$82 Find Cheap Flights from Orlando Airport to Caribbean Islands - Compare and Save

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Cheap Flights from Orlando to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stop$311
Santo Domingo
Santo Domingo2 stops$407
Montego Bay
Montego Bay1 stop$418
Oranjestad
Oranjestad1 stop$327
Nassau
Nassau1 stop$311
Kingston
Kingston1 stop$476
Simpson Bay
Simpson Bay1 stop$337
Providenciales
Providenciales1 stop$361
Port of Spain
Port of Spain1 stop$476
Bridgetown
Bridgetown1 stop$458
George Town
George Town1 stop$397
Willemstad
Willemstad1 stop$546
Castries
Castries2 stops$758
Aguadilla
Aguadillanonstop$175
St. John's
St. John's1 stop$496
Puerto Plata
Puerto Plata1 stop$511
Punta Cana
Punta Cana1 stop$311
Santo Domingo
Santo Domingo2 stops$407
Montego Bay
Montego Bay1 stop$418
Oranjestad
Oranjestad1 stop$327
Nassau
Nassau1 stop$311
Kingston
Kingston1 stop$476
Simpson Bay
Simpson Bay1 stop$337
Providenciales
Providenciales1 stop$361
Port of Spain
Port of Spain1 stop$476
Bridgetown
Bridgetown1 stop$458
George Town
George Town1 stop$397
Willemstad
Willemstad1 stop$546
Castries
Castries2 stops$758
Aguadilla
Aguadillanonstop$175
St. John's
St. John's1 stop$496
Puerto Plata
Puerto Plata1 stop$511
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?

The cheapest ticket to Caribbean Islands from Orlando Airport found in the last 5 days was to San Juan, at $122 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 $122.

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 $275 on average. Morning departures are around 3% cheaper than evening flights, on average. 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 $326.

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

No, with an average price for the route of $425, prices are generally cheapest when you fly direct.

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

The cheapest month for flights from Orlando Airport to Caribbean Islands is January, when tickets cost $355 (return) on average. On the other hand, the most expensive months are July and August, when the average cost of round-trip tickets is $547 and $491 respectively.

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

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 Sundays for better deals.

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

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 5 weeks before departure.

Good to know

Low season

August

Cheapest flight

$82
Best time to beat the crowds but there is an average 9% increase in price.
Most popular time to fly with an average 7% increase in price.
Flight from Orlando Airport to San Juan Airport

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.

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 $108 one-way - $183 round-trip

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

 
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 4194 reviews
8.0Comfort
7.5Entertainment
8.6Crew
7.0Food
8.1Boarding
Airline reviews

Delayed and once landed waited very long for the luggage

6.0 GoodIngeborg, Sep 2026
Read more Southwest reviews

Delayed and once landed waited very long for the luggage

Eveeyrime I fly they are begging for bags due to cabin overhead space. What they should so ia take the bags that are clearly too big to fit wheels first on their side. And those of us who give up the bag should really get their bags first. When boarding, nobody wants stupid jokes about how hot it is on board. Give us some cool air. Im usually sick from the heat by the time we take off.

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

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.

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.

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

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

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.

if it's a mobile only entertainment experience, please provide a place to hold the device in the back of the seat.

Not great. I understand delays happen due to weather and crew issues, but it was unacceptable that no agents were available at the counters inside the airport for customer service or help getting on a standby list. The app was not helpful either. I stood in line for an hour waiting for someone to show up at the gate to help me get on a standby flight. Customer care does not seem to be a priority.

It was awful. My first flight was delayed and as a consequence I lost my second flight to Greensboro. I did not know what to do so I rebook myself a flight to Charlotte . It was very inconvenient I not to have anybody form corporate assisting me either from PwC or from kayak . It is a very disappointing experience that American did not wait 1 minute or told me to rebook before making the first flight

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

It was great. Smooth flight, comfortable, left on time and landed on time.

Really good. I accidentally left my duffel on the plane and the reps were so friendly in retrieving it.

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.

Wish they didnt delay off-boarding for 10 minutes so i could connect to my flight from miami to tampa

I have a gluten allergy so didn't have any food

Delays were crazy long (over an hour) both for boarding and baggage claim

awful expereince. boarding was a mess and not communicated, then we sat on a hot plane and were at risk of getting kicked off

2 hour delay and a lack of air conditioning on the plane. Not a good combination

First time flying JetBlue and my perception changed. Love it.

Poor, had a 5+ hours delay. Kept sitting in the aircraft with three kids. It was terrible

They cancelled the flight after 5 hours at the airport and the only flight they offered was for the next day with a 7.5 layover in fll. This was not going to work for me as this was only a weekend trip and getting into providence at 10 pm a day later caused me to lose Mo ey on hotels money on airport parking a dog sitter etc. they wouldn’t offer any type of a voucher or anything else. All they did was refund the flight which didn’t help me with all the money in time I lost. I was going to see my very sick father

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

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!

WiFi was not eorkig (again) And the plane was from 1990 with the screens which were.not touch and most didn’t even work and if lucky could tune in tv

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.

They don’t offer food on the flight just water but when arrived on time and landed perfectly

Poor poor, airline people are rude unfriendly and unhelpful, they need to be trained to be customer friendly and gelpful

Poor, every time it’s Delays, delayed by 3 hrs to depart and still waiting in airport as another delay with no updates , Bahamasair is the worst and they are not interested in improving.

I love everything about bahamasair. Especially the safety they have for the people. I don't care how long they delay once I reach safe that's all. They made me not afraid to fly anymore

Flight was delayed more than 2 hours in departure. Boarding was lengthy and passengers were very rude. I waited on the plane for almost an hour once boarded and it was very hot. The passenger next to me was clearly I’ll: coughing and sneezing the entire flight.

I feel that I was scammed by BahamasAir. Both on flights 202 and 207, to and from Nassau - Fort Lauderdale June 2, June 6. I paid for 2 full size bags and selected seats. On both flights they told me I had not paid for luggage or seats. I was charged $100 extra each way without seat assignment. BahamasAir does not participate in TSA Pre Check. Even if you have it you cannot use it. Instead endure long lines because BahamasAir will not pay their share of PreCheck.

Booked thru you. Paid and was supposed to have 1 checked bag and seat 3 C; with the same for my wife sitting on the opposite side of the aisle in 3D. At airport we had to pay $ 25 each for 1 bag each.. we’d were given seats inn row 17

Nothing to add! I will definately use your website again. Thank you

No matter how many times I gave a try to this company it’s always a bad experience. Never, never leave on time, the shortest delay it’s an hour, but I had passed more time at Nassau airport than any other airport in the world. Saving a few dollars flying with Bahama air, it’s not worth it.

It was a safe flight and am happy to be back on the ground in my island.

When I was boarding my departure from Raleigh to Orlando I was inappropriately scolded by a female dog named Mia because I didn’t pay in advance for my carry on bag ($75). Frontiers website is confusing regarding pre-paying for carryons so it was a simple mistake. I also had paid for “upfront plus” meaning me and my son were seated in the front row with no one in the middle seat ($450 upgrade). When we were boarding Mia said “sir, you didn’t pay for your carryon” in a not so polite tone and told me to get out of line and come back to the counter to pay for my carryon. The way they had the retractable rope left me no room to circle back without making the people behind me move so I just stood there and then she said a second time “sir!! Go pay for your carryon” in an embarrassing tone. I then moved their rope so I could get back to the counter when a second female dog then asked “are you done!?!?” because I had said “do you want me to bulldoze the people behind me?” I then said you do realize I paid over $400 for upfront plus so I was certainly not trying to sneak a carryon bag without paying. Long story short, I am soooo done with discount airlines!!! By the time you pay for all the “extras” you might as well have paid for Delta Southwest or American! Frontier airlines sucks and I was embarrassed by a female dog named Mia!!!

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

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.

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.

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.

More options for your flight to Caribbean Islands

Complete your trip to Caribbean Islands with a hotel stay or car rental