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Caribbean

$139+ Cheap flights from Key West (EYW) 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 3/24. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJU
Apr 16 — Apr 231
Thu 4/16
Thu 4/23
1 adult, Economy
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Cheap flight deals from Key West to Caribbean

Cheapest flights from Key West to Caribbean
Explore the most affordable flight options available from Key West to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 17, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/2911:01 am
EYW
-
SJU
1 stop23h 09m
Multiple Airlines
Thu 4/28:47 pm
SJU
-
EYW
1 stop12h 22m
Multiple Airlines
Deal found 3/14$348
This Kiwi.com deal was found by Cheapflights users on 3/13. 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 4/69:49 am
EYW
-
SJU
1 stop24h 21m
Multiple Airlines
Fri 5/155:15 pm
SJU
-
EYW
2 stops41h 09m
Multiple Airlines
Deal found 3/13$386
This Kiwi.com deal was found by Cheapflights users on 3/15. 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.
Wed 8/511:46 am
EYW
-
SJU
1 stop25h 44m
Multiple Airlines
Tue 8/116:10 am
SJU
-
EYW
1 stop28h 56m
Multiple Airlines
Deal found 3/15$423
This Kiwi.com deal was found by Cheapflights users on 3/15. 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.
Thu 8/1311:04 am
EYW
-
SJU
2 stops13h 43m
Multiple Airlines
Wed 8/198:06 pm
SJU
-
EYW
1 stop15h 19m
Multiple Airlines
Deal found 3/15$431
This American Airlines deal was found by Cheapflights users on 3/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/61:29 pm
EYW
-
SJU
1 stop10h 11m
American Airlines
Wed 8/128:00 am
SJU
-
EYW
1 stop8h 20m
American Airlines
Deal found 3/15$436
This Kiwi.com deal was found by Cheapflights users on 3/15. 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.
Thu 8/611:04 am
EYW
-
SJU
2 stops13h 43m
Multiple Airlines
Wed 8/126:10 am
SJU
-
EYW
1 stop28h 14m
Multiple Airlines
Deal found 3/15$439
This American Airlines deal was found by Cheapflights users on 3/17. 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.
Wed 9/27:09 pm
EYW
-
SJU
1 stop14h 33m
American Airlines
Sun 9/66:00 am
SJU
-
EYW
1 stop12h 39m
American Airlines
Deal found 3/17$441
This American Airlines deal was found by Cheapflights users on 3/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:40 pm
EYW
-
SJU
1 stop13h 59m
American Airlines
Fri 5/296:00 am
SJU
-
EYW
2 stops12h 49m
American Airlines
Deal found 3/16$456
This Mytrip deal was found by Cheapflights users on 3/14. 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.
Sun 3/2912:25 pm
EYW
-
SJU
1 stop6h 30m
Spirit Airlines
Thu 4/211:03 am
SJU
-
EYW
3 stops26h 34m
Spirit Airlines
Deal found 3/14$481
This Kiwi.com deal was found by Cheapflights users on 3/12. 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.
Thu 6/1112:05 pm
EYW
-
NAS
1 stop4h 20m
Multiple Airlines
Sun 6/1412:00 pm
NAS
-
EYW
1 stop26h 35m
Multiple Airlines
Deal found 3/12$495
This Kiwi.com deal was found by Cheapflights users on 3/15. 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.
Wed 4/2911:51 am
EYW
-
NAS
1 stop4h 34m
Multiple Airlines
Wed 5/612:00 pm
NAS
-
EYW
1 stop23h 25m
Multiple Airlines
Deal found 3/15$497
This Kiwi.com deal was found by Cheapflights users on 3/12. 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.
Thu 3/269:46 am
EYW
-
NAS
1 stop6h 39m
Multiple Airlines
Sun 3/2912:00 pm
NAS
-
EYW
1 stop24h 26m
Multiple Airlines
Deal found 3/12$511

Find flight deals from Key West to Caribbean

Keep the following information in mind while searching for Key West to Caribbean flight deals. Data was last updated March 17, 2026.

Round-trip from

$348
(Kiwi.com)

One-way from

$139
(Cheapflightsfares)
From Key West to Caribbean
Search Deals
One-way flight from Key West to Caribbean
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Key West 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 17, 2026.
Use the filters below to find and compare flights from Key West to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Mon 4/6

9:49 am-10:10 am

1 stop24h 21m

San Juan Luis Munoz Marin Intl

Fri 5/15

5:15 pm-10:24 am

2 stops41h 09m

$386

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Thu 8/6

12:50 pm-10:56 pm

1 stop10h 06m

San Juan Luis Munoz Marin Intl

Wed 8/12

6:00 am-10:52 am

1 stop4h 52m

$436

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Sun 3/29

12:25 pm-6:55 pm

1 stop6h 30m

San Juan Luis Munoz Marin Intl

Thu 4/2

7:54 pm-12:26 pm

2 stops16h 32m

$437

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Wed 9/2

4:51 pm-9:42 am

2 stops16h 51m

San Juan Luis Munoz Marin Intl

Sun 9/6

6:00 am-6:39 pm

1 stop12h 39m

$441

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Wed 5/27

7:40 pm-9:39 am

1 stop13h 59m

San Juan Luis Munoz Marin Intl

Fri 5/29

6:00 am-6:49 pm

2 stops12h 49m

$456

Key WestNassau

EYW - NAS

EYWNAS

Key West

Thu 6/11

12:05 pm-4:25 pm

1 stop4h 20m

Nassau Intl

Sun 6/14

12:00 pm-2:35 pm

1 stop26h 35m

$495

Key WestNassau

EYW - NAS

EYWNAS

Key West

Wed 4/29

11:51 am-4:25 pm

1 stop4h 34m

Nassau Intl

Wed 5/6

12:00 pm-11:25 am

1 stop23h 25m

$497

Key WestNassau

EYW - NAS

EYWNAS

Key West

Sun 7/12

11:28 am-3:04 pm

1 stop3h 36m

Nassau Intl

Wed 7/15

7:39 am-7:06 pm

1 stop11h 27m

$536
Quickest round-trip

Key WestNassau

EYW - NAS

EYWNAS

Key West

Sun 4/26

12:26 pm-7:15 pm

1 stop6h 49m

Nassau Intl

Sun 5/3

7:15 am-11:31 am

1 stop4h 16m

$536

Key WestMarsh Harbour

EYW - MHH

EYWMHH

Key West

Tue 5/19

6:45 am-1:20 pm

1 stop6h 35m

Marsh Harbour

Mon 5/25

12:51 pm-7:10 pm

1 stop6h 19m

$542

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/17

Showing 1-10 of 27 resultsSorted by cheapest first
1
2
3

Best time to book a flight from Key West to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean 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
No data available for this route at this time. Please check back soon.

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 17, 2026.
Read reviews from past customers who have flown American Airlines from Key West to Caribbean. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.1
Good
11,468 reviews

Overall

7.1

Entertainment

6.9

Food

6.4

Boarding

7.5

Comfort

7.2

Crew

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes
American Airlines
7.1
Good
11,468 reviews
American Airlines
7.1
Good
11,468 reviews

Overall

7.1

Entertainment

6.9

Food

6.4

Boarding

7.5

Comfort

7.2

Crew

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes

Related info for your journey

Find useful and relevant information for your journey from Key West to Caribbean. 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?

    For a flight from Key West to Caribbean, 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?

    There are many flights that can get you from Key West to Caribbean in 10h 06m. Fly via American Airlines or United Airlines to get the fastest option. Key West and Caribbean are separated by a distance of 1096 mi. This flight may include one or multiple stops.

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

    When deciding which route to take from Key West to Caribbean consider Key West - San Juan Luis Munoz Marin Intl, Key West - Nassau Intl or Key West - Road Town Beef Island as they are the most popular.

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

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

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

    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.

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

    Yes. Cheapflights offers flight deals from Key West 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.

See more FAQs

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Top airline flying from Key West to Caribbean

Discover the top airline that operate flights from Key West 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 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$390Average$495FlexibilityNo cancel feeOn-time71%

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