$152 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 8/19. 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.
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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$408
George Town
George Town1 stop$408

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.

Recent round-trip flight deals from Orlando to the Cayman Islands

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Orlando to the Cayman Islands.
Discover the best prices for you by selecting your travel dates on KAYAK.
American Airlines Logo
6:39 am - 11:05 amMCO-GCM
5h 26m1 stop
American Airlines Logo
3:15 pm - 11:41 pmGCM-MCO
7h 26m1 stop
$408American Airlines
Find Deal
Mon, Sep 8 - Thu, Sep 18
American Airlines Logo
5:58 pm - 12:35 pmMCO-GCM
19h 37m2 stops
American Airlines Logo
3:15 pm - 8:47 pmGCM-MCO
4h 32m1 stop
$412American Airlines
Find Deal
Mon, Sep 8 - Thu, Sep 18
Delta Logo
7:00 am - 11:31 amMCO-GCM
5h 31m1 stop
Delta Logo
1:02 pm - 8:36 pmGCM-MCO
6h 34m1 stop
$457Delta
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Sun, Sep 7 - Sat, Nov 1
Delta Logo
7:00 am - 11:25 amMCO-GCM
5h 25m1 stop
Delta Logo
12:40 pm - 10:16 pmGCM-MCO
8h 36m1 stop
$493Delta
Find Deal
Wed, Jul 2 - Mon, Jul 7
Southwest Logo
10:55 am - 11:50 amMCO-GCM
1h 55mnonstop
Southwest Logo
12:45 pm - 3:50 pmGCM-MCO
2h 05mnonstop
$531Southwest
Find Deal
Thu, Jul 3 - Mon, Jul 7
Southwest Logo
10:55 am - 11:50 amMCO-GCM
1h 55mnonstop
Southwest Logo
12:45 pm - 3:50 pmGCM-MCO
2h 05mnonstop
$541Southwest
Find Deal
Sun, Jun 15 - Fri, Jun 20
 Logo
5:15 am - 9:20 pmMCO-GCM
17h 05m2 stops
 Logo
12:40 pm - 8:37 pmGCM-MCO
30h 57m2 stops
Thu, May 29 - Sun, Jun 1
United Airlines Logo
7:06 am - 12:30 pmMCO-GCM
6h 24m1 stop
United Airlines Logo
4:45 pm - 10:52 amGCM-MCO
17h 07m1 stop
$583United Airlines
Find Deal
Wed, Jul 2 - Sat, Jul 5
United Airlines Logo
5:03 pm - 12:30 pmMCO-GCM
20h 27m1 stop
United Airlines Logo
4:45 pm - 10:52 amGCM-MCO
17h 07m1 stop
$594United Airlines
Find Deal
Thu, Jul 3 - Sat, Jul 5
 Logo
5:15 am - 9:20 pmMCO-GCM
17h 05m2 stops
 Logo
12:40 pm - 8:27 pmGCM-MCO
30h 47m3 stops
Thu, May 29 - Sun, Jun 1
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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 $393 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 $393.

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 $411 (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 Sundays 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 19 weeks before departure.


Good to know

Low seasonSeptember
High seasonMay
Cheapest flight$152
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 2% increase in price.
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 $582 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 $582.

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 4294 reviews
7.1Food
8.2Boarding
8.6Crew
8.0Comfort
7.6Entertainment
Airline reviews

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.

6.0 GoodJennifer, Apr 2025FLL - RDU
Read more Southwest reviews

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:

Glad flight made it out. So many delays due to hurricane. everyone did a great job.

The flight was delayed about 20 minutes, but this was an evening flight, so it comes as no surprise. This flight came a good 1.5 days ahead of hurricane Helene which was still far out in the gulf. However, the flight never removed the seated buckle light. The staff announced from the beginning that due to the bad weather (I suppose the hurricane a day and a half away) they would have to do an abbreviated service with water and a snack. I am fine with their water and snack offering, but this was one of the smoothest flights I've had in years. If Southwest believes a flight like this requires everyone to remain seated, then all of their flights should remain buckled for the entire flight. I cannot help but wonder if things like this are a sneaky way to cut back on expenses since the airline is currently under a lot of pressure to reduce costs.

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

Crew professional. Easy bag drop off. On time. Good entertainment.

Nice modern plane. Can use your own device for entertainment. Get a snack on the plane.

Flight was late and missed connecting flight. They could have better accommodated, but instead did an overnight and had to arrive the next afternoon.

The boarding crew was incredibly helpful getting me on an earlier flight

They have lost any customer service care and support. Terrible airline now and been for awhile.

The flight was delayed leaving Miami. When we arrived in Charlotte, we were unable to park at our scheduled gate. We had to wait another 30-45 minutes before we could park at a different gate. All in all, we were delayed by almost two hours arriving in Charlotte.

the pilot that landed this flight in Philadelphia did an amazing job, the weather was absolutely terrible and we landed safely.

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

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