$101 Find Cheap Flights from Orlando to Grand Cayman

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 Grand Cayman departing on 12/7. 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 Grand Cayman

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Orlando to Grand Cayman, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Orlando to Grand Cayman, as well as popular online travel agencies
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Cheap Flights from Orlando to Grand Cayman

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
George Town
George Town1 stop$442
George Town
George Town1 stop$442

Book Cheap Orlando to Grand Cayman 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 Grand Cayman 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 Grand Cayman

Sun, Nov 9 - Fri, Nov 14
American Airlines Logo
6:01 am - 11:57 amMCO-GCM
5h 56m1 stop
American Airlines Logo
3:40 pm - 11:59 pmGCM-MCO
8h 19m1 stop
$442American Airlines
Find Deal
Sat, Oct 11 - Thu, Oct 16
American Airlines Logo
8:35 pm - 1:10 pmMCO-GCM
17h 35m1 stop
American Airlines Logo
8:25 am - 1:50 pmGCM-MCO
4h 25m1 stop
$450American Airlines
Find Deal
Wed, Dec 24 - Wed, Dec 31
United Airlines Logo
9:00 am - 4:00 pmMCO-GCM
7h 00m1 stop
United Airlines Logo
5:45 pm - 10:44 amGCM-MCO
16h 59m1 stop
$458United Airlines
Find Deal
Tue, Dec 23 - Tue, Dec 30
Delta Logo
7:00 am - 2:20 pmMCO-GCM
7h 20m1 stop
Delta Logo
1:55 pm - 10:26 pmGCM-MCO
8h 31m1 stop
$477Delta
Find Deal
Thu, Nov 6 - Sun, Nov 9
United Airlines Logo
9:00 am - 4:30 pmMCO-GCM
7h 30m1 stop
United Airlines Logo
5:45 pm - 8:15 pmGCM-MCO
26h 30m1 stop
$484United Airlines
Find Deal
Sat, Nov 8 - Mon, Nov 10
Southwest Logo
11:05 am - 1:00 pmMCO-GCM
1h 55mnonstop
Southwest Logo
1:30 pm - 3:25 pmGCM-MCO
1h 55mnonstop
$491Southwest
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Mon, Jan 5 - Sun, Jan 18
Delta Logo
8:00 am - 2:20 pmMCO-GCM
6h 20m1 stop
Delta Logo
2:00 pm - 8:38 pmGCM-MCO
6h 38m1 stop
$494Delta
Find Deal
Wed, Dec 17 - Wed, Dec 24
Southwest Logo
10:40 am - 12:35 pmMCO-GCM
1h 55mnonstop
Southwest Logo
1:30 pm - 3:25 pmGCM-MCO
1h 55mnonstop
$499Southwest
Find Deal
Sat, Oct 11 - Thu, Oct 16
 Logo
6:15 pm - 2:45 pmMCO-GCM
21h 30m1 stop
 Logo
4:45 pm - 4:05 pmGCM-MCO
22h 20m2 stops
Sat, Oct 11 - Thu, Oct 16
 Logo
1:08 pm - 11:35 amMCO-GCM
23h 27m2 stops
 Logo
12:50 pm - 8:41 amGCM-MCO
18h 51m2 stops
Booking Insights

KAYAK's insights & trends for Orlando to Grand Cayman flights

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

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

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.

No, with an average price for the route of $627, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Orlando Airport to Grand Cayman, 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 Grand Cayman is September, when tickets cost $398 (return) on average. On the other hand, the most expensive months are July and March, when the average cost of round-trip tickets is $631 and $623 respectively.

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

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

Your flight ticket price will generally be cheaper if you fly to Grand Cayman on a Monday and more expensive on a Sunday. On your return trip to Orlando, you should consider flying back on a Thursday, and avoid Sundays for better deals.

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

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 Grand Cayman, 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 Grand Cayman, you should book around 4 weeks before departure, which saves you about 26% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$101
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from Orlando to George Town

FAQs - booking Grand Cayman flights

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

    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 Grand Cayman.

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

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

    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 Grand Cayman 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 Grand Cayman?

    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 Grand Cayman 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 Grand Cayman?

    The cheapest time of day to fly to Grand Cayman is generally in the morning, when round-trip flights cost $584 on average. The most expensive time of day to fly to Grand Cayman is generally in the morning, which is peak travel time and where the average cost of a ticket is $584.

Reviews of the top airlines flying from Orlando to Grand Cayman

 
See real verified KAYAK customer reviews for airlines flying from Orlando to Grand Cayman. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Orlando to Grand Cayman? 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 4241 reviews
7.0Food
8.0Comfort
8.6Crew
7.5Entertainment
8.1Boarding
Airline reviews

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

2.0 MediocreMike, Aug 2025AUS - BWI
Read more Southwest reviews

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

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.

Internet was a bit expensive and did not work ask that week otherwise a good flight

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

The plane was broken so we had to change planes.

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

Everything you need to know for your flight to Grand Cayman

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