$69 Find Cheap Flights from Orlando to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Orlando to Caribbean departing on 8/16. 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

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Cheap Flights from Orlando to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Montego Bay
Montego Baynonstop$238
Montego Bay
Montego Baynonstop$238

Book Cheap Orlando to Caribbean Plane Tickets

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

Thu, Oct 23 - Mon, Oct 27
Frontier Logo
11:40 pm - 2:34 amMCO-SJU
2h 54mnonstop
Frontier Logo
3:40 am - 6:42 amSJU-MCO
3h 02mnonstop
$146Frontier
Find Deal
Mon, Sep 1 - Mon, Sep 8
Spirit Airlines Logo
10:47 am - 1:48 pmMCO-STT
3h 01mnonstop
Spirit Airlines Logo
4:02 pm - 7:25 pmSTT-MCO
3h 23mnonstop
$152Spirit Airlines
Find Deal
Wed, Aug 27 - Wed, Sep 3
Spirit Airlines Logo
10:47 am - 1:48 pmMCO-STT
3h 01mnonstop
Spirit Airlines Logo
2:43 pm - 6:05 pmSTT-MCO
3h 22mnonstop
$158Spirit Airlines
Find Deal
Thu, Oct 9 - Mon, Oct 20
Frontier Logo
11:40 pm - 2:34 amMCO-SJU
2h 54mnonstop
Frontier Logo
3:40 am - 6:42 amSJU-MCO
3h 02mnonstop
$166Frontier
Find Deal
Mon, Aug 18 - Fri, Aug 22
JetBlue Logo
9:04 pm - 11:59 pmMCO-BQN
2h 55mnonstop
JetBlue Logo
5:01 am - 7:52 amBQN-MCO
2h 51mnonstop
$198JetBlue
Find Deal
Wed, Aug 27 - Wed, Sep 3
JetBlue Logo
8:55 pm - 11:50 pmMCO-BQN
2h 55mnonstop
JetBlue Logo
8:07 pm - 10:59 pmBQN-MCO
2h 52mnonstop
$215JetBlue
Find Deal
Fri, Oct 17 - Fri, Oct 24
American Airlines Logo
6:00 am - 10:05 amMCO-NAS
4h 05m1 stop
American Airlines Logo
6:45 pm - 11:43 pmNAS-MCO
4h 58m1 stop
$284American Airlines
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Fri, Sep 19 - Tue, Sep 23
American Airlines Logo
8:30 pm - 5:58 pmMCO-NAS
21h 28m1 stop
American Airlines Logo
6:40 pm - 4:50 pmNAS-MCO
22h 10m1 stop
$293American Airlines
Find Deal
Mon, Nov 17 - Fri, Nov 21
Southwest Logo
10:50 am - 12:15 pmMCO-NAS
1h 25mnonstop
Southwest Logo
1:10 pm - 2:30 pmNAS-MCO
1h 20mnonstop
$305Southwest
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Mon, Aug 25 - Fri, Aug 29
Southwest Logo
11:50 am - 1:20 pmMCO-NAS
1h 30mnonstop
Southwest Logo
2:15 pm - 3:45 pmNAS-MCO
1h 30mnonstop
$334Southwest
Find Deal
Booking Insights

KAYAK's insights & trends for Orlando to Caribbean flights

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

What is the cheapest Orlando to Caribbean flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Orlando to Caribbean.

The cheapest ticket to Caribbean from Orlando found in the last 72 hours was to Nassau, at $103 round-trip. The most popular route is from Orlando Airport (MCO) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $135.

Can I save money by flying with a layover from Orlando to Caribbean?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $502, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Orlando to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Orlando to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Orlando to Caribbean is October, when tickets cost $199 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $345 and $278 respectively.

What’s the cheapest day of the week to fly from Orlando to Caribbean?

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

When flying from Orlando to Caribbean, you should consider leaving on a Thursday and avoid Sundays if you are looking for the best rates. For your return to Orlando, you’ll find the best rates on Fridays and the most expensive ones on Mondays.

How far in advance should I book a flight from Orlando to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Orlando to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Orlando to Caribbean, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.


Good to know

Low seasonSeptember
Cheapest flight$69
Best time to beat the crowds with an average 0% drop in price.
Most popular time to fly with an average 22% increase in price.
Flight from Orlando Airport to San Juan Airport

FAQs - booking Caribbean flights

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

    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 from Orlando to Caribbean.

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

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

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

    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 from Orlando to Caribbean 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 from Orlando to Caribbean?

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

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $232 on average. Morning departures are around 2% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the evening, which is peak travel time and where the average cost of a ticket is $281.

Reviews of the top 5 airlines serving from Orlando to Caribbean

 
Need help choosing which airline to fly with from Orlando to Caribbean? 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.
8.0
SouthwestOverall score based on 4246 reviews
8.0Comfort
8.1Boarding
7.0Food
8.6Crew
7.5Entertainment
Airline reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

10.0 ExcellentKevin, Jul 2025MDW - PUJ
Read more Southwest reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

WiFi on the flight was not working. Thus, entertainment options were limited.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

I had a wonderful flight, but the only thing that annoyed me was how crowded TSA was. I still believe airports and all planes work together to bunch everyone together to drive up cost.

The captain gave good announcements and the flight attendants were friendly. The WiFi was pretty good. The plane itself looked very old inside and the seats were very uncomfortable. The screens in the seat backs were the smallest I’ve ever seen. There were so many loud and obnoxious kids on this flight and the parents didn’t do much to try to quiet them down. Some had videos and games on tablets with higher than necessary volume going the whole time.

Spend hours delayed with no food, water anything sitting on the aieplane with no ability to eat or use the restroom. My entire experience was the absolute worst. I will never fly jet Blue again.

It would have been nice if they had offered more than one set of snacks

Flight was delayed several 3 hours - no reason was given and no communication what so ever.

No overhead baggage room even though I was seated in row 2. Consequently had to check in my carry on bag. Baggage carousel was jammed. Took 45 min to get my bag.

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

Except for the 28 minute delay leaving and the earlier reschedule to a later takeoff time the flight was good.

Loved the leg room and tvs screens on the seats and free WiFi. Wish the price was lower and could save by rebooking

The flight was delayed for 4 hours. Once onboard the crew was wonderful.

Very well organized both boarding and deplaning. Very satisfied with the service I received.

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

The plane was broken so we had to change planes.

Food was terrible, all served at once, poor quality . Wine and bread offered only once.

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

No entertainment yatem in flight at seat 51H. Would not shut down either leaving a self moving and openin and changing menus with changes in colors,images brightness levels sort of the type when you get sleep deprivation and image overload when being tortured during an interrogation. 8 hours worth of it. Unable to place backpack underneath seat on that chair. One female stewardess was excellent as she gave up her carryon's space for my backpack but the rest of the iberia crew were very sharp an chtting during the whole flight. The plane did not have hot water so nobody had coffee nor tea. The plane was not up to par to be flying.

I was late from Jacksonville, FL but the limited interaction I had with the Philly crew was great.

The delays and cancellations kept me stuck in Miami for an additional 24 hours, and the whole thing seemed extremely disorganized

The chicken adobo was a little too spicy but good otherwise. My personal opinion. Movie selection could be improved, too many horror movies. Could add a few more chick flicks! The flight was bumpy at times. We arrived a little early too! Flight attendants friendly.

really bad they refused to check in luggages that I had purchased, even showing them the transaction receipt from british airways app the staff in miami was MEDIOCRE

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

Friendly employees, good seat, on time, Great flight. Pilot and attendants greeted passengers as we deplaned. However, I could not ever understand what the flight attendant was saying on the mic. It was too fast, and too loud.

The flight was canceled and was bounced around time wise with my elderly parents. That being said the gentleman in custody service was amazingly helpful

Easy boarding and good flight. Need to work on the beverage and snack situation

While on the flight we had a delay and had to sit on the plane while maintenance fixed it. It’s ended up taking an hour and a half longer to leave than expected. I had an unruly passenger sitting behind me that vaped during the flight and was rude and loud for the majority of the flight.

Not great. Overpriced and charge you for everything. All but breathing was an extra charge. Never again! Oh if you didn’t check a carry on, you couldn’t use the overhead bins. Crew said those spaces were not available. Personal items MUST go on floor. Yet, there was only 50% capacity at best! So ridiculous.

It was fine, Can’t blame you about airport issues.

The flight was fine however what started as a reasonable priced ticket could have become an overpriced ticket with additional charge for carry on as well as checked bag $79 per bag per person each way. Additional charge for choosing one’s seat, additional charge for beverage and snack, we were on what was described as a new plane yet there were no audio/visual on the jet. A bare bones service but not at a bare bones price. Will think twice before flying Spirit again. 😕

I paid for streaming wifi and the connection was poor.

Very efficient process and boarding, seats felt standard. Flight conditions from take off to landing had been very smooth. Alcohol on the menu however was not available… Will fly Spirit in the future for the price, you can’t really complain if you fly light.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

My flight was delayed by two hours which made it so that I would miss my layover flight. I stood in line for customer service for over an hour and when I reached the agent she told me to scan a QR code and it'll give me options. I wasn't offered any help, guidance or compensation, only told that I have options but that I had to figure it all out myself. I was refunded part of the trip and had to buy an expensive same day ticket from another airline in order to get home. I will never fly Frontier again.

The confirmation # CK8GNW and my name was not recognized/in Frontier system. I was able to check in on Frintier app so i went to the Frontier ticket agent, at time they told me that my name/ confirmation did not show up as a purchased ticket. I had to purchase a new ticket that cost $289.00 one way.

Although an hour and a half early was told by staff at check in they had overbooked and could not check us in for the flight.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

Worst airline experience. They were rude and kept changing our seats and/or giving our seats away so our family didn’t get to sit with each other. Almost everyone we dealt with at both airports with this airline was rude. The app kept giving us wrong information making things take longer. Dealing with them before TSA can take close to an hour…longer than I’ve ever had to deal with before. Never using this airline again.

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

They switched my flight to Spirit, Never using Kayak again,

Everything you need to know for your flight to Caribbean

Cabin class types available on flights to Orlando

Cabin classes available on flights to Orlando. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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