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$154+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJU
May 4 — May 111
Sun 5/4
Sun 5/11
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 April 29, 2025.

Round-trip from

$439
(JetBlue)

One-way from

$154
(Delta)
From Key West to Caribbean
Search Deals
One-way flight from Key West to Caribbean
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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 April 29, 2025.

This American Airlines deal was found by Cheapflights users on 4/28. 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.
Thu 5/87:29 pmEYW - NAS
2 stops14h 01mAmerican Airlines
Mon 5/1212:10 pmNAS - EYW
1 stop4h 42mAmerican Airlines
Deal found 4/28$428
This JetBlue deal was found by Cheapflights users on 4/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/128:45 amEYW - SJU
1 stop5h 05mJetBlue
Sun 5/187:10 amSJU - EYW
1 stop6h 50mJetBlue
Deal found 4/29$439
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/125:24 pmEYW - SJU
1 stop17h 46mAmerican Airlines
Sun 5/186:10 amSJU - EYW
2 stops10h 30mAmerican Airlines
Deal found 4/29$525
This Mytrip deal was found by Cheapflights users on 4/29. 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.
Fri 6/2710:12 amEYW - NAS
2 stops33h 03mMultiple Airlines
Sun 6/294:25 pmNAS - EYW
1 stop20h 52mMultiple Airlines
Deal found 4/29$636
This United Airlines deal was found by Cheapflights users on 4/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/128:45 amEYW - SJU
2 stops30h 55mUnited Airlines
Sat 5/171:05 amSJU - EYW
2 stops17h 00mUnited Airlines
Deal found 4/29$643

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 April 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

Mon 5/12

8:45 am-1:50 pm

1 stop5h 05m

San Juan Luis Munoz Marin Intl

Sun 5/18

7:10 am-2:00 pm

1 stop6h 50m

$439

Key WestNassau

EYW - NAS

EYWNAS

Key West

Wed 6/11

1:24 pm-9:26 pm

1 stop8h 02m

Nassau Intl

Wed 6/18

1:10 pm-7:02 pm

1 stop5h 52m

$486

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Mon 5/12

5:24 pm-11:10 am

1 stop17h 46m

San Juan Luis Munoz Marin Intl

Sun 5/18

6:10 am-4:40 pm

2 stops10h 30m

$525

Key WestNassau

EYW - NAS

EYWNAS

Key West

Fri 6/27

10:12 am-7:15 pm

2 stops33h 03m

Nassau Intl

Sun 6/29

4:25 pm-1:17 pm

1 stop20h 52m

$636

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Mon 5/12

8:45 am-3:40 pm

2 stops30h 55m

San Juan Luis Munoz Marin Intl

Sat 5/17

1:05 am-6:05 pm

2 stops17h 00m

$643

Key WestNassau

EYW - NAS

EYWNAS

Key West

Mon 9/15

7:00 am-11:54 am

1 stop4h 54m

$154

Key WestNassau

EYW - NAS

EYWNAS

Key West

Fri 9/12

8:47 am-4:25 pm

1 stop7h 38m

$178

Key WestNassau

EYW - NAS

EYWNAS

Key West

Sat 9/13

8:45 am-5:01 pm

1 stop8h 16m

$199

Key WestNassau

EYW - NAS

EYWNAS

Key West

Sat 7/5

7:51 pm-5:40 pm

1 stop21h 49m

$215

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Fri 8/8

1:29 pm-12:05 am

1 stop10h 36m

$223

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 12 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 April 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.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 April 29, 2025.
Delta
8.0
Very good
7,929 reviews

Food

7.3

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Delta
8.0
Very good
7,929 reviews
Delta
8.0
Very good
7,929 reviews

Food

7.3

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
United Airlines
7.4
Good
8,696 reviews
Delta
8.0
Very good
7,929 reviews

Food

7.3

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
JetBlue
7.3
Good
2,922 reviews
Delta
8.0
Very good
7,929 reviews

Food

7.3

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,929 reviews

Food

7.3

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

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 cheapest airlines to fly from Key West to Caribbean one-way?

    One-way options have recently been found by users for as low as $154 on Delta. Other airlines that offer cheap prices include JetBlue from $199 and American Airlines from $215 one-way.

  • 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 December is currently the most expensive (average of $336). 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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See prices for flight routes from nearby airports that may be better suited for you.
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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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$246Average$557FlexibilityNo cancel feeOn-time71%

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