$166 Find Cheap Flights from Orlando to Cayman Islands

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 5/30. 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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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 25 - Sat, Aug 29
American Airlines Logo
8:03 am - 1:10 pm
MCO
-
GCM
6h 07m
1 stop
American Airlines Logo
11:55 am - 6:17 pm
GCM
-
MCO
5h 22m
1 stop
$520American Airlines
Tue, Aug 25 - Sat, Aug 29
American Airlines Logo
8:03 am - 11:00 am
MCO
-
GCM
3h 57m
1 stop
American Airlines Logo
2:10 pm - 12:21 am
GCM
-
MCO
9h 11m
2 stops
$525American Airlines
Sat, Aug 22 - Sat, Aug 29
American Airlines Logo
3:45 pm - 11:00 am
MCO
-
GCM
20h 15m
1 stop
American Airlines Logo
12:30 pm - 11:14 pm
GCM
-
MCO
9h 44m
1 stop
$529American Airlines
Sat, Oct 3 - Sat, Oct 10
Air Canada Logo
1:55 pm - 11:30 am
MCO
-
GCM
46h 35m
2 stops
Air Canada Logo
12:25 pm - 10:32 pm
GCM
-
MCO
33h 07m
2 stops
$533Air Canada
Tue, Oct 6 - Tue, Oct 13
American Airlines Logo
5:00 am - 11:00 am
MCO
-
GCM
7h 00m
1 stop
American Airlines Logo
9:25 am - 6:36 pm
GCM
-
MCO
8h 11m
1 stop
$540American Airlines
Fri, Jun 19 - Fri, Jun 26
Southwest Logo
11:05 am - 11:55 am
MCO
-
GCM
1h 50mnonstop
Southwest Logo
12:50 pm - 3:45 pm
GCM
-
MCO
1h 55mnonstop
$543Southwest
Tue, Oct 6 - Tue, Oct 13
American Airlines Logo
5:00 am - 12:35 pm
MCO
-
GCM
8h 35m
2 stops
American Airlines Logo
9:25 am - 11:35 pm
GCM
-
MCO
13h 10m
1 stop
$545American Airlines
Tue, Jul 28 - Fri, Jul 31
American Airlines Logo
5:00 am - 11:25 am
MCO
-
GCM
7h 25m
1 stop
American Airlines Logo
5:10 pm - 8:50 am
GCM
-
MCO
14h 40m
1 stop
$547American Airlines
Tue, Jul 28 - Fri, Jul 31
American Airlines Logo
10:00 am - 4:10 pm
MCO
-
GCM
7h 10m
1 stop
American Airlines Logo
5:10 pm - 11:57 am
GCM
-
MCO
17h 47m
2 stops
$552American Airlines
Sat, Aug 22 - Sat, Aug 29
Southwest Logo
11:10 am - 12:05 pm
MCO
-
GCM
1h 55mnonstop
Southwest Logo
1:00 pm - 3:55 pm
GCM
-
MCO
1h 55mnonstop
$553Southwest
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 3 days was to George Town, at $552 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 3 days was $552.

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 $622.

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 July, when the average cost of round-trip tickets is $746 and $505 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 Friday, 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 Wednesday and avoiding Tuesdays for the best deals.

Good to know

Low seasonMarch
Cheapest flight$124
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 4% 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 4268 reviews
8.6Crew
7.5Entertainment
7.0Food
8.1Boarding
8.0Comfort
Airline reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

4.0 OkayAnonymous, May 2026
MDW - LAX
Read more Southwest reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

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

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

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.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

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.

There were flight delays making our flight arrive at our destination after midnight didn’t seem to have enough crew or airplanes for the flights laid over in Dallas should’ve had plenty of time to make it to our next flight only made it because that flight was also delayed because our plane wasn’t even at the airport yet overall have not had a good experience on American

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

We had several flights and they were all on-time and flawless

For a 4 1/2 hour international flight all we got was 1 small pack of cookies and a drink. You had to watch movies on your own devise.

The seats need better cushioning for a nearly 5-hour flight, it was a bit uncomfortable. I'm glad American has free wi-fi but there were was a bout 30 minutes in the middle of the flight when there was no connection which was frustrating.

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

I’m sure Business Class would be excellent. I feel like I got what I paid for. Overall it was good and well worth it. I would do it again.

This short sector between Miami and JFK was undertaken purely for business purposes, with efficiency as the primary objective rather than a full inflight experience. Overall, the journey met its intended purpose; however, the ground experience at Miami stood out significantly. During check-in, I was unable to link my frequent flyer details from Qatar Airways (oneworld alliance) through either the self-service kiosk or web check-in. The situation was handled exceptionally well by the check-in agent, who demonstrated remarkable ownership. She coordinated across multiple counters, ensured my frequent flyer number was correctly reflected, reissued the boarding pass, and confirmed that mileage accrual would be recognized. Additionally, she ensured the boarding pass reflected priority status, enabling a seamless priority check-in experience without delays. This level of proactive service was both commendable and impactful. Boarding and the inflight experience, operated by American Airlines under a codeshare arrangement, were efficient but largely transactional. While operational delivery was smooth, there was no visible recognition of oneworld frequent flyer status onboard. In comparison to the consistently personalized engagement typically experienced with Qatar Airways, this absence was noticeable—though understandably a potential limitation of codeshare alignment rather than a direct service shortfall. In summary, while the flight itself fulfilled its operational intent, the exceptional professionalism and commitment demonstrated at the Miami check-in counter was the defining highlight of this journey. Greater consistency in elite recognition across partner airlines would further enhance the overall experience.

Business class was very good, one of my best flights

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

Information on your arrival and departure airports