$249 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 9/16. 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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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, Nov 11 - Mon, Nov 16
United Airlines Logo
5:45 pm - 10:00 pm
GCM
-
MCO
28h 15m
1 stop
United Airlines Logo
6:55 pm - 4:30 pm
MCO
-
GCM
21h 35m
1 stop
$428United Airlines
Wed, Aug 19 - Mon, Aug 24
American Airlines Logo
12:00 pm - 6:17 pm
GCM
-
MCO
5h 17m
1 stop
American Airlines Logo
6:00 am - 11:27 am
MCO
-
GCM
6h 27m
1 stop
$437American Airlines
Wed, Aug 26 - Wed, Sep 2
Delta Logo
1:04 pm - 8:35 pm
GCM
-
MCO
6h 31m
1 stop
Delta Logo
7:00 am - 11:39 am
MCO
-
GCM
5h 39m
1 stop
$442Delta
Tue, Aug 25 - Wed, Sep 2
American Airlines Logo
12:00 pm - 11:14 pm
GCM
-
MCO
10h 14m
2 stops
American Airlines Logo
6:00 am - 1:10 pm
MCO
-
GCM
8h 10m
2 stops
$447American Airlines
Sat, Aug 29 - Wed, Sep 2
Delta Logo
1:04 pm - 9:44 pm
GCM
-
MCO
7h 40m
1 stop
Delta Logo
6:15 am - 11:39 am
MCO
-
GCM
6h 24m
1 stop
$464Delta
Tue, Aug 25 - Sun, Aug 30
Delta Logo
1:04 pm - 9:44 pm
GCM
-
MCO
7h 40m
1 stop
Delta Logo
8:55 pm - 11:39 am
MCO
-
GCM
15h 44m
1 stop
$487Delta
Mon, Aug 31 - Wed, Sep 2
Air Canada Logo
12:25 pm - 11:12 pm
GCM
-
MCO
33h 47m
2 stops
Air Canada Logo
7:00 am - 11:25 am
MCO
-
GCM
29h 25m
2 stops
$489Air Canada
Tue, Aug 25 - Mon, Sep 7
Delta Logo
1:04 pm - 8:35 pm
GCM
-
MCO
6h 31m
1 stop
Delta Logo
7:00 am - 11:39 am
MCO
-
GCM
5h 39m
1 stop
$490Delta
Mon, Aug 24 - Sun, Aug 30
Air Canada Logo
12:25 pm - 11:12 pm
GCM
-
MCO
33h 47m
2 stops
Air Canada Logo
8:30 pm - 11:25 am
MCO
-
GCM
15h 55m
1 stop
$499Air Canada
Mon, Aug 24 - Mon, Aug 31
Delta Logo
1:04 pm - 11:05 pm
GCM
-
MCO
9h 01m
1 stop
Delta Logo
7:00 am - 11:39 am
MCO
-
GCM
5h 39m
1 stop
$500Delta
Useful Info

Good to know

Low seasonApril
Cheapest flight$249
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 16% 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.
7.9
SouthwestOverall score based on 4242 reviews
8.1Boarding
7.0Food
8.6Crew
7.5Entertainment
8.0Comfort
Airline reviews

Crew was rude, flight was late, wifi didn't work, no food, basically nothing about this flight was good.

2.0 MediocreIrene, Jun 2026
CMH - DEN
Read more Southwest reviews

Crew was rude, flight was late, wifi didn't work, no food, basically nothing about this flight was good.

It was just okay, no frills, basic transportation with no luxury. No screens on the seats, no water or drinks on a short flight. Full flight but at least it was on time.

Flight was constantly delayed with significant changes in time, it was supposed to get to Colorado Springs at 8:30 PM but it got there after midnight.

Over a 3 hour flight. The turbulence was almost imperceptible except for 2 short periods which were not bad and over quickly. The attendants claimed "Safety first" and sat looking at their phones for 3 hours with no drink or snack service. This isn't the first time with Southwest. I thinkit may be there new plan of operation. Oh, and it was June 18, Southwest's Birthday which offered free drinks. NOT.

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

It was awful. The communication between corporate and the crew on the ground left more to be desired. The crew even said that Corporate was waiting on answers because they themselves didn't know. Every hour, there was a new excuse. I also understood that passengers were angry, but the crew should have done a better job at crowd control. There was a racial exchange between passengers that could've been avoided has the crew acted sooner.

We sat on plane at gate delayed without communication as to why we were just sitting there

Flight was delayed by 6 hours... the level of incompetence was truly astounding. I won't be flying American Airlines again. I don't care if AA is direct and there is a layover with another airline, I'll take the layover.

Check in was easy. Flights were smooth. Flight attendants were courteous and friendly.

Little time between flight from Dallas to flight to Gainesville. We chose this one, 43 minutes between, because the price for a connection with at least an hour between, was so much higher. Had to ask passengers on the Dallas flight to please allow us to deplane ahead of them. The economy passengers allowed this. We had to walk very fast to the next gate, 35 gates away. Thankfully all in the same terminal. Getting to the small Gainesville plane was a little confusing as you enter an area that is boarding many small planes at the same time. We stood in the wrong line for about 15 seconds before realizing it was not our Gainesville flight. Since I had boarded at this gate in the past, I knew to check the signs carefully so we weren’t lost. The first class seat experience was wonderful. I really enjoyed the upgrade. We were offered an alcohol drink as soon as we sat down. I got something different but it was a great gesture especially since we really had to hurry to make the flight. We had packed expecting we might miss this connection, but made it. Our luggage didn’t miss the flight. American Airlines delivered our bags to our home the next day. That was very convenient!

The plane was large, not full, but one with 3 seats near each window and 4 in a row in the middle of the plane. There were screens on the backs of the seats for entertainment and information. To use the entertainment one needs ear plugs that physically plug into the screen. My husband had some he let me use as I only had blue tooth type. The stewards gave out some headphones to some, but when my neighbor asked for some, the steward said no. So maybe they ran out? Idk. Bring the old kind of headphones or earbuds if you want entertainment in case this is the type of entertainment offered. We had a very tight connection in Miami. 43 minutes. The other economy passengers allowed us to get ahead of them because I asked if we could since we were near boarding time for our next flight and 35 gates away. They were extremely kind. First class wasn’t going to allow us to pass through. We did make the next flight. Our baggage didn’t, but they were delivered to us the next day and we were prepared with essentials in our carry on packs.

We departed early and arrived early The plane was clean and the crew was incredibly efficient another positive experience with American airlines for me.

Flight left on time. Captain provided relevant announcements. We had to wait 45 minutes to desembark due to the ramp closed because of lightening.

So overall the flight was just average and nothing special. They overbooked some of the flights and they ended up running out of overhead storage space so we had to check our carry-ons which wasn't terrible but we were inconvenienced because of the second connecting flight with a long layover we couldn't get our bags until the final destination. Most of the flight attendants were pretty good and overall the meals were not that great because the chicken was dry and overcooked. They also didn't provide butter or any kind of spread with the bread which is cheap and concerning. The American airlines staff at the check-in counter was kind of unprofessional because this lady just started singing in the middle of checking us in and that's weird. The worst part of the flights was the terrible conditions of the bathrooms which were unclean and did not have toilet paper or toilet tissue available which is kind of insane for a 14-hour and 8 and 1/2 hour flight.

Everything was fine except the end of the flight. We spent more than an hour circling around Miami due to weather conditions. That was not good.

Traveling to a place near Orlando?

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