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Cheap flights from Massachusetts to Anguilla from $259

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 3/7. 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
6:50 am - 4:26 pm
BOS
-
AXA
8h 36m1 stop
American Airlines Logo
5:06 pm - 10:01 am
AXA
-
BOS
17h 55m1 stop
$478American Airlines
Mon, Jan 12 - Wed, Jan 21
American Airlines Logo
5:15 am - 4:26 pm
BOS
-
AXA
10h 11m1 stop
American Airlines Logo
5:24 pm - 9:49 am
AXA
-
BOS
17h 25m1 stop
$485American Airlines
Tue, Feb 10 - Tue, Feb 17
American Airlines Logo
6:00 am - 4:26 pm
BOS
-
AXA
9h 26m2 stops
American Airlines Logo
5:24 pm - 9:49 am
AXA
-
BOS
17h 25m1 stop
$490American Airlines
Tue, Feb 10 - Tue, Feb 17
American Airlines Logo
6:17 pm - 2:23 pm
BOS
-
AXA
19h 06m1 stop
American Airlines Logo
5:06 pm - 10:01 am
AXA
-
BOS
17h 55m1 stop
$515American Airlines
Sat, Jan 24 - Sat, Jan 31
American Airlines Logo
7:17 pm - 2:23 pm
BOS
-
AXA
18h 06m2 stops
American Airlines Logo
5:06 pm - 12:59 am
AXA
-
BOS
8h 53m1 stop
$517American Airlines
Mon, Jan 5 - Tue, Jan 13
American Airlines Logo
8:51 pm - 2:23 pm
BOS
-
AXA
16h 32m2 stops
American Airlines Logo
5:06 pm - 12:59 am
AXA
-
BOS
8h 53m1 stop
$518American Airlines
Mon, Jan 12 - Wed, Jan 21
American Airlines Logo
8:47 pm - 4:26 pm
BOS
-
AXA
18h 39m2 stops
American Airlines Logo
5:06 pm - 8:41 am
AXA
-
BOS
16h 35m2 stops
$520American Airlines
Sat, Jan 24 - Sat, Jan 31
BermudAir Logo
10:20 am - 4:00 pm
BOS
-
AXA
4h 40mnonstop
BermudAir Logo
5:05 pm - 8:50 pm
AXA
-
BOS
4h 45mnonstop
$523BermudAir
Wed, Dec 31 - Wed, Jan 7
American Airlines Logo
6:17 pm - 4:44 pm
BOS
-
AXA
21h 27m1 stop
American Airlines Logo
5:24 pm - 9:49 am
AXA
-
BOS
17h 25m1 stop
$527American Airlines
Sat, Feb 21 - Sat, Feb 28
American Airlines Logo
5:00 am - 2:19 pm
BOS
-
AXA
8h 19m1 stop
American Airlines Logo
4:18 pm - 12:59 am
AXA
-
BOS
8h 41m1 stop
$529American Airlines
Tue, Feb 24 - Tue, Mar 10

BermudAir flights from Massachusetts to Anguilla

Our best BermudAir deals on Massachusetts to Anguilla flight tickets
BermudAir
Dec 31
BOS10:20 amBoston Logan Intl
4h 40m
AXA4:00 pmThe Valley Wallblake Intl
Jan 7
AXA5:05 pmThe Valley Wallblake Intl
4h 45m
BOS8:50 pmBoston Logan Intl
$523
Find similar
BermudAir
Mar 14
BOS10:20 amBoston Logan Intl
4h 40m
AXA3:00 pmThe Valley Wallblake Intl
Mar 21
AXA4:05 pmThe Valley Wallblake Intl
4h 45m
BOS8:50 pmBoston Logan Intl
$531
Find similar
BermudAir
Jan 7
BOS10:20 amBoston Logan Intl
4h 40m
AXA4:00 pmThe Valley Wallblake Intl
Jan 14
AXA5:05 pmThe Valley Wallblake Intl
4h 45m
BOS8:50 pmBoston Logan Intl
$551
Find similar

United Airlines flights from Massachusetts to Anguilla

Our best United Airlines deals on Massachusetts to Anguilla flight tickets
United Airlines
Feb 9
BDL6:00 amHartford Bradley Intl
10h 45m
2 stops
AXA5:45 pmThe Valley Wallblake Intl
Feb 13
AXA9:00 amThe Valley Wallblake Intl
16h 07m
2 stops
BDL12:07 amHartford Bradley Intl
$1,567
Find similar
United Airlines
Apr 25
BDL6:15 amHartford Bradley Intl
35h 30m
2 stops
AXA5:45 pmThe Valley Wallblake Intl
May 2
AXA9:00 amThe Valley Wallblake Intl
30h 38m
3 stops
BDL3:38 pmHartford Bradley Intl
$1,608
Find similar
United Airlines
Apr 25
BDL6:15 amHartford Bradley Intl
35h 30m
2 stops
AXA5:45 pmThe Valley Wallblake Intl
May 2
AXA9:00 amThe Valley Wallblake Intl
30h 38m
3 stops
BDL3:38 pmHartford Bradley Intl
$1,640
Find similar

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 December 18, 2025.
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

Mon 1/12

6:50 am-4:26 pm

1 stop8h 36m

The Valley Wallblake Intl

Wed 1/21

5:06 pm-10:01 am

1 stop17h 55m

$478

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Tue 2/10

5:15 am-4:26 pm

1 stop10h 11m

The Valley Wallblake Intl

Tue 2/17

5:24 pm-9:49 am

1 stop17h 25m

$485

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Tue 2/10

6:00 am-4:26 pm

2 stops9h 26m

The Valley Wallblake Intl

Tue 2/17

5:24 pm-9:49 am

1 stop17h 25m

$490

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Sat 1/24

6:17 pm-2:23 pm

1 stop19h 06m

The Valley Wallblake Intl

Sat 1/31

5:06 pm-10:01 am

1 stop17h 55m

$515

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Mon 1/5

7:17 pm-2:23 pm

2 stops18h 06m

The Valley Wallblake Intl

Tue 1/13

5:06 pm-12:59 am

1 stop8h 53m

$517

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Mon 1/12

8:51 pm-2:23 pm

2 stops16h 32m

The Valley Wallblake Intl

Wed 1/21

5:06 pm-12:59 am

1 stop8h 53m

$518

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Sat 1/24

8:47 pm-4:26 pm

2 stops18h 39m

The Valley Wallblake Intl

Sat 1/31

5:06 pm-8:41 am

2 stops16h 35m

$520

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Wed 12/31

10:20 am-4:00 pm

Nonstop4h 40m

The Valley Wallblake Intl

Wed 1/7

5:05 pm-8:50 pm

Nonstop4h 45m

$523

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Sat 2/21

6:17 pm-4:44 pm

1 stop21h 27m

The Valley Wallblake Intl

Sat 2/28

5:24 pm-9:49 am

1 stop17h 25m

$527

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Tue 2/24

5:00 am-2:19 pm

1 stop8h 19m

The Valley Wallblake Intl

Tue 3/10

4:18 pm-12:59 am

1 stop8h 41m

$529

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 $547. The most expensive day to fly to Anguilla is Friday, with ticket prices averaging around $870.

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

Flying to Anguilla from Massachusetts in the morning is the least expensive time of day to depart. momondo users have found prices as low as $551 when looking at flights departing in the morning. Flights in the evening are often more expensive with an average ticket price of $799.

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 $759 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 $583 on momondo.

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

There is only 1 cabin class 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

$299

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 $299. The best round-trip flight deal from Massachusetts to Anguilla found on momondo in the last 72 hours is $506.
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 $450Free CancellationRating
0.0
0 reviews
Search BermudAir flights
American AirlinesPriceFrom $627Free CancellationRating
7.2
11,054 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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Popular flights according to clicks in the last 7 days on momondo
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