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$390+ Cheap flights from Caribbean to Key West (EYW)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — EYW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Caribbean to Key West

Keep the following information in mind while searching for Caribbean to Key West flight deals. Data was last updated September 11, 2025.

Round-trip from

$390
(American Airlines)
From Caribbean to Key West
Search Deals

Find flight deals from Caribbean to Key West

Cheapest flights from Caribbean to Key West
Explore the most affordable flight options available from Caribbean to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

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.
Sat 11/17:10 amSJU - EYW
1 stop14h 46mAmerican Airlines
Sat 11/87:53 pmEYW - SJU
1 stop15h 12mAmerican Airlines
Deal found 9/11$390
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.
Tue 12/3010:03 pmSJU - EYW
1 stop19h 41mAmerican Airlines
Fri 1/24:03 pmEYW - SJU
1 stop6h 36mAmerican Airlines
Deal found 9/10$733
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/14:50 pmSJU - EYW
3 stops46h 14mUnited Airlines
Sat 11/84:00 pmEYW - SJU
1 stop28h 00mUnited Airlines
Deal found 9/11$883
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.
Mon 9/157:05 pmSJU - EYW
2 stops16h 08mAmerican Airlines
Wed 9/176:17 pmEYW - SJU
2 stops16h 54mAmerican Airlines
Deal found 9/11$991
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/308:30 amSJU - EYW
2 stops30h 43mUnited Airlines
Fri 1/212:22 pmEYW - SJU
2 stops33h 00mUnited Airlines
Deal found 9/10$1,159
This United 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/311:05 amSJU - EYW
1 stop12h 59mMultiple Airlines
Sat 11/83:00 pmEYW - SJU
2 stops43h 07mMultiple Airlines
Deal found 9/11$1,768

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean to Key West 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 Caribbean to Key West that are best for you.

Fly from

Caribbean

Fly to

Key West

Route

Depart

Return

Price

San JuanKey West

SJU - EYW

SJUEYW

San Juan Luis Munoz Marin Intl

Sat 11/1

7:10 am-9:56 pm

1 stop14h 46m

Key West

Sat 11/8

7:53 pm-12:05 pm

1 stop15h 12m

$390

San JuanKey West

SJU - EYW

SJUEYW

San Juan Luis Munoz Marin Intl

Sat 11/1

4:50 pm-3:04 pm

3 stops46h 14m

Key West

Sat 11/8

4:00 pm-9:00 pm

1 stop28h 00m

$883

San JuanKey West

SJU - EYW

SJUEYW

San Juan Luis Munoz Marin Intl

Mon 9/15

7:05 pm-11:13 am

2 stops16h 08m

Key West

Wed 9/17

11:25 am-6:14 pm

1 stop6h 49m

$991

San JuanKey West

SJU - EYW

SJUEYW

San Juan Luis Munoz Marin Intl

Fri 10/31

1:05 am-2:04 pm

1 stop12h 59m

Key West

Sat 11/8

3:00 pm-11:07 am

2 stops43h 07m

$1,768

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Best time to book a flight from Caribbean to Key West

Have a flexible travel schedule? Discover the best time to fly to Key West from Caribbean 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 Caribbean to Key West

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

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

Related info for your journey

Find useful and relevant information for your journey from Caribbean to Key West. 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 into for flights to Key West from Caribbean?

    Most people fly into Key West (EYW) if they book a flight to Key West from Caribbean. Key West is conveniently located just 2.6 mi from Key West’s city center.

  • How long is the flight from Caribbean to Key West?

    Departing from Caribbean to Key West will take you 14h 46m. Caribbean and Key West are separated by a distance of 1096 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • Can I find deals for flights from Caribbean to Key West that include hotel bookings?

    Yes. In addition to deals on Caribbean to Key West flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Caribbean to Key West?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Caribbean to Key West.

  • Can I find deals for business class flights from Caribbean to Key West?

    Yes. Cheapflights offers flight deals from Caribbean to Key West 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 Caribbean to Key West?

    Currently, August is the cheapest month in which you can book a flight from Caribbean to Key West (average of $328). Flying from Caribbean to Key West in March is currently the most expensive (average of $491). 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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