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$189+ 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 11/26. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJU
nov. 29 — dic. 61
sáb. 11/29
sáb. 12/6
1 adult, Economy
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Find 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 octubre 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/267:47 amEYW - SJU
1 stop14h 22mMultiple Airlines
mié. 12/39:15 amSJU - EYW
2 stops31h 29mMultiple Airlines
Deal found 10/29$377
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/28:55 amEYW - SJU
1 stop25h 24mMultiple Airlines
mar. 11/49:00 amSJU - EYW
2 stops26h 07mMultiple Airlines
Deal found 10/29$473
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/132:30 pmEYW - NAS
1 stop4h 45mMultiple Airlines
sáb. 12/204:00 pmNAS - EYW
1 stop19h 20mMultiple Airlines
Deal found 10/29$473
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
mié. 11/267:47 amEYW - NAS
2 stops6h 03mMultiple Airlines
mié. 12/34:00 pmNAS - EYW
1 stop19h 20mMultiple Airlines
Deal found 10/27$516
This Mytrip deal was found by Cheapflights users on 10/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/3012:20 pmEYW - NAS
1 stop6h 55mMultiple Airlines
jue. 1/17:15 amNAS - EYW
1 stop4h 05mMultiple Airlines
Deal found 10/29$517
This American Airlines deal was found by Cheapflights users on 10/27. 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.
mié. 11/2611:44 amEYW - NAS
1 stop8h 27mAmerican Airlines
mié. 12/37:49 amNAS - EYW
1 stop9h 08mAmerican Airlines
Deal found 10/27$555
This American Airlines deal was found by Cheapflights users on 10/29. 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.
dom. 11/27:53 pmEYW - SJU
1 stop13h 24mAmerican Airlines
mar. 11/411:13 amSJU - EYW
1 stop9h 10mAmerican Airlines
Deal found 10/29$645
This American Airlines deal was found by Cheapflights users on 10/29. 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.
dom. 12/218:30 pmEYW - SJU
1 stop12h 05mAmerican Airlines
dom. 12/285:24 amSJU - EYW
1 stop15h 15mAmerican Airlines
Deal found 10/29$667
This Mytrip deal was found by Cheapflights users on 10/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/292:30 pmEYW - SJU
1 stop6h 35mMultiple Airlines
sáb. 1/36:00 amSJU - EYW
2 stops16h 45mMultiple Airlines
Deal found 10/29$700
This American Airlines deal was found by Cheapflights users on 10/29. 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.
lun. 12/291:46 pmEYW - SJU
1 stop6h 25mAmerican Airlines
sáb. 1/35:24 amSJU - EYW
1 stop13h 20mAmerican Airlines
Deal found 10/29$740

Cheap 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 octubre 30, 2025.

Round-trip from

$365
(American Airlines)

One-way from

$189
(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 octubre 30, 2025.
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 WestKingston

EYW - KIN

EYWKIN

Key West

vie. 1/9

2:25 pm-12:13 pm

1 stop21h 48m

Kingston Norman Manley

mar. 1/13

1:28 pm-1:30 pm

1 stop24h 02m

$412

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

mié. 2/18

2:25 pm-3:06 pm

2 stops23h 41m

San Juan Luis Munoz Marin Intl

dom. 2/22

9:37 pm-12:26 pm

1 stop15h 49m

$422

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

mié. 11/26

7:47 am-11:09 pm

1 stop14h 22m

San Juan Luis Munoz Marin Intl

mié. 12/3

11:55 am-11:20 am

1 stop24h 25m

$430

Key WestKingston

EYW - KIN

EYWKIN

Key West

vie. 1/9

2:25 pm-12:13 pm

1 stop21h 48m

Kingston Norman Manley

mar. 1/13

1:28 pm-10:09 am

2 stops20h 41m

$452

Key WestNassau

EYW - NAS

EYWNAS

Key West

sáb. 12/13

2:30 pm-7:15 pm

1 stop4h 45m

Nassau Intl

sáb. 12/20

4:00 pm-11:20 am

1 stop19h 20m

$473

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

mié. 2/18

2:25 pm-7:21 pm

3 stops27h 56m

San Juan Luis Munoz Marin Intl

dom. 2/22

8:28 pm-1:30 pm

2 stops18h 02m

$476

Key WestNassau

EYW - NAS

EYWNAS

Key West

dom. 4/5

6:31 am-7:45 pm

1 stop13h 14m

Nassau Intl

mié. 4/8

3:05 pm-6:21 pm

1 stop3h 16m

$489

Key WestNassau

EYW - NAS

EYWNAS

Key West

vie. 1/23

2:25 pm-7:15 pm

1 stop4h 50m

Nassau Intl

lun. 1/26

7:45 am-1:30 pm

3 stops29h 45m

$504

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

mar. 3/10

1:23 pm-8:36 am

2 stops19h 13m

San Juan Luis Munoz Marin Intl

mié. 3/11

3:45 pm-11:31 am

2 stops19h 46m

$514

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

mar. 3/3

6:28 pm-1:33 pm

2 stops18h 05m

San Juan Luis Munoz Marin Intl

mié. 3/4

4:37 pm-12:07 pm

2 stops20h 30m

$514

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 26 results
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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

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

Find hourly flight availability from Key West 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 octubre 30, 2025.

When flying from Key West to Caribbean, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 15% versus a flight at noon.

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 octubre 30, 2025.
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
11,034 reviews

Comfort

7.2

Entertainment

6.9

Crew

8.0

Overall

7.2

Boarding

7.5

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
11,034 reviews
American Airlines
7.2
Good
11,034 reviews

Comfort

7.2

Entertainment

6.9

Crew

8.0

Overall

7.2

Boarding

7.5

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. 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 13h 14m. Fly via Spirit Airlines, American Airlines, or JetBlue 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 - Nassau Intl or Key West - Marsh Harbour 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 octubre 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$360Average$526FlexibilityNo cancel feeOn-time71%

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