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Cheap flights from Massachusetts to Anguilla from $271

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 2/21. 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
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.
American Airlines Logo
8:45 am - 4:17 pm
BOS
-
AXA
7h 32m
1 stop
American Airlines Logo
4:57 pm - 12:59 am
AXA
-
BOS
8h 02m
1 stop
$548American Airlines
Tue, May 5 - Tue, May 19
American Airlines Logo
5:09 pm - 1:15 pm
BOS
-
AXA
20h 06m
2 stops
American Airlines Logo
4:57 pm - 10:01 am
AXA
-
BOS
17h 04m
2 stops
$553American Airlines
Sat, May 2 - Wed, May 6
American Airlines Logo
12:44 pm - 4:17 pm
BOS
-
AXA
27h 33m
1 stop
American Airlines Logo
4:57 pm - 10:02 am
AXA
-
BOS
17h 05m
1 stop
$561American Airlines
Sat, May 2 - Wed, May 6
American Airlines Logo
5:05 am - 1:11 pm
BOS
-
AXA
8h 06m
1 stop
American Airlines Logo
4:41 pm - 12:59 am
AXA
-
BOS
8h 18m
1 stop
$571American Airlines
Sun, May 31 - Fri, Jun 5
American Airlines Logo
6:34 am - 4:01 pm
BOS
-
AXA
9h 27m
1 stop
American Airlines Logo
4:41 pm - 10:27 am
AXA
-
BOS
17h 46m
2 stops
$576American Airlines
Sun, May 31 - Fri, Jun 5
American Airlines Logo
7:00 am - 4:28 pm
BOS
-
AXA
8h 28m
1 stop
American Airlines Logo
4:09 pm - 12:59 am
AXA
-
BOS
8h 50m
1 stop
$578American Airlines
Tue, Feb 24 - Tue, Mar 10
American Airlines Logo
7:50 pm - 4:28 pm
BOS
-
AXA
19h 38m
2 stops
American Airlines Logo
4:09 pm - 12:59 am
AXA
-
BOS
8h 50m
1 stop
$583American Airlines
Tue, Feb 24 - Tue, Mar 10
American Airlines Logo
5:40 am - 4:17 pm
BOS
-
AXA
10h 37m
2 stops
American Airlines Logo
1:55 pm - 9:21 am
AXA
-
BOS
19h 26m
2 stops
$588American Airlines
Wed, May 6 - Sun, May 10
American Airlines Logo
6:00 am - 3:29 pm
BOS
-
AXA
9h 29m
1 stop
American Airlines Logo
4:09 pm - 10:01 am
AXA
-
BOS
17h 52m
1 stop
$594American Airlines
Wed, Mar 25 - Tue, Mar 31
American Airlines Logo
6:25 pm - 2:30 pm
BOS
-
AXA
19h 05m
1 stop
American Airlines Logo
5:10 pm - 10:01 am
AXA
-
BOS
17h 51m
1 stop
$596American Airlines
Mon, Feb 16 - Thu, Feb 19

American Airlines flights from Massachusetts to Anguilla

Our best American Airlines deals on Massachusetts to Anguilla flight tickets
American Airlines
Feb 10
BOS6:49 amBoston Logan Intl
8h 37m
1 stop
AXA4:26 pmThe Valley Wallblake Intl
Feb 17
AXA5:10 pmThe Valley Wallblake Intl
8h 49m
1 stop
BOS12:59 amBoston Logan Intl
$542
American Airlines
Feb 10
BOS5:45 pmBoston Logan Intl
19h 38m
2 stops
AXA2:23 pmThe Valley Wallblake Intl
Feb 17
AXA5:10 pmThe Valley Wallblake Intl
15h 37m
2 stops
BOS7:47 amBoston Logan Intl
$547
American Airlines
May 5
BOS8:45 amBoston Logan Intl
7h 32m
1 stop
AXA4:17 pmThe Valley Wallblake Intl
May 19
AXA4:57 pmThe Valley Wallblake Intl
8h 02m
1 stop
BOS12:59 amBoston Logan Intl
$548

BermudAir flights from Massachusetts to Anguilla

Our best BermudAir deals on Massachusetts to Anguilla flight tickets
BermudAir
Feb 7
BOS10:20 amBoston Logan Intl
4h 40m
AXA4:00 pmThe Valley Wallblake Intl
Feb 14
AXA5:05 pmThe Valley Wallblake Intl
4h 45m
BOS8:50 pmBoston Logan Intl
$623
BermudAir
Feb 28
BOS10:20 amBoston Logan Intl
4h 40m
AXA4:00 pmThe Valley Wallblake Intl
Mar 7
AXA5:05 pmThe Valley Wallblake Intl
4h 45m
BOS8:50 pmBoston Logan Intl
$638
BermudAir
Mar 14
BOS10:20 amBoston Logan Intl
4h 40m
AXA3:00 pmThe Valley Wallblake Intl
Mar 18
AXA4:05 pmThe Valley Wallblake Intl
4h 45m
BOS8:50 pmBoston Logan Intl
$639

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 February 5, 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

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Tue 5/5

8:45 am-4:17 pm

1 stop7h 32m

The Valley Wallblake Intl

Tue 5/19

4:57 pm-12:59 am

1 stop8h 02m

$548

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Sat 5/2

5:09 pm-1:15 pm

2 stops20h 06m

The Valley Wallblake Intl

Wed 5/6

4:57 pm-10:01 am

2 stops17h 04m

$553

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Sat 5/2

12:44 pm-4:17 pm

1 stop27h 33m

The Valley Wallblake Intl

Wed 5/6

4:57 pm-10:02 am

1 stop17h 05m

$561

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Sun 5/31

5:05 am-1:11 pm

1 stop8h 06m

The Valley Wallblake Intl

Fri 6/5

4:41 pm-12:59 am

1 stop8h 18m

$571

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Sun 5/31

6:34 am-4:01 pm

1 stop9h 27m

The Valley Wallblake Intl

Fri 6/5

4:41 pm-10:27 am

2 stops17h 46m

$576

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Tue 2/24

7:00 am-4:28 pm

1 stop8h 28m

The Valley Wallblake Intl

Tue 3/10

4:09 pm-12:59 am

1 stop8h 50m

$578

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Tue 2/24

7:50 pm-4:28 pm

2 stops19h 38m

The Valley Wallblake Intl

Tue 3/10

4:09 pm-12:59 am

1 stop8h 50m

$583

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Wed 5/6

5:40 am-4:17 pm

2 stops10h 37m

The Valley Wallblake Intl

Sun 5/10

1:55 pm-9:21 am

2 stops19h 26m

$588

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Wed 3/25

6:00 am-3:29 pm

1 stop9h 29m

The Valley Wallblake Intl

Tue 3/31

4:09 pm-10:01 am

1 stop17h 52m

$594

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Mon 2/16

6:25 pm-2:30 pm

1 stop19h 05m

The Valley Wallblake Intl

Thu 2/19

5:10 pm-10:01 am

1 stop17h 51m

$596

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 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 $561. The most expensive day to fly to Anguilla is Saturday, with ticket prices averaging around $590.

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 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 $765 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 $556 on momondo.

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

There are 2 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?

You could potentially save up to 30% on your flight if you consider stops on a Massachusetts to Anguilla flight.

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

$330

Fastest flight time

4h 40m

Direct flights

Thu and Sun

Airports in Anguilla

2 airports
The best one-way flight to Anguilla from Massachusetts in the past 72 hours is $330. The best round-trip flight deal from Massachusetts to Anguilla found on momondo in the last 72 hours is $669.
The fastest flight from Massachusetts to Anguilla takes 4h 40m
Direct flights go from Massachusetts to Anguilla on Thursday and Sunday. The only airline offering direct flights is BermudAir.
There are 2 airports in Anguilla. From Massachusetts there are direct flights to The Valley Wallblake Intl (AXA).
Search flight deals

  • 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 $622Free CancellationRating
7.2
11,229 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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