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Caribbean Islands

$198+ Cheap flights from Key West (EYW) to Caribbean Islands

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 11/27. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJU
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheap flight deals from Key West to Caribbean Islands

Keep the following information in mind while searching for Key West to Caribbean Islands flight deals. Data was last updated July 3, 2025.

Round-trip from

$319
(Delta)

One-way from

$198
(Kiwi.com)
From Key West to Caribbean Islands
Search Deals
One-way flight from Key West to Caribbean Islands
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Find flight deals from Key West to Caribbean Islands

Cheapest flights from Key West to Caribbean Islands
Explore the most affordable flight options available from Key West to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2025.

This Delta deal was found by Cheapflights users on 7/1. 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.
Wed 10/111:50 amEYW - SJU
1 stop10h 10mDelta
Mon 10/67:30 amSJU - EYW
1 stop9h 42mDelta
Deal found 7/1$319
This American Airlines deal was found by Cheapflights users on 7/2. 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 stops16h 54mAmerican Airlines
Mon 10/611:56 amSJU - EYW
1 stop7h 26mAmerican Airlines
Deal found 7/2$365
This American Airlines deal was found by Cheapflights users on 7/1. 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 9/2011:25 amEYW - NAS
1 stop22h 20mAmerican Airlines
Mon 9/292:50 pmNAS - EYW
1 stop4h 09mAmerican Airlines
Deal found 7/1$476
This Mytrip deal was found by Cheapflights users on 7/1. 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.
Wed 7/1610:02 amEYW - SJU
2 stops25h 30mMultiple Airlines
Sat 7/192:40 amSJU - EYW
1 stop10h 27mMultiple Airlines
Deal found 7/1$542
This American Airlines deal was found by Cheapflights users on 7/2. 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 12/1112:07 pmEYW - FPO
1 stop4h 18mAmerican Airlines
Sun 12/141:05 pmFPO - EYW
1 stop5h 33mAmerican Airlines
Deal found 7/2$660
This United Airlines deal was found by Cheapflights users on 7/1. 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.
Wed 10/13:11 pmEYW - SJU
2 stops21h 23mUnited Airlines
Mon 10/63:56 pmSJU - EYW
2 stops22h 23mUnited Airlines
Deal found 7/1$731
This American Airlines deal was found by Cheapflights users on 7/2. 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 8/182:31 pmEYW - EIS
2 stops22h 45mAmerican Airlines
Thu 8/211:56 pmEIS - EYW
2 stops22h 36mAmerican Airlines
Deal found 7/2$802

Cheapflights Fare Finder

Customize your flight search to find flights from Key West to Caribbean Islands 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 July 3, 2025.
Use the filters below to find and compare flights from Key West to Caribbean Islands that are best for you.

Fly from

Key West

Fly to

Caribbean Islands

Route

Depart

Return

Price

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Wed 10/1

11:50 am-10:00 pm

1 stop10h 10m

San Juan Luis Munoz Marin Intl

Mon 10/6

7:30 am-5:12 pm

1 stop9h 42m

$319

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Wed 10/1

11:25 am-6:14 pm

1 stop6h 49m

San Juan Luis Munoz Marin Intl

Mon 10/6

11:56 am-5:16 pm

1 stop5h 20m

$365

Key WestNassau

EYW - NAS

EYWNAS

Key West

Sat 9/20

11:25 am-9:45 am

1 stop22h 20m

Nassau Intl

Mon 9/29

2:50 pm-6:59 pm

1 stop4h 09m

$476

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Wed 7/16

10:02 am-11:32 am

2 stops25h 30m

San Juan Luis Munoz Marin Intl

Sat 7/19

2:40 am-1:07 pm

1 stop10h 27m

$542

Key WestFreeport

EYW - FPO

EYWFPO

Key West

Thu 12/11

12:07 pm-4:25 pm

1 stop4h 18m

Freeport Grand Bahama Intl

Sun 12/14

1:05 pm-6:38 pm

1 stop5h 33m

$660

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Wed 10/1

3:11 pm-12:34 pm

2 stops21h 23m

San Juan Luis Munoz Marin Intl

Mon 10/6

3:56 pm-2:19 pm

2 stops22h 23m

$731

Key WestRoad Town

EYW - EIS

EYWEIS

Key West

Mon 8/18

2:31 pm-1:16 pm

2 stops22h 45m

Road Town Beef Island

Thu 8/21

1:56 pm-12:32 pm

2 stops22h 36m

$802

Key WestNassau

EYW - NAS

EYWNAS

Key West

Thu 11/27

8:55 am-4:25 pm

1 stop7h 30m

$198

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Wed 12/10

3:55 pm-9:05 pm

1 stop4h 10m

$448

Key WestNassau

EYW - NAS

EYWNAS

Key West

Thu 11/27

4:00 pm-1:48 pm

2 stops21h 48m

$1,791

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Best time to book a flight from Key West to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Islands

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

Find hourly flight availability from Key West to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 3, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Key West to Caribbean Islands as you normally would.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated July 3, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American Airlines from Key West to Caribbean Islands by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,982 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Food

7.3

Overall

8.0

Comfort

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Delta
8.0
Very good
7,982 reviews
Delta
8.0
Very good
7,982 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Food

7.3

Overall

8.0

Comfort

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
United Airlines
7.4
Good
8,861 reviews
Delta
8.0
Very good
7,982 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Food

7.3

Overall

8.0

Comfort

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,982 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Food

7.3

Overall

8.0

Comfort

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.

Related info for your journey

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

    For a flight from Key West to Caribbean Islands, you will be flying from Key West. Key West (EYW) is just 2.6 mi from the center of the city.

  • What are the most popular routes from Key West to Caribbean Islands?

    While some choose either Key West - Nassau Intl or Key West - Freeport Grand Bahama Intl, Key West - San Juan Luis Munoz Marin Intl is the most popular route from Key West to Caribbean Islands.

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

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

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

    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 Islands.

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

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

    Currently, September is the cheapest month in which you can book a flight from Key West to Caribbean Islands (average of $254). Flying from Key West to Caribbean Islands 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 Islands

Discover the top airline that operate flights from Key West to Caribbean Islands. 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$246Average$488FlexibilityNo cancel feeOn-time71%

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