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$179+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJU
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Round-trip from

$303
(Mytrip)

One-way from

$179
(JetBlue)
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 February 20, 2025.

This Mytrip deal was found by Cheapflights users on 2/20. 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.
Thu 5/84:24 pmEYW - SJU
3 stops32h 47mMultiple Airlines
Tue 5/131:10 amSJU - EYW
2 stops14h 46mMultiple Airlines
Deal found 2/20$303
This American Airlines deal was found by Cheapflights users on 2/20. 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 5/811:28 amEYW - SJU
1 stop5h 08mAmerican Airlines
Wed 5/146:10 amSJU - EYW
1 stop10h 42mAmerican Airlines
Deal found 2/20$335
This Priceline deal was found by Cheapflights users on 2/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/2010:55 amEYW - MHH
1 stop6h 15mSilver Airways
Thu 3/271:40 pmMHH - EYW
1 stop5h 15mSilver Airways
Deal found 2/20$376
This JetBlue deal was found by Cheapflights users on 2/20. 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.
Fri 3/77:40 pmEYW - SJU
1 stop6h 04mJetBlue
Tue 3/111:25 pmSJU - EYW
1 stop5h 30mJetBlue
Deal found 2/20$426
This JetBlue deal was found by Cheapflights users on 2/19. 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.
Thu 5/110:55 amEYW - NAS
1 stop6h 04mJetBlue
Mon 5/510:02 amNAS - EYW
1 stop8h 53mJetBlue
Deal found 2/19$488
This American Airlines deal was found by Cheapflights users on 2/19. 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 5/23:56 pmEYW - NAS
1 stop3h 45mAmerican Airlines
Mon 5/57:45 amNAS - EYW
1 stop3h 05mAmerican Airlines
Deal found 2/19$507
This United Airlines deal was found by Cheapflights users on 2/19. 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 4/154:04 pmEYW - NAS
1 stop22h 55mUnited Airlines
Fri 4/184:01 pmNAS - EYW
1 stop19h 14mUnited Airlines
Deal found 2/19$516
This United Airlines deal was found by Cheapflights users on 2/20. 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.
Fri 3/71:54 pmEYW - SJU
1 stop9h 42mUnited Airlines
Mon 3/101:05 amSJU - EYW
2 stops17h 50mUnited Airlines
Deal found 2/20$549
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Fri 5/210:55 amEYW - NAS
2 stops24h 55mMultiple Airlines
Mon 5/54:00 pmNAS - EYW
1 stop26h 55mMultiple Airlines
Deal found 2/19$620
This CheapOair deal was found by Cheapflights users on 2/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/1510:55 amEYW - NAS
2 stops25h 40mSilver Airways
Fri 4/181:20 pmNAS - EYW
1 stop3h 55mSilver Airways
Deal found 2/19$728
This United Airlines deal was found by Cheapflights users on 2/20. 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.
Sun 4/62:03 pmEYW - EIS
2 stops24h 32mUnited Airlines
Sun 4/138:00 amEIS - EYW
2 stops55h 04mUnited Airlines
Deal found 2/20$1,705

Find flights from Key West to Caribbean within your budget

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 February 20, 2025.

Fly from

Key West

Fly to

Caribbean

Route

Depart

Return

Price

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Thu 5/8

4:24 pm-1:11 am

3 stops32h 47m

San Juan Luis Munoz Marin Intl

Tue 5/13

1:10 am-3:56 pm

2 stops14h 46m

$303

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Thu 5/8

11:28 am-4:36 pm

1 stop5h 08m

San Juan Luis Munoz Marin Intl

Wed 5/14

6:10 am-4:52 pm

1 stop10h 42m

$335

Key WestMarsh Harbour

EYW - MHH

EYWMHH

Key West

Thu 3/20

10:55 am-5:10 pm

1 stop6h 15m

Marsh Harbour

Thu 3/27

1:40 pm-6:55 pm

1 stop5h 15m

$376

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Fri 3/7

7:40 pm-2:44 am

1 stop6h 04m

San Juan Luis Munoz Marin Intl

Tue 3/11

1:25 pm-6:55 pm

1 stop5h 30m

$426

Key WestNassau

EYW - NAS

EYWNAS

Key West

Thu 5/1

10:55 am-4:59 pm

1 stop6h 04m

Nassau Intl

Mon 5/5

10:02 am-6:55 pm

1 stop8h 53m

$488

Key WestNassau

EYW - NAS

EYWNAS

Key West

Fri 5/2

3:56 pm-7:41 pm

1 stop3h 45m

Nassau Intl

Mon 5/5

7:45 am-10:50 am

1 stop3h 05m

$507

Key WestNassau

EYW - NAS

EYWNAS

Key West

Tue 4/15

4:04 pm-2:59 pm

1 stop22h 55m

Nassau Intl

Fri 4/18

4:01 pm-11:15 am

1 stop19h 14m

$516

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Fri 3/7

1:54 pm-12:36 am

1 stop9h 42m

San Juan Luis Munoz Marin Intl

Mon 3/10

1:05 am-6:55 pm

2 stops17h 50m

$549

Key WestNassau

EYW - NAS

EYWNAS

Key West

Fri 5/2

10:55 am-11:50 am

2 stops24h 55m

Nassau Intl

Mon 5/5

4:00 pm-6:55 pm

1 stop26h 55m

$620

Key WestNassau

EYW - NAS

EYWNAS

Key West

Tue 4/15

10:55 am-12:35 pm

2 stops25h 40m

Nassau Intl

Fri 4/18

1:20 pm-5:15 pm

1 stop3h 55m

$728

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 16 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.

Travel insights for flights from Key West to Caribbean

Get recent, data-driven insights about flights from Key West to Caribbean including ideal travel times, pricing trends, and more.

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 February 20, 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 February 20, 2025.
JetBlue
7.4
Good
3,070 reviews

Comfort

7.7

Entertainment

7.3

Food

6.8

Overall

7.4

Crew

8.1

Boarding

7.6

Reviews

1 / 20

4.0
Okay

Anonymous,Feb 2025

BOS - SFO

Flight was delayed an hour due to a flight plan issue. Then additional fuel was needed. The crew did communicate well. Upon departure there was not food available for purchase, at least not by the time they got to row 23. Wifi didn't work consistently. Not the normal Jetblue experience. The Captain and crew were great though.

JetBlue
7.4
Good
3,070 reviews
JetBlue
7.4
Good
3,070 reviews

Comfort

7.7

Entertainment

7.3

Food

6.8

Overall

7.4

Crew

8.1

Boarding

7.6

Reviews

1 / 20

4.0
Okay

Anonymous,Feb 2025

BOS - SFO

Flight was delayed an hour due to a flight plan issue. Then additional fuel was needed. The crew did communicate well. Upon departure there was not food available for purchase, at least not by the time they got to row 23. Wifi didn't work consistently. Not the normal Jetblue experience. The Captain and crew were great though.

United Airlines
7.4
Good
8,765 reviews
JetBlue
7.4
Good
3,070 reviews

Comfort

7.7

Entertainment

7.3

Food

6.8

Overall

7.4

Crew

8.1

Boarding

7.6

Reviews

1 / 20

4.0
Okay

Anonymous,Feb 2025

BOS - SFO

Flight was delayed an hour due to a flight plan issue. Then additional fuel was needed. The crew did communicate well. Upon departure there was not food available for purchase, at least not by the time they got to row 23. Wifi didn't work consistently. Not the normal Jetblue experience. The Captain and crew were great though.

American Airlines
7.2
Good
10,000 reviews
JetBlue
7.4
Good
3,070 reviews

Comfort

7.7

Entertainment

7.3

Food

6.8

Overall

7.4

Crew

8.1

Boarding

7.6

Reviews

1 / 20

4.0
Okay

Anonymous,Feb 2025

BOS - SFO

Flight was delayed an hour due to a flight plan issue. Then additional fuel was needed. The crew did communicate well. Upon departure there was not food available for purchase, at least not by the time they got to row 23. Wifi didn't work consistently. Not the normal Jetblue experience. The Captain and crew were great though.

Silver Airways
6.0
Okay
259 reviews
JetBlue
7.4
Good
3,070 reviews

Comfort

7.7

Entertainment

7.3

Food

6.8

Overall

7.4

Crew

8.1

Boarding

7.6

Reviews

1 / 20

4.0
Okay

Anonymous,Feb 2025

BOS - SFO

Flight was delayed an hour due to a flight plan issue. Then additional fuel was needed. The crew did communicate well. Upon departure there was not food available for purchase, at least not by the time they got to row 23. Wifi didn't work consistently. Not the normal Jetblue experience. The Captain and crew were great though.

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 March is currently the most expensive (average of $363). 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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Alternative routes for Key West to Caribbean

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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$246Average$528FlexibilityNo cancel feeOn-time71%
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