$148 Find Cheap Flights from Orlando to Cayman Islands

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 the Cayman Islands departing on 11/3. 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

KAYAK searches hundreds of travel sites at once for deals on flights to the Cayman Islands

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 20% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Useful Info
Flights Deals

Best Cayman Islands Flight Deals from Orlando

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
George Town
George Town1 stop$458
George Town
George Town1 stop$458

Cheap Flights from Orlando to the Cayman Islands

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Orlando to the Cayman Islands 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 the Cayman Islands

Sun, Sep 7 - Sat, Nov 1
Delta Logo
6:00 am - 11:37 amMCO-GCM
6h 37m1 stop
Delta Logo
1:02 pm - 8:36 pmGCM-MCO
6h 34m1 stop
$458Delta
Find Deal
Sun, Sep 7 - Sat, Nov 1
American Airlines Logo
5:27 pm - 11:10 amMCO-GCM
18h 43m2 stops
American Airlines Logo
12:15 pm - 8:42 pmGCM-MCO
7h 27m1 stop
$462American Airlines
Find Deal
Wed, Aug 6 - Wed, Aug 13
United Airlines Logo
7:12 am - 12:30 pmMCO-GCM
6h 18m1 stop
United Airlines Logo
1:35 pm - 10:00 pmGCM-MCO
7h 25m1 stop
$498United Airlines
Find Deal
Tue, Jul 22 - Tue, Jul 29
Southwest Logo
10:55 am - 11:50 amMCO-GCM
1h 55mnonstop
Southwest Logo
12:45 pm - 3:50 pmGCM-MCO
2h 05mnonstop
$501Southwest
Find Deal
Fri, Dec 5 - Sun, Dec 7
Southwest Logo
10:40 am - 12:35 pmMCO-GCM
1h 55mnonstop
Southwest Logo
1:30 pm - 3:25 pmGCM-MCO
1h 55mnonstop
$531Southwest
Find Deal
Wed, Aug 13 - Sat, Aug 16
 Logo
10:24 pm - 9:20 pmMCO-GCM
23h 56m2 stops
 Logo
8:50 am - 9:02 amGCM-MCO
23h 12m2 stops
Wed, Aug 13 - Sat, Aug 16
 Logo
6:28 am - 11:40 amMCO-GCM
30h 12m2 stops
 Logo
8:50 am - 9:02 amGCM-MCO
23h 12m2 stops
Sat, Jul 12 - Sat, Jul 19
United Airlines Logo
7:12 am - 3:35 pmMCO-GCM
9h 23m1 stop
United Airlines Logo
4:45 pm - 10:52 amGCM-MCO
17h 07m1 stop
$626United Airlines
Find Deal
Fri, Nov 21 - Fri, Nov 28
Air Canada Logo
6:10 pm - 12:20 pmMCO-GCM
42h 10m2 stops
Air Canada Logo
1:35 pm - 11:51 pmGCM-MCO
10h 16m1 stop
$738Air Canada
Find Deal
Sat, Nov 22 - Fri, Nov 28
Air Canada Logo
10:15 pm - 12:20 pmMCO-GCM
14h 05m1 stop
Air Canada Logo
1:35 pm - 11:51 pmGCM-MCO
10h 16m1 stop
$747Air Canada
Find Deal
Useful Info

KAYAK's insights & trends for Orlando to the Cayman Islands flights

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

What is the cheapest Orlando Airport to the Cayman Islands flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Orlando Airport to the Cayman Islands.

The cheapest ticket to the Cayman Islands from Orlando Airport found in the last 72 hours was to George Town, at $491 round-trip. The most popular route is from Orlando Airport (MCO) to George Town (GCM), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $491.

Can I save money by flying with a layover from Orlando Airport to the Cayman Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $651 on average.

What is the cheapest month to fly from Orlando Airport to the Cayman Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Orlando Airport to the Cayman Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Orlando Airport to the Cayman Islands is November, when tickets cost $399 (return) on average. On the other hand, the most expensive months are April and March, when the average cost of round-trip tickets is $603 and $596 respectively.

What’s the cheapest day of the week to fly from Orlando to Cayman Islands?

The average price of all round-trip flights from Orlando Airport to the Cayman Islands clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Cayman Islands on a Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Orlando to Cayman Islands. For your return ticket, we recommend flying on a Thursday and avoiding Saturdays for the best deals.

How far in advance should I book a flight from Orlando Airport to the Cayman Islands?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Orlando Airport to the Cayman Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Orlando Airport to the Cayman Islands, you should book around 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.


Good to know

Low seasonSeptember
High seasonJanuary
Cheapest flight$148
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from Orlando to George Town

FAQs - booking Cayman Islands flights

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

    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 Cayman Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Orlando to Cayman Islands 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 Cayman Islands?

    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 Cayman Islands 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 Cayman Islands?

    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 Cayman Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to the Cayman Islands?

    The cheapest time of day to fly to the Cayman Islands is generally in the morning, when round-trip flights cost $583 on average. The most expensive time of day to fly to the Cayman Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $583.

Reviews of the top airlines flying from Orlando to the Cayman Islands

 
Need help choosing which airline to fly with from Orlando to the Cayman Islands? 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.
8.0
SouthwestOverall score based on 4278 reviews
8.2Boarding
7.6Entertainment
8.6Crew
8.0Comfort
7.0Food
Airline reviews

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

8.0 ExcellentMichael, Jun 2025PHX - SAN
Read more Southwest reviews

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

WiFi on the flight was not working. Thus, entertainment options were limited.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

I had a wonderful flight, but the only thing that annoyed me was how crowded TSA was. I still believe airports and all planes work together to bunch everyone together to drive up cost.

Easy to book and to get check in and get on and off.

Everything worked well. Crew was as entertaining as is possible on a plane flight. Southwest still has good legroom:

Food was terrible, all served at once, poor quality . Wine and bread offered only once.

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

No entertainment yatem in flight at seat 51H. Would not shut down either leaving a self moving and openin and changing menus with changes in colors,images brightness levels sort of the type when you get sleep deprivation and image overload when being tortured during an interrogation. 8 hours worth of it. Unable to place backpack underneath seat on that chair. One female stewardess was excellent as she gave up her carryon's space for my backpack but the rest of the iberia crew were very sharp an chtting during the whole flight. The plane did not have hot water so nobody had coffee nor tea. The plane was not up to par to be flying.

I was late from Jacksonville, FL but the limited interaction I had with the Philly crew was great.

The delays and cancellations kept me stuck in Miami for an additional 24 hours, and the whole thing seemed extremely disorganized

The chicken adobo was a little too spicy but good otherwise. My personal opinion. Movie selection could be improved, too many horror movies. Could add a few more chick flicks! The flight was bumpy at times. We arrived a little early too! Flight attendants friendly.

really bad they refused to check in luggages that I had purchased, even showing them the transaction receipt from british airways app the staff in miami was MEDIOCRE

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

Uncomfortable seats and flight attendant was rude as she insisted on waking up my husband to ask him if he wanted a drink. When he said that he was sleeping, she replied “without an attitude “. He was seated at 8c

No food/snack served during the flight. Crew wasn’t interested at all. Flew American First but flying low cost with Ryanair is even better

Everything you need to know for your flight from Orlando to the Cayman Islands

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.