Flights To Anguilla - Cheap Flights Starting at CA $205

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Jet to one of Anguilla's top cities

Palm tree in Shoal Bay beach, Caribbean dream landscape in Anguilla island, British West Indies panoramic web banner

West End Village

Flights
West End Village

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.

Mon, Jun 29 - Mon, Jul 6
SXM
Princess Juliana Intl.
AXA
Clayton J. Lloyd Intl.
CA $401 Roundtrip, found 1 day ago
CA $401
Roundtrip
found 1 day ago
Select World Ticket Ltd flight, departing Mon, Jun 29 from Princess Juliana Intl. to Clayton J. Lloyd Intl., returning Mon, Jul 6, priced at CA $401 found 1 day ago
Sat, Mar 28 - Wed, Apr 1
SXM
Princess Juliana Intl.
AXA
Clayton J. Lloyd Intl.
CA $425 Roundtrip, found 2 days ago
CA $425
Roundtrip
found 2 days ago
Select World Ticket Ltd flight, departing Sat, Mar 28 from Princess Juliana Intl. to Clayton J. Lloyd Intl., returning Wed, Apr 1, priced at CA $425 found 2 days ago
Mon, Jun 29 - Mon, Jul 6
SXM
Princess Juliana Intl.
AXA
Clayton J. Lloyd Intl.
CA $430 Roundtrip, found 1 day ago
CA $430
Roundtrip
found 1 day ago
Select World Ticket Ltd flight, departing Mon, Jun 29 from Princess Juliana Intl. to Clayton J. Lloyd Intl., returning Mon, Jul 6, priced at CA $430 found 1 day ago
Thu, Mar 19 - Sun, Mar 22
SXM
Princess Juliana Intl.
AXA
Clayton J. Lloyd Intl.
CA $433 Roundtrip, found 3 days ago
CA $433
Roundtrip
found 3 days ago
Select Hahn Air Systems flight, departing Thu, Mar 19 from Princess Juliana Intl. to Clayton J. Lloyd Intl., returning Sun, Mar 22, priced at CA $433 found 3 days ago
Sat, Mar 28 - Wed, Apr 1
SXM
Princess Juliana Intl.
AXA
Clayton J. Lloyd Intl.
CA $441 Roundtrip, found 2 days ago
CA $441
Roundtrip
found 2 days ago
Select Hahn Air Systems flight, departing Sat, Mar 28 from Princess Juliana Intl. to Clayton J. Lloyd Intl., returning Wed, Apr 1, priced at CA $441 found 2 days ago
Mon, Jun 29 - Mon, Jul 6
SXM
Princess Juliana Intl.
AXA
Clayton J. Lloyd Intl.
CA $447 Roundtrip, found 1 day ago
CA $447
Roundtrip
found 1 day ago
Select Hahn Air Systems flight, departing Mon, Jun 29 from Princess Juliana Intl. to Clayton J. Lloyd Intl., returning Mon, Jul 6, priced at CA $447 found 1 day ago
Thu, Mar 19 - Sun, Mar 22
SXM
Princess Juliana Intl.
AXA
Clayton J. Lloyd Intl.
CA $450 Roundtrip, found 3 days ago
CA $450
Roundtrip
found 3 days ago
Select Hahn Air Systems flight, departing Thu, Mar 19 from Princess Juliana Intl. to Clayton J. Lloyd Intl., returning Sun, Mar 22, priced at CA $450 found 3 days ago
Sat, Apr 11 - Fri, Apr 17
YYZ
Pearson Intl.
AXA
Clayton J. Lloyd Intl.
CA $453 Roundtrip, found 6 days ago
CA $453
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Apr 11 from Pearson Intl. to Clayton J. Lloyd Intl., returning Fri, Apr 17, priced at CA $453 found 6 days ago
Sat, Jan 2 - Sat, Jan 9
YVR
Vancouver Intl.
AXA
Clayton J. Lloyd Intl.
CA $2,139 Roundtrip, found 22 hours ago
CA $2,139
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Sat, Jan 2 from Vancouver Intl. to Clayton J. Lloyd Intl., returning Sat, Jan 9, priced at CA $2,139 found 22 hours ago
OriginDestinationTravel datesFlights from*
SXMThe ValleyJune 29 to July 6CA $401
BOSThe ValleyApril 4 to April 11CA $1,135
EWRThe ValleyApril 2 to April 6CA $1,147
JFKThe ValleyApril 2 to April 6CA $1,214
*Prices include taxes and fees
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

May 2 - May 9

7 night stay

Toronto (YTO) to The Valley (AXA)

American Airlines • Non-stop roundtrip • Coach
Price was CA $9,319, price is now CA $5,540 per person
CA $5,540
per person
found 1 day ago
Malliouhana Resort Anguilla
5.0-star property

Malliouhana Resort Anguilla

May 2 - May 9

7 night stay

Toronto (YTO) to The Valley (AXA)

American Airlines • Non-stop roundtrip • Coach
Price was CA $21,303, price is now CA $15,828 per person
CA $15,828
per person
found 1 day ago
Zemi Beach House, LXR Hotels & Resorts
5.0-star property

Zemi Beach House, LXR Hotels & Resorts

May 2 - May 9

7 night stay

Toronto (YTO) to The Valley (AXA)

American Airlines • Non-stop roundtrip • Coach
Price was CA $8,008, price is now CA $6,641 per person
CA $6,641
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Toronto to Anguilla
View all trips

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.
9.6/10 Exceptional! (247 reviews)
Great Service!!!

Reviewed on Feb 4, 2026

Opens in a new windowFour Seasons Resort and Residences Anguilla
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

4 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! (297 reviews)
The location is great, very quiet and beautiful. The staff are not friendly or helpful. They do the minimum to get buy.

Reviewed on Mar 15, 2026

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.
9.6/10 Exceptional! (137 reviews)
Besides the obvious natural beauty of the property, the beachfront’s glorious views, the fine restaurants and food, it is the warm, inviting and outgoing staff that sets Cap Juluca apart. It is one of a kind on the island, in a class by itself.

Reviewed on Feb 2, 2026

Opens in a new windowCap Juluca, A Belmond Hotel, Anguilla
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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! (194 reviews)
Beautiful oceanfront hotel with two golf courses, amazing restaurants, quiet pool area an the a waterpark for kids.

Reviewed on Mar 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 CA $401 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 16 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, June 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 CA $401. 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 CA $401 and CA $2,139 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.