$83 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 7/26. 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 Cana1 stop$313
Santo Domingo
Santo Domingo1 stop$378
Montego Bay
Montego Baynonstop$392
Oranjestad
Oranjestadnonstop$357
Nassau
Nassaunonstop$301
Kingston
Kingston1 stop$430
Simpson Bay
Simpson Bay1 stop$362
Providenciales
Providenciales1 stop$399
Port of Spain
Port of Spain1 stop$468
Bridgetown
Bridgetown1 stop$480
George Town
George Town2 stops$454
Willemstad
Willemstad1 stop$590
Castries
Castries1 stop$894
Aguadilla
Aguadillanonstop$241
Puerto Plata
Puerto Plata1 stop$518
St. John's
St. John's2 stops$588
Punta Cana
Punta Cana1 stop$313
Santo Domingo
Santo Domingo1 stop$378
Montego Bay
Montego Baynonstop$392
Oranjestad
Oranjestadnonstop$357
Nassau
Nassaunonstop$301
Kingston
Kingston1 stop$430
Simpson Bay
Simpson Bay1 stop$362
Providenciales
Providenciales1 stop$399
Port of Spain
Port of Spain1 stop$468
Bridgetown
Bridgetown1 stop$480
George Town
George Town2 stops$454
Willemstad
Willemstad1 stop$590
Castries
Castries1 stop$894
Aguadilla
Aguadillanonstop$241
Puerto Plata
Puerto Plata1 stop$518
St. John's
St. John's2 stops$588

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 20 - Thu, Aug 20
Frontier Logo
10:17 am - 1:16 pm
MCO
-
SJU
2h 59mnonstop
Frontier Logo
4:05 pm - 7:20 pm
SJU
-
MCO
3h 15mnonstop
$223Frontier
Thu, Aug 20 - Sun, Aug 23
Frontier Logo
5:15 am - 8:09 am
MCO
-
SJU
2h 54mnonstop
Frontier Logo
6:00 am - 9:12 am
SJU
-
MCO
3h 12mnonstop
$226Frontier
Wed, Aug 19 - Wed, Aug 26
JetBlue Logo
5:14 am - 8:00 am
MCO
-
BQN
2h 46mnonstop
JetBlue Logo
8:30 pm - 11:27 pm
BQN
-
MCO
2h 57mnonstop
$248JetBlue
Thu, Jul 23 - Tue, Jul 28
JetBlue Logo
6:25 pm - 11:59 pm
MCO
-
PSE
5h 34m
1 stop
JetBlue Logo
5:01 am - 11:08 am
PSE
-
MCO
6h 07m
1 stop
$248JetBlue
Thu, Oct 1 - 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
$301Bahamasair
Mon, Aug 17 - Mon, Aug 24
American Airlines Logo
9:10 am - 3:52 pm
MCO
-
STT
6h 42m
1 stop
American Airlines Logo
4:42 pm - 11:41 pm
STT
-
MCO
6h 59m
1 stop
$304American Airlines
Sat, Nov 7 - Fri, Nov 13
American Airlines Logo
7:49 pm - 10:00 am
MCO
-
NAS
14h 11m
1 stop
American Airlines Logo
3:15 pm - 9:44 pm
NAS
-
MCO
6h 29m
1 stop
$306American Airlines
Wed, Sep 23 - Sat, Sep 26
Bahamasair Logo
2:45 pm - 4:15 pm
MCO
-
NAS
1h 30mnonstop
Bahamasair Logo
12:00 pm - 1:30 pm
NAS
-
MCO
1h 30mnonstop
$310Bahamasair
Tue, Aug 25 - Wed, Sep 2
Southwest Logo
11:40 am - 2:45 pm
MCO
-
AUA
3h 05mnonstop
Southwest Logo
3:40 pm - 6:55 pm
AUA
-
MCO
3h 15mnonstop
$357Southwest
Sat, Sep 5 - Sat, Sep 12
Southwest Logo
10:15 am - 11:20 am
MCO
-
MBJ
2h 05mnonstop
Southwest Logo
11:40 am - 8:05 pm
MBJ
-
MCO
7h 25m
1 stop
$392Southwest
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 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 $239.

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

The average price for all round-trip flights from Orlando Airport 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 $272 on average. Morning departures are around 1% more expensive 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 $321.

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 $406, 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 August, when tickets cost $271 (return) on average. On the other hand, the most expensive months are March and July, when the average cost of round-trip tickets is $479 and $459 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 Sundays 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 2 weeks before departure, which saves you about 8% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$83
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 13% 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.

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 $176 one-way - $315 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.
7.9
SouthwestOverall score based on 4240 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.5Entertainment
7.0Food
Airline reviews

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

10.0 ExcellentAnonymous, Jun 2026
OKC - LAS
Read more Southwest reviews

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

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

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’m sure Business Class would be excellent. I feel like I got what I paid for. Overall it was good and well worth it. I would do it again.

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!

The flight was delayed 4 hours and the JetBlue people at the counter kept lying to us and telling us it was due to weather however all other flights were going in and out of NY and FL. Then they lied that the plane had to stop to refuel. Then they lied and said the plane needed a tire change. JetBlue is the worst. Then they gave a lot of people meal vouchers however I didn’t know they did that and they didn’t offer anything to me.

Jet Blue has excellent everything, Friendly customer service and staff, clean aircraft’s and is always on time.

They could give you a snack or at least something to drink during the flight. The flight was also delayed.

They cut off check in at 1 hr, while we were in line, & sold our seats.

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

Delays, changing flight times and screws us up when connecting with another flight . It’s the same ole story. Bahamasair don’t care and no one holds them accountable.

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

I love bahamasair safety always blown away. They made my fears from travel so much better. Bahamasair #1 Highly recommend We don't just fly here. We live here Pilots and crew keep up the good work.

Going the plane was late and then Bahamas Air chartered another plane to take the passengers to San Salvador.

4 hour delay Noisy passengers Tight seats Missed connecting flight in Ft. Lauderdale

We were scheduled to travel at 12pm. The flight got delayed with no updates until 11:30am. They advised that we will receive an update at 1pm. However, the flight was then delayed until 6pm with no clear indication as to if that was the departure time. It was NOT! They decided to combine two of their scheduled flights into one due to the smaller number of passengers. If you do not wish to be inconvenienced, “STAY AWAY FROM THIS AIRLINE”!!!!!!They do have a track record of 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

Information on your arrival and departure airports