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Anguilla

$284+ Cheap flights from Boston (BOS) to Anguilla

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/23. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — AXA
Feb 14 — Feb 211
Sat 2/14
Sat 2/21
1 adult, Economy
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Cheap flight deals from Boston to Anguilla

Keep the following information in mind while searching for Boston to Anguilla flight deals. Data was last updated January 15, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$586
(American Airlines)

One-way from

$284
(Kiwi.com)

Popular in

August

Cheapest in

December

Average price

$587

Good round-trip deal

$557 or less
Provider with most accurate pricing for Boston Logan Intl-The Valley Wallblake Intl flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-The Valley Wallblake Intl flights.
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From Boston Logan Intl to Anguilla
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One-way flight from Boston Logan Intl to Anguilla
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Highest demand for flights based on searches. 28% potential increase in price ($306 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($68 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Price to beat on a round-trip flight from Boston Logan Intl to Anguilla.
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Find flight deals from Boston to Anguilla

Cheapest flights from Boston to Anguilla
Explore the most affordable flight options available from Boston to Anguilla. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 15, 2026.

This American Airlines deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/96:00 am
BOS
-
AXA
1 stop9h 28m
American Airlines
Tue 3/174:08 pm
AXA
-
BOS
2 stops15h 39m
American Airlines
Deal found 1/13$586
This American Airlines deal was found by Cheapflights users on 1/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/175:00 am
BOS
-
AXA
1 stop8h 30m
American Airlines
Wed 3/254:08 pm
AXA
-
BOS
1 stop8h 51m
American Airlines
Deal found 1/15$594
This American Airlines deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/25:40 pm
BOS
-
AXA
2 stops19h 35m
American Airlines
Thu 5/74:57 pm
AXA
-
BOS
1 stop8h 02m
American Airlines
Deal found 1/14$599
This American Airlines deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:22 pm
BOS
-
AXA
1 stop21h 55m
American Airlines
Wed 5/61:55 pm
AXA
-
BOS
1 stop9h 12m
American Airlines
Deal found 1/14$608
This American Airlines deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:00 am
BOS
-
AXA
1 stop9h 28m
American Airlines
Mon 3/164:08 pm
AXA
-
BOS
1 stop17h 54m
American Airlines
Deal found 1/14$619
This American Airlines deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/248:30 pm
BOS
-
AXA
2 stops18h 58m
American Airlines
Tue 3/104:08 pm
AXA
-
BOS
1 stop8h 51m
American Airlines
Deal found 1/14$629
This American Airlines deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/61:17 pm
BOS
-
AXA
1 stop23h 48m
American Airlines
Sat 10/172:35 pm
AXA
-
BOS
1 stop9h 59m
American Airlines
Deal found 1/14$633
This American Airlines deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/412:44 pm
BOS
-
AXA
1 stop24h 46m
American Airlines
Wed 3/114:08 pm
AXA
-
BOS
1 stop17h 53m
American Airlines
Deal found 1/14$634
This American Airlines deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/284:32 pm
BOS
-
AXA
1 stop20h 58m
American Airlines
Thu 3/53:10 pm
AXA
-
BOS
1 stop10h 49m
American Airlines
Deal found 1/14$640
This American Airlines deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/195:00 am
BOS
-
AXA
1 stop8h 30m
American Airlines
Mon 3/234:08 pm
AXA
-
BOS
1 stop8h 51m
American Airlines
Deal found 1/14$644

Cheapflights Fare Finder

 
Customize your flight search to find flights from Boston 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, Cheapflights users made 2,558,603 searches. Data last updated January 15, 2026.
Use the filters below to find and compare flights from Boston to Anguilla that are best for you.

Fly from

Boston

Fly to

Anguilla

Route

Depart

Return

Price

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Sat 5/2

6:53 pm-1:15 pm

2 stops18h 22m

The Valley Wallblake Intl

Wed 5/6

4:57 pm-10:01 am

2 stops17h 04m

$599

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Wed 3/11

6:00 am-3:28 pm

2 stops9h 28m

The Valley Wallblake Intl

Mon 3/16

4:08 pm-8:44 am

2 stops16h 36m

$624

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Fri 3/6

5:49 am-4:28 pm

2 stops9h 39m

The Valley Wallblake Intl

Fri 3/13

4:08 pm-10:47 am

2 stops18h 39m

$624

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Wed 3/4

6:54 pm-2:30 pm

2 stops18h 36m

The Valley Wallblake Intl

Wed 3/11

4:08 pm-10:01 am

1 stop17h 53m

$624

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Tue 2/24

5:49 am-4:28 pm

2 stops9h 39m

The Valley Wallblake Intl

Tue 3/10

4:08 pm-9:29 am

2 stops17h 21m

$629

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Wed 2/25

6:00 am-4:28 pm

2 stops9h 28m

The Valley Wallblake Intl

Wed 3/4

5:10 pm-7:47 am

2 stops15h 37m

$629

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Sat 2/28

4:32 pm-2:30 pm

1 stop20h 58m

The Valley Wallblake Intl

Thu 3/5

3:10 pm-12:59 am

1 stop10h 49m

$640

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Sat 3/14

10:20 am-3:00 pm

Nonstop4h 40m

The Valley Wallblake Intl

Sat 3/21

4:05 pm-8:50 pm

Nonstop4h 45m

$670

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Tue 2/24

6:00 am-4:28 pm

1 stop9h 28m

The Valley Wallblake Intl

Sat 2/28

5:10 pm-10:01 am

1 stop17h 51m

$679

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Mon 3/23

5:49 pm-3:40 pm

2 stops21h 51m

$284

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/14

Showing 1-10 of 19 results
1
2

Best time to book a flight from Boston to Anguilla

Have a flexible travel schedule? Discover the best time to fly to Anguilla from Boston with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Boston to Anguilla

What is the cheapest time of day to fly from BOS to AI?

Find hourly flight availability from Boston to Anguilla. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 15, 2026.

When flying from Boston to Anguilla, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Anguilla

Get insights into the airlines that provide service to Anguilla. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Anguilla. Reviews last updated January 15, 2026.
Get a feel of what it's like to fly with American Airlines from Boston to Anguilla by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,132 reviews

Entertainment

6.9

Boarding

7.5

Comfort

7.2

Crew

8.0

Overall

7.2

Food

6.4

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.
American Airlines
7.2
Good
11,132 reviews
American Airlines
7.2
Good
11,132 reviews

Entertainment

6.9

Boarding

7.5

Comfort

7.2

Crew

8.0

Overall

7.2

Food

6.4

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.

Related info for your journey

Find useful and relevant information for your journey from Boston to Anguilla. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Boston to Anguilla?

    For a flight from Boston to Anguilla, you will be flying from Logan Intl. Boston Logan Intl (BOS) is just 2.6 mi from the center of the city.

  • How long is the flight from Boston to Anguilla?

    There are many flights that can get you from Boston to Anguilla in 9h 28m. Fly via American Airlines to get the fastest option. Airlines will cover a distance of 1732 mi.

  • What are the cheapest flights from Boston to Anguilla?

    Looking at all options, your cheapest flight can be booked for $548. While the most popular route (Boston Logan Intl - The Valley Wallblake Intl) can be booked for $594 on average, our data indicates $634 when flying from Boston to Anguilla.

  • Can I find deals for flights from Boston to Anguilla that include hotel bookings?

    Yes. In addition to deals on Boston to Anguilla flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Boston to Anguilla?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to Anguilla.

  • Can I find deals for business class flights from Boston to Anguilla?

    Yes. Cheapflights offers flight deals from Boston to Anguilla by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Alternative routes for Boston to Anguilla

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Top 2 airlines flying from Boston to Anguilla

Discover the top 2 airlines that operate flights from Boston to Anguilla. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
BermudAirCheapest$457Average$564FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$627Average$764FlexibilityNo cancel feeOn-time71%

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