Cheap Flights to Anguilla from $212 (2026/2027)

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Jet to one of Anguilla's top cities

A beach with clear turquoise water, white sand, and a few buildings in the distance.

Rendezvous Bay

Flights
Rendezvous Bay

How Much Does it Cost To Fly To Anguilla?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Thu, Sep 3 - Sun, Sep 6
SXM
Princess Juliana Intl.
AXA
Clayton J. Lloyd Intl.
$358 Roundtrip, found 11 hours ago
$358
Roundtrip
found 11 hours ago
Select World Ticket Ltd flight, departing Thu, Sep 3 from Princess Juliana Intl. to Clayton J. Lloyd Intl., returning Sun, Sep 6, priced at $358 found 11 hours ago
Thu, Oct 1 - Mon, Oct 19
ANU
V.C. Bird Intl.
AXA
Clayton J. Lloyd Intl.
$612 Roundtrip, found 7 hours ago
$612
Roundtrip
found 7 hours ago
Select FlexFlight flight, departing Thu, Oct 1 from V.C. Bird Intl. to Clayton J. Lloyd Intl., returning Mon, Oct 19, priced at $612 found 7 hours ago
Sun, Sep 13 - Sat, Sep 19
STT
Cyril E. King
AXA
Clayton J. Lloyd Intl.
$624 Roundtrip, found 17 hours ago
$624
Roundtrip
found 17 hours ago
Select Cape Air flight, departing Sun, Sep 13 from Cyril E. King to Clayton J. Lloyd Intl., returning Sat, Sep 19, priced at $624 found 17 hours ago
Fri, Feb 19 - Sat, Feb 27
EWR
Newark Liberty Intl. Airport
AXA
Clayton J. Lloyd Intl.
$642 Roundtrip, found 9 hours ago
$642
Roundtrip
found 9 hours ago
Select BermudAir flight, departing Fri, Feb 19 from Newark Liberty Intl. Airport to Clayton J. Lloyd Intl., returning Sat, Feb 27, priced at $642 found 9 hours ago
Fri, Feb 5 - Mon, Feb 15
BOS
Logan Intl.
AXA
Clayton J. Lloyd Intl.
$642 Roundtrip, found 22 hours ago
$642
Roundtrip
found 22 hours ago
Select BermudAir flight, departing Fri, Feb 5 from Logan Intl. to Clayton J. Lloyd Intl., returning Mon, Feb 15, priced at $642 found 22 hours ago
Thu, May 13 - Thu, May 20
CLT
Charlotte-Douglas Intl.
AXA
Clayton J. Lloyd Intl.
$680 Roundtrip, found 2 days ago
$680
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, May 13 from Charlotte-Douglas Intl. to Clayton J. Lloyd Intl., returning Thu, May 20, priced at $680 found 2 days ago
Tue, Jan 19 - Tue, Jan 26
BWI
Baltimore Washington Intl. Thurgood Marshall
AXA
Clayton J. Lloyd Intl.
$696 Roundtrip, found 5 days ago
$696
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Jan 19 from Baltimore Washington Intl. Thurgood Marshall to Clayton J. Lloyd Intl., returning Tue, Jan 26, priced at $696 found 5 days ago
Tue, Jul 6 - Tue, Jul 13
JFK
John F. Kennedy Intl.
AXA
Clayton J. Lloyd Intl.
$712 Roundtrip, found 9 hours ago
$712
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Jul 6 from John F. Kennedy Intl. to Clayton J. Lloyd Intl., returning Tue, Jul 13, priced at $712 found 9 hours ago
OriginDestinationTravel DatesFlights From*
SXMThe ValleySeptember 18 to September 20$358
MIAThe ValleyNovember 1 to November 5$669
JFKThe ValleyNovember 28 to December 4$710
JFKThe ValleyNovember 28 to December 4$710
BOSThe ValleyNovember 3 to November 17$712
IADThe ValleyNovember 4 to November 8$781
SJUThe ValleyNovember 11 to November 15$796
ATLThe ValleyNovember 22 to November 25$846
LHRThe ValleyNovember 1 to November 5$1,009
LAXThe ValleyNovember 21 to November 28$1,464
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
SXMThe ValleySeptember 4 to September 11$358
SJUThe ValleySeptember 4 to September 7$897
BOSThe ValleySeptember 4 to September 7$1,537
*Prices include taxes and fees

Best Anguilla Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Aurora Anguilla Resort & Golf Club
5.0-star property

Aurora Anguilla Resort & Golf Club

Nov 23 - Nov 30

7 night stay

Boston (BOS) to The Valley (AXA)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $7,580, price is now $4,192 per person
$4,192
per person
found 1 day ago
Malliouhana Resort Anguilla
5.0-star property

Malliouhana Resort Anguilla

Nov 23 - Nov 30

7 night stay

Boston (BOS) to The Valley (AXA)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $7,794, price is now $5,659 per person
$5,659
per person
found 1 day ago
Ceblue Luxury Villas
5.0-star property

Ceblue Luxury Villas

Nov 23 - Nov 30

7 night stay

Boston (BOS) to The Valley (AXA)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $6,728, price is now $5,453 per person
$5,453
per person
found 1 day ago
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See all available trips from Boston to Anguilla
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Travelers ❤️ These Anguilla 🏨

Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
Barnes Bay West End Village
Book a stay at this luxury resort in West End Village. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Meads Bay and Meads Bay Beach are located nearby.
Opens in a new windowFour Seasons Resort and Residences Anguilla
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

3.5 out of 5
Rendezvous Bay Rendezvous Bay
Book a stay at this beach hotel in Rendezvous Bay. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Meads Bay and Rendezvous Bay Beach are located nearby.
Opens in a new windowAnguilla Great House Beach Resort
Cap Juluca, A Belmond Hotel, Anguilla

Cap Juluca, A Belmond Hotel, Anguilla

5 out of 5
Maundays Bay Maunday's Bay
Book a stay at this luxury resort in Maunday's Bay. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Meads Bay and Maundays Bay are located nearby.
Opens in a new windowCap Juluca, A Belmond Hotel, Anguilla
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Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Rendezvous Bay Rendezvous Bay
Book a stay at this luxury resort in Rendezvous Bay. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Meads Bay and Aurora International Golf Club are located nearby.
9.6/10 Exceptional! (205 reviews)
"This property is very well kept. The facilities are excellent. Great golf courses. The water park is an excellent option for families. There are several good restaurant options on site. We had a relaxing and enjoyable stay."

Reviewed on Aug 24, 2026

Opens in a new windowAurora Anguilla Resort & Golf Club
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much is the cheapest flight to Anguilla?
A roundtrip flight to Anguilla cost as little as $358 over the last seven days. When you're ready to book, we'll help you find an amazing deal. This price was available on Travelocity for flights to Anguilla departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Anguilla?
Find your ideal fare with one of the 15 airlines that fly to Anguilla. If you're staying in The Valley, let Anguilla Air Services whisk you away to this lively city to explore its top sights. This popular carrier offers 30 flights there per month.
What is the cheapest month to fly to Anguilla?
If you've been dreaming of a break in Anguilla, September is the cheapest month to make your way there. This is according to Travelocity's direct return flight demand between January and December last year. Pick your preferred travel dates and lock in your seat today.
How can I check my flight status to Anguilla?
There are a couple of handy ways to look up your flight status. You can find all the necessary info in our "Trips" portal, which is located at the top right of our homepage. Log in or open a new account — you'll then be able to browse and manage your bookings whenever you need. If you're already on the go, the Travelocity app can also help you look up the status of your flight to Anguilla, as well as share details with any members of your family flying with you.
How do I find the best deals on flights to Anguilla?
Being flexible with your travel dates is one way to land an awesome deal. Travelocity makes it a piece of cake to find your ideal fare through the "Flexible dates" function. First, search for your flight to Anguilla, then compare prices for surrounding days by clicking the "Flexible dates" dropdown box above. Booking earlier and avoiding vacation periods are some other suggestions. In the last seven days, the best price for a return flight to Anguilla was $358. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Anguilla with Travelocity?
Pack your bags and get set for an awesome vacation with Travelocity. It's our job to track down fantastic deals on cheap flights to Anguilla. Whether you're seeking flexible airfares or cheap family flights from low-cost carriers, we've got you covered.
How much is a flight to Anguilla on average?
Passengers were picking up roundtrip flights to Anguilla for between $358 and $1,537 with Travelocity in the last seven days. Whether you're planning to fly economy or first class, we'll help you get a fantastic deal. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
What can I expect on a flight to Anguilla?
This depends mostly on your carrier and the duration of your flight. Generally, most airlines provide warm meals, drinks and entertainment on long-haul journeys. Whether you're searching for first class flights to Anguilla or cheap flights for family vacations, you'll be well looked after from boarding to touchdown.