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$66+ Cheap flights from Orlando (ORL) to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — SJU
Apr 26 — May 31
Sun 4/26
Sun 5/3
1 adult, Economy
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Cheap flight deals from Orlando to Caribbean

Cheapest flights from Orlando to Caribbean
Explore the most affordable flight options available from Orlando to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 27, 2026.

This eDestinos deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/2911:25 pm
MCO
-
SJU
Nonstop2h 48m
Frontier
Sat 4/45:21 pm
SJU
-
MCO
Nonstop3h 22m
Frontier
Deal found 3/22$152
This Kiwi.com deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3111:15 pm
MCO
-
SJU
Nonstop2h 48m
Multiple Airlines
Sat 4/47:00 am
SJU
-
MCO
Nonstop3h 14m
Multiple Airlines
Deal found 3/23$154
This Cheapflightsfares deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/287:19 pm
MCO
-
SJU
Nonstop2h 40m
Spirit Airlines
Sat 4/46:55 pm
SJU
-
MCO
1 stop16h 00m
Spirit Airlines
Deal found 3/24$155
This Kiwi.com deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/3011:10 pm
MCO
-
SJU
Nonstop2h 48m
Multiple Airlines
Sat 4/410:00 am
SJU
-
MCO
1 stop12h 31m
Multiple Airlines
Deal found 3/23$157
This eDestinos deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/316:10 am
MCO
-
SJU
Nonstop2h 43m
Spirit Airlines
Mon 4/61:45 am
SJU
-
MCO
Nonstop3h 15m
Spirit Airlines
Deal found 3/26$158
This eDestinos deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/75:15 pm
MCO
-
SJU
1 stop22h 44m
Frontier
Thu 5/148:30 am
SJU
-
MCO
1 stop15h 37m
Frontier
Deal found 3/25$159
This Cheapflightsfares deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:10 am
MCO
-
SJU
Nonstop2h 43m
Spirit Airlines
Thu 4/91:45 am
SJU
-
MCO
Nonstop3h 15m
Spirit Airlines
Deal found 3/26$160
This CheapOair deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/2811:25 pm
MCO
-
SJU
Nonstop2h 48m
Multiple Airlines
Sat 4/410:00 am
SJU
-
MCO
1 stop12h 31m
Multiple Airlines
Deal found 3/24$161
This Cheapflightsfares deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/37:19 pm
MCO
-
SJU
Nonstop2h 40m
Spirit Airlines
Sat 4/41:45 am
SJU
-
MCO
Nonstop3h 15m
Spirit Airlines
Deal found 3/26$162
This Priceline deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:10 am
MCO
-
SJU
Nonstop2h 43m
Multiple Airlines
Thu 4/96:00 am
SJU
-
MCO
1 stop8h 19m
Multiple Airlines
Deal found 3/26$163
This CheapOair deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2411:00 pm
MCO
-
BQN
Nonstop2h 43m
Frontier
Tue 4/282:38 am
BQN
-
MCO
Nonstop2h 59m
Frontier
Deal found 3/23$164
This Travelocity deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2911:00 pm
MCO
-
BQN
Nonstop2h 43m
Frontier
Sat 5/22:48 am
BQN
-
MCO
Nonstop2h 59m
Frontier
Deal found 3/25$166

Find flight deals from Orlando to Caribbean

Keep the following information in mind while searching for Orlando to Caribbean flight deals. Data was last updated March 27, 2026.

Round-trip from

$159
(eDestinos)

One-way from

$66
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$266

Good round-trip deal

$179 or less

Good one-way deal

$96 or less
From Orlando (ORL) to Caribbean
Search Deals
One-way flight from Orlando (ORL) to Caribbean
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($32 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip flight from Orlando (ORL) to Caribbean.
Search Deals
Price to beat on a one-way flight from Orlando (ORL) to Caribbean.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Orlando to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 27, 2026.
Use the filters below to find and compare flights from Orlando to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Fri 5/8

6:05 am-9:02 am

Nonstop2h 57m

Ponce Mercedita

Wed 5/13

10:02 am-1:23 pm

Nonstop3h 21m

$178

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Thu 5/14

6:10 am-9:07 am

Nonstop2h 57m

Ponce Mercedita

Mon 5/18

9:47 am-1:02 pm

Nonstop3h 15m

$178

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Thu 5/14

6:10 am-9:07 am

Nonstop2h 57m

Ponce Mercedita

Tue 5/19

10:02 am-1:23 pm

Nonstop3h 21m

$209

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Tue 5/5

7:30 am-10:28 am

Nonstop2h 58m

Ponce Mercedita

Tue 5/19

10:02 am-1:23 pm

Nonstop3h 21m

$228

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Mon 7/27

6:55 am-9:52 am

Nonstop2h 57m

Ponce Mercedita

Sat 8/15

10:37 am-1:59 pm

Nonstop3h 22m

$244

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Mon 7/27

6:55 am-9:52 am

Nonstop2h 57m

Ponce Mercedita

Mon 8/31

10:37 am-1:59 pm

Nonstop3h 22m

$244

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Sat 5/9

6:10 am-9:07 am

Nonstop2h 57m

Ponce Mercedita

Sat 5/16

10:02 am-1:23 pm

Nonstop3h 21m

$247

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Thu 4/9

9:00 am-11:49 am

Nonstop2h 49m

Ponce Mercedita

Mon 4/13

7:59 pm-11:10 pm

Nonstop3h 11m

$269

OrlandoSaint Thomas Island

MCO - STT

MCOSTT

Orlando

Thu 5/21

7:00 am-1:09 pm

1 stop6h 09m

Saint Thomas Island Cyril E King

Sun 5/24

10:49 am-2:12 pm

Nonstop3h 23m

$286

OrlandoSaint Thomas Island

MCO - STT

MCOSTT

Orlando

Mon 4/20

5:01 am-12:26 pm

1 stop7h 25m

Saint Thomas Island Cyril E King

Sat 4/25

12:25 pm-8:37 pm

1 stop8h 12m

$286

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

Showing 1-10 of 60 resultsSorted by cheapest first
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6

Best time to book a flight from Orlando to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Orlando with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Orlando to Caribbean

What is the cheapest month to book a flight from Orlando to Caribbean?

Currently, October is the cheapest month in which you can book a flight from Orlando to Caribbean (average of $89). Flying from Orlando to Caribbean in July is currently the most expensive (average of $119). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ORL to CB?

Find hourly flight availability from Orlando to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 27, 2026.

It’s typically best to fly out from Orlando to Caribbean in the afternoon. Doing so could potentially save you 16% on the flight price compared to flying in the morning, which is usually more expensive.

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

Use this chart to determine the cheapest time to fly round-trip from Orlando to Caribbean. Price data was last updated on March 23, 2026.

Travelers seeking maximum savings on their Orlando to Caribbean flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Orlando to Caribbean

Explore weekly flight availability from Orlando to Caribbean. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 27, 2026.

The most flights from ORL to 0CB are scheduled on a Thursday (27 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (7 on average).

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated March 27, 2026.
Peruse reviews from past customers who have flown with Southwest,JetBlue, andAmerican Airlines from Orlando to Caribbean to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,331 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,331 reviews
Southwest
8.0
Very good
4,331 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
JetBlue
7.2
Good
2,905 reviews
Southwest
8.0
Very good
4,331 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,496 reviews
Southwest
8.0
Very good
4,331 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Spirit Airlines
6.3
Okay
8,546 reviews
Southwest
8.0
Very good
4,331 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
3,015 reviews
Southwest
8.0
Very good
4,331 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Orlando to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Orlando to Caribbean?

    Departing from Orlando to Caribbean will take you 2h 50m. The distance between Orlando and Caribbean is about 1188 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Orlando to Caribbean one-way?

    One-way options have recently been found by users for as low as $66 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $71 and Arajet from $77 one-way.

  • What are the most popular routes from Orlando to Caribbean?

    The most popular route from Orlando to Caribbean is Orlando - San Juan Luis Munoz Marin Intl. You may also consider Orlando - Punta Cana or Orlando - Santo Domingo Las Americas.

  • What are the most reliable airlines from Orlando to Caribbean?

    The top 3 most reliable airlines when flying from Orlando to Caribbean are Spirit Airlines (83%), JetBlue (79%) and Azul (78%).

  • What are the cheapest flights from Orlando to Caribbean?

    The cheapest flight price from Orlando to Caribbean is $95. On average you can expect to pay $330. The most popular route, (Orlando - San Juan Luis Munoz Marin Intl), can usually be booked for $141.

  • Can I find deals for flights from Orlando to Caribbean that include hotel bookings?

    Yes. In addition to deals on Orlando to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Orlando to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Orlando to Caribbean.

  • Can I find deals for business class flights from Orlando to Caribbean?

    Yes. Cheapflights offers flight deals from Orlando to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Orlando to Caribbean?

    Currently, October is the cheapest month in which you can book a flight from Orlando to Caribbean (average of $89). Flying from Orlando to Caribbean in July is currently the most expensive (average of $119). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Orlando to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
Miami to John F Kennedy Intl flights
Fort Lauderdale to LaGuardia flights
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Tampa to Boston flights
Fort Lauderdale to Jose Maria Cordova Intl flights
Orlando to Baltimore flights
West Palm Beach to LaGuardia flights
Miami to Reagan-National flights
Miami to Denver flights
Miami to Heathrow flights
Fort Lauderdale to O'Hare Intl flights
Miami to Baltimore flights

Top 9 airlines flying from Orlando to Caribbean

Discover the top 9 airlines that operate flights from Orlando to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$99Average$289FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$103Average$420FlexibilityNo cancel feeOn-time62%
FrontierCheapest$116Average$283FlexibilityNo cancel feeOn-time62%
BahamasairCheapest$141Average$338FlexibilityNo cancel feeOn-time33%
DeltaCheapest$142Average$406FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$142Average$424FlexibilityNo cancel feeOn-time70%
ArajetCheapest$204Average$237FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$245Average$522FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$253Average$459FlexibilityNo cancel feeOn-time71%

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