$51 Find Cheap Flights from Orlando Airport to Caribbean Islands

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 3/21. 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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Cheap Flights from Orlando to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cananonstop$225
Santo Domingo
Santo Domingononstop$242
Montego Bay
Montego Bay1 stop$316
Oranjestad
Oranjestad1 stop$276
Nassau
Nassaunonstop$268
Kingston
Kingston1 stop$334
Simpson Bay
Simpson Bay1 stop$275
Providenciales
Providenciales1 stop$317
Port of Spain
Port of Spain1 stop$280
Bridgetown
Bridgetown1 stop$450
George Town
George Town1 stop$314
Willemstad
Willemstad1 stop$479
Castries
Castries1 stop$665
St. John's
St. John's1 stop$496
Puerto Plata
Puerto Plata1 stop$527
Aguadilla
Aguadillanonstop$142
Punta Cana
Punta Cananonstop$225
Santo Domingo
Santo Domingononstop$242
Montego Bay
Montego Bay1 stop$316
Oranjestad
Oranjestad1 stop$276
Nassau
Nassaunonstop$268
Kingston
Kingston1 stop$334
Simpson Bay
Simpson Bay1 stop$275
Providenciales
Providenciales1 stop$317
Port of Spain
Port of Spain1 stop$280
Bridgetown
Bridgetown1 stop$450
George Town
George Town1 stop$314
Willemstad
Willemstad1 stop$479
Castries
Castries1 stop$665
St. John's
St. John's1 stop$496
Puerto Plata
Puerto Plata1 stop$527
Aguadilla
Aguadillanonstop$142

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

Fri, Apr 3 - Sat, Apr 11
Frontier Logo
11:10 pm - 1:53 am
MCO
-
BQN
2h 43mnonstop
Frontier Logo
6:28 pm - 9:43 pm
BQN
-
MCO
3h 15mnonstop
$142Frontier
Fri, Apr 3 - Sat, Apr 11
Frontier Logo
11:10 pm - 1:53 am
MCO
-
BQN
2h 43mnonstop
Frontier Logo
2:43 am - 5:42 am
BQN
-
MCO
2h 59mnonstop
$144Frontier
Tue, May 12 - Mon, May 18
Spirit Airlines Logo
9:03 am - 11:52 am
MCO
-
SJU
2h 49mnonstop
Spirit Airlines Logo
2:59 am - 6:02 am
SJU
-
MCO
3h 03mnonstop
$166Spirit Airlines
Sat, Apr 11 - Wed, Apr 15
Spirit Airlines Logo
6:00 am - 3:28 pm
MCO
-
STT
9h 28m
1 stop
Spirit Airlines Logo
10:49 am - 2:12 pm
STT
-
MCO
3h 23mnonstop
$167Spirit Airlines
Wed, Apr 15 - Tue, Apr 21
JetBlue Logo
12:09 pm - 1:34 pm
MCO
-
NAS
1h 25mnonstop
JetBlue Logo
2:39 pm - 4:12 pm
NAS
-
MCO
1h 33mnonstop
$268JetBlue
Tue, Apr 14 - Fri, Apr 17
Southwest Logo
5:05 pm - 6:30 pm
MCO
-
NAS
1h 25mnonstop
Southwest Logo
8:45 am - 10:10 am
NAS
-
MCO
1h 25mnonstop
$273Southwest
Tue, May 5 - Wed, May 6
American Airlines Logo
6:00 am - 10:59 am
MCO
-
NAS
4h 59m
1 stop
American Airlines Logo
3:46 pm - 8:10 am
NAS
-
MCO
16h 24m
1 stop
$287American Airlines
Mon, Apr 13 - Fri, Apr 17
JetBlue Logo
1:01 pm - 2:26 pm
MCO
-
NAS
1h 25mnonstop
JetBlue Logo
2:39 pm - 4:12 pm
NAS
-
MCO
1h 33mnonstop
$288JetBlue
Sun, Apr 19 - Thu, Apr 23
American Airlines Logo
9:00 am - 2:46 pm
MCO
-
NAS
5h 46m
1 stop
American Airlines Logo
3:46 pm - 8:10 am
NAS
-
MCO
16h 24m
1 stop
$295American Airlines
Sun, Apr 19 - Fri, Apr 24
Southwest Logo
10:55 pm - 11:15 am
MCO
-
MBJ
13h 20m
1 stop
Southwest Logo
12:35 pm - 11:10 pm
MBJ
-
MCO
9h 35m
1 stop
$320Southwest
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 Airport 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 Airport found in the last 72 hours was to San Juan, at $138 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 $138.

Can I save money by flying with a layover from Orlando Airport 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 $350, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Orlando Airport 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 Airport 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 Airport to Caribbean Islands is February, when tickets cost $204 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $332 and $274 respectively.

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

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

Your flight ticket price will generally be cheaper if you fly to Caribbean Islands on a Thursday and more expensive on a Sunday. On your return trip to Orlando Airport, you should consider flying back on a Friday, and avoid Mondays for better deals.

How far in advance should I book a flight from Orlando Airport 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 Airport 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 Airport to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 2 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$51
Best time to beat the crowds with an average 4% 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 Airport 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 Airport to Caribbean Islands.

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

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

    The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $238 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 $293.

Top tips for finding cheap flights to Caribbean Islands

  • Looking for a cheap flight? 25% of our users found tickets from Orlando Airport to the following destinations at these prices or less: San Juan $106 one-way - $206 round-trip

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.
8.0
SouthwestOverall score based on 4314 reviews
8.0Comfort
7.5Entertainment
8.6Crew
7.0Food
8.1Boarding
Airline reviews

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

8.0 ExcellentAnonymous, Mar 2026
MCO - IND
Read more Southwest reviews

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

An entire day of delays. Cost lots of money. Meals and a hotel.

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

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.

They made me check my bag and I didn't need to as there was overhead space available. I paid for a seat towards the front of the plane and it didn't recline. I requested a refund and they declined to give me one.

I have to congratulate Kayak (and Dylan the Chatdeal agent) because because when we decided extended our trip in Florida by two days, there were many direct flights oprions back to Boston available on the Friday we wanted to fly on the JetBlue website, but once I canceled the original JetBlue flight on their website, those direct return options disappeared immediatley! I think it's a game JetBlue plays. . Luckily, I checked Kayak and they had a direct flight that wasn't appearing on JetBlue's website and so I booked it, and we were able to fly home direct through the Kayak booking when JetBlue was offering nothing (even though I have been a True Blue member for 20 years, and also am a Mosaic member). So much for loyalty- their algorithm for booking is like a shell game. JetBlue used to be a good company but now they're worse than anyone. Also I was originally booked this trip to Florida, two months before the departure date, I booked the trip on JetBlue's website and then after the payment part, they said there was a problem and that I needed to do the booking again, so when I immediately went to rebook , the price had gone up 30%! I called them and it sounded like they had heard this so many times before and the guy told me to check back in 10 minutes and the price would be back to where it was when I was booking- it but it never was. How could the price go up 30% in one minute two months before the flight???? They're playing a game with their customers. Anyways, I booked a cheaper flight then at a less convenient time. So fast forward two months the night before the 7 AM flight, they sent me an email at midnight when I was sleeping to let me know that my flight at 7 AM had been canceled. The only thing they offered was a flight that night from from a different airport (Providence) to a different airport in Florida (West Palm Beach) or a flight two days later. No compensation, nothing. They couldn't of tried to get another plane to the Boston airport? They had all night to do it. I passed on their ridiculous options and flew with Delta and it was a great experience. Of course, I had to pay a lot more booking on the same day, but JetBlue doesn't care. I put in a lengthy complaint with the agent who assured me someone would get back to me by email within three days and I haven't heard a thing. JetBlue used to be a good company but now they're among the worst. The only thing they still have is decent legroom, but the corporate bean counters will probably start taking that away too.

We were made to wait in the airport for six hours for a flight that was ultimately canceled.

Friendly crew, efficient boarding and flight arrived early. Couldn’t ask for a better experience

Horribly rude check in at airport, worst in 25 years of flying. All over a simple issue they could have googled to resolve.

1) No pilot available for 1 hour 2) no room for most passengers careyon in overhead—-> stowed below 3) when we landed we had to wait 45 min. Before docking at gate as gate was not ready

Good. No issues except a slight delay. Crew came in late.

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

There was a fowl odour coming from the lavatory the entire flight

very difficult boarding process - aggressive passengers not the friendliest crew

Other than nearly three hour delay for maintenance issues, everything went smooth

why would I bother with this airline and pick seats when I am asked to move for a weight imbalance

Overall good. The pilots and flight attendants are excellent! The equipment was the issue on my First flight as they had to wait for a part to be installed. So the take off was at least 30 minutes later.

For my arriving destination, we were delayed multiple times to the point that we arrived 6 hours after we were originally scheduled. On my flight home, they overbooked and involuntarily removed passengers (including me) from the plane. It was not a good experience.

Boarding is always an ordeal. Less dogs on flights. I am highly allergic to dogs and cats. Why are there so many animals these days?

Horrible. Got delayed many hours because their pilot wasn't trained for night landing at the airport and a rain delay made it a night landing. We have to wait hours for a qualified crew. They give us 12 dollar meal vouchers but most everything in the airport was closed and definitely more expensive than the vouchers.

I am an AA flyer for a very long time... AA has yet to disappoint.

Everything was good. Flight was very full so crew was busy. After we boarded and plane pulled away from the gate, we were delayed about 40 minutes- sitting on the runway - due to weather en route or at the destination. While weather is not the fault of the airline- it’s terrible to sit on a plane and not moving.

The smell from the bathroom kept wafting through the cabin. It made people sick.

Waited for oxygen tanks for 30 minutes after boarding was complete.

It’s was a cheap flight and they got us there safely. It’s just their whole business model that make the experience “meh.” They make you paranoid about whether your personal item is too big. They make you paranoid about being crammed into a middle seat at the back of the plane. They purposely cram people together leaving multiple rows completely empty and even after the door closes the FA’s announce that everyone has to sit in their assigned seat. We knew what we were buying and in that regard we got a cheap and safe flight but it felt like they do their best to take any enjoyment out of the experience. That’s all on management, not the crew.

Spirit Airlines at Laguardia is a small terminal so it is quick to get to your gate and to get your luggage. The flight is short enough to orlando and the price was very inexpensive. The seats do not move so you can't recline. Drinks and snakcks should be complimentary.

The flight time did not match my original email on time of flight. Missed the first flight. The representative I got on the phone was so incompetent it was unbelievable. My guess is it was AI but it told me it was not AI. They did get me rebooked which I was very thankful of. The return flight was delayed because of staffing issues for the plane and when we reached our destination the jet bridge would not work so we sat on the plane another 40 minutes. I did get to my destination and I did get home but not a good experience.

They charged late fees for selecting seats (no $0 options). They also changed my gate within the last half hour and are refusing to reimburse my costs to drive across the country with two small children in a rental car.

The flight itself and the crew were great. Sitting on the tarmac for over an hour until our gate opened up was really frustrating. Missed our scheduled bus and got home two hours later

There absolutely needs to be WiFi on flights. Not sure why this new aircraft did not have the capability, but it made for a very frustrating flight. I honestly would have paid twice as much for another airline to have WiFi as an option, especially as a mom with kids who have disabilities.

Flight out was great but this flight was canceled and nothing was available for 2 days after this so I had to purchase an expensive ticket from another airline so I could go home. The flight cancellation was said to be a crew issue, it wasn’t weather or maintenance.

the fligh was delay form 9am to 10, delayed again from 10 to 11, than delay and gate change to 12 and delay another gate change to 3;25 pm

Missed flight cause tsa took so long, overbooked flight, left terminal earlier than posted departure ridiculous upcharges stayed at airport additional 6 hours to catch next available flight. Had to make other arrangements to be picked up for later flight. Terrible experience!

Cancelled my flight, said next flight was 30hrs later. Had to come out of pocket $500 to get on a SW flight

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

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

Flight got delayed for 5 hours no good explanation was offered ;(

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

The experience was good. No frills but I got there safe and sound and on time.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

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.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports