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Caribbean

$150+ 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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJU
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/269:46 am
EYW
-
SJU
1 stop12h 23m
Multiple Airlines
Wed 3/43:53 am
SJU
-
EYW
1 stop6h 13m
Multiple Airlines
Deal found 1/27$266
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 3/59:46 am
EYW
-
SJU
1 stop12h 23m
Multiple Airlines
Wed 3/113:08 am
SJU
-
EYW
1 stop5h 58m
Multiple Airlines
Deal found 1/27$283
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Fri 2/271:06 pm
EYW
-
SJU
1 stop9h 03m
Multiple Airlines
Fri 3/66:30 am
SJU
-
EYW
1 stop6h 56m
Multiple Airlines
Deal found 1/28$289
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Sat 2/1411:53 am
EYW
-
SJU
2 stops34h 31m
Multiple Airlines
Wed 2/185:25 pm
SJU
-
EYW
1 stop22h 54m
Multiple Airlines
Deal found 1/27$341
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 1/2910:06 am
EYW
-
SJU
2 stops25h 21m
Multiple Airlines
Wed 2/48:05 pm
SJU
-
EYW
1 stop14h 01m
Multiple Airlines
Deal found 1/27$348
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Thu 2/129:46 am
EYW
-
SJU
1 stop16h 07m
Multiple Airlines
Sun 2/153:53 am
SJU
-
EYW
1 stop9h 33m
Multiple Airlines
Deal found 1/28$360
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Sat 1/3110:49 am
EYW
-
SJU
2 stops23h 56m
Multiple Airlines
Sat 2/78:05 pm
SJU
-
EYW
1 stop14h 01m
Multiple Airlines
Deal found 1/27$385
This American Airlines deal was found by Cheapflights users on 1/28. 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 6/211:28 am
EYW
-
NAS
1 stop6h 04m
American Airlines
Sat 6/138:00 am
NAS
-
EYW
1 stop5h 04m
American Airlines
Deal found 1/28$493
This Delta deal was found by Cheapflights users on 1/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/267:30 am
EYW
-
NAS
1 stop9h 15m
Delta
Mon 3/301:18 pm
NAS
-
EYW
1 stop6h 23m
Delta
Deal found 1/29$510
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 3/199:46 am
EYW
-
NAS
1 stop6h 39m
Multiple Airlines
Mon 3/234:00 pm
NAS
-
EYW
2 stops20h 21m
Multiple Airlines
Deal found 1/27$516
This Mytrip deal was found by Cheapflights users on 1/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/1512:25 pm
EYW
-
NAS
1 stop6h 50m
Multiple Airlines
Sun 3/227:15 am
NAS
-
EYW
1 stop4h 15m
Multiple Airlines
Deal found 1/28$536
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Mon 11/912:00 pm
EYW
-
NAS
1 stop8h 09m
American Airlines
Thu 11/1210:40 am
NAS
-
EYW
1 stop5h 59m
American Airlines
Deal found 1/27$537

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 January 29, 2026.

Round-trip from

$266
(Kiwi.com)

One-way from

$150
(Kiwi.com)

Popular in

March

Cheapest in

April

Average price

$710
From Key West to Caribbean
Search Deals
One-way flight from Key West to Caribbean
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($53 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($39 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
Use the filters below to find and compare flights from Key West to Caribbean that are best for you.

Fly from

Key West

Fly to

Caribbean

Route

Depart

Return

Price

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Thu 2/26

9:46 am-11:09 pm

1 stop12h 23m

San Juan Luis Munoz Marin Intl

Wed 3/4

3:53 am-9:06 am

1 stop6h 13m

$266

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Thu 3/5

9:46 am-11:09 pm

1 stop12h 23m

San Juan Luis Munoz Marin Intl

Wed 3/11

3:08 am-9:06 am

1 stop5h 58m

$283

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Fri 2/27

1:06 pm-11:09 pm

1 stop9h 03m

San Juan Luis Munoz Marin Intl

Fri 3/6

6:30 am-12:26 pm

1 stop6h 56m

$289

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Sat 2/14

11:53 am-11:24 pm

2 stops34h 31m

San Juan Luis Munoz Marin Intl

Wed 2/18

5:25 pm-3:19 pm

1 stop22h 54m

$341

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Thu 2/12

9:46 am-2:53 am

1 stop16h 07m

San Juan Luis Munoz Marin Intl

Sun 2/15

3:53 am-12:26 pm

1 stop9h 33m

$360

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Sun 3/15

7:42 pm-10:56 am

1 stop15h 14m

San Juan Luis Munoz Marin Intl

Sun 3/22

6:00 am-7:12 pm

1 stop13h 12m

$426

Key WestNassau

EYW - NAS

EYWNAS

Key West

Tue 6/2

11:28 am-5:32 pm

1 stop6h 04m

Nassau Intl

Sat 6/13

8:00 am-1:04 pm

1 stop5h 04m

$493

Key WestNassau

EYW - NAS

EYWNAS

Key West

Thu 3/26

7:30 am-4:45 pm

1 stop9h 15m

Nassau Intl

Mon 3/30

1:18 pm-7:41 pm

1 stop6h 23m

$510

Key WestNassau

EYW - NAS

EYWNAS

Key West

Thu 3/19

9:46 am-4:25 pm

1 stop6h 39m

Nassau Intl

Mon 3/23

4:00 pm-12:21 pm

2 stops20h 21m

$516

Key WestNassau

EYW - NAS

EYWNAS

Key West

Sun 3/15

12:25 pm-7:15 pm

1 stop6h 50m

Nassau Intl

Sun 3/22

7:15 am-11:30 am

1 stop4h 15m

$536

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 20 results
1
2

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 January 29, 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
7.2
Good
11,206 reviews

Overall

7.2

Food

6.4

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.
American Airlines
7.2
Good
11,206 reviews
American Airlines
7.2
Good
11,206 reviews

Overall

7.2

Food

6.4

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.

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 04m. Fly via American Airlines or Delta to get the fastest option. Key West and Caribbean are separated by a distance of 271 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 - Marsh Harbour or Key West - Nassau Intl 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$376Average$495FlexibilityNo cancel feeOn-time71%

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