$86+ Cheap flights from Caribbean
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
Find flights from Caribbean within your budget
Fly to
Route
Depart
Return
San JuanOrlando
SJU San Juan Luis Munoz Marin Intl - MCO Orlando
SJUMCO
San Juan Luis Munoz Marin Intl
Thu 11/12
12:40 pm-2:50 pm
Nonstop3h 10m
Orlando
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
San JuanOrlando
SJU San Juan Luis Munoz Marin Intl - MCO Orlando
SJUMCO
San Juan Luis Munoz Marin Intl
Fri 11/6
7:30 am-9:40 am
Nonstop3h 10m
Orlando
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
San JuanOrlando
SJU San Juan Luis Munoz Marin Intl - MCO Orlando
SJUMCO
San Juan Luis Munoz Marin Intl
Sun 11/8
9:40 pm-11:55 pm
Nonstop3h 15m
Orlando
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
San JuanOrlando
SJU San Juan Luis Munoz Marin Intl - MCO Orlando
SJUMCO
San Juan Luis Munoz Marin Intl
Fri 11/13
6:35 am-3:55 pm
2 stops10h 20m
Orlando
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
San JuanOrlando
SJU San Juan Luis Munoz Marin Intl - MCO Orlando
SJUMCO
San Juan Luis Munoz Marin Intl
Sat 11/14
6:45 am-8:35 pm
2 stops14h 50m
Orlando
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
San JuanOrlando
SJU San Juan Luis Munoz Marin Intl - MCO Orlando
SJUMCO
San Juan Luis Munoz Marin Intl
Fri 12/4
5:15 pm-7:32 pm
Nonstop3h 17m
Orlando
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
San JuanOrlando
SJU San Juan Luis Munoz Marin Intl - MCO Orlando
SJUMCO
San Juan Luis Munoz Marin Intl
Wed 12/2
12:30 pm-2:45 pm
Nonstop3h 15m
Orlando
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
San JuanOrlando
SJU San Juan Luis Munoz Marin Intl - MCO Orlando
SJUMCO
San Juan Luis Munoz Marin Intl
Mon 12/7
10:45 am-12:55 pm
Nonstop3h 10m
Orlando
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
San JuanNew York
SJU San Juan Luis Munoz Marin Intl - JFK New York John F Kennedy Intl
SJUJFK
San Juan Luis Munoz Marin Intl
Mon 12/21
6:01 am-12:46 pm
1 stop7h 45m
New York John F Kennedy Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
San JuanNew York
SJU San Juan Luis Munoz Marin Intl - JFK New York John F Kennedy Intl
SJUJFK
San Juan Luis Munoz Marin Intl
Sat 11/14
7:00 am-10:04 am
Nonstop4h 04m
New York John F Kennedy Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
Best time to book a flight from Caribbean
Have a flexible travel schedule? Discover the best time to fly from Caribbean with our price prediction graph.
Travel insights for flights from Caribbean
Get recent, data-driven insights about flights from Caribbean including ideal travel times, pricing trends, and more.
What is the cheapest month to book a flight from Caribbean?
Currently, February is the cheapest month in which you can book a flight from Caribbean (average of $221). Flying from Caribbean in July will prove the most costly (average of $340). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.
Which airlines fly from Caribbean?
For flights departing from Caribbean check dates and pricing for the following: Frontier, JetBlue, Bahamasair, Southwest, American Airlines. These airlines depart to the following popular destinations: Orlando.
What is the cheapest place to fly to from Caribbean?
The cheapest city to fly to from Caribbean is Scarborough ANR Robinson Intl, with prices starting at $28. Explore other affordable destinations below.
When is the best time to book a flight from Caribbean?
To ensure you get the cheapest price possible for a flight from Caribbean, you should look to book at least 24 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
When is the cheapest time to fly from Caribbean?
Use this chart to determine the cheapest time to fly round-trip from Caribbean to Orlando. Price data was last updated on October 24, 2026.
Those who are seeking the cheapest fare on flights departing from Caribbean would be wise to consider leaving during Tuesday at noon when prices are typically at their lowest. When considering other options, price-conscious travelers should avoid Sunday at noon when fares are usually the most expensive.
Airline reviews for flights from Caribbean
Read reviews and ratings of airlines operating flights from Caribbean. Gain insights into the quality of service, in-flight amenities, customer experiences, and overall satisfaction to choose the best airline for your Caribbean travel. Please note that the reviews are sourced from user searches and were last updated on October 30, 2026. In the last 7 days, Cheapflights users made a total of 7,457,451 searches.
Read through reviews of airlines servicing Caribbean, such as Southwest,JetBlue, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
Boarding
Entertainment
Food
Crew
Overall
Reviews
Patricia,Oct 2026
DAL - TPA
Comfort
Boarding
Entertainment
Food
Crew
Overall
Reviews
Patricia,Oct 2026
DAL - TPA
Comfort
Boarding
Entertainment
Food
Crew
Overall
Reviews
Patricia,Oct 2026
DAL - TPA
Comfort
Boarding
Entertainment
Food
Crew
Overall
Reviews
Patricia,Oct 2026
DAL - TPA
Comfort
Boarding
Entertainment
Food
Crew
Overall
Reviews
Patricia,Oct 2026
DAL - TPA
Comfort
Boarding
Entertainment
Food
Crew
Overall
Reviews
Patricia,Oct 2026
DAL - TPA
Browse thousands of different options on Cheapflights for your next trip
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Popular international destinations from Caribbean
The most popular international flight routes departing from Caribbean we’ve come across at this time.
Fly from Caribbean countries
Fly from one of these departure points in Caribbean.
Fly from other continents
Choose from these other continents to depart from.
Popular Round-Trip Flight Destinations
Consider these popular destinations that Cheapflights users have chosen when departing from Caribbean. Routes are based on user searches and were last updated on October 30, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Related info for your journey
Access useful and relevant information related to your journey from Caribbean. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated October 30, 2026.