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$134+ 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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJU
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
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 December 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/14. 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.
Thu 12/188:55 amEYW - NAS
1 stop8h 45mMultiple Airlines
Sat 12/204:00 pmNAS - EYW
1 stop19h 20mMultiple Airlines
Deal found 12/14$604
This American Airlines deal was found by Cheapflights users on 12/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1811:47 amEYW - NAS
1 stop8h 41mAmerican Airlines
Sat 12/207:45 amNAS - EYW
1 stop5h 41mAmerican Airlines
Deal found 12/14$920
This Expedia deal was found by Cheapflights users on 12/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/181:12 pmEYW - NAS
2 stops20h 08mJetBlue
Sat 12/206:01 pmNAS - EYW
2 stops18h 16mJetBlue
Deal found 12/14$1,009

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 December 16, 2025.

Round-trip from

$298
(Kiwi.com)

One-way from

$134
(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 December 16, 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 WestSan Juan

EYW - SJU

EYWSJU

Key West

Thu 2/5

11:01 am-4:57 pm

2 stops28h 56m

San Juan Luis Munoz Marin Intl

Mon 2/9

6:00 am-12:26 pm

1 stop7h 26m

$298

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Sat 2/14

7:35 pm-10:07 am

1 stop13h 32m

San Juan Luis Munoz Marin Intl

Sun 2/22

7:00 am-7:20 pm

1 stop13h 20m

$365

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Wed 1/14

10:49 am-11:40 pm

2 stops35h 51m

San Juan Luis Munoz Marin Intl

Sun 1/18

3:58 am-12:26 pm

1 stop9h 28m

$384

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Wed 1/21

10:49 am-7:26 pm

2 stops31h 37m

San Juan Luis Munoz Marin Intl

Sun 1/25

8:05 pm-12:26 pm

1 stop17h 21m

$397

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Tue 1/13

7:08 am-6:22 pm

2 stops10h 14m

San Juan Luis Munoz Marin Intl

Tue 1/27

4:49 pm-11:56 pm

1 stop8h 07m

$405

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Wed 1/21

6:06 am-3:59 pm

1 stop8h 53m

San Juan Luis Munoz Marin Intl

Sun 1/25

6:00 am-7:10 pm

1 stop14h 10m

$405

Key WestNassau

EYW - NAS

EYWNAS

Key West

Wed 2/4

7:08 am-1:22 pm

1 stop6h 14m

Nassau Intl

Thu 2/5

2:22 pm-9:47 pm

1 stop7h 25m

$496

Key WestNassau

EYW - NAS

EYWNAS

Key West

Fri 3/6

11:47 am-7:56 pm

1 stop8h 09m

Nassau Intl

Tue 3/10

3:43 pm-11:56 pm

1 stop8h 13m

$500

Key WestNassau

EYW - NAS

EYWNAS

Key West

Thu 2/5

1:33 pm-5:55 pm

1 stop4h 22m

Nassau Intl

Mon 2/9

2:22 pm-9:47 pm

1 stop7h 25m

$517

Key WestNassau

EYW - NAS

EYWNAS

Key West

Tue 1/13

6:06 am-1:52 pm

1 stop7h 46m

Nassau Intl

Tue 1/20

7:45 am-4:49 pm

1 stop9h 04m

$530

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

Showing 1-10 of 27 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 December 16, 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 December 16, 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
11,048 reviews

Food

6.5

Comfort

7.2

Boarding

7.5

Overall

7.2

Entertainment

6.9

Crew

8.0

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
11,048 reviews
American Airlines
7.2
Good
11,048 reviews

Food

6.5

Comfort

7.2

Boarding

7.5

Overall

7.2

Entertainment

6.9

Crew

8.0

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 32m. 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 - 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 December 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$360Average$526FlexibilityNo cancel feeOn-time71%

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