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Caribbean

$172+ 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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJU
May 30 — Jun 61
Sat 5/30
Sat 6/6
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 April 30, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/25. 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 5/1012:05 pm
EYW
-
SJU
1 stop12h 14m
Multiple Airlines
Thu 5/147:00 am
SJU
-
EYW
2 stops28h 27m
Multiple Airlines
Deal found 4/25$367
This American Airlines deal was found by Cheapflights users on 4/30. 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 9/21:49 pm
EYW
-
SJU
1 stop4h 35m
American Airlines
Sun 9/66:00 am
SJU
-
EYW
1 stop13h 39m
American Airlines
Deal found 4/30$441
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Tue 8/411:28 am
EYW
-
NAS
1 stop6h 26m
American Airlines
Thu 8/62:36 pm
NAS
-
EYW
1 stop5h 03m
American Airlines
Deal found 4/28$536
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 6/1212:07 pm
EYW
-
NAS
1 stop4h 18m
Multiple Airlines
Mon 6/154:00 pm
NAS
-
EYW
2 stops20h 34m
Multiple Airlines
Deal found 4/26$561
This Kiwi.com deal was found by Cheapflights users on 4/27. 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
2 stops31h 10m
Multiple Airlines
Thu 6/1812:00 pm
NAS
-
EYW
1 stop23h 27m
Multiple Airlines
Deal found 4/27$567
This American Airlines deal was found by Cheapflights users on 4/26. 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 6/101:39 pm
EYW
-
NAS
1 stop4h 11m
American Airlines
Wed 6/178:00 am
NAS
-
EYW
1 stop11h 10m
American Airlines
Deal found 4/26$571
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 6/1011:46 am
EYW
-
NAS
2 stops7h 29m
Multiple Airlines
Wed 6/1712:00 pm
NAS
-
EYW
1 stop23h 25m
Multiple Airlines
Deal found 4/26$588
This American Airlines deal was found by Cheapflights users on 4/29. 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 7/97:40 pm
EYW
-
NAS
1 stop13h 47m
American Airlines
Mon 7/137:39 am
NAS
-
EYW
1 stop5h 29m
American Airlines
Deal found 4/29$606
This American Airlines deal was found by Cheapflights users on 4/26. 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.
Fri 6/1211:28 am
EYW
-
NAS
1 stop8h 28m
American Airlines
Mon 6/1510:17 am
NAS
-
EYW
1 stop8h 53m
American Airlines
Deal found 4/26$636
This American Airlines deal was found by Cheapflights users on 4/27. 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.
Sat 5/24:53 pm
EYW
-
SJU
1 stop17h 55m
American Airlines
Sat 5/96:02 pm
SJU
-
EYW
1 stop4h 56m
American Airlines
Deal found 4/27$711
This American Airlines deal was found by Cheapflights users on 4/26. 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.
Tue 5/267:40 pm
EYW
-
MHH
1 stop13h 50m
American Airlines
Tue 6/210:10 am
MHH
-
EYW
1 stop9h 00m
American Airlines
Deal found 4/26$727
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 8/41:14 pm
EYW
-
NAS
2 stops6h 01m
Multiple Airlines
Thu 8/69:55 am
NAS
-
EYW
1 stop9h 18m
Multiple Airlines
Deal found 4/28$763

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 April 30, 2026.

Round-trip from

$367
(Kiwi.com)

One-way from

$172
(Kiwi.com)
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 April 30, 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

Sun 5/10

12:05 pm-12:19 am

1 stop12h 14m

San Juan Luis Munoz Marin Intl

Thu 5/14

7:00 am-11:27 am

2 stops28h 27m

$367

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Wed 9/2

11:30 am-6:24 pm

1 stop6h 54m

San Juan Luis Munoz Marin Intl

Sun 9/6

1:38 pm-7:39 pm

1 stop6h 01m

$441

Key WestNassau

EYW - NAS

EYWNAS

Key West

Fri 6/12

12:07 pm-4:25 pm

1 stop4h 18m

Nassau Intl

Mon 6/15

4:00 pm-12:34 pm

2 stops20h 34m

$561

Key WestNassau

EYW - NAS

EYWNAS

Key West

Thu 6/11

12:05 pm-4:25 pm

1 stop4h 20m

Nassau Intl

Thu 6/18

12:00 pm-11:27 am

1 stop23h 27m

$567

Key WestNassau

EYW - NAS

EYWNAS

Key West

Wed 6/10

1:39 pm-5:50 pm

1 stop4h 11m

Nassau Intl

Wed 6/17

8:00 am-7:10 pm

1 stop11h 10m

$571

Key WestNassau

EYW - NAS

EYWNAS

Key West

Wed 6/10

11:46 am-7:15 pm

2 stops7h 29m

Nassau Intl

Wed 6/17

12:00 pm-11:25 am

1 stop23h 25m

$588

Key WestNassau

EYW - NAS

EYWNAS

Key West

Thu 7/9

7:40 pm-9:27 am

1 stop13h 47m

Nassau Intl

Mon 7/13

7:39 am-1:08 pm

1 stop5h 29m

$606

Key WestMarsh Harbour

EYW - MHH

EYWMHH

Key West

Tue 5/26

7:40 pm-9:30 am

1 stop13h 50m

Marsh Harbour

Tue 6/2

10:10 am-7:10 pm

1 stop9h 00m

$727
Quickest round-trip

Key WestFreeport

EYW - FPO

EYWFPO

Key West

Wed 5/20

6:45 am-9:42 am

1 stop2h 57m

Freeport Grand Bahama Intl

Mon 5/25

11:53 am-7:10 pm

1 stop7h 17m

$829

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Fri 5/15

2:49 pm-12:34 pm

2 stops21h 45m

San Juan Luis Munoz Marin Intl

Tue 5/19

7:20 am-1:45 pm

2 stops30h 25m

$871

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/25

Showing 1-10 of 24 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 April 30, 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
11,681 reviews

Crew

7.9

Food

6.4

Overall

7.1

Comfort

7.2

Boarding

7.5

Entertainment

6.9

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
11,681 reviews
American Airlines
7.1
Good
11,681 reviews

Crew

7.9

Food

6.4

Overall

7.1

Comfort

7.2

Boarding

7.5

Entertainment

6.9

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 6h 54m. Fly via American Airlines to get the fastest option. Key West and Caribbean are separated by a distance of 1096 mi.

  • 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 - Nassau Intl, Key West - San Juan Luis Munoz Marin Intl or Key West - Kingston Norman Manley 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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See prices for flight routes from nearby airports that may be better suited for you.
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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 April 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$390Average$495FlexibilityNo cancel feeOn-time71%

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