$172 Find Cheap Flights from Orlando to Cayman Islands - Compare and Save

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 8/10. 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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Book Cheap Orlando to the Cayman Islands 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 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

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

Tue, Aug 11 - Tue, Aug 18
Delta Logo
7:00 am - 11:39 am
MCO
-
GCM
5h 39m
1 stop
Delta Logo
1:04 pm - 12:24 am
GCM
-
MCO
10h 20m
1 stop
$449Delta
Tue, Aug 11 - Tue, Aug 25
American Airlines Logo
8:00 am - 11:00 am
MCO
-
GCM
4h 00m
1 stop
American Airlines Logo
12:00 pm - 11:14 pm
GCM
-
MCO
10h 14m
2 stops
$454American Airlines
Wed, Sep 9 - Wed, Sep 16
American Airlines Logo
7:49 am - 11:00 am
MCO
-
GCM
4h 11m
1 stop
American Airlines Logo
12:00 pm - 10:17 am
GCM
-
MCO
21h 17m
2 stops
$459American Airlines
Sat, Aug 15 - Tue, Aug 25
American Airlines Logo
9:59 am - 1:10 pm
MCO
-
GCM
4h 11m
1 stop
American Airlines Logo
2:10 pm - 11:33 pm
GCM
-
MCO
8h 23m
1 stop
$489American Airlines
Tue, Nov 10 - Sat, Nov 14
Southwest Logo
10:35 am - 12:35 pm
MCO
-
GCM
2h 00mnonstop
Southwest Logo
1:55 pm - 3:55 pm
GCM
-
MCO
2h 00mnonstop
$490Southwest
Tue, Nov 10 - Sat, Nov 14
American Airlines Logo
6:00 am - 8:20 pm
MCO
-
GCM
14h 20m
1 stop
American Airlines Logo
1:00 pm - 8:02 pm
GCM
-
MCO
7h 02m
1 stop
$491American Airlines
Tue, Aug 18 - Sat, Aug 22
American Airlines Logo
6:00 am - 1:10 pm
MCO
-
GCM
8h 10m
2 stops
American Airlines Logo
2:10 pm - 9:10 am
GCM
-
MCO
18h 00m
2 stops
$494American Airlines
Tue, Sep 1 - Tue, Sep 8
Delta Logo
6:15 am - 11:39 am
MCO
-
GCM
6h 24m
1 stop
Delta Logo
1:00 pm - 12:23 am
GCM
-
MCO
10h 23m
1 stop
$498Delta
Wed, Aug 19 - Sat, Aug 22
American Airlines Logo
6:00 am - 1:10 pm
MCO
-
GCM
8h 10m
2 stops
American Airlines Logo
2:10 pm - 11:14 pm
GCM
-
MCO
8h 04m
2 stops
$499American Airlines
Tue, Sep 1 - Tue, Sep 8
American Airlines Logo
5:36 pm - 11:00 am
MCO
-
GCM
18h 24m
2 stops
American Airlines Logo
2:10 pm - 11:14 pm
GCM
-
MCO
8h 04m
2 stops
$503American Airlines
Booking Insights

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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to the Cayman Islands from Orlando Airport found in the last 5 days was to George Town, at $602 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 5 days was $602.

What is the cheapest time of day to fly to the Cayman Islands?

The average price for all round-trip flights from Orlando Airport to the Cayman Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to the Cayman Islands is generally in the afternoon, when round-trip flights cost $489 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 $626.

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

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 $602, prices are generally cheapest when you fly direct.

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 June, when tickets cost $201 (return) on average. On the other hand, the most expensive months are December and January, when the average cost of round-trip tickets is $724 and $521 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 Thursday, as we generally find the cheapest rates on that day for this route. On the other hand, Tuesday is the most expensive day to fly from Orlando to Cayman Islands. For your return ticket, we recommend flying on a Tuesday and avoiding Fridays for the best deals.

Good to know

Low seasonMarch
Cheapest flight$172
Best time to beat the crowds but there is an average 10% increase 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.

Reviews of the 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.
7.9
SouthwestOverall score based on 4249 reviews
7.5Entertainment
8.0Comfort
7.0Food
8.6Crew
8.1Boarding
Airline reviews

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

8.0 ExcellentValerie, Jun 2026
MCO - ATL
Read more Southwest reviews

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

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

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

I liked it better when you were truer to your roots Am paying more for less fun

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

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.

My original flight got delayed day of so I had to rebook it from one layover to two layovers. The flight also left earlier which was a slight inconvenience but manageable. Then my first connection flight got delayed 3 separate times for a total of 2 hours delayed, causing me to miss my second connection flight back to Santa Barbara. Now, because of this missed flight, I am missing my college classes that I pay for.

Flight: Started on time. Comfortable flight. Arrived on time. Crew: Very cordial and helpful. Drinks and snack was served with a smile. Overall enjoyed the trip. Regards, Hari Doss Chanchala Doss

It was great. Smooth flight, comfortable, left on time and landed on time.

Really good. I accidentally left my duffel on the plane and the reps were so friendly in retrieving it.

Overall good. The pilots and flight attendants are excellent! The equipment was the issue on my First flight as they had to wait for a part to be installed. So the take off was at least 30 minutes later.

Wish they didnt delay off-boarding for 10 minutes so i could connect to my flight from miami to tampa

I have a gluten allergy so didn't have any food

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

We had 3 flights. 1 & 2 were on the same plane but we had to de-board just to re-board 30 mins later. That may have been due to a crew change though. Our 3rd flight had a couple “maintenance” issues that held us up. They were quickly resolved but it took forever for someone to bring the paperwork needed so we could leave. Apparently there was a computer glitch so a driver had to bring a physical copy. It delayed us about 1 1/2 hrs. The flights themselves were smooth & no problems. For boarding, I don’t know why they don’t start with the back of the plane & move forward. It would eliminate the back up from people trying to find their seats & put their bags in the overhead bins. Unless you’re on an overseas flight, there is no food, you get a beverage & either a small bag of pretzels or a biscuit cookie. Take your own food or snacks of you want something more.

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

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

Information on your arrival and departure airports