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$365+ Cheap flights from Key West (EYW) to Caribbean

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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJU
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 July 29, 2025.

Round-trip from

$365
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$448
From Key West to Caribbean
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($29 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 29, 2025.

This American Airlines deal was found by Cheapflights users on 7/27. 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.
Wed 10/11:59 pmEYW - SJU
1 stop4h 15mAmerican Airlines
Mon 10/61:35 pmSJU - EYW
1 stop5h 47mAmerican Airlines
Deal found 7/27$365
This American Airlines deal was found by Cheapflights users on 7/27. 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.
Wed 9/1011:25 amEYW - NAS
1 stop6h 30mAmerican Airlines
Wed 9/1710:26 amNAS - EYW
1 stop3h 03mAmerican Airlines
Deal found 7/27$471
This Mytrip deal was found by Cheapflights users on 7/29. 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.
Wed 8/1310:02 amEYW - SJU
3 stops30h 40mMultiple Airlines
Sat 8/162:11 amSJU - EYW
1 stop10h 56mMultiple Airlines
Deal found 7/29$559
This American Airlines deal was found by Cheapflights users on 7/28. 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 9/126:17 pmEYW - EIS
2 stops42h 49mAmerican Airlines
Fri 9/191:46 pmEIS - EYW
2 stops21h 27mAmerican Airlines
Deal found 7/28$898
This Mytrip deal was found by Cheapflights users on 7/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/110:02 amEYW - NAS
1 stop10h 58mMultiple Airlines
Mon 8/44:00 pmNAS - EYW
2 stops17h 22mMultiple Airlines
Deal found 7/27$933

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 July 29, 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

Wed 10/1

1:59 pm-6:14 pm

1 stop4h 15m

San Juan Luis Munoz Marin Intl

Mon 10/6

1:35 pm-7:22 pm

1 stop5h 47m

$365

Key WestNassau

EYW - NAS

EYWNAS

Key West

Wed 9/10

11:25 am-5:55 pm

1 stop6h 30m

Nassau Intl

Wed 9/17

10:26 am-1:29 pm

1 stop3h 03m

$471

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Wed 8/13

10:02 am-4:42 pm

3 stops30h 40m

San Juan Luis Munoz Marin Intl

Sat 8/16

2:11 am-1:07 pm

1 stop10h 56m

$559

Key WestRoad Town

EYW - EIS

EYWEIS

Key West

Fri 9/12

6:17 pm-1:06 pm

2 stops42h 49m

Road Town Beef Island

Fri 9/19

1:46 pm-11:13 am

2 stops21h 27m

$898

Key WestNassau

EYW - NAS

EYWNAS

Key West

Fri 8/1

10:02 am-9:00 pm

1 stop10h 58m

Nassau Intl

Mon 8/4

4:00 pm-9:22 am

2 stops17h 22m

$933

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

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 July 29, 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 July 29, 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

Comfort

7.2

Boarding

7.5

Crew

8.0

Entertainment

6.9

Food

6.5

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Bama,Oct 2024

MIA - PNS

I paid for first class and it was nothing more than a 36" long curtain between first and business class, nothing extra, nothing fancy and a waste of money. Would have been better off just getting a regular seat and saving the money. Also had one of my eardrums rupture because of the take off and had to sit in uncomfortable pain with a bleeding ear the entire flight. Had to go to the doctor and it's been 5 days and still having difficulty hearing like it just happened.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Boarding

7.5

Crew

8.0

Entertainment

6.9

Food

6.5

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Bama,Oct 2024

MIA - PNS

I paid for first class and it was nothing more than a 36" long curtain between first and business class, nothing extra, nothing fancy and a waste of money. Would have been better off just getting a regular seat and saving the money. Also had one of my eardrums rupture because of the take off and had to sit in uncomfortable pain with a bleeding ear the entire flight. Had to go to the doctor and it's been 5 days and still having difficulty hearing like it just happened.

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.

  • 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 - Nassau Intl, Key West - San Juan Luis Munoz Marin 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.

  • 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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$304Average$491FlexibilityNo cancel feeOn-time71%

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