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$74+ Cheap flights from Florida Keys 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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJU
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
1 adult, Economy
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Cheap flight deals from Florida Keys to Caribbean

Keep the following information in mind while searching for Florida Keys to Caribbean flight deals. Data was last updated septiembre 16, 2025.

Round-trip from

$145
(Kiwi.com)

One-way from

$74
(eDestinos)

Popular in

January

Cheapest in

April

Average price

$489
From Florida Keys to Caribbean
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One-way flight from Florida Keys to Caribbean
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Highest demand for flights based on searches. 23% potential increase in price ($148 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($38 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Florida Keys to Caribbean

Cheapest flights from Florida Keys to Caribbean
Explore the most affordable flight options available from Florida Keys to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
jue. 10/165:13 pmMIA - SJU
Nonstop2h 43mFrontier
dom. 10/195:30 amSJU - MIA
Nonstop2h 48mFrontier
Deal found 9/15$145
This Frontier deal was found by Cheapflights users on 9/15. 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.
lun. 10/205:13 pmMIA - SJU
Nonstop2h 43mFrontier
mar. 10/216:22 amSJU - MIA
2 stops12h 23mFrontier
Deal found 9/15$146
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
vie. 10/175:13 pmMIA - SJU
Nonstop2h 43mFrontier
dom. 10/195:30 amSJU - MIA
Nonstop2h 48mFrontier
Deal found 9/15$148
This Mytrip deal was found by Cheapflights users on 9/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/297:10 amMIA - SJU
Nonstop2h 42mFrontier
vie. 10/37:50 pmSJU - MIA
Nonstop2h 47mFrontier
Deal found 9/14$149
This Frontier deal was found by Cheapflights users on 9/15. 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.
vie. 10/175:13 pmMIA - SJU
Nonstop2h 43mFrontier
lun. 11/39:30 amSJU - MIA
Nonstop2h 47mFrontier
Deal found 9/15$150
This eDestinos deal was found by Cheapflights users on 9/15. 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.
dom. 10/57:10 amMIA - SJU
Nonstop2h 42mFrontier
dom. 10/195:30 amSJU - MIA
Nonstop2h 48mFrontier
Deal found 9/15$153
This SmartFares deal was found by Cheapflights users on 9/15. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/3010:45 pmMIA - SJU
Nonstop2h 47mFrontier
jue. 11/66:54 pmSJU - MIA
Nonstop2h 51mFrontier
Deal found 9/15$155
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
dom. 10/199:18 amMIA - SJU
Nonstop2h 43mFrontier
lun. 10/279:06 pmSJU - MIA
Nonstop2h 50mFrontier
Deal found 9/16$156
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
lun. 9/297:10 amMIA - SJU
Nonstop2h 42mFrontier
jue. 10/210:57 amSJU - MIA
Nonstop2h 53mFrontier
Deal found 9/14$157
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
jue. 12/118:59 pmMIA - SJU
Nonstop2h 38mFrontier
jue. 12/189:30 pmSJU - MIA
Nonstop3h 00mFrontier
Deal found 9/14$162
This Priceline deal was found by Cheapflights users on 9/16. 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.
dom. 10/57:10 amMIA - SJU
Nonstop2h 42mFrontier
dom. 10/125:30 amSJU - MIA
Nonstop2h 48mFrontier
Deal found 9/16$163
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
mar. 9/237:25 pmMIA - SDQ
Nonstop2h 20mArajet
sáb. 9/273:35 pmSDQ - MIA
Nonstop2h 20mArajet
Deal found 9/14$220

Cheapflights Fare Finder

 
Customize your flight search to find flights from Florida Keys 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 septiembre 16, 2025.
Use the filters below to find and compare flights from Florida Keys to Caribbean that are best for you.

Fly from

Florida Keys

Fly to

Caribbean

Route

Depart

Return

Price

MiamiSan Juan

MIA - SJU

MIASJU

Miami

mar. 10/21

11:45 am-10:45 pm

1 stop11h 00m

San Juan Luis Munoz Marin Intl

vie. 10/24

5:50 am-6:50 pm

1 stop13h 00m

$175

MiamiSan Juan

MIA - SJU

MIASJU

Miami

mar. 10/7

12:44 pm-12:29 am

2 stops11h 45m

San Juan Luis Munoz Marin Intl

mié. 10/8

6:22 am-6:45 pm

2 stops12h 23m

$239

MiamiSanto Domingo

MIA - SDQ

MIASDQ

Miami

sáb. 11/1

7:25 pm-9:45 pm

Nonstop2h 20m

Santo Domingo Las Americas

sáb. 11/8

3:35 pm-4:55 pm

Nonstop2h 20m

$253

MiamiNassau

MIA - NAS

MIANAS

Miami

sáb. 2/7

4:45 pm-5:40 pm

Nonstop0h 55m

Nassau Intl

sáb. 2/14

10:00 am-11:00 am

Nonstop1h 00m

$266

MiamiPunta Cana

MIA - PUJ

MIAPUJ

Miami

lun. 10/20

7:05 am-2:30 pm

1 stop7h 25m

Punta Cana

mié. 10/22

1:40 pm-9:55 pm

1 stop8h 15m

$275

MiamiMontego Bay

MIA - MBJ

MIAMBJ

Miami

lun. 10/27

12:55 pm-1:30 pm

Nonstop1h 35m

Montego Bay Sangster Intl

lun. 11/3

1:40 pm-3:25 pm

Nonstop1h 45m

$276

MiamiSan Juan

MIA - SJU

MIASJU

Miami

sáb. 11/15

8:15 am-11:15 pm

1 stop14h 00m

San Juan Luis Munoz Marin Intl

mar. 11/18

8:55 am-8:45 pm

2 stops12h 50m

$281

MiamiSan Juan

MIA - SJU

MIASJU

Miami

mié. 10/1

7:45 am-7:45 pm

2 stops12h 00m

San Juan Luis Munoz Marin Intl

sáb. 10/4

5:45 am-8:30 pm

1 stop14h 45m

$281

MiamiMontego Bay

MIA - MBJ

MIAMBJ

Miami

vie. 10/31

6:50 am-1:45 pm

1 stop7h 55m

Montego Bay Sangster Intl

dom. 11/2

3:25 pm-10:05 pm

1 stop6h 40m

$291

MiamiMontego Bay

MIA - MBJ

MIAMBJ

Miami

mié. 10/29

6:55 am-1:45 pm

1 stop7h 50m

Montego Bay Sangster Intl

mié. 11/5

3:25 pm-9:50 pm

1 stop6h 25m

$291

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 60 results
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Best time to book a flight from Florida Keys to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Florida Keys 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 Florida Keys to Caribbean

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

Find hourly flight availability from Florida Keys 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 septiembre 16, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Florida Keys to Caribbean as you normally would.

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 septiembre 16, 2025.
Get a feel of what it's like to fly with American Airlines, Spirit Airlines, and Frontier from Florida Keys to Caribbean by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Boarding

7.5

Comfort

7.2

Crew

8.0

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Boarding

7.5

Comfort

7.2

Crew

8.0

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
Spirit Airlines
6.3
Okay
8,019 reviews
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Boarding

7.5

Comfort

7.2

Crew

8.0

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
Frontier
5.8
Fair
3,174 reviews
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Boarding

7.5

Comfort

7.2

Crew

8.0

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
Bahamasair
5.2
Fair
57 reviews
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Boarding

7.5

Comfort

7.2

Crew

8.0

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

Related info for your journey

Find useful and relevant information for your journey from Florida Keys 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 Florida Keys to Caribbean?

    Southwest, Frontier, and Arajet can get you from Florida Keys to Caribbean in just under 2h 20m. Your travel time can differ by up to 9h 25m. The distance from Florida Keys to Caribbean is about 848 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    One-way options have recently been found by users for as low as $88 on Southwest. Other airlines that offer cheap prices include Delta from $94 and Copa Airlines from $94 one-way.

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

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

  • How can I find direct flights from Florida Keys to Caribbean?

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

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

    Yes. Cheapflights offers flight deals from Florida Keys 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 Florida Keys to Caribbean?

    Currently, September is the cheapest month in which you can book a flight from Florida Keys to Caribbean (average of $254). Flying from Florida Keys to Caribbean in June is currently the most expensive (average of $339). 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 Florida Keys to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Florida Keys to Caribbean

Discover the top airline that operate flights from Florida Keys 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 septiembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$360Average$526FlexibilityNo cancel feeOn-time71%

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