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$198+ 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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJU
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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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 September 11, 2025.

Round-trip from

$330
(Kiwi.com)

One-way from

$198
(Kiwi.com)

Popular in

January

Cheapest in

April

Average price

$444
From Key West to Caribbean
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One-way flight from Key West to Caribbean
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Highest demand for flights based on searches. 24% potential increase in price ($152 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($39 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/1810:47 amEYW - SJU
1 stop8h 11mMultiple Airlines
Wed 10/224:51 pmSJU - EYW
2 stops51h 04mMultiple Airlines
Deal found 9/11$330
This American Airlines deal was found by Cheapflights users on 9/11. 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 11/74:18 pmEYW - SJU
1 stop6h 40mAmerican Airlines
Wed 11/122:47 pmSJU - EYW
1 stop5h 36mAmerican Airlines
Deal found 9/11$365
This American Airlines deal was found by Cheapflights users on 9/10. 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 12/187:52 pmEYW - SJU
1 stop12h 44mAmerican Airlines
Thu 12/252:31 pmSJU - EYW
1 stop5h 51mAmerican Airlines
Deal found 9/10$405
This American Airlines deal was found by Cheapflights users on 9/9. 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 10/16:17 pmEYW - SJU
2 stops20h 36mAmerican Airlines
Mon 10/67:00 amSJU - EYW
1 stop5h 55mAmerican Airlines
Deal found 9/9$425
This Mytrip deal was found by Cheapflights users on 9/11. 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.
Fri 11/710:10 amEYW - SJU
3 stops29h 13mMultiple Airlines
Wed 11/1210:57 amSJU - EYW
3 stops27h 33mMultiple Airlines
Deal found 9/11$444
This Mytrip deal was found by Cheapflights users on 9/11. 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.
Fri 11/72:25 pmEYW - SJU
2 stops24h 58mSpirit Airlines
Wed 11/1212:10 pmSJU - EYW
3 stops26h 20mSpirit Airlines
Deal found 9/11$457
This American Airlines deal was found by Cheapflights users on 9/9. 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 11/227:58 pmEYW - SJU
1 stop13h 12mAmerican Airlines
Fri 11/282:50 pmSJU - EYW
1 stop5h 33mAmerican Airlines
Deal found 9/9$515
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/128:55 amEYW - NAS
1 stop7h 30mMultiple Airlines
Fri 10/1711:30 amNAS - EYW
2 stops22h 37mMultiple Airlines
Deal found 9/10$573
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 9/118:55 amEYW - NAS
1 stop7h 30mMultiple Airlines
Wed 9/174:00 pmNAS - EYW
2 stops40h 07mMultiple Airlines
Deal found 9/9$683
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Sun 10/1211:22 amEYW - NAS
1 stop6h 25mAmerican Airlines
Fri 10/177:45 amNAS - EYW
1 stop9h 31mAmerican Airlines
Deal found 9/10$710
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Sun 10/2611:22 amEYW - NAS
1 stop6h 25mAmerican Airlines
Sun 11/27:49 amNAS - EYW
1 stop9h 12mAmerican Airlines
Deal found 9/11$725
This American Airlines deal was found by Cheapflights users on 9/9. 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 9/111:59 pmEYW - NAS
1 stop3h 59mAmerican Airlines
Wed 9/1710:26 amNAS - EYW
1 stop8h 33mAmerican Airlines
Deal found 9/9$1,053

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 September 11, 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

Sat 10/18

10:47 am-6:58 pm

1 stop8h 11m

San Juan Luis Munoz Marin Intl

Wed 10/22

4:51 pm-7:55 pm

2 stops51h 04m

$330

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Fri 11/7

4:18 pm-11:58 pm

1 stop6h 40m

San Juan Luis Munoz Marin Intl

Wed 11/12

2:47 pm-7:23 pm

1 stop5h 36m

$365

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Wed 10/1

6:17 pm-2:53 pm

2 stops20h 36m

San Juan Luis Munoz Marin Intl

Mon 10/6

7:00 am-12:55 pm

1 stop5h 55m

$425

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Fri 11/7

10:10 am-4:23 pm

3 stops29h 13m

San Juan Luis Munoz Marin Intl

Wed 11/12

10:57 am-1:30 pm

3 stops27h 33m

$444

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Fri 11/7

2:25 pm-4:23 pm

2 stops24h 58m

San Juan Luis Munoz Marin Intl

Wed 11/12

12:10 pm-1:30 pm

3 stops26h 20m

$457

Key WestNassau

EYW - NAS

EYWNAS

Key West

Sun 10/12

8:55 am-4:25 pm

1 stop7h 30m

Nassau Intl

Fri 10/17

11:30 am-10:07 am

2 stops22h 37m

$573

Key WestNassau

EYW - NAS

EYWNAS

Key West

Sun 10/12

11:22 am-5:47 pm

1 stop6h 25m

Nassau Intl

Fri 10/17

7:45 am-5:16 pm

1 stop9h 31m

$710

Key WestNassau

EYW - NAS

EYWNAS

Key West

Sun 10/26

11:22 am-5:47 pm

1 stop6h 25m

Nassau Intl

Sun 11/2

7:49 am-5:01 pm

1 stop9h 12m

$725

Key WestKingston

EYW - KIN

EYWKIN

Key West

Tue 3/10

6:31 am-10:55 am

1 stop5h 24m

Kingston Norman Manley

Wed 3/11

12:50 pm-6:30 pm

1 stop4h 40m

$733

Key WestRoad Town

EYW - EIS

EYWEIS

Key West

Tue 9/23

3:45 pm-1:06 pm

2 stops21h 21m

Road Town Beef Island

Thu 9/25

1:46 pm-11:49 am

2 stops22h 03m

$1,112

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/8

Showing 1-10 of 13 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

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 September 11, 2025.

When flying from Key West to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 11, 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
10,000 reviews

Food

6.4

Boarding

7.5

Overall

7.2

Entertainment

6.9

Crew

8.0

Comfort

7.2

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
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Food

6.4

Boarding

7.5

Overall

7.2

Entertainment

6.9

Crew

8.0

Comfort

7.2

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 6h 40m. Fly via American Airlines or JetBlue 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 - 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.

  • What is the cheapest month to book a flight from Key West to Caribbean?

    Currently, September is the cheapest month in which you can book a flight from Key West to Caribbean (average of $254). Flying from Key West to Caribbean in June is currently the most expensive (average of $339). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$360Average$526FlexibilityNo cancel feeOn-time71%

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