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Cayman Islands

$101+ Cheap flights from Orlando (MCO) to the Cayman Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — GCM
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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Cheap flight deals from Orlando to Cayman Islands

Keep the following information in mind while searching for Orlando to Cayman Islands flight deals. Data was last updated August 20, 2025.

Round-trip from

$395
(Southwest)

One-way from

$101
(FlightHub)

Popular in

June

Cheapest in

September

Average price

$665

Good round-trip deal

$651 or less
From Orlando to Cayman Islands
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One-way flight from Orlando to Cayman Islands
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Highest demand for flights based on searches. 7% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Orlando to Cayman Islands.
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Find flight deals from Orlando to Cayman Islands

Cheapest flights from Orlando to Cayman Islands
Explore the most affordable flight options available from Orlando to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 20, 2025.

This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/910:40 amMCO - GCM
Nonstop1h 55mSouthwest
Fri 11/141:30 pmGCM - MCO
Nonstop1h 55mSouthwest
Deal found 8/18$395
This American Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/96:01 amMCO - GCM
1 stop6h 39mAmerican Airlines
Wed 11/121:25 pmGCM - MCO
1 stop9h 29mAmerican Airlines
Deal found 8/19$410
This American Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/154:26 pmMCO - GCM
2 stops19h 44mAmerican Airlines
Thu 9/1812:28 pmGCM - MCO
1 stop8h 56mAmerican Airlines
Deal found 8/19$414
This American Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/146:00 amMCO - GCM
1 stop6h 22mAmerican Airlines
Sun 9/2112:10 pmGCM - MCO
1 stop7h 25mAmerican Airlines
Deal found 8/18$440
This American Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1712:30 pmMCO - GCM
1 stop23h 40mAmerican Airlines
Wed 9/2412:25 pmGCM - MCO
1 stop6h 38mAmerican Airlines
Deal found 8/18$443
This American Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/37:35 amMCO - GCM
1 stop4h 35mAmerican Airlines
Fri 10/108:25 amGCM - MCO
1 stop9h 03mAmerican Airlines
Deal found 8/19$458
This American Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/287:35 amMCO - GCM
1 stop4h 35mAmerican Airlines
Sun 10/512:28 pmGCM - MCO
1 stop6h 38mAmerican Airlines
Deal found 8/20$461
This American Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/104:26 pmMCO - GCM
2 stops19h 44mAmerican Airlines
Wed 9/1712:10 pmGCM - MCO
2 stops19h 40mAmerican Airlines
Deal found 8/20$462
This American Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/96:10 amMCO - GCM
1 stop6h 00mAmerican Airlines
Sun 9/1412:10 pmGCM - MCO
1 stop10h 45mAmerican Airlines
Deal found 8/18$463
This American Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/256:00 amMCO - GCM
1 stop6h 22mAmerican Airlines
Sun 9/2812:10 pmGCM - MCO
1 stop7h 25mAmerican Airlines
Deal found 8/18$465

Cheapflights Fare Finder

 
Customize your flight search to find flights from Orlando to Cayman Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 20, 2025.
Use the filters below to find and compare flights from Orlando Airport to the Cayman Islands that are best for you.

Fly from

Orlando

Fly to

Cayman Islands

Route

Depart

Return

Price

OrlandoGeorge Town

MCO - GCM

MCOGCM

Orlando

Sun 11/9

10:40 am-12:35 pm

Nonstop1h 55m

George Town Owen Roberts Intl

Wed 11/12

1:30 pm-3:25 pm

Nonstop1h 55m

$395

OrlandoGeorge Town

MCO - GCM

MCOGCM

Orlando

Sun 11/9

10:40 am-12:35 pm

Nonstop1h 55m

George Town Owen Roberts Intl

Fri 11/14

1:30 pm-3:25 pm

Nonstop1h 55m

$395

OrlandoGeorge Town

MCO - GCM

MCOGCM

Orlando

Sun 11/9

8:00 am-11:58 am

1 stop3h 58m

George Town Owen Roberts Intl

Fri 11/14

8:45 am-5:12 pm

1 stop8h 27m

$410

OrlandoGeorge Town

MCO - GCM

MCOGCM

Orlando

Wed 9/10

7:35 am-11:10 am

1 stop4h 35m

George Town Owen Roberts Intl

Wed 9/17

12:25 pm-11:31 pm

1 stop10h 06m

$410

OrlandoGeorge Town

MCO - GCM

MCOGCM

Orlando

Sun 11/9

6:01 am-12:40 pm

1 stop6h 39m

George Town Owen Roberts Intl

Wed 11/12

1:25 pm-10:54 pm

1 stop9h 29m

$410

OrlandoGeorge Town

MCO - GCM

MCOGCM

Orlando

Mon 9/15

6:10 am-11:10 am

1 stop6h 00m

George Town Owen Roberts Intl

Thu 9/18

12:28 pm-10:24 pm

1 stop8h 56m

$410

OrlandoGeorge Town

MCO - GCM

MCOGCM

Orlando

Mon 10/27

6:15 am-11:25 am

1 stop6h 10m

George Town Owen Roberts Intl

Wed 10/29

8:25 am-6:28 pm

1 stop9h 03m

$410

OrlandoGeorge Town

MCO - GCM

MCOGCM

Orlando

Sat 12/6

6:55 am-11:00 am

1 stop4h 05m

$102

OrlandoGeorge Town

MCO - GCM

MCOGCM

Orlando

Thu 12/4

6:55 am-11:00 am

1 stop4h 05m

$102

OrlandoGeorge Town

MCO - GCM

MCOGCM

Orlando

Sun 12/7

6:55 am-11:00 am

1 stop4h 05m

$102

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 12 results
1
2

Best time to book a flight from Orlando to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from Orlando with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest month to book a flight from Orlando Airport to Cayman Islands?

Currently, January is the cheapest month in which you can book a flight from Orlando Airport to Cayman Islands (average of $467). Flying from Orlando Airport to Cayman Islands in March is currently the most expensive (average of $594). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MCO to KY?

Find hourly flight availability from Orlando to Cayman Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 20, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Orlando Airport to Cayman Islands as you normally would.

Reviews of airlines servicing Cayman Islands

Get insights into the airlines that provide service to Cayman Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Cayman Islands. Reviews last updated August 20, 2025.
See what other customers who have flown with Southwest and American Airlines from Orlando Airport to the Cayman Islands have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Orlando to Cayman Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    Departing from Orlando Airport to Cayman Islands will take you 1h 55m. There are 631 mi between Orlando Airport and Cayman Islands. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest flights from Orlando Airport to Cayman Islands?

    While on average a flight from Orlando Airport to Cayman Islands is generally $731, our data shows the cheapest flight currently is $581. When looking at the most popular route, (Orlando - George Town Owen Roberts Intl), you can expect to pay $372 for that flight.

  • Can I find deals for flights from Orlando to Cayman Islands that include hotel bookings?

    Yes. In addition to deals on Orlando to Cayman Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Orlando to Cayman Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Orlando to Cayman Islands.

  • Can I find deals for business class flights from Orlando to Cayman Islands?

    Yes. Cheapflights offers flight deals from Orlando to Cayman Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Orlando Airport to Cayman Islands?

    Currently, January is the cheapest month in which you can book a flight from Orlando Airport to Cayman Islands (average of $467). Flying from Orlando Airport to Cayman Islands in March is currently the most expensive (average of $594). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Orlando to Cayman Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Orlando to Cayman Islands

Discover the top 2 airlines that operate flights from Orlando to Cayman Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$379Average$588FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$404Average$507FlexibilityNo cancel feeOn-time71%

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