$491+ 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 12/27. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — AXA
Aug 5 — Aug 121
1 adult, Economy
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1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.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 July 31, 2025.
Round-trip from | $573 (American Airlines) |
|---|---|
One-way from | $491 (American Airlines) |
Popular in | August |
Cheapest in | October |
Average price | $660 |
Good round-trip deal | $528 or less |
Find flight deals from Massachusetts to Anguilla
Cheapest flights from Massachusetts to AnguillaExplore 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 July 31, 2025.
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 July 31, 2025.
This American Airlines deal was found by Cheapflights users on 7/30. 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 12/117:28 amBOS - AXA
1 stop7h 47mAmerican Airlines
Tue 12/163:25 pmAXA - BOS
1 stop8h 36mAmerican Airlines
Deal found 7/30![American Airlines logo]()
$598
This American Airlines deal was found by Cheapflights users on 7/30. 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 11/295:40 amBDL - AXA
1 stop9h 45mAmerican Airlines
Sat 12/61:00 pmAXA - BDL
1 stop10h 57mAmerican Airlines
Deal found 7/30![American Airlines logo]()
$623
This Booking.com deal was found by Cheapflights users on 7/31. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2710:05 amBOS - AXA
Nonstop5h 00mBermudAir
Sat 1/35:05 pmAXA - BOS
Nonstop4h 50mBermudAir
Deal found 7/31![BermudAir logo]()
$946
This United deal was found by Cheapflights users on 7/31. 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.
Sat 8/235:30 amBOS - AXA
2 stops11h 45mMultiple Airlines
Sat 8/309:35 amAXA - BOS
2 stops9h 12mMultiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$1,117
This United Airlines deal was found by Cheapflights users on 7/31. 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.
Fri 12/195:20 amBOS - AXA
2 stops11h 15mUnited Airlines
Fri 12/269:46 amAXA - BOS
3 stops14h 13mUnited Airlines
Deal found 7/31![United Airlines logo]()
$1,944
Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated July 31, 2025.
Use the filters below to find and compare flights from Massachusetts to Anguilla that are best for you.
Fly from
Massachusetts
Fly to
Anguilla
Route
Depart
Return
Price
BostonThe Valley
BOS - AXA
BOSAXA
Boston Logan Intl
Mon 1/12
5:24 am-2:15 pm
1 stop7h 51m
The Valley Wallblake Intl
Thu 1/15
5:25 pm-12:55 am
1 stop8h 30m
$573
HartfordThe Valley
BDL - AXA
BDLAXA
Hartford Bradley Intl
Sat 11/29
5:40 am-4:25 pm
1 stop9h 45m
The Valley Wallblake Intl
Sat 12/6
1:00 pm-10:57 pm
1 stop10h 57m
$623
BostonThe Valley
BOS - AXA
BOSAXA
Boston Logan Intl
Sat 12/27
10:05 am-4:05 pm
Nonstop5h 00m
The Valley Wallblake Intl
Sat 1/3
5:05 pm-8:55 pm
Nonstop4h 50m
$946
BostonThe Valley
BOS - AXA
BOSAXA
Boston Logan Intl
Sat 8/23
5:30 am-5:15 pm
2 stops11h 45m
The Valley Wallblake Intl
Sat 8/30
9:35 am-6:47 pm
2 stops9h 12m
$1,117
BostonThe Valley
BOS - AXA
BOSAXA
Boston Logan Intl
Fri 12/19
5:20 am-5:35 pm
2 stops11h 15m
The Valley Wallblake Intl
Fri 12/26
9:46 am-10:59 pm
3 stops14h 13m
$1,944
BostonThe Valley
BOS - AXA
BOSAXA
Boston Logan Intl
Sat 12/27
6:46 pm-2:05 pm
2 stops18h 19m
$491
BostonThe Valley
BOS - AXA
BOSAXA
Boston Logan Intl
Sat 12/27
10:05 am-4:05 pm
Nonstop5h 00m
$501
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.
Cheapflights Insights
Everything you need to know about your flight from Massachusetts to Anguilla
No data available for this route at this time. Please check back soon.
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 July 31, 2025.
Read reviews from past customers who have flown United Airlines and American Airlines from Massachusetts to Anguilla. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
6.6
Overall
7.4
Crew
8.1
Boarding
7.7
Entertainment
7.1
Comfort
7.3
Reviews
1 / 20
4.0
OkayThomas,Mar 2025
SFO - TPE
Food
6.6
Overall
7.4
Crew
8.1
Boarding
7.7
Entertainment
7.1
Comfort
7.3
Reviews
1 / 20
4.0
OkayThomas,Mar 2025
SFO - TPE
Food
6.6
Overall
7.4
Crew
8.1
Boarding
7.7
Entertainment
7.1
Comfort
7.3
Reviews
1 / 20
4.0
OkayThomas,Mar 2025
SFO - TPE
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.
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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 July 31, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$630 | Average$789 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$635 | Average$762 | FlexibilityNo cancel fee | On-time71% |