h 40mnonstop
Multiple Airlines Logo
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
$833Multiple Airlines
Fri, Dec 25 - Thu, Dec 31

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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 8
AXA1:25 pmThe Valley Wallblake Intl
4h 45m
BOS5:10 pmBoston Logan Intl
$649
BermudAir
Jan 25
BOS7:30 amBoston Logan Intl
4h 40m
AXA1:10 pmThe Valley Wallblake Intl
Jan 29
AXA1:25 pmThe Valley Wallblake Intl
4h 45m
BOS5:10 pmBoston Logan Intl
$662
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
$666

American Airlines flights from Massachusetts to Anguilla

Our best American Airlines deals on Massachusetts to Anguilla flight tickets
American Airlines
Jan 13
BOS5:15 amBoston Logan Intl
8h 08m
1 stop
AXA2:23 pmThe Valley Wallblake Intl
Jan 20
AXA5:06 pmThe Valley Wallblake Intl
17h 55m
1 stop
BOS10:01 amBoston Logan Intl
$709
American Airlines
Feb 2
BDL5:23 amHartford Bradley Intl
8h 00m
1 stop
AXA2:23 pmThe Valley Wallblake Intl
Feb 11
AXA3:00 pmThe Valley Wallblake Intl
9h 59m
1 stop
BDL11:59 pmHartford Bradley Intl
$712
American Airlines
Feb 2
BDL4:52 pmHartford Bradley Intl
20h 31m
2 stops
AXA2:23 pmThe Valley Wallblake Intl
Feb 11
AXA5:26 pmThe Valley Wallblake Intl
20h 41m
2 stops
BDL1:07 pmHartford Bradley Intl
$717

momondo Fare Finder

 
Customize your flight search to find flights from Massachusetts to Anguilla that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 14, 2026.
Use the filters below to find and compare flights from Massachusetts to Anguilla that are best for you.

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

Fri 1/8

1:25 pm-5:10 pm

Nonstop4h 45m

$649

BostonThe Valley

BOS Boston Logan Intl - AXA The Valley Wallblake Intl

BOSAXA

Boston Logan Intl

Mon 1/25

7:30 am-1:10 pm

Nonstop4h 40m

The Valley Wallblake Intl

Fri 1/29

1:25 pm-5:10 pm

Nonstop4h 45m

$662

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

$666

BostonThe Valley

BOS Boston Logan Intl - AXA The Valley Wallblake Intl

BOSAXA

Boston Logan Intl

Mon 12/21

7:30 am-1:10 pm

Nonstop4h 40m

The Valley Wallblake Intl

Mon 12/28

1:25 pm-5:10 pm

Nonstop4h 45m

$701

BostonThe Valley

BOS Boston Logan Intl - AXA The Valley Wallblake Intl

BOSAXA

Boston Logan Intl

Wed 1/13

5:15 am-2:23 pm

1 stop8h 08m

The Valley Wallblake Intl

Wed 1/20

5:06 pm-10:01 am

1 stop17h 55m

$709

BostonThe Valley

BOS Boston Logan Intl - AXA The Valley Wallblake Intl

BOSAXA

Boston Logan Intl

Tue 1/5

5:00 am-4:48 pm

1 stop10h 48m

The Valley Wallblake Intl

Tue 1/12

3:03 pm-11:05 pm

1 stop9h 02m

$712

BostonThe Valley

BOS Boston Logan Intl - AXA The Valley Wallblake Intl

BOSAXA

Boston Logan Intl

Sun 1/24

6:17 pm-2:23 pm

1 stop19h 06m

The Valley Wallblake Intl

Thu 1/28

5:06 pm-10:01 am

1 stop17h 55m

$712

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

3:30 pm-7:50 pm

2 stops29h 20m

$822

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

3:30 pm-7:50 pm

2 stops29h 20m

$830

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

$833

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Anguilla from

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

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 $561.

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 $584. The most expensive day to fly to Anguilla is Friday, with ticket prices averaging around $992.

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 $818 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 $560 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

$725

Fastest flight time

4h 40m

Direct flights

Tue and Sat

Airports in Anguilla

2 airports
The best flight deal from Massachusetts to Anguilla found on momondo in the last 72 hours is $725
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?

  • 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?

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
BermudAirPriceFrom $457Free CancellationRating
0.0
0 reviews
Search BermudAir flights
American AirlinesPriceFrom $658Free CancellationRating
7.1
11,927 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.

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