$247 Find Cheap Flights from Grand Cayman to Orlando

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Orlando departing on 11/4. 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

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Cheap Flights from Grand Cayman to Orlando

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

Wed, Sep 3 - Mon, Sep 29
American Airlines Logo
12:25 pm - 9:05 pmGCM-MCO
7h 40m1 stop
American Airlines Logo
6:10 am - 11:10 amMCO-GCM
6h 00m1 stop
$410American Airlines
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Wed, Sep 3 - Mon, Sep 29
American Airlines Logo
12:10 pm - 9:58 pmGCM-MCO
8h 48m1 stop
American Airlines Logo
4:26 pm - 11:10 amMCO-GCM
19h 44m2 stops
$414American Airlines
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Wed, Sep 3 - Mon, Sep 29
American Airlines Logo
12:25 pm - 3:32 pmGCM-MCO
26h 07m1 stop
American Airlines Logo
4:26 pm - 11:10 amMCO-GCM
19h 44m2 stops
$415American Airlines
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Thu, Aug 14 - Mon, Aug 18
Delta Logo
12:52 pm - 10:33 pmGCM-MCO
8h 41m1 stop
Delta Logo
7:00 am - 11:37 amMCO-GCM
5h 37m1 stop
$481Delta
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Wed, Aug 6 - Wed, Aug 13
United Airlines Logo
1:35 pm - 10:52 amGCM-MCO
20h 17m1 stop
United Airlines Logo
2:08 pm - 12:30 pmMCO-GCM
23h 22m1 stop
$489United Airlines
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Tue, Jul 22 - Tue, Jul 29
United Airlines Logo
1:35 pm - 6:10 pmGCM-MCO
27h 35m1 stop
United Airlines Logo
12:00 pm - 12:30 pmMCO-GCM
25h 30m1 stop
$497United Airlines
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Tue, Jul 22 - Tue, Jul 29
Southwest Logo
12:45 pm - 3:50 pmGCM-MCO
2h 05mnonstop
Southwest Logo
10:55 am - 11:50 amMCO-GCM
1h 55mnonstop
$501Southwest
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Tue, Jul 29 - Mon, Aug 11
American Airlines Logo
12:25 pm - 12:06 amGCM-MCO
10h 41m1 stop
American Airlines Logo
9:11 am - 1:12 pmMCO-GCM
5h 01m1 stop
$506American Airlines
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Wed, Aug 6 - Wed, Aug 13
 Logo
11:30 am - 12:13 pmGCM-MCO
23h 43m3 stops
 Logo
10:24 pm - 9:20 pmMCO-GCM
23h 56m2 stops
Wed, Sep 3 - Mon, Sep 29
 Logo
6:10 pm - 5:52 pmGCM-MCO
22h 42m2 stops
 Logo
5:30 am - 9:20 pmMCO-GCM
16h 50m3 stops
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Good to know

Low seasonFebruary
High seasonAugust
Cheapest flight$247
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from George Town to Orlando

FAQs for booking Grand Cayman to Orlando flights

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

    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 Grand Cayman to Orlando.

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

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

    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 to Orlando with an airline and back to Grand Cayman with another airline.

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

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

Reviews of the top airlines flying from Grand Cayman to Orlando

 
Need help choosing which airline to fly with from Grand Cayman to Orlando? 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
8.0Comfort
8.6Crew
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.

Cluster mess boarding. Can't wait for SWA reserved seating. Internet didn't seem to work on the plane.

Flights delayed by 4-6 hours. Boarding was a mess and unclear. Bags were not at arrival airport and had never even been put on the plane. No idea when I’ll get them. Don’t fly into Denver!

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

The flight crew were friendly and attentive. Food was good and they passed out ice cream and drinks awhile after Lunch was done. The ice cream was a nice treat! I found several movies to watch during the flight. There was many movies and tv shows to choose from. We flew Premium economy and there was enough leg room to be comfortable. The seats were also comfortable. I would fly AA again if the airfare isn’t expensive.

The pilots are always hauling in the sky. No issues with boarding only problem was layover was shortened too much by weather but luckily the next flight was still boarding and did not missit

During service there was a garbage/beverage spill near our seats that never was cleaned up. On a relatively short flight when we’re fortunate enough to actually have in flight movies available, the flight attendants pitching the AADVANTAGE credit card shouldn’t talk for the last 10 minutes of the flight so that we miss the end of the movie.

Waited on the runway for takeoff for 2.5 hours. Air traffic rerouted us. The plane didn't have enough fuel, so had to go back to the gate. Had to wait for a new pilot. Should have landed at 5:22. Didn't land until 9:10. Trash flight.

The boarding was pretty easy. However, the first class seats are not lay flat as other airlines (like JetBlue) has and therefore sleeping was a challenge.

Everything about the flight was lovely…We left early, arrived early, cabin crew were efficient and helpful. Flight was easy and most pleasant.

Would have thought that they would gas up plane before everyone got on board

The flight was late and we missed this connecting flight. American Airlines refused to put us anywhere for the night for their snafu. We had to find our own accommodations in Miami, and it was expensive for a crappy hotel.

Fine. On time, cabin service was fine, bag arrived. All good. Flying into DCA so did not collide with any helicopters, which is also good. Horrid incident that could have and should have been prevented.

Free wifi was available, but only some time, being at least 30 minutes into the flight. it would have been better that an announcement had been made about the delay.

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