$125+ 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 8/28. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJU
Aug 31 — Sep 71
Round-trip
1 adult, Economy
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Find cheap flights from Key West to Caribbean with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Key West to CaribbeanExplore 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 August 1, 2026.
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 August 1, 2026.
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1110:04 am
EYW
- SJU
1 stop13h 53m
Multiple Airlines
Sun 11/157:05 am
SJU
- EYW
1 stop26h 25m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$285
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1312:05 pm
EYW
- SJU
1 stop7h 27m
Multiple Airlines
Sun 8/163:10 am
SJU
- EYW
1 stop8h 17m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$364
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:53 pm
EYW
- NAS
1 stop13h 02m
Breeze Airways
Mon 8/319:55 am
NAS
- EYW
1 stop26h 39m
Breeze Airways
Deal found 7/29![Breeze Airways logo]()
$379
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/301:43 pm
EYW
- SJU
1 stop8h 39m
American Airlines
Sun 11/18:25 am
SJU
- EYW
1 stop8h 49m
American Airlines
Deal found 7/29![American Airlines logo]()
$466
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.
Tue 9/153:30 pm
EYW
- SJU
2 stops19h 30m
American Airlines
Tue 9/296:00 am
SJU
- EYW
1 stop13h 17m
American Airlines
Deal found 7/28![American Airlines logo]()
$486
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:09 pm
EYW
- NAS
1 stop15h 46m
Multiple Airlines
Mon 8/314:00 pm
NAS
- EYW
2 stops20h 34m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$493
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.
Wed 9/21:49 pm
EYW
- SJU
1 stop8h 06m
American Airlines
Sun 9/67:24 pm
SJU
- EYW
2 stops17h 31m
American Airlines
Deal found 7/28![American Airlines logo]()
$511
This American Airlines deal was found by Cheapflights users on 7/31. 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 8/2110:15 am
EYW
- SJU
1 stop5h 56m
American Airlines
Fri 8/287:22 pm
SJU
- EYW
1 stop14h 22m
American Airlines
Deal found 7/31![American Airlines logo]()
$526
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Sun 9/1312:01 pm
EYW
- NAS
1 stop20h 29m
Breeze Airways
Sun 9/2010:20 am
NAS
- EYW
1 stop25h 59m
Breeze Airways
Deal found 7/30![Breeze Airways logo]()
$535
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Sun 9/1312:01 pm
EYW
- NAS
1 stop20h 29m
Multiple Airlines
Sun 9/204:00 pm
NAS
- EYW
2 stops20h 19m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$585
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.
Wed 8/2611:30 am
EYW
- KIN
1 stop5h 56m
American Airlines
Wed 9/22:00 pm
KIN
- EYW
1 stop4h 39m
American Airlines
Deal found 7/28![American Airlines logo]()
$739
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.
Sat 8/17:55 pm
EYW
- SJU
1 stop13h 50m
American Airlines
Mon 8/36:00 am
SJU
- EYW
2 stops10h 11m
American Airlines
Deal found 7/28![American Airlines logo]()
$776
Best flights from Key West to CaribbeanDiscover carefully curated flight deals from Key West to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 1, 2026.
Discover carefully curated flight deals from Key West to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 1, 2026.
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1110:04 am
EYW
- SJU
1 stop13h 53m
Multiple Airlines
Sun 11/157:05 am
SJU
- EYW
1 stop26h 25m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$285
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.
Wed 9/28:09 pm
EYW
- SJU
1 stop13h 34m
American Airlines
Sun 9/61:38 pm
SJU
- EYW
1 stop6h 01m
American Airlines
Deal found 7/28![American Airlines logo]()
$511
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Sun 9/1312:01 pm
EYW
- NAS
1 stop20h 29m
Breeze Airways
Sun 9/2010:20 am
NAS
- EYW
1 stop25h 59m
Breeze Airways
Deal found 7/30![Breeze Airways logo]()
$535
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1312:05 pm
EYW
- SJU
1 stop7h 27m
Multiple Airlines
Sun 8/163:10 am
SJU
- EYW
1 stop8h 17m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$364
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/304:10 pm
EYW
- SJU
2 stops31h 26m
United Airlines
Sun 11/14:55 pm
SJU
- EYW
2 stops21h 57m
United Airlines
Deal found 7/29![United Airlines logo]()
$832
This American Airlines deal was found by Cheapflights users on 7/31. 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 8/2110:15 am
EYW
- SJU
1 stop5h 56m
American Airlines
Fri 8/287:22 pm
SJU
- EYW
1 stop14h 22m
American Airlines
Deal found 7/31![American Airlines logo]()
$526
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:09 pm
EYW
- NAS
1 stop15h 46m
Multiple Airlines
Mon 8/314:00 pm
NAS
- EYW
2 stops20h 34m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$493
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.
Wed 8/2611:30 am
EYW
- KIN
1 stop5h 56m
American Airlines
Wed 9/22:00 pm
KIN
- EYW
1 stop4h 39m
American Airlines
Deal found 7/28![American Airlines logo]()
$739
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/172:20 pm
EYW
- SJU
1 stop9h 30m
United Airlines
Sat 9/191:00 am
SJU
- EYW
1 stop12h 29m
United Airlines
Deal found 7/29![United Airlines logo]()
$895
This American Airlines deal was found by Cheapflights users on 7/30. 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 8/37:40 pm
EYW
- NAS
1 stop13h 47m
American Airlines
Thu 8/67:45 am
NAS
- EYW
1 stop25h 59m
American Airlines
Deal found 7/30![American Airlines logo]()
$806
This WestJet 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:15 pm
EYW
- KIN
2 stops45h 15m
WestJet
Wed 9/23:30 pm
KIN
- EYW
2 stops27h 27m
WestJet
Deal found 7/28![WestJet logo]()
$2,127
This American Airlines deal was found by Cheapflights users on 7/31. 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 8/1911:30 am
EYW
- EIS
1 stop4h 55m
American Airlines
Sun 8/2312:36 pm
EIS
- EYW
1 stop7h 03m
American Airlines
Deal found 7/31![American Airlines logo]()
$1,017
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/22:15 pm
EYW
- KIN
2 stops24h 36m
United Airlines
Sat 9/52:57 pm
KIN
- EYW
2 stops21h 32m
United Airlines
Deal found 7/27![United Airlines logo]()
$1,340
Last-minute flights from Key West to CaribbeanDiscover last-minute flight deals from Key West to Caribbean. Data last updated August 1, 2026 and is based on user searches.
Discover last-minute flight deals from Key West to Caribbean. Data last updated August 1, 2026 and is based on user searches.
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.
Thu 7/3011:28 am
EYW
- KIN
1 stop9h 44m
American Airlines
Fri 8/142:00 pm
KIN
- EYW
1 stop4h 39m
American Airlines
Deal found 7/27![American Airlines logo]()
$904
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.
Thu 7/301:47 pm
EYW
- KIN
1 stop7h 25m
American Airlines
Thu 8/132:00 pm
KIN
- EYW
1 stop4h 39m
American Airlines
Deal found 7/27![American Airlines logo]()
$1,024
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.
Thu 7/301:47 pm
EYW
- KIN
1 stop7h 25m
American Airlines
Sat 8/156:05 am
KIN
- EYW
1 stop11h 35m
American Airlines
Deal found 7/27![American Airlines logo]()
$1,034
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/307:50 am
EYW
- KIN
1 stop13h 14m
Delta
Sat 8/159:13 am
KIN
- EYW
1 stop9h 44m
Delta
Deal found 7/28![Delta logo]()
$1,107
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.
Sat 8/17:55 pm
EYW
- SJU
1 stop13h 50m
American Airlines
Mon 8/36:00 am
SJU
- EYW
2 stops10h 11m
American Airlines
Deal found 7/28![American Airlines logo]()
$776
This American Airlines deal was found by Cheapflights users on 7/30. 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 8/37:40 pm
EYW
- NAS
1 stop13h 47m
American Airlines
Thu 8/67:45 am
NAS
- EYW
1 stop25h 59m
American Airlines
Deal found 7/30![American Airlines logo]()
$806
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1312:05 pm
EYW
- SJU
1 stop7h 27m
Multiple Airlines
Sun 8/163:10 am
SJU
- EYW
1 stop8h 17m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$364
This American Airlines deal was found by Cheapflights users on 7/31. 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 8/1911:30 am
EYW
- EIS
1 stop4h 55m
American Airlines
Sun 8/2312:36 pm
EIS
- EYW
1 stop7h 03m
American Airlines
Deal found 7/31![American Airlines logo]()
$1,017
This American Airlines deal was found by Cheapflights users on 7/31. 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 8/2111:30 am
EYW
- SJU
1 stop4h 41m
American Airlines
Fri 8/286:00 am
SJU
- EYW
2 stops10h 18m
American Airlines
Deal found 7/31![American Airlines logo]()
$526
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.
Wed 8/2611:30 am
EYW
- KIN
1 stop5h 56m
American Airlines
Wed 9/22:00 pm
KIN
- EYW
1 stop4h 39m
American Airlines
Deal found 7/28![American Airlines logo]()
$739
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:53 pm
EYW
- NAS
1 stop13h 02m
Breeze Airways
Mon 8/319:55 am
NAS
- EYW
1 stop26h 39m
Breeze Airways
Deal found 7/29![Breeze Airways logo]()
$379
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:09 pm
EYW
- NAS
1 stop15h 46m
Multiple Airlines
Mon 8/314:00 pm
NAS
- EYW
2 stops20h 34m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$493
One-way flights from Key West to CaribbeanSearch for one-way flight options from Key West to Caribbean. Find affordable one-way fares based on user searches. Data last updated August 1, 2026.
Search for one-way flight options from Key West to Caribbean. Find affordable one-way fares based on user searches. Data last updated August 1, 2026.
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2810:59 am
EYW
- SJU
1 stop13h 57m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$125
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/293:52 pm
EYW
- SJU
1 stop9h 04m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$129
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.
Sun 10/188:03 pm
EYW
- MHH
1 stop15h 04m
American Airlines
Deal found 7/28![American Airlines logo]()
$282
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1810:59 am
EYW
- MHH
2 stops20h 51m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$358
This Delta deal was found by Cheapflights users on 7/30. 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.
Mon 8/37:40 am
EYW
- MHH
1 stop5h 28m
Delta
Deal found 7/30![Delta logo]()
$360
This American Airlines deal was found by Cheapflights users on 7/30. 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 8/34:41 pm
EYW
- NAS
2 stops16h 46m
American Airlines
Deal found 7/30![American Airlines logo]()
$417
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Mon 8/31:11 pm
EYW
- NAS
3 stops30h 19m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$446
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Mon 8/31:11 pm
EYW
- MHH
3 stops42h 39m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$598
Find 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 August 1, 2026.
Round-trip from | $285 (Kiwi.com) |
|---|---|
One-way from | $125 (Kiwi.com) |
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 August 1, 2026.
Use the filters below to find and compare flights from Key West to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Key WestSan Juan
EYW - SJU
EYWSJU
Key West
Wed 11/11
10:04 am-12:57 am
1 stop13h 53m
San Juan Luis Munoz Marin Intl
Sun 11/15
7:05 am-8:30 am
1 stop26h 25m
$285
Key WestSan Juan
EYW - SJU
EYWSJU
Key West
Thu 8/13
12:05 pm-7:32 pm
1 stop7h 27m
San Juan Luis Munoz Marin Intl
Sun 8/16
3:10 am-11:27 am
1 stop8h 17m
$364
Key WestNassau
EYW - NAS
EYWNAS
Key West
Thu 8/27
5:09 pm-8:55 am
1 stop15h 46m
Nassau Intl
Mon 8/31
4:00 pm-12:34 pm
2 stops20h 34m
$493
Key WestSan Juan
EYW - SJU
EYWSJU
Key West
Wed 9/2
8:09 pm-9:43 am
1 stop13h 34m
San Juan Luis Munoz Marin Intl
Sun 9/6
1:38 pm-7:39 pm
1 stop6h 01m
$511
Key WestSan Juan
EYW - SJU
EYWSJU
Key West
Fri 8/21
10:15 am-4:11 pm
1 stop5h 56m
San Juan Luis Munoz Marin Intl
Fri 8/28
7:22 pm-9:44 am
1 stop14h 22m
$526
Key WestNassau
EYW - NAS
EYWNAS
Key West
Sun 9/13
12:01 pm-8:30 am
1 stop20h 29m
Nassau Intl
Sun 9/20
10:20 am-12:19 pm
1 stop25h 59m
$535
Quickest round-trip
Key WestKingston
EYW - KIN
EYWKIN
Key West
Wed 8/26
11:30 am-4:26 pm
1 stop5h 56m
Kingston Norman Manley
Wed 9/2
2:00 pm-7:39 pm
1 stop4h 39m
$739
Key WestNassau
EYW - NAS
EYWNAS
Key West
Mon 8/3
7:40 pm-9:27 am
1 stop13h 47m
Nassau Intl
Thu 8/6
7:45 am-9:44 am
1 stop25h 59m
$806
Key WestSan Juan
EYW - SJU
EYWSJU
Key West
Fri 10/30
4:10 pm-11:36 pm
2 stops31h 26m
San Juan Luis Munoz Marin Intl
Sun 11/1
4:55 pm-1:52 pm
2 stops21h 57m
$832
Key WestSan Juan
EYW - SJU
EYWSJU
Key West
Thu 9/17
2:20 pm-11:50 pm
1 stop9h 30m
San Juan Luis Munoz Marin Intl
Sat 9/19
1:00 am-1:29 pm
1 stop12h 29m
$895
Showing 1-10 of 21 resultsSorted by cheapest first
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.
EYW-SJU
EYW-NAS
EYW-KIN
EYW-MHH
EYW-EIS
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
EYW-0CB
EYW-SJU
EYW-NAS
EYW-KIN
EYW-MHH
No data available for this route at this time. Please check back soon.
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 August 1, 2026.
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.
Crew
7.9
Comfort
7.2
Overall
7.1
Boarding
7.5
Entertainment
6.8
Food
6.4
Reviews
1 / 20
8.0
ExcellentOlwin,Jul 2026
MCO - DCA
Crew
7.9
Comfort
7.2
Overall
7.1
Boarding
7.5
Entertainment
6.8
Food
6.4
Reviews
1 / 20
8.0
ExcellentOlwin,Jul 2026
MCO - DCA
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.
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Alternative routes for Key West to Caribbean
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Complete your trip
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Key West and Caribbean flights
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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 August 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$415 | Average$570 | FlexibilityNo cancel fee | On-time71% |