Cheap Flights to Anguilla from $198 (2026/2027)

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A beach with clear turquoise waters, white sand, and a palm tree.

Shoal Bay

Flights
Shoal 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.

Sun, Aug 23 - Tue, Aug 25
SXM
Princess Juliana Intl.
AXA
Clayton J. Lloyd Intl.
$358 Roundtrip, found 22 hours ago
$358
Roundtrip
found 22 hours ago
Select World Ticket Ltd flight, departing Sun, Aug 23 from Princess Juliana Intl. to Clayton J. Lloyd Intl., returning Tue, Aug 25, priced at $358 found 22 hours ago
Fri, Aug 7 - Mon, Aug 10
SKB
Robert L. Bradshaw Intl.
AXA
Clayton J. Lloyd Intl.
$368 Roundtrip, found 1 day ago
$368
Roundtrip
found 1 day ago
Select FlexFlight flight, departing Fri, Aug 7 from Robert L. Bradshaw Intl. to Clayton J. Lloyd Intl., returning Mon, Aug 10, priced at $368 found 1 day ago
Tue, Sep 22 - Sat, Sep 26
STT
Cyril E. King
AXA
Clayton J. Lloyd Intl.
$624 Roundtrip, found 13 hours ago
$624
Roundtrip
found 13 hours ago
Select Cape Air flight, departing Tue, Sep 22 from Cyril E. King to Clayton J. Lloyd Intl., returning Sat, Sep 26, priced at $624 found 13 hours ago
Tue, Jun 1 - Tue, Jun 8
MIA
Miami Intl.
AXA
Clayton J. Lloyd Intl.
$634 Roundtrip, found 5 days ago
$634
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Jun 1 from Miami Intl. to Clayton J. Lloyd Intl., returning Tue, Jun 8, priced at $634 found 5 days 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
Mon, Apr 26 - Mon, May 3
EWR
Newark Liberty Intl. Airport
AXA
Clayton J. Lloyd Intl.
$642 Roundtrip, found 1 day ago
$642
Roundtrip
found 1 day ago
Select BermudAir flight, departing Mon, Apr 26 from Newark Liberty Intl. Airport to Clayton J. Lloyd Intl., returning Mon, May 3, priced at $642 found 1 day ago
Mon, Feb 8 - Tue, Feb 23
BWI
Baltimore Washington Intl. Thurgood Marshall
AXA
Clayton J. Lloyd Intl.
$696 Roundtrip, found 4 days ago
$696
Roundtrip
found 4 days ago
Select American Airlines flight, departing Mon, Feb 8 from Baltimore Washington Intl. Thurgood Marshall to Clayton J. Lloyd Intl., returning Tue, Feb 23, priced at $696 found 4 days ago
Wed, Oct 28 - Wed, Nov 4
IAH
George Bush Intercontinental
AXA
Clayton J. Lloyd Intl.
$701 Roundtrip, found 3 days ago
$701
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Oct 28 from George Bush Intercontinental to Clayton J. Lloyd Intl., returning Wed, Nov 4, priced at $701 found 3 days ago
OriginDestinationTravel DatesFlights From*
SXMThe ValleyAugust 15 to August 21$358
MIAThe ValleyNovember 6 to November 10$669
LGAThe ValleyOctober 24 to October 28$747
BOSThe ValleyOctober 10 to October 17$782
JFKThe ValleyOctober 24 to October 28$807
SJUThe ValleyOctober 7 to October 14$814
BWIThe ValleyNovember 8 to November 14$951
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
BOSThe ValleyAugust 8 to August 15$1,519
JFKThe ValleyAugust 8 to August 14$1,731
JFKThe ValleyAugust 8 to August 14$1,731
*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

Oct 17 - Oct 24

7 night stay

Boston (BOS) to The Valley (AXA)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $5,809, price is now $3,311 per person
$3,311
per person
found 1 day ago
6 BR Villa With Concierge Amenities Pool
2.0-star property

6 BR Villa With Concierge Amenities Pool

Oct 10 - Oct 17

7 night stay

Boston (BOS) to The Valley (AXA)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $9,395, price is now $7,622 per person
$7,622
per person
found 1 day ago
6 BR Villa On Crocus Bay With Pool Concierge
2.0-star property

6 BR Villa On Crocus Bay With Pool Concierge

Oct 17 - Oct 24

7 night stay

Boston (BOS) to The Valley (AXA)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $9,319, price is now $7,733 per person
$7,733
per person
found 1 day ago
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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.
9.8/10 Exceptional! (259 reviews)
"I love the four seasons in Anguilla!! This is my 3rd time going to the island and I wouldn't stay anywhere else!’Nothing but top notch service!! Amazing time!!"

Reviewed on Jul 28, 2026

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.
8.2/10 Very Good! (334 reviews)
"Charming spot on a beautiful Rendezvous Bay! Staff were super nice and helpful and the property location can’t be beat. The actual room could use some upgrades from plumbing to cleanliness but the location was perfect to explore the island."

Reviewed on Jul 27, 2026

Opens in a new windowAnguilla Great House Beach Resort
Zemi Beach House, LXR Hotels & Resorts

Zemi Beach House, LXR Hotels & Resorts

5 out of 5
Shoal Bay East Shoal Bay
Book a stay at this luxury resort in Shoal Bay. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Shoal Bay Beach and Scrub Island are located nearby.
Opens in a new windowZemi Beach House, LXR Hotels & Resorts
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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! (202 reviews)
"Asian restaurant hostess was rude."

Reviewed on Jul 16, 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, August 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 $1,731 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.