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

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Price, demand and travel trends for Orlando Airport to the Cayman Islands flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

Are flights from Orlando Airport to the Cayman Islands cheaper or more expensive than last year?

Fares from Orlando Airport to the Cayman Islands are running about 4% higher than they were around this time last year, averaging $606 round-trip.

What are the cheapest fares from Orlando Airport to the Cayman Islands right now?

The cheapest fare from Orlando Airport to the Cayman Islands in the last week was $438 round-trip, to George Town Owen Roberts Intl (GCM).

What’s the cheapest month to fly from Orlando Airport to the Cayman Islands?

November is the cheapest time of year to fly, with average fares of $505. Prices are highest in June, when average flight costs increase to around $777.

Which airport in the Cayman Islands is the cheapest to fly to from Orlando Airport?

All flights from Orlando Airport to the Cayman Islands arrive at George Town Owen Roberts Intl (GCM). On average, round-trip fares are around $611.

What’s the cheapest day to fly from Orlando Airport to the Cayman Islands?

Tuesday tends to be the cheapest day to fly from Orlando Airport to the Cayman Islands, while Saturday is the most expensive. Fares run about 24% higher that day, based on the past 12 months of KAYAK data.

What's the cheapest time of day to fly from Orlando Airport to the Cayman Islands?

Data from the past 12 months shows it's cheapest to fly to the Cayman Islands during the morning with average prices of $612. The night is the most expensive time to fly, with average prices of $1,268.

Key details for Orlando Airport to the Cayman Islands flights

Low season

February

Cheapest flight

$172
Beat the crowds with an average 43% drop in travelers.
The most popular month to fly with an average 23% increase in travelers.
One-way flight from Orlando Airport to George Town

Your Orlando Airport to the Cayman Islands flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Orlando Airport to the Cayman Islands?

    Yes. Fares from Orlando Airport to the Cayman Islands are low right now. As a rule of thumb, a round-trip under $529 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Orlando Airport to the Cayman Islands?

    Over the past 12 months, round-trip fares from Orlando Airport to the Cayman Islands have ranged from $529 to $702.

  • What airlines fly nonstop from Orlando Airport to the Cayman Islands?

    Based on the flight schedule for the next 3 months, just one airline regularly flies nonstop from Orlando Airport to the Cayman Islands: Southwest.

  • Where in the Cayman Islands can I fly nonstop from Orlando Airport?

    Based on the flight schedule for the next 3 months, you can only fly nonstop from Orlando Airport to George Town.

  • Is it cheaper to fly with a layover from Orlando Airport to the Cayman Islands?

    Yes. Nonstop flights from Orlando Airport to the Cayman Islands average $640 over the past 12 months, but flights with a layover can cost less. The most affordable connecting airports are:

    • Atlanta Hartsfield-Jackson (ATL) from $319
    • Fort Lauderdale (FLL) from $328
    • Miami (MIA) from $586

  • How long is a flight from Orlando Airport to the Cayman Islands?

    Flights from Orlando Airport to the Cayman Islands take 2h on average.

  • Which cabin classes are available on flights from Orlando Airport to the Cayman Islands?

    On flights from Orlando Airport to the Cayman Islands you can only book Economy Class.

  • What are the earliest and latest flights from Orlando Airport to the Cayman Islands?

    The earliest nonstop flight from Orlando Airport to the Cayman Islands departs at 10:30 am and the latest departs at 11:25 am. Nonstop flights take about 2h.

Your guide to booking Orlando Airport to the Cayman Islands flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your travel dates are flexible, book your trip for November when flights are typically cheapest and avoid June when prices are at their highest.
  • Flying on Tuesday is usually the cheapest. Flights on Saturday cost about 24% more on average, so being flexible with your travel dates could help you save.
  • Start your trip in George Town, which is the most popular destination in the Cayman Islands. From there, it's easy to continue on to other popular destinations such as West Bay, East End and North Side.
  • If you want the shortest trip, choose the Orlando Airport to the Cayman Islands nonstop route. If you'd rather save money, the route via Atlanta Hartsfield-Jackson (ATL) is usually the cheapest.

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 4216 reviews
7.0Food
7.5Entertainment
8.1Boarding
8.0Comfort
8.6Crew
Airline reviews

Wasn't expecting this, but, we actually ended up getting assigned to the first row of seats!!!!! The extra legroom came in handy

10.0 ExcellentAnonymous, Sep 2026
Read more Southwest reviews

Wasn't expecting this, but, we actually ended up getting assigned to the first row of seats!!!!! The extra legroom came in handy

Flights delays were communicated timely and helpfully, but there was a significant delay without any real effort to make up for that. Also, the in-flight WiFi was very spotty. That said, this was my first time with Southwest and I was quite happy with the service and staff otherwise.

Delayed and once landed waited very long for the luggage

Eveeyrime I fly they are begging for bags due to cabin overhead space. What they should so ia take the bags that are clearly too big to fit wheels first on their side. And those of us who give up the bag should really get their bags first. When boarding, nobody wants stupid jokes about how hot it is on board. Give us some cool air. Im usually sick from the heat by the time we take off.

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

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

Flight was 2+ hours delayed and they “misplaced” all 3 of our checked-in bags.

I have executive platinum status with American Airlines. It seems impossible to be upgraded anymore and I’m never offered a cheese plate or thanked for my loyalty.

In premium economy I was expecting a bit cleaner area. Tables were not very clean. Only one of us received a blanket and pillow. The food was okay. Probably a smidgen better than coach. The crew were very nice but should have done more walk through to at least pick up trash.

if it's a mobile only entertainment experience, please provide a place to hold the device in the back of the seat.

Not great. I understand delays happen due to weather and crew issues, but it was unacceptable that no agents were available at the counters inside the airport for customer service or help getting on a standby list. The app was not helpful either. I stood in line for an hour waiting for someone to show up at the gate to help me get on a standby flight. Customer care does not seem to be a priority.

It was awful. My first flight was delayed and as a consequence I lost my second flight to Greensboro. I did not know what to do so I rebook myself a flight to Charlotte . It was very inconvenient I not to have anybody form corporate assisting me either from PwC or from kayak . It is a very disappointing experience that American did not wait 1 minute or told me to rebook before making the first flight

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.

More options for your flight from Orlando to the Cayman Islands

Complete your trip to the Cayman Islands with a hotel stay or car rental