$271 Find Cheap Flights from Cayman Islands to Orlando

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Orlando departing on 6/15. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Orlando Airport

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Orlando, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Orlando, as well as popular online travel agencies
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Flight Deals

Cheap Flights from the Cayman Islands to Orlando

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from the Cayman Islands to Orlando 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 the Cayman Islands to Orlando

Thu, Sep 24 - Sun, Sep 27
Delta Logo
12:55 pm - 11:04 pm
GCM
-
MCO
9h 09m
1 stop
Delta Logo
7:00 am - 11:40 am
MCO
-
GCM
5h 40m
1 stop
$464Delta
Tue, Sep 22 - Sat, Sep 26
American Airlines Logo
1:20 pm - 8:49 am
GCM
-
MCO
18h 29m
2 stops
American Airlines Logo
8:05 pm - 10:50 am
MCO
-
GCM
15h 45m
2 stops
$478American Airlines
Tue, Sep 22 - Sat, Sep 26
American Airlines Logo
1:20 pm - 8:16 am
GCM
-
MCO
17h 56m
1 stop
American Airlines Logo
8:05 pm - 11:10 am
MCO
-
GCM
16h 05m
1 stop
$482American Airlines
Sun, Aug 2 - Sat, Aug 8
American Airlines Logo
12:02 pm - 6:59 pm
GCM
-
MCO
5h 57m
1 stop
American Airlines Logo
6:00 am - 1:10 pm
MCO
-
GCM
8h 10m
1 stop
$526American Airlines
Thu, Jun 11 - Mon, Jun 15
Southwest Logo
12:50 pm - 3:45 pm
GCM
-
MCO
1h 55mnonstop
Southwest Logo
11:05 am - 11:55 am
MCO
-
GCM
1h 50mnonstop
$533Southwest
Fri, Jun 12 - Mon, Jun 15
Delta Logo
12:59 pm - 10:51 pm
GCM
-
MCO
8h 52m
1 stop
Delta Logo
6:15 am - 11:34 am
MCO
-
GCM
6h 19m
1 stop
$538Delta
Sat, Aug 1 - Sun, Aug 9
American Airlines Logo
11:56 am - 8:01 pm
GCM
-
MCO
7h 05m
1 stop
American Airlines Logo
7:30 am - 11:00 am
MCO
-
GCM
4h 30m
1 stop
$545American Airlines
Thu, Jun 11 - Mon, Jun 15
American Airlines Logo
12:33 pm - 12:13 am
GCM
-
MCO
10h 40m
1 stop
American Airlines Logo
7:34 am - 11:01 am
MCO
-
GCM
4h 27m
1 stop
$547American Airlines
Sat, Jun 13 - Tue, Jun 16
United Airlines Logo
1:50 pm - 9:45 am
GCM
-
MCO
18h 55m
1 stop
United Airlines Logo
7:20 pm - 12:30 pm
MCO
-
GCM
18h 10m
1 stop
$548United Airlines
Thu, Jun 11 - Mon, Jun 15
American Airlines Logo
12:01 pm - 10:00 pm
GCM
-
MCO
8h 59m
2 stops
American Airlines Logo
6:00 am - 11:01 am
MCO
-
GCM
6h 01m
1 stop
$552American Airlines
Booking Insights

KAYAK's insights & trends for flights to Orlando

Get data-powered insights and trends for flights to Orlando to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest flight to Orlando?

These are the best round-trip prices found by users searching on KAYAK in the last 3 days.

In the last 3 days, the cheapest flight deal to Orlando was found on the route from George Town, at $464 return. The most popular connection is from Newark to Orlando and KAYAK users have found round-trip deals for as low as $141 in the last 3 days.

What is the cheapest day to fly to Orlando?

The average price of all round-trip flights to Orlando Airport clicked on KAYAK for each day over the last 12 months.

Based on KAYAK data, the cheapest day to fly to Orlando is Wednesday where round-trip tickets can be as cheap as $491. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $731 on average.

What is the cheapest time of day to fly to Orlando Airport?

The average price for all round-trip flights to Orlando Airport depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Orlando Airport is generally in the afternoon, when round-trip flights cost $622 on average. The most expensive time of day to fly to Orlando Airport is generally in the morning, which is peak travel time and where the average cost of a ticket is $656.

What is a good deal for flights to Orlando Airport?

If you’re looking for cheap airfare to Orlando Airport, 25% of our users found tickets to Orlando Airport for the following prices or less: From George Town $523 round-trip.

Good to know

Low seasonApril
Cheapest flight$271
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly and prices are also 16% lower on average.
Flight from George Town to Orlando

FAQs - booking Orlando flights

  • What is the cheapest flight to Orlando?

    In the last 3 days, the cheapest flight deal to Orlando was found on the route from George Town, at $464 return. The most popular connection is from Newark to Orlando and KAYAK users have found round-trip deals for as low as $141 in the last 3 days.

  • How far is Orlando Airport from central Orlando?

    You’ll need to travel 9 miles to reach the Orlando city center from Orlando Airport.

  • How much is a flight to Orlando?

    On average, a flight to Orlando costs $495. The cheapest price found on KAYAK in the last 2 weeks cost $283 and departed from George Town Owen Roberts Intl Airport.

  • How does KAYAK find such low prices on flights to Orlando?

    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 to Orlando.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Orlando?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Orlando is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Orlando?

    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 to Orlando 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 to Orlando?

    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 to Orlando up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Orlando

  • Looking for cheap airfare to Orlando? 25% of our users found round-trip tickets to Orlando for the following prices or less: From George Town $434
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Orlando flight deals.

Reviews of the top airlines flying from the Cayman Islands to Orlando

 
See real verified KAYAK customer reviews for airlines flying to Orlando. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from the Cayman Islands to Orlando. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Orlando? 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 4277 reviews
8.6Crew
8.1Boarding
7.0Food
7.5Entertainment
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.

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

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.

So overall the flight was just average and nothing special. They overbooked some of the flights and they ended up running out of overhead storage space so we had to check our carry-ons which wasn't terrible but we were inconvenienced because of the second connecting flight with a long layover we couldn't get our bags until the final destination. Most of the flight attendants were pretty good and overall the meals were not that great because the chicken was dry and overcooked. They also didn't provide butter or any kind of spread with the bread which is cheap and concerning. The American airlines staff at the check-in counter was kind of unprofessional because this lady just started singing in the middle of checking us in and that's weird. The worst part of the flights was the terrible conditions of the bathrooms which were unclean and did not have toilet paper or toilet tissue available which is kind of insane for a 14-hour and 8 and 1/2 hour flight.

Everything was fine except the end of the flight. We spent more than an hour circling around Miami due to weather conditions. That was not good.

They lost my bag. ... And I asked them 3 times to 3 different people if my checked bag will maKe it all the way - they all confirmed and at the end it was left at the connection... Bravo

Cancelled BOYH legs of our flight home 30 min before initial boarding

Poor... food was horrible, boarding very slow, service on board mediocre

Flight left early and arrived 30 MINUTES early at the destination. Smooth trip.

Departed late but made up the time en route. Uncrowded and clean aircraft.

I was able to get the AA customer Service desk to put me on an earlier flight without any issues.

Incredibly delayed. First delay was due to plane coming in being late. Resulted in 30 minute delay. Boarded and then had multiple mechanical issues. Was on plane for an hour until they told people they could get off if they wanted but couldn't come back. Then gate agent rushed in and said they had lost control of who went off and we would all have to deplane and then get back on. They said flight had not been cancelled. Then while sitting waiting to board again they announced it would take two hours to get new plane and to wait at new gate. New plane arrived, reboarded only to find out that pilots had timed out. Waited for new pilots. In that time one of the flight attendants timed out. Never received food or water while waiting. Was confusing mess as to what was happening. Even flight attendants and gate agents were getting frustrated. Almost 6 hours delayed. Called American to received flight credit but can't get anywhere as Kayak reservation and don't have a ticket number. Reached out to Kayak but never heard back.

Very disappointing. Flight was delayed by 1.5 hours and food options are very underwhelming even for first class seats (same food given to economy seats)

Traveling to a place near Orlando?

Book flights to Orlando if you plan to visit one of these locations
Bay Lake
Cocoa
Lake Wales
River Ranch
Union Park
Belle Isle
Bartow
Oviedo
Montverde

Everything you need to know for your flight to Orlando

Information on the airport you'll fly into in Orlando