$278 Find Cheap Flights from Orlando to Anguilla

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Orlando to Anguilla departing on 5/14. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Flight Deals

Book Cheap Orlando to Anguilla Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Orlando to Anguilla that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Orlando to Anguilla

Di, Jul 21 - Di, Jul 28
American Airlines Logo
6:00 am - 4:19 pm
MCO
-
AXA
10h 19m
1 stop
American Airlines Logo
4:59 pm - 11:59 pm
AXA
-
MCO
7h 00m
1 stop
$616American Airlines
Di, Jul 21 - Di, Jul 28
American Airlines Logo
10:00 am - 4:19 pm
MCO
-
AXA
6h 19m
1 stop
American Airlines Logo
4:59 pm - 1:01 pm
AXA
-
MCO
20h 02m
2 stops
$621American Airlines
Fr, Jul 3 - Do, Jul 9
American Airlines Logo
8:45 am - 4:19 pm
MCO
-
AXA
7h 34m
1 stop
American Airlines Logo
4:59 pm - 11:59 pm
AXA
-
MCO
7h 00m
1 stop
$651American Airlines
Fr, Jul 3 - Do, Jul 9
American Airlines Logo
7:34 pm - 12:01 pm
MCO
-
AXA
16h 27m
2 stops
American Airlines Logo
4:59 pm - 9:44 am
AXA
-
MCO
16h 45m
2 stops
$656American Airlines
Di, Jul 21 - Mi, Jul 29
American Airlines Logo
6:00 am - 1:11 pm
MCO
-
AXA
7h 11m
1 stop
American Airlines Logo
4:59 pm - 7:55 am
AXA
-
MCO
14h 56m
1 stop
$676American Airlines
Di, Jul 21 - Mi, Jul 29
American Airlines Logo
7:34 am - 1:11 pm
MCO
-
AXA
5h 37m
1 stop
American Airlines Logo
1:55 pm - 9:13 am
AXA
-
MCO
19h 18m
2 stops
$681American Airlines
Mi, Mai 20 - Mi, Mai 27
American Airlines Logo
7:00 am - 4:17 pm
MCO
-
AXA
9h 17m
1 stop
American Airlines Logo
4:55 pm - 11:59 pm
AXA
-
MCO
7h 04m
1 stop
$731American Airlines
Sa, Jul 25 - Fr, Jul 31
American Airlines Logo
6:58 pm - 4:19 pm
MCO
-
AXA
21h 21m
1 stop
American Airlines Logo
4:59 pm - 7:55 am
AXA
-
MCO
14h 56m
1 stop
$734American Airlines
Mi, Mai 20 - Mi, Mai 27
American Airlines Logo
7:00 am - 1:15 pm
MCO
-
AXA
6h 15m
1 stop
American Airlines Logo
4:55 pm - 11:10 am
AXA
-
MCO
18h 15m
2 stops
$736American Airlines
Do, Jul 30 - Mo, Aug 3
American Airlines Logo
7:34 am - 4:19 pm
MCO
-
AXA
8h 45m
1 stop
American Airlines Logo
4:59 pm - 11:59 pm
AXA
-
MCO
7h 00m
1 stop
$746American Airlines
Booking Insights

KAYAK's insights & trends for Orlando to Anguilla flights

Get data-powered insights and trends into flights from Orlando to Anguilla to help you find the cheapest flights, the best time to fly and much more.

How long does a flight from Orlando Airport to Anguilla take?

The duration of a flight to Anguilla depends on your arrival airport. The shortest route to Anguilla from Orlando Airport is to The Valley, which takes 6h 17m.

Good to know

Low seasonDecember
Cheapest flight$278
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly with an average 20% increase in price.
Flight from Orlando to The Valley

FAQs - booking Anguilla flights

  • How does KAYAK find such low prices on flights from Orlando to Anguilla?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Orlando to Anguilla.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Orlando to Anguilla?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Orlando to Anguilla is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Orlando to Anguilla?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Orlando to Anguilla with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Orlando to Anguilla?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Orlando to Anguilla up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Orlando to Anguilla

 
Need help choosing which airline to fly with from Orlando to Anguilla? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
American AirlinesOverall score based on 11659 reviews
7.2Comfort
7.5Boarding
6.9Entertainment
7.9Crew
6.4Food
Airline reviews

For a 4 1/2 hour international flight all we got was 1 small pack of cookies and a drink. You had to watch movies on your own devise.

4.0 OkayAnonymous, Apr 2026
MIA - UIO
Read more American Airlines reviews

For a 4 1/2 hour international flight all we got was 1 small pack of cookies and a drink. You had to watch movies on your own devise.

The seats need better cushioning for a nearly 5-hour flight, it was a bit uncomfortable. I'm glad American has free wi-fi but there were was a bout 30 minutes in the middle of the flight when there was no connection which was frustrating.

My original flight got delayed day of so I had to rebook it from one layover to two layovers. The flight also left earlier which was a slight inconvenience but manageable. Then my first connection flight got delayed 3 separate times for a total of 2 hours delayed, causing me to miss my second connection flight back to Santa Barbara. Now, because of this missed flight, I am missing my college classes that I pay for.

Flight: Started on time. Comfortable flight. Arrived on time. Crew: Very cordial and helpful. Drinks and snack was served with a smile. Overall enjoyed the trip. Regards, Hari Doss Chanchala Doss

I’m sure Business Class would be excellent. I feel like I got what I paid for. Overall it was good and well worth it. I would do it again.

This short sector between Miami and JFK was undertaken purely for business purposes, with efficiency as the primary objective rather than a full inflight experience. Overall, the journey met its intended purpose; however, the ground experience at Miami stood out significantly. During check-in, I was unable to link my frequent flyer details from Qatar Airways (oneworld alliance) through either the self-service kiosk or web check-in. The situation was handled exceptionally well by the check-in agent, who demonstrated remarkable ownership. She coordinated across multiple counters, ensured my frequent flyer number was correctly reflected, reissued the boarding pass, and confirmed that mileage accrual would be recognized. Additionally, she ensured the boarding pass reflected priority status, enabling a seamless priority check-in experience without delays. This level of proactive service was both commendable and impactful. Boarding and the inflight experience, operated by American Airlines under a codeshare arrangement, were efficient but largely transactional. While operational delivery was smooth, there was no visible recognition of oneworld frequent flyer status onboard. In comparison to the consistently personalized engagement typically experienced with Qatar Airways, this absence was noticeable—though understandably a potential limitation of codeshare alignment rather than a direct service shortfall. In summary, while the flight itself fulfilled its operational intent, the exceptional professionalism and commitment demonstrated at the Miami check-in counter was the defining highlight of this journey. Greater consistency in elite recognition across partner airlines would further enhance the overall experience.

Business class was very good, one of my best flights

Incredibly delayed. First delay was due to plane coming in being late. Resulted in 30 minute delay. Boarded and then had multiple mechanical issues. Was on plane for an hour until they told people they could get off if they wanted but couldn't come back. Then gate agent rushed in and said they had lost control of who went off and we would all have to deplane and then get back on. They said flight had not been cancelled. Then while sitting waiting to board again they announced it would take two hours to get new plane and to wait at new gate. New plane arrived, reboarded only to find out that pilots had timed out. Waited for new pilots. In that time one of the flight attendants timed out. Never received food or water while waiting. Was confusing mess as to what was happening. Even flight attendants and gate agents were getting frustrated. Almost 6 hours delayed. Called American to received flight credit but can't get anywhere as Kayak reservation and don't have a ticket number. Reached out to Kayak but never heard back.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

Flight was delayed and they gave up my seat on my connection, even when I could still make the flight

Everything you need to know for your flight from Orlando to Anguilla

Information on your arrival and departure airports