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Cayman Islands

$103+ Cheap flights from Orlando (ORL) 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — GCM
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$409
(Southwest)

One-way from

$103
(Priceline)

Popular in

August

Cheapest in

September

Average price

$487
From Orlando (ORL) to Cayman Islands
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One-way flight from Orlando (ORL) to Cayman Islands
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Highest demand for flights based on searches. 7% potential increase in price ($47 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($23 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 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 September 17, 2025.

This Southwest deal was found by Cheapflights users on 9/16. 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.
Tue 11/1110:40 amMCO - GCM
Nonstop1h 55mSouthwest
Fri 11/141:30 pmGCM - MCO
Nonstop1h 55mSouthwest
Deal found 9/16$409
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/136:00 amMCO - GCM
1 stop6h 10mAmerican Airlines
Thu 10/1612:10 pmGCM - MCO
1 stop10h 49mAmerican Airlines
Deal found 9/16$424
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Wed 11/269:15 pmMCO - GCM
1 stop16h 29mMultiple Airlines
Thu 12/411:55 amGCM - MCO
1 stop20h 35mMultiple Airlines
Deal found 9/16$437
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Thu 10/309:00 amMCO - GCM
1 stop7h 30mUnited Airlines
Thu 11/65:45 pmGCM - MCO
1 stop28h 13mUnited Airlines
Deal found 9/15$439
This Expedia deal was found by Cheapflights users on 9/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/286:15 pmMCO - GCM
2 stops42h 10mAir Canada
Sun 11/21:30 pmGCM - MCO
1 stop19h 50mAir Canada
Deal found 9/16$444
This American Airlines deal was found by Cheapflights users on 9/16. 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 12/306:45 amMCO - GCM
1 stop5h 20mAmerican Airlines
Wed 12/313:45 pmGCM - MCO
1 stop8h 32mAmerican Airlines
Deal found 9/16$449
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Thu 11/208:35 amMCO - GCM
2 stops12h 40mMultiple Airlines
Thu 12/411:55 amGCM - MCO
1 stop22h 09mMultiple Airlines
Deal found 9/16$453
This Mytrip deal was found by Cheapflights users on 9/15. 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.
Thu 10/308:00 amMCO - GCM
1 stop28h 25mMultiple Airlines
Thu 11/61:30 pmGCM - MCO
2 stops34h 23mMultiple Airlines
Deal found 9/15$455
This Priceline deal was found by Cheapflights users on 9/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/316:00 amMCO - GCM
1 stop8h 31mJetBlue
Fri 11/73:45 pmGCM - MCO
1 stop27h 09mJetBlue
Deal found 9/16$457
This Priceline deal was found by Cheapflights users on 9/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/266:00 amMCO - GCM
1 stop8h 31mJetBlue
Mon 10/272:45 pmGCM - MCO
1 stop17h 39mJetBlue
Deal found 9/16$466
This United Airlines deal was found by Cheapflights users on 9/16. 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 12/249:00 amMCO - GCM
1 stop7h 00mUnited Airlines
Wed 12/315:10 pmGCM - MCO
1 stop7h 35mUnited Airlines
Deal found 9/16$469

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 September 17, 2025.
Use the filters below to find and compare flights from Orlando 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

Tue 11/11

10:40 am-12:35 pm

Nonstop1h 55m

George Town Owen Roberts Intl

Fri 11/14

1:30 pm-3:25 pm

Nonstop1h 55m

$409

OrlandoGeorge Town

MCO - GCM

MCOGCM

Orlando

Mon 10/20

8:00 am-11:10 am

1 stop4h 10m

George Town Owen Roberts Intl

Tue 10/28

8:25 am-6:28 pm

1 stop9h 03m

$424

OrlandoGeorge Town

MCO - GCM

MCOGCM

Orlando

Wed 10/22

6:02 am-11:20 am

1 stop6h 18m

George Town Owen Roberts Intl

Fri 10/24

2:00 pm-11:59 pm

1 stop8h 59m

$424

OrlandoGeorge Town

MCO - GCM

MCOGCM

Orlando

Mon 10/13

6:00 am-7:20 pm

1 stop14h 20m

George Town Owen Roberts Intl

Thu 10/16

8:25 am-8:17 pm

2 stops10h 52m

$428

OrlandoGeorge Town

MCO - GCM

MCOGCM

Orlando

Thu 10/30

9:00 am-3:30 pm

1 stop7h 30m

George Town Owen Roberts Intl

Thu 11/6

5:45 pm-9:58 pm

1 stop28h 13m

$439

OrlandoGeorge Town

MCO - GCM

MCOGCM

Orlando

Fri 3/13

6:00 am-1:02 pm

1 stop8h 02m

George Town Owen Roberts Intl

Wed 3/18

2:10 pm-11:38 pm

1 stop8h 28m

$452

OrlandoGeorge Town

MCO - GCM

MCOGCM

Orlando

Wed 3/11

6:00 am-1:02 pm

1 stop8h 02m

George Town Owen Roberts Intl

Mon 3/16

2:10 pm-11:38 pm

1 stop8h 28m

$452

OrlandoGeorge Town

MCO - GCM

MCOGCM

Orlando

Wed 3/4

6:00 am-2:02 pm

1 stop8h 02m

George Town Owen Roberts Intl

Sun 3/8

2:10 pm-11:38 pm

1 stop8h 28m

$452

OrlandoGeorge Town

MCO - GCM

MCOGCM

Orlando

Tue 3/3

6:00 am-2:02 pm

1 stop8h 02m

George Town Owen Roberts Intl

Sun 3/8

2:10 pm-11:38 pm

1 stop8h 28m

$452

OrlandoGeorge Town

MCO - GCM

MCOGCM

Orlando

Fri 3/13

6:00 am-1:02 pm

1 stop8h 02m

George Town Owen Roberts Intl

Tue 3/17

2:10 pm-11:38 pm

1 stop8h 28m

$452

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 21 results
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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 to the Cayman Islands

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

Currently, January is the cheapest month in which you can book a flight from Orlando to Cayman Islands (average of $467). Flying from Orlando 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 ORL 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 September 17, 2025.

When flying from Orlando to Cayman Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 17, 2025.
Read through reviews of airlines operating flights from Orlando to the Cayman Islands, such as Southwest and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Food

7.0

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

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Food

7.0

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

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Food

7.0

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 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 to Cayman Islands?

    A quick flight from Orlando to Cayman Islands can take about 1h 55m. Southwest provides one of the quickest options available for as low as $409. The distance from Orlando to Cayman Islands is about 631 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 to Cayman Islands?

    Currently, January is the cheapest month in which you can book a flight from Orlando to Cayman Islands (average of $467). Flying from Orlando 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$379Average$589FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$434Average$525FlexibilityNo cancel feeOn-time71%

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