$271+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — AXA
Mar 7 — Mar 141
1 adult, Economy
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Find cheap flights from Massachusetts to Anguilla with Cheapflights
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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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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 February 5, 2026.
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 5, 2026.
This American Airlines deal was found by Cheapflights users on 2/3. 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 2/105:15 am
BOS
- AXA
1 stop8h 08m
American Airlines
Tue 2/175:10 pm
AXA
- BOS
1 stop17h 51m
American Airlines
Deal found 2/3![American Airlines logo]()
$542
This American Airlines deal was found by Cheapflights users on 2/3. 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 5/25:09 pm
BOS
- AXA
2 stops20h 06m
American Airlines
Wed 5/64:57 pm
AXA
- BOS
2 stops17h 42m
American Airlines
Deal found 2/3![American Airlines logo]()
$553
This American Airlines deal was found by Cheapflights users on 2/3. 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 5/315:05 am
BOS
- AXA
1 stop8h 06m
American Airlines
Fri 6/54:41 pm
AXA
- BOS
1 stop8h 18m
American Airlines
Deal found 2/3![American Airlines logo]()
$571
This American Airlines deal was found by Cheapflights users on 2/1. 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 2/85:15 am
BOS
- AXA
1 stop10h 11m
American Airlines
Mon 2/165:10 pm
AXA
- BOS
1 stop8h 49m
American Airlines
Deal found 2/1![American Airlines logo]()
$572
This American Airlines deal was found by Cheapflights users on 2/1. 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 2/85:15 am
BOS
- AXA
1 stop8h 08m
American Airlines
Sun 2/155:10 pm
AXA
- BOS
1 stop17h 51m
American Airlines
Deal found 2/1![American Airlines logo]()
$577
This American Airlines deal was found by Cheapflights users on 2/3. 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 2/247:00 am
BOS
- AXA
1 stop8h 28m
American Airlines
Tue 3/104:09 pm
AXA
- BOS
1 stop8h 50m
American Airlines
Deal found 2/3![American Airlines logo]()
$578
This American Airlines deal was found by Cheapflights users on 2/4. 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 2/116:00 am
BOS
- AXA
2 stops9h 26m
American Airlines
Tue 2/175:10 pm
AXA
- BOS
2 stops18h 10m
American Airlines
Deal found 2/4![American Airlines logo]()
$587
This American Airlines deal was found by Cheapflights users on 2/2. 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 3/256:03 am
BDL
- AXA
2 stops9h 26m
American Airlines
Tue 3/314:09 pm
AXA
- BDL
2 stops22h 42m
American Airlines
Deal found 2/2![American Airlines logo]()
$599
This American Airlines deal was found by Cheapflights users on 2/1. 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 5/65:45 am
BDL
- AXA
1 stop10h 32m
American Airlines
Sun 5/101:55 pm
AXA
- BDL
1 stop10h 04m
American Airlines
Deal found 2/1![American Airlines logo]()
$624
This American Airlines deal was found by Cheapflights users on 2/5. 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.
Thu 4/165:45 am
BDL
- AXA
1 stop10h 32m
American Airlines
Mon 4/201:55 pm
AXA
- BDL
2 stops20h 17m
American Airlines
Deal found 2/5![American Airlines logo]()
$649
This American Airlines deal was found by Cheapflights users on 2/3. 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 4/257:29 pm
BDL
- AXA
2 stops17h 46m
American Airlines
Sat 5/24:57 pm
AXA
- BDL
2 stops17h 15m
American Airlines
Deal found 2/3![American Airlines logo]()
$684
This American Airlines deal was found by Cheapflights users on 2/3. 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 2/255:45 am
BDL
- AXA
1 stop9h 43m
American Airlines
Sat 3/75:10 pm
AXA
- BDL
2 stops15h 22m
American Airlines
Deal found 2/3![American Airlines logo]()
$714
Best flights from Massachusetts to AnguillaDiscover carefully curated flight deals from Massachusetts to Anguilla that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 5, 2026.
Discover carefully curated flight deals from Massachusetts to Anguilla that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 5, 2026.
This American Airlines deal was found by Cheapflights users on 2/4. 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 5/26:40 pm
BOS
- AXA
2 stops18h 35m
American Airlines
Wed 5/64:57 pm
AXA
- BOS
1 stop17h 05m
American Airlines
Deal found 2/4![American Airlines logo]()
$553
This American Airlines deal was found by Cheapflights users on 2/3. 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 5/316:34 am
BOS
- AXA
1 stop9h 27m
American Airlines
Fri 6/54:41 pm
AXA
- BOS
2 stops17h 46m
American Airlines
Deal found 2/3![American Airlines logo]()
$576
This American Airlines deal was found by Cheapflights users on 2/1. 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 2/255:00 am
BOS
- AXA
1 stop10h 28m
American Airlines
Wed 3/45:10 pm
AXA
- BOS
1 stop17h 51m
American Airlines
Deal found 2/1![American Airlines logo]()
$578
This American Airlines deal was found by Cheapflights users on 2/2. 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 2/246:00 am
BOS
- AXA
2 stops9h 28m
American Airlines
Tue 3/104:09 pm
AXA
- BOS
2 stops17h 20m
American Airlines
Deal found 2/2![American Airlines logo]()
$583
This American Airlines deal was found by Cheapflights users on 2/2. 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 3/255:43 am
BDL
- AXA
1 stop9h 46m
American Airlines
Tue 3/314:09 pm
AXA
- BDL
2 stops20h 51m
American Airlines
Deal found 2/2![American Airlines logo]()
$599
This American Airlines deal was found by Cheapflights users on 2/1. 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 5/65:45 am
BDL
- AXA
1 stop10h 32m
American Airlines
Sun 5/101:55 pm
AXA
- BDL
1 stop10h 04m
American Airlines
Deal found 2/1![American Airlines logo]()
$624
This American Airlines deal was found by Cheapflights users on 2/5. 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.
Thu 4/165:45 am
BDL
- AXA
1 stop10h 32m
American Airlines
Mon 4/201:55 pm
AXA
- BDL
2 stops20h 17m
American Airlines
Deal found 2/5![American Airlines logo]()
$649
This American Airlines deal was found by Cheapflights users on 2/2. 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 4/253:06 pm
BDL
- AXA
1 stop25h 11m
American Airlines
Sat 5/24:57 pm
AXA
- BDL
2 stops17h 15m
American Airlines
Deal found 2/2![American Airlines logo]()
$698
Last-minute flights from Massachusetts to AnguillaDiscover last-minute flight deals from Massachusetts to Anguilla. Data last updated February 5, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Anguilla. Data last updated February 5, 2026 and is based on user searches.
This Gotogate deal was found by Cheapflights users on 2/1. 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 2/710:20 am
BOS
- AXA
Nonstop4h 40m
BermudAir
Sat 2/145:05 pm
AXA
- BOS
Nonstop4h 45m
BermudAir
Deal found 2/1![BermudAir logo]()
$623
This American Airlines deal was found by Cheapflights users on 2/1. 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 2/85:15 am
BOS
- AXA
1 stop10h 11m
American Airlines
Mon 2/165:10 pm
AXA
- BOS
1 stop8h 49m
American Airlines
Deal found 2/1![American Airlines logo]()
$572
This American Airlines deal was found by Cheapflights users on 2/1. 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 2/85:15 am
BOS
- AXA
1 stop8h 08m
American Airlines
Sun 2/155:10 pm
AXA
- BOS
1 stop17h 51m
American Airlines
Deal found 2/1![American Airlines logo]()
$577
This American Airlines deal was found by Cheapflights users on 2/3. 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 2/105:15 am
BOS
- AXA
1 stop8h 08m
American Airlines
Tue 2/175:10 pm
AXA
- BOS
1 stop17h 51m
American Airlines
Deal found 2/3![American Airlines logo]()
$542
This American Airlines deal was found by Cheapflights users on 2/4. 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 2/115:15 am
BOS
- AXA
1 stop10h 11m
American Airlines
Tue 2/175:10 pm
AXA
- BOS
2 stops17h 20m
American Airlines
Deal found 2/4![American Airlines logo]()
$587
This American Airlines deal was found by Cheapflights users on 2/5. 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.
Sat 2/145:59 pm
BDL
- AXA
2 stops19h 31m
American Airlines
Sat 2/215:10 pm
AXA
- BDL
2 stops18h 58m
American Airlines
Deal found 2/5![American Airlines logo]()
$969
This American Airlines deal was found by Cheapflights users on 2/3. 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 2/247:00 am
BOS
- AXA
1 stop8h 28m
American Airlines
Tue 3/104:09 pm
AXA
- BOS
1 stop8h 50m
American Airlines
Deal found 2/3![American Airlines logo]()
$578
This American Airlines deal was found by Cheapflights users on 2/3. 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 2/255:28 am
BDL
- AXA
2 stops10h 00m
American Airlines
Sat 3/75:10 pm
AXA
- BDL
2 stops17h 58m
American Airlines
Deal found 2/3![American Airlines logo]()
$714
This American Airlines deal was found by Cheapflights users on 2/2. 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 2/287:51 pm
BOS
- AXA
2 stops19h 37m
American Airlines
Sat 3/75:10 pm
AXA
- BOS
2 stops14h 37m
American Airlines
Deal found 2/2![American Airlines logo]()
$608
This American Airlines deal was found by Cheapflights users on 2/4. 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 stop22h 56m
American Airlines
Mon 3/94:09 pm
AXA
- BOS
1 stop8h 50m
American Airlines
Deal found 2/4![American Airlines logo]()
$616
This American Airlines deal was found by Cheapflights users on 2/2. 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 3/45:45 am
BDL
- AXA
1 stop9h 43m
American Airlines
Wed 3/114:09 pm
AXA
- BDL
2 stops16h 58m
American Airlines
Deal found 2/2![American Airlines logo]()
$769
This American Airlines deal was found by Cheapflights users on 2/2. 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 3/255:43 am
BDL
- AXA
1 stop9h 46m
American Airlines
Tue 3/314:09 pm
AXA
- BDL
2 stops20h 51m
American Airlines
Deal found 2/2![American Airlines logo]()
$599
One-way flights from Massachusetts to AnguillaSearch for one-way flight options from Massachusetts to Anguilla. Find affordable one-way fares based on user searches. Data last updated February 5, 2026.
Search for one-way flight options from Massachusetts to Anguilla. Find affordable one-way fares based on user searches. Data last updated February 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:32 pm
BOS
- AXA
2 stops19h 38m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/206:10 pm
BOS
- AXA
2 stops22h 00m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/255:49 pm
BOS
- AXA
2 stops43h 41m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$306
This Gotogate deal was found by Cheapflights users on 2/3. 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 2/2110:20 am
BOS
- AXA
Nonstop4h 40m
BermudAir
Deal found 2/3![BermudAir logo]()
$308
This Booking.com deal was found by Cheapflights users on 2/3. 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 3/1410:20 am
BOS
- AXA
Nonstop4h 40m
BermudAir
Deal found 2/3![BermudAir logo]()
$316
This Booking.com deal was found by Cheapflights users on 2/2. 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.
Wed 3/2510:20 am
BOS
- AXA
Nonstop4h 40m
BermudAir
Deal found 2/2![BermudAir logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/45:49 pm
BOS
- AXA
2 stops22h 51m
Multiple Airlines
Deal found 2/4![Multiple Airlines logo]()
$328
This FlightHub deal was found by Cheapflights users on 2/3. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/710:20 am
BOS
- AXA
Nonstop4h 40m
BermudAir
Deal found 2/3![BermudAir logo]()
$330
This Gotogate deal was found by Cheapflights users on 2/5. 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 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
Deal found 2/5![BermudAir logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/225:49 pm
BOS
- AXA
2 stops21h 51m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$333
This American Airlines deal was found by Cheapflights users on 2/2. 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 3/255:28 am
BDL
- AXA
2 stops10h 01m
American Airlines
Deal found 2/2![American Airlines logo]()
$345
This American Airlines deal was found by Cheapflights users on 2/3. 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 3/307:00 am
BOS
- AXA
1 stop8h 29m
American Airlines
Deal found 2/3![American Airlines logo]()
$345
Find 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 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $553 (American Airlines) |
One-way from | $271 (Kiwi.com) |
Popular in | August |
Cheapest in | December |
Average price | $679 |
Good round-trip deal | $669 or less |
Good one-way deal | $330 or less |
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 February 5, 2026.
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
Sat 5/2
6:40 pm-1:15 pm
2 stops18h 35m
The Valley Wallblake Intl
Wed 5/6
4:57 pm-10:02 am
1 stop17h 05m
$553
BostonThe Valley
BOS - AXA
BOSAXA
Boston Logan Intl
Sun 5/31
6:34 am-4:01 pm
1 stop9h 27m
The Valley Wallblake Intl
Fri 6/5
4:41 pm-10:27 am
2 stops17h 46m
$576
BostonThe Valley
BOS - AXA
BOSAXA
Boston Logan Intl
Wed 2/25
5:00 am-4:28 pm
1 stop10h 28m
The Valley Wallblake Intl
Wed 3/4
5:10 pm-10:01 am
1 stop17h 51m
$578
BostonThe Valley
BOS - AXA
BOSAXA
Boston Logan Intl
Tue 2/24
6:00 am-4:28 pm
2 stops9h 28m
The Valley Wallblake Intl
Tue 3/10
4:09 pm-9:29 am
2 stops17h 20m
$583
HartfordThe Valley
BDL - AXA
BDLAXA
Hartford Bradley Intl
Wed 3/25
5:43 am-3:29 pm
1 stop9h 46m
The Valley Wallblake Intl
Tue 3/31
4:09 pm-1:00 pm
2 stops20h 51m
$599
HartfordThe Valley
BDL - AXA
BDLAXA
Hartford Bradley Intl
Wed 5/6
5:45 am-4:17 pm
1 stop10h 32m
The Valley Wallblake Intl
Sun 5/10
1:55 pm-11:59 pm
1 stop10h 04m
$624
HartfordThe Valley
BDL - AXA
BDLAXA
Hartford Bradley Intl
Thu 4/16
5:45 am-4:17 pm
1 stop10h 32m
The Valley Wallblake Intl
Mon 4/20
1:55 pm-10:12 am
2 stops20h 17m
$649
HartfordThe Valley
BDL - AXA
BDLAXA
Hartford Bradley Intl
Sat 4/25
3:06 pm-4:17 pm
1 stop25h 11m
The Valley Wallblake Intl
Sat 5/2
4:57 pm-10:12 am
2 stops17h 15m
$698
BostonThe Valley
BOS - AXA
BOSAXA
Boston Logan Intl
Sat 2/21
8:32 pm-5:10 pm
2 stops19h 38m
$271
BostonThe Valley
BOS - AXA
BOSAXA
Boston Logan Intl
Fri 2/20
6:10 pm-5:10 pm
2 stops22h 00m
$285
Showing 1-10 of 18 results
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.
BOS-AXA
BDL-AXA
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
USMA-AI0
BOS-AXA
BDL-AXA
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 5, 2026.
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.
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
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Complete your trip
Complete your trip to Anguilla by adding a car rental and/or hotel reservation to your travel itinerary.
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Massachusetts and Anguilla flights
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Massachusetts to Anguilla flights
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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 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$457 | Average$581 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$622 | Average$770 | FlexibilityNo cancel fee | On-time71% |