Anguilla

$361+ Cheap flights from Massachusetts 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — AXA
Feb 28 — Mar 71
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Cheap flight deals from Massachusetts to Anguilla

Keep the following information in mind while searching for Massachusetts to Anguilla flight deals. Data was last updated February 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$670
(Mytrip)

One-way from

$361
(Kiwi.com)

Popular in

December

Cheapest in

May

Average price

$1,030
Provider with most accurate pricing for Boston Logan Intl-The Valley Wallblake Intl flight deals.
Provider most trusted by Cheapflights users for Boston Logan Intl-The Valley Wallblake Intl flights.
From Massachusetts to Anguilla
One-way flight from Massachusetts to Anguilla
Highest demand for flights based on searches. 12% potential increase in price ($114 potential increase over avg. RT price).
Cheapest flight prices on average. 6% potential price decrease ($50 potential savings vs. average RT price).
Average for round-trip flights in February 2025

Find flight deals from Massachusetts to Anguilla

Cheapest flights from Massachusetts to Anguilla
Explore the most affordable flight options available from Massachusetts to Anguilla. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 23, 2025.

This Mytrip deal was found by Cheapflights users on 2/22. 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.
Sun 4/209:05 pmBOS - AXA
2 stops17h 35mMultiple Airlines
Sat 4/2612:45 pmAXA - BOS
3 stops42h 38mMultiple Airlines
Deal found 2/22$670
This American Airlines deal was found by Cheapflights users on 2/23. 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 5/46:00 amBOS - AXA
1 stop9h 15mAmerican Airlines
Thu 5/83:51 pmAXA - BOS
1 stop8h 29mAmerican Airlines
Deal found 2/23$677
This American Airlines deal was found by Cheapflights users on 2/22. 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 5/85:44 amBDL - AXA
1 stop8h 08mAmerican Airlines
Tue 5/132:38 pmAXA - BDL
1 stop8h 36mAmerican Airlines
Deal found 2/22$702
This United Airlines deal was found by Cheapflights users on 2/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/126:00 amBDL - AXA
2 stops11h 35mMultiple Airlines
Mon 5/1910:35 amAXA - BDL
3 stops13h 24mMultiple Airlines
Deal found 2/21$1,269
This United Airlines deal was found by Cheapflights users on 2/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/126:00 amBDL - AXA
2 stops11h 35mUnited Airlines
Tue 5/2010:35 amAXA - BDL
2 stops23h 00mUnited Airlines
Deal found 2/21$1,459
This United deal was found by Cheapflights users on 2/22. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/255:30 amBOS - AXA
2 stops11h 25mUnited Airlines
Tue 7/299:35 amAXA - BOS
3 stops35h 19mUnited Airlines
Deal found 2/22$1,718

Find flights from Massachusetts to Anguilla within your budget

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, Cheapflights users made 2,558,603 searches. Data last updated February 23, 2025.

Fly from

Massachusetts

Fly to

Anguilla

Route

Depart

Return

Price

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Sun 4/20

9:05 pm-2:40 pm

2 stops17h 35m

The Valley Wallblake Intl

Sat 4/26

12:45 pm-7:23 am

3 stops42h 38m

$670

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Sun 5/4

6:00 am-3:15 pm

1 stop9h 15m

The Valley Wallblake Intl

Thu 5/8

3:51 pm-12:20 am

1 stop8h 29m

$677

HartfordThe Valley

BDL - AXA

BDLAXA

Hartford Bradley Intl

Thu 5/8

5:44 am-1:52 pm

1 stop8h 08m

The Valley Wallblake Intl

Tue 5/13

2:38 pm-11:14 pm

1 stop8h 36m

$702

HartfordThe Valley

BDL - AXA

BDLAXA

Hartford Bradley Intl

Mon 5/12

6:00 am-5:35 pm

2 stops11h 35m

The Valley Wallblake Intl

Mon 5/19

10:35 am-11:59 pm

3 stops13h 24m

$1,269

HartfordThe Valley

BDL - AXA

BDLAXA

Hartford Bradley Intl

Mon 5/12

6:00 am-5:35 pm

2 stops11h 35m

The Valley Wallblake Intl

Tue 5/20

10:35 am-9:35 am

2 stops23h 00m

$1,459

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Fri 7/25

5:30 am-4:55 pm

2 stops11h 25m

The Valley Wallblake Intl

Tue 7/29

9:35 am-8:54 pm

3 stops35h 19m

$1,718

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Tue 3/4

4:47 pm-5:10 pm

2 stops23h 23m

$361

BostonThe Valley

BOS - AXA

BOSAXA

Boston Logan Intl

Tue 3/4

5:25 am-4:19 pm

1 stop9h 54m

$487

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

Best time to book a flight from Massachusetts to Anguilla

Have a flexible travel schedule? Discover the best time to fly to Anguilla from Massachusetts 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.

Travel insights for flights from Massachusetts to Anguilla

Get recent, data-driven insights about flights from Massachusetts to Anguilla including ideal travel times, pricing trends, and more.

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

Find hourly flight availability from Massachusetts 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 February 23, 2025.

When flying from Massachusetts 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.

Rainfall in Anguilla by month

Plan your trip to Anguilla by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Anguilla ranges from 1.6 - 4.3 inches per month. August is typically the wettest month, when rainfall can reach 4.3 in. February is typically the driest time to visit Anguilla when rainfall is around 1.6 in.

Temperature in Anguilla by month

Plan your trip to Anguilla by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Anguilla, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 78.8 F).

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 February 23, 2025.
Read reviews from past customers who have flown United Airlines and American Airlines from Massachusetts to Anguilla. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

Entertainment

7.1

Food

6.7

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20

2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Entertainment

7.1

Food

6.7

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20

2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Entertainment

7.1

Food

6.7

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20

2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Anguilla. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • Can I find deals for flights from Massachusetts to Anguilla that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Massachusetts 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.

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Alternative routes for Massachusetts to Anguilla

See prices for flight routes from nearby airports that may be better suited for you.

Top 2 airlines flying from Massachusetts to Anguilla

Discover the top 2 airlines that operate flights from Massachusetts 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 February 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$585Average$792FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$630Average$789FlexibilityNo cancel feeOn-time62%
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