$84 Find Cheap Flights from Orlando to Caribbean Islands - Compare and Save

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 Islands departing on 8/9. 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 Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Orlando to Caribbean Islands.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Orlando to Caribbean Islands.
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Flight Deals

Book Cheap Orlando to Caribbean Islands 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 Islands 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 Islands

Thu, Aug 13 - Tue, Aug 18
Frontier Logo
4:25 pm - 7:32 pm
MCO
-
SJU
3h 07mnonstop
Frontier Logo
6:00 am - 9:12 am
SJU
-
MCO
3h 12mnonstop
$201Frontier
Thu, Aug 20 - Sun, Aug 23
Frontier Logo
5:15 am - 8:09 am
MCO
-
SJU
2h 54mnonstop
Frontier Logo
6:16 pm - 9:30 pm
SJU
-
MCO
3h 14mnonstop
$202Frontier
Fri, Aug 14 - Sat, Aug 15
Frontier Logo
6:35 pm - 9:43 pm
MCO
-
SJU
3h 08mnonstop
Frontier Logo
3:10 am - 6:10 am
SJU
-
MCO
3h 00mnonstop
$203Frontier
Thu, Oct 15 - Mon, Oct 19
Bahamasair Logo
2:45 pm - 4:15 pm
MCO
-
NAS
1h 30mnonstop
Bahamasair Logo
12:00 pm - 1:30 pm
NAS
-
MCO
1h 30mnonstop
$301Bahamasair
Thu, Aug 27 - Mon, Aug 31
JetBlue Logo
7:00 am - 3:32 pm
MCO
-
STT
8h 32m
1 stop
JetBlue Logo
4:27 pm - 11:53 pm
STT
-
MCO
7h 26m
1 stop
$307JetBlue
Thu, Oct 1 - Tue, Oct 6
JetBlue Logo
7:25 am - 2:41 pm
MCO
-
STT
7h 16m
1 stop
JetBlue Logo
3:40 pm - 9:51 pm
STT
-
MCO
6h 11m
1 stop
$309JetBlue
Fri, Oct 2 - Sun, Oct 4
Bahamasair Logo
2:45 pm - 4:15 pm
MCO
-
NAS
1h 30mnonstop
Bahamasair Logo
12:00 pm - 1:30 pm
NAS
-
MCO
1h 30mnonstop
$316Bahamasair
Tue, Aug 25 - Sat, Sep 5
American Airlines Logo
6:00 am - 12:53 pm
MCO
-
STT
6h 53m
1 stop
American Airlines Logo
12:08 pm - 12:28 am
STT
-
MCO
12h 20m
1 stop
$329American Airlines
Sun, Aug 16 - Sun, Aug 23
American Airlines Logo
7:30 am - 12:53 pm
MCO
-
STT
5h 23m
1 stop
American Airlines Logo
1:48 pm - 11:41 pm
STT
-
MCO
9h 53m
1 stop
$339American Airlines
Fri, Sep 11 - Sun, Sep 13
Southwest Logo
7:50 am - 1:40 pm
MCO
-
MBJ
6h 50m
1 stop
Southwest Logo
3:25 pm - 6:30 pm
MBJ
-
MCO
2h 05mnonstop
$396Southwest
Booking Insights

KAYAK's insights & trends for Orlando to Caribbean Islands flights

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

What is the cheapest Orlando to Caribbean Islands flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean Islands from Orlando found in the last 5 days was to Montego Bay, at $224 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 5 days was $244.

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

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

The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $274 on average. On average, there is no price difference when choosing to fly in the morning or the evening on this flight route. The most expensive time of day to fly to Caribbean Islands is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $322.

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

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 $346, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Orlando to Caribbean Islands, 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 Islands is January, when tickets cost $335 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $467 and $434 respectively.

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

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

When flying from Orlando to Caribbean Islands, 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 Sundays.

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

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 Islands, 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 Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$84
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 19% increase in price.
Flight from Orlando to Aguadilla

FAQs - booking Caribbean Islands flights

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

    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 Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Orlando to Caribbean Islands 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 Islands?

    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 Islands 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 Islands?

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

Reviews of the top 5 airlines serving from Orlando to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Orlando to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Orlando to Caribbean Islands? 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 4235 reviews
7.0Food
7.5Entertainment
8.6Crew
8.1Boarding
8.0Comfort
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

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.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

I liked it better when you were truer to your roots Am paying more for less fun

Trash. Sat on the runway for 40 mins…missed connecting flight because of it now I’m stuck. Thanks…a whole fkn lot.

Little time between flight from Dallas to flight to Gainesville. We chose this one, 43 minutes between, because the price for a connection with at least an hour between, was so much higher. Had to ask passengers on the Dallas flight to please allow us to deplane ahead of them. The economy passengers allowed this. We had to walk very fast to the next gate, 35 gates away. Thankfully all in the same terminal. Getting to the small Gainesville plane was a little confusing as you enter an area that is boarding many small planes at the same time. We stood in the wrong line for about 15 seconds before realizing it was not our Gainesville flight. Since I had boarded at this gate in the past, I knew to check the signs carefully so we weren’t lost. The first class seat experience was wonderful. I really enjoyed the upgrade. We were offered an alcohol drink as soon as we sat down. I got something different but it was a great gesture especially since we really had to hurry to make the flight. We had packed expecting we might miss this connection, but made it. Our luggage didn’t miss the flight. American Airlines delivered our bags to our home the next day. That was very convenient!

It was what i expected. I like the movies you can access from your phone. It would be nice if there was a gluten free snack offered. But I did bring my own snack knowing there would not be a gluten free option

There were flight delays making our flight arrive at our destination after midnight didn’t seem to have enough crew or airplanes for the flights laid over in Dallas should’ve had plenty of time to make it to our next flight only made it because that flight was also delayed because our plane wasn’t even at the airport yet overall have not had a good experience on American

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

We had several flights and they were all on-time and flawless

For a 4 1/2 hour international flight all we got was 1 small pack of cookies and a drink. You had to watch movies on your own devise.

The seats need better cushioning for a nearly 5-hour flight, it was a bit uncomfortable. I'm glad American has free wi-fi but there were was a bout 30 minutes in the middle of the flight when there was no connection which was frustrating.

My original flight got delayed day of so I had to rebook it from one layover to two layovers. The flight also left earlier which was a slight inconvenience but manageable. Then my first connection flight got delayed 3 separate times for a total of 2 hours delayed, causing me to miss my second connection flight back to Santa Barbara. Now, because of this missed flight, I am missing my college classes that I pay for.

Flight: Started on time. Comfortable flight. Arrived on time. Crew: Very cordial and helpful. Drinks and snack was served with a smile. Overall enjoyed the trip. Regards, Hari Doss Chanchala Doss

I tried to book a flight with Jet Blue. Your third party company hijacked my attempt with a website that looked like I was booking with Jet Blue. I realized it when I paid. I tried to cancel and was told by a man in India that there were no refunds. $735 stolen, Thanks Kayak!

The flight out was delayed from 3:40pm to 5pm and again to 8pm. We boarded after 5pm, had to disembark because they could not get the Engine started, then we switched gates and got a new plane and did not board until after 8pm.

Boarding was easy. Provided drinks and snacks. Good aircraft and staff

Flight was quick, less time than expected, and the attendants all friendly and helpful. We had paid extra for more leg room and were very comfortable. Haven't flown JetBlue in quite a while. Glad to be back!

JetBlue not only has the most comfortable planes, but also used to have the best customer service. Lorie Wright, the lady at the gate was very rude not only to me, but to other passengers as well. Her colleague, the gentleman was also not very friendly. They both were acting like they were doing passengers a favor. The crew on board was very nice.

Direct tv did not work on flight Short flight so no good service offered Arrived early to destination and had to wait for gate to open. Deplaned LATER than if we arrived on time!! Poor planning Jet blue has had something go wrong on every flight I’ve taken with them in last five years. Terribly run airline

My experience with JetBlue was fine BUT I am very upset with Kayak! JetBlue had delayed our scheduled departure by an hour and you NEVER notified me of the change. I did not hear directly from JetBlue because the trip was booked through Kayak, a mistake I will not repeat. Your reminder of the our trip last week still had the WRONG departure time. Our return trip has also changed, and again no notice from you.

Not having an assigned seat until boarding and then having to check my bag.

I purchased ticket so our daughter ( a minor) can sit next to her mother. No help at gate after kayak insisted that this could be done. She ended sitting by herself

Terrible. There was a lot of misleading information regarding ticketing, seat upgrades, & boarding group. I also expect my seat will recline. I have back problems & it is very painful for me of the seat doesn’t recline. In addition, when I choose a fare that allows me a carry-on bag, I expect to be able to carry it on. Not be forced to check it. Thos happened on my flight to MCO & back to Boston. Not sure I will ever fly JetBlue again. Further I bought the ticket through hat deal. I will NEVER do that again. They were incapable of providing an accurate record locator # for either leg of the trip. I had to call them before each flight with me VERY stressed about whether I would actually be able to get on my flight. Who does that? Who books flight & then FAILS to give an accurate record locator? Twice!

Awful. Not water, or chargers or space under the seats, the plane was very old and poor maintenance, seats really dirty, sticky, seats pockets with wires pinching your knees. Connection with no announcements, plane departed 1.30 hour earlier for an extra stop to refueling in Trinidad & Tobago. Even that we had a 3 hrs delay, seated in the plane in the runway.

Really bad. Uncommunicated stop in Trinidad & Tobago for refueling. Extra stop added 3 hours of discomfort without allowing off the seat. Not even water, or chargers or boarding groups.

Staff were unfriendly and rude. Was stuck on runway for 2 hours after arrival in Boston.

Horrible service. No communication from the crew as to why a 6 hour delay then cancellation

We waited in an overcrowded bus for over a half hour. It was uncomfortable. It would have been better to have waited in the terminal in a line

The food for sale on board has opportunity for improvement.

I paid extra for a comfortable seat in the second flight, but the plane didn't have those seats, the first one did

The Arajet person who greeted us initially was unhelpful & rude about the mandatory migration form which has to be completed digitally but the systems don’t work properly. The boarding gate was changed twice and initial boarding was delayed. Once on board we we had to wait an hour and a half before take off. It was hot and there was very little room for tall-ish people to fit their knees in. The crew were pleasant but working in a poor situation. The plane was delayed because we were waiting for people from a delayed interconnecting flight. Arajet must have known that before we were asked to board. Better information, decisions & communication were needed.

My seat was broken and the crew had to find me somewhere else to sit. The crew was extremely courteous about this

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

It was an early flight and most people napped/slept and the crew let us which was nice.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

Everything you need to know for your flight to Caribbean Islands

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.