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$92+ 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 6/4. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — SJU
Jun 7 — Jun 141
Sun 6/7
Sun 6/14
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 May 8, 2026.

This eDestinos deal was found by Cheapflights users on 5/8. 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.
Wed 8/195:10 pm
MCO
-
SJU
1 stop23h 24m
Frontier
Sat 8/223:35 pm
SJU
-
MCO
1 stop26h 04m
Frontier
Deal found 5/8$199
This Cheapflightsfares deal was found by Cheapflights users on 5/4. 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.
Thu 6/411:37 am
MCO
-
SJU
1 stop16h 24m
Frontier
Tue 6/98:00 am
SJU
-
MCO
1 stop8h 32m
Frontier
Deal found 5/4$201
This Orbitz deal was found by Cheapflights users on 5/3. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/411:37 am
MCO
-
SJU
1 stop16h 24m
Frontier
Sat 6/68:32 am
SJU
-
MCO
1 stop13h 21m
Frontier
Deal found 5/3$202
This eDestinos deal was found by Cheapflights users on 5/4. 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 6/49:04 am
MCO
-
SJU
1 stop18h 57m
Frontier
Sun 6/76:00 am
SJU
-
MCO
Nonstop3h 16m
Frontier
Deal found 5/4$206
This eDestinos deal was found by Cheapflights users on 5/3. 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.
Sat 6/610:11 am
MCO
-
SJU
1 stop7h 03m
Frontier
Sat 7/45:15 pm
SJU
-
MCO
1 stop13h 29m
Frontier
Deal found 5/3$209
This Cheapflightsfares deal was found by Cheapflights users on 5/4. 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 6/610:11 am
MCO
-
SJU
1 stop7h 03m
Frontier
Sat 6/138:50 am
SJU
-
MCO
1 stop13h 05m
Frontier
Deal found 5/4$210
This Expedia deal was found by Cheapflights users on 5/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/610:11 am
MCO
-
SJU
1 stop7h 03m
Frontier
Wed 6/106:44 am
SJU
-
MCO
1 stop13h 10m
Frontier
Deal found 5/3$211
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 7/711:12 pm
MCO
-
BQN
Nonstop2h 53m
Frontier
Tue 7/1412:19 pm
BQN
-
MCO
Nonstop3h 01m
Frontier
Deal found 5/3$212
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Sat 8/225:15 am
MCO
-
SJU
Nonstop2h 54m
Frontier
Sat 8/293:06 am
SJU
-
MCO
Nonstop3h 04m
Frontier
Deal found 5/5$213
This Frontier deal was found by Cheapflights users on 5/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/711:12 pm
MCO
-
BQN
Nonstop2h 53m
Frontier
Sun 8/93:00 am
BQN
-
MCO
Nonstop2h 51m
Frontier
Deal found 5/3$214
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Fri 8/75:01 am
MCO
-
SJU
Nonstop2h 56m
Frontier
Sun 8/93:06 am
SJU
-
MCO
Nonstop3h 00m
Frontier
Deal found 5/5$214
This Cheapflightsfares deal was found by Cheapflights users on 5/5. 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.
Tue 8/410:17 am
MCO
-
SJU
Nonstop3h 03m
Frontier
Tue 8/116:31 pm
SJU
-
MCO
Nonstop3h 12m
Frontier
Deal found 5/5$215

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 May 8, 2026.

Round-trip from

$199
(eDestinos)

One-way from

$92
(eDestinos)

Popular in

December

Cheapest in

February

Average price

$249

Good round-trip deal

$240 or less

Good one-way deal

$105 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. 9% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 8, 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

Wed 8/5

7:55 am-10:57 am

Nonstop3h 02m

Ponce Mercedita

Sat 8/8

10:31 am-1:38 pm

Nonstop3h 07m

$239

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Thu 8/6

6:45 am-9:46 am

Nonstop3h 01m

Ponce Mercedita

Tue 8/11

10:31 am-1:38 pm

Nonstop3h 07m

$292

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Wed 7/1

7:55 am-10:56 am

Nonstop3h 01m

Ponce Mercedita

Mon 7/6

10:31 am-1:38 pm

Nonstop3h 07m

$293

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Tue 5/26

6:10 am-9:07 am

Nonstop2h 57m

Ponce Mercedita

Tue 6/2

10:02 am-1:23 pm

Nonstop3h 21m

$293

OrlandoNassau

MCO - NAS

MCONAS

Orlando

Sun 7/5

7:00 am-4:37 pm

1 stop9h 37m

Nassau Intl

Fri 7/10

6:04 pm-11:02 pm

1 stop4h 58m

$314

OrlandoNassau

MCO - NAS

MCONAS

Orlando

Tue 6/2

5:30 am-2:04 pm

1 stop8h 34m

Nassau Intl

Tue 6/9

6:02 pm-10:51 pm

1 stop4h 49m

$314

OrlandoNassau

MCO - NAS

MCONAS

Orlando

Mon 7/20

10:05 am-4:39 pm

1 stop6h 34m

Nassau Intl

Sat 7/25

6:04 pm-12:15 am

1 stop6h 11m

$314

OrlandoNassau

MCO - NAS

MCONAS

Orlando

Tue 6/23

7:00 am-2:04 pm

1 stop7h 04m

Nassau Intl

Wed 6/24

3:29 pm-8:35 pm

1 stop5h 06m

$314

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Sun 6/14

6:45 am-9:42 am

Nonstop2h 57m

Ponce Mercedita

Sun 7/19

10:31 am-1:38 pm

Nonstop3h 07m

$316

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Thu 7/16

6:45 am-9:46 am

Nonstop3h 01m

Ponce Mercedita

Mon 7/20

10:31 am-1:38 pm

Nonstop3h 07m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/4

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

How far ahead should I book a flight from Orlando to Caribbean?

Booking 14 days in advance of your planned departure date is, on average, the best time to get cheap flights from Orlando to Caribbean. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, February is the cheapest month in which you can book a flight from Orlando to Caribbean (average of $247). Flying from Orlando to Caribbean in December is currently the most expensive (average of $367). 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 May 8, 2026.

It’s typically best to fly out from Orlando to Caribbean in the afternoon. Doing so could potentially save you 15% 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 May 2, 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 May 8, 2026.

The most flights from ORL to 0CB are scheduled on a Thursday (25 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (15 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 May 8, 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
7.9
Good
4,302 reviews

Overall

7.9

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

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
7.9
Good
4,302 reviews
Southwest
7.9
Good
4,302 reviews

Overall

7.9

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

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
2,979 reviews
Southwest
7.9
Good
4,302 reviews

Overall

7.9

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

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
11,669 reviews
Southwest
7.9
Good
4,302 reviews

Overall

7.9

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

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
8,638 reviews
Southwest
7.9
Good
4,302 reviews

Overall

7.9

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

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
5.6
Fair
2,961 reviews
Southwest
7.9
Good
4,302 reviews

Overall

7.9

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

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 46m. The distance between Orlando and Caribbean is about 1128 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 $61 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $71 and American Airlines from $88 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 - Montego Bay Sangster Intl.

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

    The top 3 most reliable airlines when flying from Orlando to Caribbean are Azul (85%), JetBlue (83%) and Aer Lingus (78%).

  • What are the cheapest flights from Orlando to Caribbean?

    The cheapest flight price from Orlando to Caribbean is $71. On average you can expect to pay $234. The most popular route, (Orlando - San Juan Luis Munoz Marin Intl), can usually be booked for $230.

  • 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, February is the cheapest month in which you can book a flight from Orlando to Caribbean (average of $247). Flying from Orlando to Caribbean in December is currently the most expensive (average of $367). 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.
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Miami to Las Vegas flights
Miami to Hobby 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 May 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$89Average$502FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$98Average$291FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$103Average$432FlexibilityNo cancel feeOn-time62%
FrontierCheapest$116Average$286FlexibilityNo cancel feeOn-time62%
BahamasairCheapest$119Average$337FlexibilityNo cancel feeOn-time33%
Copa AirlinesCheapest$142Average$390FlexibilityNo cancel feeOn-time70%
ArajetCheapest$204Average$253FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$244Average$519FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$253Average$447FlexibilityNo cancel feeOn-time71%

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