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$232+ Cheap flights from the Cayman Islands to Orlando (ORL)

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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — ORL
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Cayman Islands to Orlando

Keep the following information in mind while searching for Cayman Islands to Orlando flight deals. Data was last updated September 15, 2025.

Round-trip from

$424
(American Airlines)

One-way from

$232
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$448
From Cayman Islands to Orlando (ORL)
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One-way flight from Cayman Islands to Orlando (ORL)
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Highest demand for flights based on searches. 12% potential increase in price ($77 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 September 2025
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Find flight deals from Cayman Islands to Orlando

Cheapest flights from Cayman Islands to Orlando
Explore the most affordable flight options available from Cayman Islands to Orlando. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This American Airlines deal was found by Cheapflights users on 9/14. 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 10/2312:10 pmGCM - MCO
1 stop8h 50mAmerican Airlines
Mon 10/2710:10 amMCO - GCM
1 stop10h 10mAmerican Airlines
Deal found 9/14$424
This American Airlines deal was found by Cheapflights users on 9/12. 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 10/2312:10 pmGCM - MCO
2 stops8h 50mAmerican Airlines
Tue 10/286:02 amMCO - GCM
2 stops8h 08mAmerican Airlines
Deal found 9/12$428
This United Airlines deal was found by Cheapflights users on 9/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/294:45 pmGCM - MCO
1 stop26h 30mUnited Airlines
Wed 11/57:05 pmMCO - GCM
1 stop21h 25mUnited Airlines
Deal found 9/13$439
This American Airlines deal was found by Cheapflights users on 9/13. 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.
Sat 10/118:25 amGCM - MCO
1 stop9h 03mAmerican Airlines
Mon 10/205:00 amMCO - GCM
1 stop7h 25mAmerican Airlines
Deal found 9/13$475
This American Airlines deal was found by Cheapflights users on 9/13. 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.
Sat 10/113:15 pmGCM - MCO
1 stop5h 45mAmerican Airlines
Sun 10/191:28 pmMCO - GCM
1 stop22h 42mAmerican Airlines
Deal found 9/13$483
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/122:00 pmGCM - MCO
1 stop7h 00mAmerican Airlines
Sun 10/193:14 pmMCO - GCM
1 stop20h 56mAmerican Airlines
Deal found 9/14$488
This American Airlines deal was found by Cheapflights users on 9/13. 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 10/108:25 amGCM - MCO
1 stop12h 35mAmerican Airlines
Mon 10/205:00 amMCO - GCM
1 stop7h 25mAmerican Airlines
Deal found 9/13$505
This American Airlines deal was found by Cheapflights users on 9/14. 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 11/61:20 pmGCM - MCO
2 stops8h 38mAmerican Airlines
Sun 11/98:00 amMCO - GCM
1 stop4h 13mAmerican Airlines
Deal found 9/14$509
This American Airlines deal was found by Cheapflights users on 9/13. 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 10/108:25 amGCM - MCO
1 stop10h 58mAmerican Airlines
Sun 10/191:28 pmMCO - GCM
1 stop22h 42mAmerican Airlines
Deal found 9/13$513
This Mytrip deal was found by Cheapflights users on 9/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/186:10 pmGCM - MCO
1 stop13h 31mMultiple Airlines
Sun 11/21:54 pmMCO - GCM
2 stops24h 06mMultiple Airlines
Deal found 9/13$519
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/48:50 amGCM - MCO
2 stops22h 06mMultiple Airlines
Sat 10/118:21 pmMCO - GCM
1 stop19h 24mMultiple Airlines
Deal found 9/14$523
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/116:10 pmGCM - MCO
1 stop17h 42mMultiple Airlines
Sat 10/1810:18 pmMCO - GCM
2 stops14h 17mMultiple Airlines
Deal found 9/14$527

Cheapflights Fare Finder

 
Customize your flight search to find flights from Cayman Islands to Orlando 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 September 15, 2025.
Use the filters below to find and compare flights from the Cayman Islands to Orlando that are best for you.

Fly from

Cayman Islands

Fly to

Orlando

Route

Depart

Return

Price

George TownOrlando

GCM - MCO

GCMMCO

George Town Owen Roberts Intl

Wed 10/22

8:25 am-6:28 pm

1 stop9h 03m

Orlando

Sun 10/26

5:00 am-11:25 am

1 stop7h 25m

$424

George TownOrlando

GCM - MCO

GCMMCO

George Town Owen Roberts Intl

Thu 10/23

8:25 am-1:50 pm

1 stop4h 25m

Orlando

Tue 10/28

6:00 am-11:10 am

1 stop6h 10m

$424

George TownOrlando

GCM - MCO

GCMMCO

George Town Owen Roberts Intl

Fri 10/31

8:25 am-10:02 pm

2 stops12h 37m

Orlando

Sun 11/2

10:03 am-2:46 pm

1 stop4h 43m

$428

George TownOrlando

GCM - MCO

GCMMCO

George Town Owen Roberts Intl

Thu 10/23

8:25 am-8:58 pm

2 stops11h 33m

Orlando

Mon 10/27

3:14 pm-7:20 pm

1 stop5h 06m

$428

George TownOrlando

GCM - MCO

GCMMCO

George Town Owen Roberts Intl

Wed 10/29

4:45 pm-8:15 pm

1 stop26h 30m

Orlando

Wed 11/5

7:05 pm-4:30 pm

1 stop21h 25m

$439

George TownOrlando

GCM - MCO

GCMMCO

George Town Owen Roberts Intl

Sat 10/18

12:10 pm-6:28 pm

1 stop5h 18m

Orlando

Sun 11/2

7:00 am-2:46 pm

1 stop7h 46m

$475

George TownOrlando

GCM - MCO

GCMMCO

George Town Owen Roberts Intl

Tue 3/10

2:10 pm-11:38 pm

1 stop8h 28m

Orlando

Wed 3/11

6:00 am-1:02 pm

1 stop8h 02m

$480

George TownOrlando

GCM - MCO

GCMMCO

George Town Owen Roberts Intl

Sat 10/11

3:15 pm-10:00 pm

1 stop5h 45m

Orlando

Sun 10/19

1:28 pm-11:10 am

1 stop22h 42m

$483

George TownOrlando

GCM - MCO

GCMMCO

George Town Owen Roberts Intl

Sat 10/11

12:10 pm-6:28 pm

1 stop5h 18m

Orlando

Sat 10/18

8:35 pm-11:10 am

1 stop15h 35m

$483

George TownOrlando

GCM - MCO

GCMMCO

George Town Owen Roberts Intl

Wed 2/11

1:50 pm-3:45 pm

Nonstop1h 55m

$254

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 20 results
1
2

Best time to book a flight from Cayman Islands to Orlando

Have a flexible travel schedule? Discover the best time to fly to Orlando from Cayman Islands 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 the Cayman Islands to Orlando

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

Currently, May is the cheapest month in which you can book a flight from Cayman Islands to Orlando (average of $206). Flying from Cayman Islands to Orlando in November is currently the most expensive (average of $289). 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 KY to ORL?

Find hourly flight availability from Cayman Islands to Orlando. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

It’s optimal to fly from Cayman Islands to Orlando at noon. By choosing this option you can save up to 4% on the cost of your flight, compared to a flight in the morning.

Reviews of airlines servicing Orlando

Get insights into the airlines that provide service to Orlando. 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 Orlando. Reviews last updated September 15, 2025.
Get a feel of what it's like to fly with Southwest and American Airlines from the Cayman Islands to Orlando by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Cayman Islands to Orlando. 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 Cayman Islands to Orlando?

    A quick flight from Cayman Islands to Orlando can take about 9h 03m. American Airlines provides one of the quickest options available for as low as $424. Cayman Islands and Orlando are separated by a distance of 631 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Cayman Islands to Orlando 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 Cayman Islands to Orlando?

    Currently, May is the cheapest month in which you can book a flight from Cayman Islands to Orlando (average of $206). Flying from Cayman Islands to Orlando in November is currently the most expensive (average of $289). 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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Top 2 airlines flying from Cayman Islands to Orlando

Discover the top 2 airlines that operate flights from Cayman Islands to Orlando. 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$335Average$540FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$441Average$505FlexibilityNo cancel feeOn-time71%

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