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Anguilla

$370+ 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 3/30. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — AXA
Apr 9 — Apr 161
Thu 4/9
Thu 4/16
1 adult, Economy
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Cheap 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 March 10, 2026.

This Gotogate deal was found by Cheapflights users on 3/6. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/410:20 am
BOS
-
AXA
Nonstop4h 40m
BermudAir
Wed 4/84:05 pm
AXA
-
BOS
Nonstop4h 45m
BermudAir
Deal found 3/6$643
This American Airlines deal was found by Cheapflights users on 3/8. 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.
Sun 7/198:00 am
BOS
-
AXA
1 stop8h 19m
American Airlines
Thu 7/234:59 pm
AXA
-
BOS
1 stop8h 00m
American Airlines
Deal found 3/8$644
This American Airlines deal was found by Cheapflights users on 3/6. 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 4/257:32 pm
BOS
-
AXA
2 stops17h 43m
American Airlines
Fri 5/14:57 pm
AXA
-
BOS
2 stops17h 06m
American Airlines
Deal found 3/6$649
This American Airlines deal was found by Cheapflights users on 3/5. 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 4/296:00 am
BOS
-
AXA
2 stops10h 17m
American Airlines
Tue 5/51:55 pm
AXA
-
BOS
1 stop11h 04m
American Airlines
Deal found 3/5$654
This American Airlines deal was found by Cheapflights users on 3/10. 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.
Sun 7/126:00 am
BOS
-
AXA
1 stop10h 19m
American Airlines
Fri 7/174:59 pm
AXA
-
BOS
1 stop17h 08m
American Airlines
Deal found 3/10$664
This American Airlines deal was found by Cheapflights users on 3/9. 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.
Fri 5/18:45 am
BOS
-
AXA
1 stop7h 32m
American Airlines
Wed 5/64:57 pm
AXA
-
BOS
1 stop17h 05m
American Airlines
Deal found 3/9$669
This Mytrip deal was found by Cheapflights users on 3/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/45:45 am
BOS
-
AXA
2 stops9h 25m
Multiple Airlines
Wed 4/84:05 pm
AXA
-
BOS
Nonstop4h 45m
Multiple Airlines
Deal found 3/6$678
This American Airlines deal was found by Cheapflights users on 3/5. 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 4/218:45 am
BOS
-
AXA
1 stop7h 32m
American Airlines
Tue 4/284:57 pm
AXA
-
BOS
2 stops19h 25m
American Airlines
Deal found 3/5$679
This American Airlines deal was found by Cheapflights users on 3/10. 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.
Sun 7/51:45 pm
BOS
-
AXA
1 stop26h 34m
American Airlines
Wed 7/84:59 pm
AXA
-
BOS
1 stop8h 00m
American Airlines
Deal found 3/10$680
This American Airlines deal was found by Cheapflights users on 3/7. 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 5/206:00 am
BOS
-
AXA
2 stops10h 17m
American Airlines
Sun 5/244:49 pm
AXA
-
BOS
2 stops14h 50m
American Airlines
Deal found 3/7$684

Find flight deals from Boston to Anguilla

Keep the following information in mind while searching for Boston to Anguilla flight deals. Data was last updated March 10, 2026.

Round-trip from

$643
(Gotogate)

One-way from

$370
(American Airlines)

Popular in

August

Cheapest in

December

Average price

$691

Good round-trip deal

$668 or less
From Boston Logan Intl to Anguilla
Search Deals
One-way flight from Boston Logan Intl to Anguilla
Search Deals
Highest demand for flights based on searches. 28% potential increase in price ($304 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($68 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip flight from Boston Logan Intl to Anguilla.
Search Deals

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 March 10, 2026.
Use the filters below to find and compare flights from Boston to Anguilla that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Mon 5/4

7:04 pm-1:15 pm

2 stops18h 11m

The Valley Wallblake Intl

Fri 5/8

4:57 pm-10:02 am

1 stop17h 05m

$679

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Sat 6/27

6:57 pm-4:15 pm

2 stops21h 18m

The Valley Wallblake Intl

Wed 7/1

4:55 pm-12:59 am

1 stop8h 04m

$701

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Sat 4/4

5:49 pm-1:10 pm

2 stops43h 21m

The Valley Wallblake Intl

Wed 4/8

4:05 pm-8:50 pm

Nonstop4h 45m

$731

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Sat 5/30

5:22 pm-1:14 pm

2 stops19h 52m

The Valley Wallblake Intl

Sat 6/6

5:02 pm-12:59 am

1 stop7h 57m

$784

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Sat 5/23

6:57 pm-4:05 pm

2 stops21h 08m

The Valley Wallblake Intl

Sat 5/30

5:02 pm-12:59 am

1 stop7h 57m

$834

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Sat 6/6

3:18 pm-4:15 pm

1 stop24h 57m

The Valley Wallblake Intl

Sat 6/13

5:02 pm-9:29 am

2 stops16h 27m

$971

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Thu 6/4

5:00 am-4:15 pm

1 stop11h 15m

The Valley Wallblake Intl

Sat 6/13

5:02 pm-11:16 am

2 stops18h 14m

$979

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Sat 4/18

6:22 pm-4:17 pm

1 stop21h 55m

The Valley Wallblake Intl

Sat 4/25

4:57 pm-12:26 pm

2 stops19h 29m

$1,226
Quickest round-trip

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Sat 3/21

10:20 am-3:00 pm

Nonstop4h 40m

The Valley Wallblake Intl

Sat 3/28

4:05 pm-8:50 pm

Nonstop4h 45m

$1,300

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Tue 4/28

10:07 am-5:45 pm

1 stop7h 38m

The Valley Wallblake Intl

Mon 5/4

9:00 am-10:54 pm

2 stops13h 54m

$1,415

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/7

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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 March 10, 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 March 10, 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
7.1
Good
11,414 reviews

Entertainment

6.9

Food

6.4

Comfort

7.2

Overall

7.1

Crew

7.9

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes
American Airlines
7.1
Good
11,414 reviews
American Airlines
7.1
Good
11,414 reviews

Entertainment

6.9

Food

6.4

Comfort

7.2

Overall

7.1

Crew

7.9

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes

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 18h 11m. 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 $645. While the most popular route (Boston Logan Intl - The Valley Wallblake Intl) can be booked for $644 on average, our data indicates $688 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

Browse thousands of different options on Cheapflights for your next trip

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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 March 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
BermudAirCheapest$457Average$588FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$602Average$738FlexibilityNo cancel feeOn-time71%

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