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Caribbean Islands

$198+ Cheap flights from Key West (EYW) to Caribbean Islands

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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJU
oct. 11 — oct. 181
sam. 10/11
sam. 10/18
1 adult, Economy
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Cheap flight deals from Key West to Caribbean Islands

Keep the following information in mind while searching for Key West to Caribbean Islands flight deals. Data was last updated septembre 11, 2025.

Round-trip from

$330
(Kiwi.com)

One-way from

$198
(Kiwi.com)

Popular in

January

Cheapest in

April

Average price

$444
From Key West to Caribbean Islands
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One-way flight from Key West to Caribbean Islands
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Highest demand for flights based on searches. 24% potential increase in price ($152 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($39 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 Key West to Caribbean Islands

Cheapest flights from Key West to Caribbean Islands
Explore the most affordable flight options available from Key West to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septembre 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
sam. 10/1810:47 amEYW - SJU
1 stop8h 11mMultiple Airlines
mer. 10/224:51 pmSJU - EYW
2 stops51h 04mMultiple Airlines
Deal found 9/11$330
This American Airlines deal was found by Cheapflights users on 9/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 11/74:18 pmEYW - SJU
1 stop6h 40mAmerican Airlines
mer. 11/122:47 pmSJU - EYW
1 stop5h 36mAmerican Airlines
Deal found 9/11$365
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 12/187:52 pmEYW - SJU
1 stop12h 44mAmerican Airlines
jeu. 12/252:31 pmSJU - EYW
1 stop5h 51mAmerican Airlines
Deal found 9/10$405
This American Airlines deal was found by Cheapflights users on 9/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 10/16:17 pmEYW - SJU
2 stops20h 36mAmerican Airlines
lun. 10/67:00 amSJU - EYW
1 stop5h 55mAmerican Airlines
Deal found 9/9$425
This Mytrip deal was found by Cheapflights users on 9/11. 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.
ven. 11/710:10 amEYW - SJU
3 stops29h 13mMultiple Airlines
mer. 11/1210:57 amSJU - EYW
3 stops27h 33mMultiple Airlines
Deal found 9/11$444
This Mytrip deal was found by Cheapflights users on 9/11. 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.
ven. 11/72:25 pmEYW - SJU
2 stops24h 58mSpirit Airlines
mer. 11/1212:10 pmSJU - EYW
3 stops26h 20mSpirit Airlines
Deal found 9/11$457
This American Airlines deal was found by Cheapflights users on 9/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 11/227:58 pmEYW - SJU
1 stop13h 12mAmerican Airlines
ven. 11/282:50 pmSJU - EYW
1 stop5h 33mAmerican Airlines
Deal found 9/9$515
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
dim. 10/128:55 amEYW - NAS
1 stop7h 30mMultiple Airlines
ven. 10/1711:30 amNAS - EYW
2 stops22h 37mMultiple Airlines
Deal found 9/10$573
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
jeu. 9/118:55 amEYW - NAS
1 stop7h 30mMultiple Airlines
mer. 9/174:00 pmNAS - EYW
2 stops40h 07mMultiple Airlines
Deal found 9/9$683
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 10/1211:22 amEYW - NAS
1 stop6h 25mAmerican Airlines
ven. 10/177:45 amNAS - EYW
1 stop9h 31mAmerican Airlines
Deal found 9/10$710
This American Airlines deal was found by Cheapflights users on 9/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 10/2611:22 amEYW - NAS
1 stop6h 25mAmerican Airlines
dim. 11/27:49 amNAS - EYW
1 stop9h 12mAmerican Airlines
Deal found 9/11$725
This American Airlines deal was found by Cheapflights users on 9/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 9/111:59 pmEYW - NAS
1 stop3h 59mAmerican Airlines
mer. 9/1710:26 amNAS - EYW
1 stop8h 33mAmerican Airlines
Deal found 9/9$1,053

Cheapflights Fare Finder

 
Customize your flight search to find flights from Key West to Caribbean Islands 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 septembre 11, 2025.
Use the filters below to find and compare flights from Key West to Caribbean Islands that are best for you.

Fly from

Key West

Fly to

Caribbean Islands

Route

Depart

Return

Price

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

sam. 10/18

10:47 am-6:58 pm

1 stop8h 11m

San Juan Luis Munoz Marin Intl

mer. 10/22

4:51 pm-7:55 pm

2 stops51h 04m

$330

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

ven. 11/7

4:18 pm-11:58 pm

1 stop6h 40m

San Juan Luis Munoz Marin Intl

mer. 11/12

2:47 pm-7:23 pm

1 stop5h 36m

$365

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

mer. 10/1

6:17 pm-2:53 pm

2 stops20h 36m

San Juan Luis Munoz Marin Intl

lun. 10/6

7:00 am-12:55 pm

1 stop5h 55m

$425

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

ven. 11/7

10:10 am-4:23 pm

3 stops29h 13m

San Juan Luis Munoz Marin Intl

mer. 11/12

10:57 am-1:30 pm

3 stops27h 33m

$444

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

ven. 11/7

2:25 pm-4:23 pm

2 stops24h 58m

San Juan Luis Munoz Marin Intl

mer. 11/12

12:10 pm-1:30 pm

3 stops26h 20m

$457

Key WestNassau

EYW - NAS

EYWNAS

Key West

dim. 10/12

8:55 am-4:25 pm

1 stop7h 30m

Nassau Intl

ven. 10/17

11:30 am-10:07 am

2 stops22h 37m

$573

Key WestNassau

EYW - NAS

EYWNAS

Key West

dim. 10/12

11:22 am-5:47 pm

1 stop6h 25m

Nassau Intl

ven. 10/17

7:45 am-5:16 pm

1 stop9h 31m

$710

Key WestNassau

EYW - NAS

EYWNAS

Key West

dim. 10/26

11:22 am-5:47 pm

1 stop6h 25m

Nassau Intl

dim. 11/2

7:49 am-5:01 pm

1 stop9h 12m

$725

Key WestKingston

EYW - KIN

EYWKIN

Key West

mar. 3/10

6:31 am-10:55 am

1 stop5h 24m

Kingston Norman Manley

mer. 3/11

12:50 pm-6:30 pm

1 stop4h 40m

$733

Key WestRoad Town

EYW - EIS

EYWEIS

Key West

mar. 9/23

3:45 pm-1:06 pm

2 stops21h 21m

Road Town Beef Island

jeu. 9/25

1:46 pm-11:49 am

2 stops22h 03m

$1,112

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/8

Showing 1-10 of 13 results
1
2

Best time to book a flight from Key West to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Key West 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 Key West to Caribbean Islands

What is the cheapest time of day to fly from EYW to EPX?

Find hourly flight availability from Key West to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septembre 11, 2025.

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

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated septembre 11, 2025.
Get a feel of what it's like to fly with American Airlines from Key West to Caribbean Islands 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.

Related info for your journey

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

  • What airport do you fly from for flights from Key West to Caribbean Islands?

    For a flight from Key West to Caribbean Islands, you will be flying from Key West. Key West (EYW) is just 2.6 mi from the center of the city.

  • How long is the flight from Key West to Caribbean Islands?

    For as low as $365, American Airlines can have you in Caribbean Islands from Key West in 6h 40m. The distance between Key West and Caribbean Islands is about 1096 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Key West to Caribbean Islands?

    While some choose either Key West - Nassau Intl or Key West - Marsh Harbour, Key West - San Juan Luis Munoz Marin Intl is the most popular route from Key West to Caribbean Islands.

  • Can I find deals for flights from Key West to Caribbean Islands that include hotel bookings?

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

  • How can I find direct flights from Key West to Caribbean Islands?

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

  • Can I find deals for business class flights from Key West to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Key West to Caribbean Islands 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 Key West to Caribbean Islands?

    Currently, September is the cheapest month in which you can book a flight from Key West to Caribbean Islands (average of $254). Flying from Key West to Caribbean Islands 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.

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Top airline flying from Key West to Caribbean Islands

Discover the top airline that operate flights from Key West to Caribbean Islands. 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 septembre 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$360Average$526FlexibilityNo cancel feeOn-time71%

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