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Cheap flights from Massachusetts to Anguilla from $294

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 4/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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
8:00 am - 5:01 pmBOS-AXA
8h 01m1 stop
American Airlines Logo
3:03 pm - 11:08 pmAXA-BOS
9h 05m1 stop
$469American Airlines
Find Deal
Thu, Nov 27 - Wed, Dec 3
American Airlines Logo
5:34 am - 2:23 pmBOS-AXA
7h 49m1 stop
American Airlines Logo
1:20 pm - 11:08 pmAXA-BOS
10h 48m1 stop
$479American Airlines
Find Deal
Wed, Dec 3 - Sat, Dec 6
American Airlines Logo
6:00 am - 4:40 pmBOS-AXA
9h 40m2 stops
American Airlines Logo
1:20 pm - 12:59 amAXA-BOS
12h 39m1 stop
$484American Airlines
Find Deal
Wed, Dec 3 - Sat, Dec 6
BermudAir Logo
10:20 am - 3:00 pmBOS-AXA
4h 40mnonstop
BermudAir Logo
4:05 pm - 8:50 pmAXA-BOS
4h 45mnonstop
$526BermudAir
Find Deal
Sat, Mar 28 - Wed, Apr 1
BermudAir Logo
10:20 am - 4:00 pmBOS-AXA
4h 40mnonstop
BermudAir Logo
4:05 pm - 8:50 pmAXA-BOS
4h 45mnonstop
$551BermudAir
Find Deal
Wed, Mar 4 - Wed, Mar 11
American Airlines Logo
6:00 am - 2:31 pmBOS-AXA
31h 31m2 stops
American Airlines Logo
3:03 pm - 12:15 amAXA-BOS
10h 12m2 stops
$557American Airlines
Find Deal
Thu, Nov 27 - Wed, Dec 3
Multiple Airlines Logo
10:20 am - 4:00 pmBOS-AXA
4h 40mnonstop
Multiple Airlines Logo
2:45 pm - 1:04 amAXA-BOS
35h 19m3 stops
$713Multiple Airlines
Find Deal
Wed, Jan 14 - Fri, Jan 23
Multiple Airlines Logo
10:20 am - 4:00 pmBOS-AXA
4h 40mnonstop
Multiple Airlines Logo
2:45 pm - 12:40 amAXA-BOS
10h 55m2 stops
$716Multiple Airlines
Find Deal
Wed, Jan 14 - Wed, Jan 21
United Airlines Logo
6:00 am - 5:45 pmBDL-AXA
11h 45m2 stops
United Airlines Logo
9:00 am - 5:24 pmAXA-BDL
32h 24m3 stops
$1,712United Airlines
Find Deal
Sat, Apr 25 - Sat, May 2
United Airlines Logo
6:30 pm - 5:45 pmBDL-AXA
47h 15m2 stops
United Airlines Logo
9:00 am - 5:24 pmAXA-BDL
32h 24m2 stops
$1,868United Airlines
Find Deal
Sat, Apr 11 - Sat, Apr 18

United Airlines flights from Massachusetts to Anguilla

Our best United Airlines deals on Massachusetts to Anguilla flight tickets
United Airlines
Nov 7
BOS3:37 pmBoston Logan Intl
25h 08m
2 stops
AXA5:45 pmThe Valley Wallblake Intl
Nov 10
AXA9:00 amThe Valley Wallblake Intl
14h 42m
2 stops
BOS10:42 pmBoston Logan Intl
$1,342
Find similar
United Airlines
Nov 7
BOS3:37 pmBoston Logan Intl
25h 08m
2 stops
AXA5:45 pmThe Valley Wallblake Intl
Nov 13
AXA9:00 amThe Valley Wallblake Intl
15h 42m
2 stops
BOS11:42 pmBoston Logan Intl
$1,349
Find similar
United Airlines
Nov 10
BOS5:30 amBoston Logan Intl
11h 15m
2 stops
AXA5:45 pmThe Valley Wallblake Intl
Nov 13
AXA9:00 amThe Valley Wallblake Intl
15h 42m
2 stops
BOS11:42 pmBoston Logan Intl
$1,457
Find similar

American Airlines flights from Massachusetts to Anguilla

Our best American Airlines deals on Massachusetts to Anguilla flight tickets
American Airlines
Nov 27
BOS8:00 amBoston Logan Intl
8h 01m
1 stop
AXA5:01 pmThe Valley Wallblake Intl
Dec 3
AXA3:03 pmThe Valley Wallblake Intl
9h 05m
1 stop
BOS11:08 pmBoston Logan Intl
$469
Find similar
American Airlines
Dec 3
BOS5:34 amBoston Logan Intl
7h 49m
1 stop
AXA2:23 pmThe Valley Wallblake Intl
Dec 6
AXA1:20 pmThe Valley Wallblake Intl
10h 48m
1 stop
BOS11:08 pmBoston Logan Intl
$479
Find similar
American Airlines
Dec 3
BOS6:00 amBoston Logan Intl
9h 40m
2 stops
AXA4:40 pmThe Valley Wallblake Intl
Dec 6
AXA1:20 pmThe Valley Wallblake Intl
12h 39m
1 stop
BOS12:59 amBoston Logan Intl
$484
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 November 3, 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

Thu 11/27

8:00 am-5:01 pm

1 stop8h 01m

The Valley Wallblake Intl

Wed 12/3

3:03 pm-11:08 pm

1 stop9h 05m

$469

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Wed 12/3

5:34 am-2:23 pm

1 stop7h 49m

The Valley Wallblake Intl

Sat 12/6

1:20 pm-11:08 pm

1 stop10h 48m

$479

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Wed 12/3

6:00 am-4:40 pm

2 stops9h 40m

The Valley Wallblake Intl

Sat 12/6

1:20 pm-12:59 am

1 stop12h 39m

$484

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Sat 3/28

10:20 am-3:00 pm

Nonstop4h 40m

The Valley Wallblake Intl

Wed 4/1

4:05 pm-8:50 pm

Nonstop4h 45m

$526

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Wed 3/4

10:20 am-4:00 pm

Nonstop4h 40m

The Valley Wallblake Intl

Wed 3/11

4:05 pm-8:50 pm

Nonstop4h 45m

$551

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Thu 11/27

6:00 am-2:31 pm

2 stops31h 31m

The Valley Wallblake Intl

Wed 12/3

3:03 pm-12:15 am

2 stops10h 12m

$557

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Wed 1/14

10:20 am-4:00 pm

Nonstop4h 40m

The Valley Wallblake Intl

Fri 1/23

2:45 pm-1:04 am

3 stops35h 19m

$713

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Wed 1/14

10:20 am-4:00 pm

Nonstop4h 40m

The Valley Wallblake Intl

Wed 1/21

2:45 pm-12:40 am

2 stops10h 55m

$716

HartfordThe Valley

BDL - AXA

BDLAXA

Hartford Bradley Intl

Sat 4/25

6:00 am-5:45 pm

2 stops11h 45m

The Valley Wallblake Intl

Sat 5/2

9:00 am-5:24 pm

3 stops32h 24m

$1,712

HartfordThe Valley

BDL - AXA

BDLAXA

Hartford Bradley Intl

Sat 4/11

6:30 pm-5:45 pm

2 stops47h 15m

The Valley Wallblake Intl

Sat 4/18

9:00 am-5:24 pm

2 stops32h 24m

$1,868

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 $620 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 $855 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 $601 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

$347

Fastest flight time

4h 40m

Direct flights

Thu and Sun

Airports in Anguilla

1 airport
The best one-way flight to Anguilla from Massachusetts in the past 72 hours is $347. The best round-trip flight deal from Massachusetts to Anguilla found on momondo in the last 72 hours is $551.
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 is 1 airport near Anguilla: 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 $497Free CancellationRating
0.0
0 reviews
Search BermudAir flights
American AirlinesPriceFrom $632Free CancellationRating
7.2
11,035 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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