$243 Find Cheap Flights from Grand Cayman to Orlando - Compare and Save

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Cheap Flights from Grand Cayman to Orlando

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Grand Cayman to Orlando

Tue, Oct 20 - Tue, Oct 27
American Airlines Logo
8:00 am - 2:54 pmGCM  George Town Owen Roberts Intl-MCO Orlando
5h 54m1 stop Miami
American Airlines Logo
7:15 am - 2:23 pmMCO  Orlando-GCM George Town Owen Roberts Intl
8h 08m1 stop Miami
$397American Airlines
Tue, Oct 20 - Tue, Oct 27
American Airlines Logo
8:00 am - 11:15 pmGCM  George Town Owen Roberts Intl-MCO Orlando
14h 15m2 stops Miami Charlotte Douglas
American Airlines Logo
5:50 am - 2:23 pmMCO  Orlando-GCM George Town Owen Roberts Intl
9h 33m2 stops Charlotte Douglas Miami
$402American Airlines
Tue, Oct 20 - Tue, Oct 27
American Airlines Logo
8:00 am - 5:54 pmGCM  George Town Owen Roberts Intl-MCO Orlando
8h 54m1 stop Miami
American Airlines Logo
5:50 am - 2:23 pmMCO  Orlando-GCM George Town Owen Roberts Intl
9h 33m2 stops Charlotte Douglas Miami
$402American Airlines
Wed, Nov 25 - Mon, Nov 30
American Airlines Logo
3:40 pm - 10:47 pmGCM  George Town Owen Roberts Intl-MCO Orlando
7h 07m1 stop Miami
American Airlines Logo
8:25 pm - 2:40 pmMCO  Orlando-GCM George Town Owen Roberts Intl
18h 15m1 stop Miami
$405American Airlines
Wed, Nov 25 - Mon, Nov 30
Air Canada Logo
1:10 pm - 11:58 pmGCM  George Town Owen Roberts Intl-MCO Orlando
10h 48m1 stop Toronto Pearson Intl
Air Canada Logo
10:35 am - 12:10 pmMCO  Orlando-GCM George Town Owen Roberts Intl
25h 35m1 stop Toronto Pearson Intl
$447Air Canada
Sat, Sep 19 - Tue, Sep 22
Air Canada Logo
10:40 am - 11:49 pmGCM  George Town Owen Roberts Intl-MCO Orlando
12h 09m1 stop Toronto Pearson Intl
Air Canada Logo
1:55 pm - 11:25 amMCO  Orlando-GCM George Town Owen Roberts Intl
46h 30m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
$465Air Canada
Thu, Nov 5 - Mon, Nov 9
Southwest Logo
1:30 pm - 3:25 pmGCM  George Town Owen Roberts Intl-MCO Orlando
1h 55mnonstop
Southwest Logo
10:35 am - 12:35 pmMCO  Orlando-GCM George Town Owen Roberts Intl
2h 00mnonstop
$488Southwest
Thu, Jan 14 - Mon, Jan 18
Southwest Logo
1:50 pm - 3:45 pmGCM  George Town Owen Roberts Intl-MCO Orlando
1h 55mnonstop
Southwest Logo
10:55 am - 12:55 pmMCO  Orlando-GCM George Town Owen Roberts Intl
2h 00mnonstop
$489Southwest
Thu, Dec 17 - Sun, Jan 10
United Airlines Logo
2:55 pm - 11:44 pmGCM  George Town Owen Roberts Intl-MCO Orlando
8h 49m1 stop Chicago O'Hare Intl
United Airlines Logo
8:10 pm - 1:45 pmMCO  Orlando-GCM George Town Owen Roberts Intl
17h 35m1 stop Chicago O'Hare Intl
$492United Airlines
Fri, Dec 18 - Fri, Jan 8
Southwest Logo
1:30 pm - 3:25 pmGCM  George Town Owen Roberts Intl-MCO Orlando
1h 55mnonstop
Southwest Logo
10:55 am - 12:55 pmMCO  Orlando-GCM George Town Owen Roberts Intl
2h 00mnonstop
$526Southwest
Useful Info

Good to know

Low season

October

Cheapest flight

$243
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly with an average 8% increase in price.
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 4202 reviews
8.1Boarding
8.6Crew
7.0Food
7.5Entertainment
8.0Comfort
Airline reviews

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

6.0 GoodGordon, Jul 2026
Read more Southwest reviews

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

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

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

It went well. Plane wasn't full. Will be great when assigned seating is in place

Excellent experience. WiFi worked on this leg of My trip

Flight was great, but golf bag never made it until later in the day. Even though I had a nonstop flight it was placed on a different one. They made it right with flight credits and I was able to get it the same day.

Pretty standard flight. We left late, but arrived early. The wifi entertainment is always nice. The free snacks and beverages are simple, but appreciated. I'm tall and the seats are an issue. I can deal with a short flight, but any longer, I have to find another airline where I know beforehand I have extra legroom.

The flight was promptly on schedule and Southwest delivered everything they promised. No excuses for any shortfalls just 100% ownership of their responsibilities and business. The boarding and seating policy is a complete shambles. What started out as a great idea when Southwest first hit the market has been turned into a disaster due to the lack of integrity in many of the people who fly Southwest and take advantage of Southwest generosity at the expense of their fellow passengers.

The actual flight was great! The 3 hour delay not so much.

I have yet to come across an AA agent or flight attendant that is friendly. They really inhibit a good experience.

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.

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

I was able to get the AA customer Service desk to put me on an earlier flight without any issues.

It was a train wreck but on an airplane. First off, flight was delayed then we board only to hear two announcements, First weather delays in Orlando and second backup battery warning on emergency lights. After sitting on the plane for almost 2 hours they have us deplane due to the maintenance issue. We were told they were getting another plane. In the mean time, I notice another American- Orlando flight and ask the gate agent if I can switch. He says he cant help me and I'd have to walk to A13 from A37. Really!? I get down there and get a seat only to get an announcement my original flight was RE-boarding. The Then inflight there's no communication and I notice on flightaware were circling over the Gulf of America. I call the flight attendant and of course she has no clue and apparently 5m later the pilot finally tells us about another delay. Why does American always have these service and delay issues? They are my LAST choice in flights now!

No gates avail at DFW so our incoming had to wait 30 mins for a plane to push back because they Had mechanical. We boarded 90 mins delayed and then we had a mechanical. Come on American…do better. Also at my seat the tray table had not been cleaned. Floor had not been cleaned. But captain and flight Att were very picture and apologetic.

On the plus side, crew was attentive, drinks were cold, and in-flight entertainment selection was better than some other airlines. On the negative aide, Plane was delayed almost an hour, either no announcements from the gate crew. Biscoff cookies are gross, appreciate airlines that give a choice. Also, crew had no personality or enthusiasm at all.

Wish they had the seat-back video screens for watching movies or playing games.

Very good but wish they had the seat-back video screens for movies & games

Flight was delayed not sure why no explanation given and no apologies either. Otherwise the flight was fine

Traveling to a place near Orlando?

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Bay Lake
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