$171+ 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 7/5. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJU
Apr 5 — Apr 121
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Key West to Caribbean
Cheapest
Best
Last-minute
One-way
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 March 6, 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 March 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/4. 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 3/239:49 am
EYW
- SJU
1 stop25h 21m
Multiple Airlines
Fri 3/278:47 pm
SJU
- EYW
1 stop17h 56m
Multiple Airlines
Deal found 3/4![Multiple Airlines logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 4/812:25 pm
EYW
- SJU
1 stop6h 30m
Multiple Airlines
Thu 4/91:45 am
SJU
- EYW
1 stop10h 41m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 3/239:49 am
EYW
- SJU
1 stop25h 21m
Multiple Airlines
Thu 3/267:54 pm
SJU
- EYW
1 stop17h 43m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$343
This Mytrip deal was found by Cheapflights users on 3/3. 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 4/812:25 pm
EYW
- SJU
1 stop6h 30m
Spirit Airlines
Thu 4/91:45 am
SJU
- EYW
2 stops11h 52m
Spirit Airlines
Deal found 3/3![Spirit Airlines logo]()
$350
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1311:04 am
EYW
- SJU
2 stops13h 43m
Multiple Airlines
Wed 8/1910:50 am
SJU
- EYW
1 stop24h 35m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$367
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 8/67:53 pm
EYW
- SJU
1 stop17h 37m
Multiple Airlines
Wed 8/126:10 am
SJU
- EYW
1 stop28h 14m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$401
This Kiwi.com deal was found by Cheapflights users on 3/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/171:01 pm
EYW
- SJU
1 stop22h 09m
Multiple Airlines
Sat 3/217:54 pm
SJU
- EYW
2 stops19h 48m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$402
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 4/171:06 pm
EYW
- NAS
1 stop27h 19m
Multiple Airlines
Fri 4/247:15 am
NAS
- EYW
1 stop6h 20m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$494
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 4/1912:26 pm
EYW
- NAS
1 stop6h 49m
Multiple Airlines
Sun 4/2612:00 pm
NAS
- EYW
1 stop24h 26m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$496
This American Airlines deal was found by Cheapflights users on 3/2. 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.
Fri 4/246:45 am
EYW
- NAS
1 stop9h 49m
American Airlines
Wed 4/298:18 am
NAS
- EYW
1 stop8h 12m
American Airlines
Deal found 3/2![American Airlines logo]()
$521
This American Airlines deal was found by Cheapflights users on 3/1. 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.
Wed 3/253:56 pm
EYW
- MHH
1 stop23h 34m
American Airlines
Wed 4/11:04 pm
MHH
- EYW
1 stop6h 08m
American Airlines
Deal found 3/1![American Airlines logo]()
$531
This Kiwi.com deal was found by Cheapflights users on 3/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3112:25 pm
EYW
- KIN
1 stop24h 10m
Spirit Airlines
Tue 4/712:32 pm
KIN
- EYW
1 stop21h 58m
Spirit Airlines
Deal found 3/1![Spirit Airlines logo]()
$533
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 March 6, 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 March 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/171:01 pm
EYW
- SJU
1 stop22h 09m
Multiple Airlines
Sat 3/217:54 pm
SJU
- EYW
2 stops19h 48m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$402
This American Airlines deal was found by Cheapflights users on 3/2. 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 8/137:09 pm
EYW
- SJU
1 stop4h 31m
American Airlines
Wed 8/191:35 pm
SJU
- EYW
1 stop5h 04m
American Airlines
Deal found 3/2![American Airlines logo]()
$406
This Mytrip deal was found by Cheapflights users on 3/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/112:25 pm
EYW
- SJU
3 stops35h 33m
Spirit Airlines
Wed 4/87:54 pm
SJU
- EYW
1 stop15h 36m
Spirit Airlines
Deal found 3/2![Spirit Airlines logo]()
$458
This United Airlines deal was found by Cheapflights users on 3/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/94:47 pm
EYW
- NAS
1 stop21h 00m
United Airlines
Wed 5/133:59 pm
NAS
- EYW
1 stop23h 08m
United Airlines
Deal found 3/2![United Airlines logo]()
$750
This Kiwi.com deal was found by Cheapflights users on 3/5. 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.
Tue 3/171:01 pm
EYW
- SJU
1 stop22h 09m
Multiple Airlines
Fri 3/209:12 pm
SJU
- EYW
2 stops37h 09m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$445
This Mytrip deal was found by Cheapflights users on 3/5. 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.
Mon 3/232:35 pm
EYW
- SJU
3 stops24h 44m
Spirit Airlines
Thu 3/268:47 pm
SJU
- EYW
2 stops16h 50m
Spirit Airlines
Deal found 3/5![Spirit Airlines logo]()
$485
This American Airlines deal was found by Cheapflights users on 3/2. 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 4/17:42 pm
EYW
- SJU
1 stop13h 18m
American Airlines
Wed 4/87:25 am
SJU
- EYW
1 stop15h 11m
American Airlines
Deal found 3/2![American Airlines logo]()
$496
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 3/194:22 pm
EYW
- SJU
1 stop17h 48m
Multiple Airlines
Mon 3/237:54 pm
SJU
- EYW
2 stops16h 27m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$464
This American Airlines deal was found by Cheapflights users on 3/1. 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.
Wed 3/253:56 pm
EYW
- MHH
1 stop23h 34m
American Airlines
Wed 4/11:04 pm
MHH
- EYW
1 stop6h 08m
American Airlines
Deal found 3/1![American Airlines logo]()
$531
This Kiwi.com deal was found by Cheapflights users on 3/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3112:25 pm
EYW
- KIN
1 stop24h 10m
Spirit Airlines
Tue 4/712:32 pm
KIN
- EYW
1 stop21h 58m
Spirit Airlines
Deal found 3/1![Spirit Airlines logo]()
$533
This American Airlines deal was found by Cheapflights users on 3/5. 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 4/82:29 pm
EYW
- SJU
1 stop14h 03m
American Airlines
Fri 4/105:45 am
SJU
- EYW
1 stop10h 45m
American Airlines
Deal found 3/5![American Airlines logo]()
$531
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 4/1912:26 pm
EYW
- NAS
1 stop6h 49m
Multiple Airlines
Sun 4/267:15 am
NAS
- EYW
2 stops25h 54m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$540
This Mytrip deal was found by Cheapflights users on 3/1. 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.
Tue 3/1712:25 pm
EYW
- SJU
2 stops21h 45m
Spirit Airlines
Thu 3/191:39 am
SJU
- EYW
2 stops11h 58m
Spirit Airlines
Deal found 3/1![Spirit Airlines logo]()
$600
This American Airlines deal was found by Cheapflights users on 3/1. 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.
Thu 7/91:34 pm
EYW
- NAS
1 stop3h 58m
American Airlines
Mon 7/132:34 pm
NAS
- EYW
1 stop4h 47m
American Airlines
Deal found 3/1![American Airlines logo]()
$546
This Kiwi.com deal was found by Cheapflights users on 3/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/311:01 pm
EYW
- KIN
2 stops23h 34m
Multiple Airlines
Tue 4/712:32 pm
KIN
- EYW
1 stop21h 58m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$547
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 4/172:30 pm
EYW
- NAS
1 stop4h 45m
Multiple Airlines
Fri 4/244:50 pm
NAS
- EYW
2 stops41h 31m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$561
This American Airlines deal was found by Cheapflights users on 3/5. 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 5/1511:24 am
EYW
- FPO
1 stop24h 37m
American Airlines
Sun 5/1712:41 pm
FPO
- EYW
1 stop3h 49m
American Airlines
Deal found 3/5![American Airlines logo]()
$633
This United Airlines deal was found by Cheapflights users on 3/5. 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 3/236:28 pm
EYW
- NAS
1 stop17h 22m
United Airlines
Tue 3/243:35 pm
NAS
- EYW
1 stop23h 20m
United Airlines
Deal found 3/5![United Airlines logo]()
$935
This American Airlines deal was found by Cheapflights users on 3/5. 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 4/196:45 am
EYW
- FPO
1 stop2h 57m
American Airlines
Sun 4/2612:41 pm
FPO
- EYW
1 stop10h 17m
American Airlines
Deal found 3/5![American Airlines logo]()
$709
This American Airlines deal was found by Cheapflights users on 3/1. 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.
Sun 4/193:58 pm
EYW
- KIN
1 stop3h 56m
American Airlines
Sat 4/257:00 am
KIN
- EYW
1 stop14h 58m
American Airlines
Deal found 3/1![American Airlines logo]()
$714
This United Airlines deal was found by Cheapflights users on 3/1. 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.
Sun 4/195:23 pm
EYW
- KIN
2 stops21h 29m
United Airlines
Sat 4/252:59 pm
KIN
- EYW
2 stops22h 52m
United Airlines
Deal found 3/1![United Airlines logo]()
$1,186
This American Airlines deal was found by Cheapflights users on 3/1. 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.
Mon 5/116:45 am
EYW
- EIS
1 stop4h 33m
American Airlines
Tue 5/199:00 am
EIS
- EYW
1 stop13h 58m
American Airlines
Deal found 3/1![American Airlines logo]()
$716
This United Airlines deal was found by Cheapflights users on 3/1. 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.
Sun 4/124:38 pm
EYW
- KIN
2 stops46h 14m
United Airlines
Sat 4/182:59 pm
KIN
- EYW
2 stops47h 58m
United Airlines
Deal found 3/1![United Airlines logo]()
$1,215
This United Airlines deal was found by Cheapflights users on 3/1. 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.
Tue 3/315:23 pm
EYW
- KIN
2 stops21h 29m
United Airlines
Tue 4/72:59 pm
KIN
- EYW
2 stops47h 58m
United Airlines
Deal found 3/1![United Airlines logo]()
$1,348
This United Airlines deal was found by Cheapflights users on 3/4. 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 3/306:22 pm
EYW
- KIN
2 stops20h 29m
United Airlines
Wed 4/12:59 pm
KIN
- EYW
2 stops47h 58m
United Airlines
Deal found 3/4![United Airlines logo]()
$1,416
This Mytrip deal was found by Cheapflights users on 3/1. 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.
Sun 4/1212:25 pm
EYW
- KIN
3 stops25h 50m
Multiple Airlines
Sat 4/1811:00 am
KIN
- EYW
3 stops23h 31m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$1,341
This United Airlines deal was found by Cheapflights users on 2/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/313:50 pm
EYW
- KIN
2 stops47h 04m
United Airlines
Wed 6/32:59 pm
KIN
- EYW
2 stops47h 08m
United Airlines
Deal found 2/28![United Airlines logo]()
$5,393
Last-minute flights from Key West to CaribbeanDiscover last-minute flight deals from Key West to Caribbean. Data last updated March 6, 2026 and is based on user searches.
Discover last-minute flight deals from Key West to Caribbean. Data last updated March 6, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 3/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/171:01 pm
EYW
- SJU
1 stop22h 09m
Multiple Airlines
Sat 3/217:54 pm
SJU
- EYW
2 stops19h 48m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$402
This Kiwi.com deal was found by Cheapflights users on 3/4. 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 3/239:49 am
EYW
- SJU
1 stop25h 21m
Multiple Airlines
Fri 3/278:47 pm
SJU
- EYW
1 stop17h 56m
Multiple Airlines
Deal found 3/4![Multiple Airlines logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 3/239:49 am
EYW
- SJU
1 stop25h 21m
Multiple Airlines
Thu 3/267:54 pm
SJU
- EYW
1 stop17h 43m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/2511:51 am
EYW
- SJU
1 stop10h 08m
Multiple Airlines
Tue 3/317:54 pm
SJU
- EYW
1 stop15h 36m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$424
This American Airlines deal was found by Cheapflights users on 3/1. 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.
Wed 3/253:56 pm
EYW
- MHH
1 stop23h 34m
American Airlines
Wed 4/11:04 pm
MHH
- EYW
1 stop6h 08m
American Airlines
Deal found 3/1![American Airlines logo]()
$531
This Kiwi.com deal was found by Cheapflights users on 3/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3112:25 pm
EYW
- KIN
1 stop24h 10m
Spirit Airlines
Tue 4/712:32 pm
KIN
- EYW
1 stop21h 58m
Spirit Airlines
Deal found 3/1![Spirit Airlines logo]()
$533
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/112:25 pm
EYW
- SJU
2 stops20h 28m
Multiple Airlines
Wed 4/88:47 pm
SJU
- EYW
1 stop18h 55m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$426
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 4/812:25 pm
EYW
- SJU
1 stop6h 30m
Multiple Airlines
Thu 4/91:45 am
SJU
- EYW
1 stop10h 41m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$334
This Mytrip deal was found by Cheapflights users on 3/3. 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 4/812:25 pm
EYW
- SJU
1 stop6h 30m
Spirit Airlines
Thu 4/91:45 am
SJU
- EYW
2 stops11h 52m
Spirit Airlines
Deal found 3/3![Spirit Airlines logo]()
$350
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 4/171:06 pm
EYW
- NAS
1 stop27h 19m
Multiple Airlines
Fri 4/247:15 am
NAS
- EYW
1 stop6h 20m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$494
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 4/1912:26 pm
EYW
- NAS
1 stop6h 49m
Multiple Airlines
Sun 4/2612:00 pm
NAS
- EYW
1 stop24h 26m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$496
This American Airlines deal was found by Cheapflights users on 3/2. 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.
Fri 4/246:45 am
EYW
- NAS
1 stop9h 49m
American Airlines
Wed 4/298:18 am
NAS
- EYW
1 stop8h 12m
American Airlines
Deal found 3/2![American Airlines logo]()
$521
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 March 6, 2026.
Search for one-way flight options from Key West to Caribbean. Find affordable one-way fares based on user searches. Data last updated March 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/57:53 pm
EYW
- NAS
1 stop13h 02m
Breeze Airways
Deal found 3/2![Breeze Airways logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 5/2912:10 pm
EYW
- SJU
1 stop20h 39m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/112:44 pm
EYW
- NAS
1 stop18h 11m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 3/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/611:04 am
EYW
- NAS
1 stop21h 51m
Breeze Airways
Deal found 3/1![Breeze Airways logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/911:04 am
EYW
- NAS
1 stop21h 51m
Breeze Airways
Deal found 3/2![Breeze Airways logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/103:27 pm
EYW
- NAS
1 stop24h 58m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 3/201:06 pm
EYW
- SJU
2 stops29h 49m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 3/202:35 pm
EYW
- SJU
1 stop28h 20m
Spirit Airlines
Deal found 3/3![Spirit Airlines logo]()
$192
This Delta deal was found by Cheapflights users on 3/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/77:00 am
EYW
- NAS
1 stop6h 43m
Delta
Deal found 3/2![Delta logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/111:51 am
EYW
- SJU
3 stops37h 26m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/811:46 am
EYW
- NAS
2 stops7h 29m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 3/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/611:04 am
EYW
- NAS
2 stops27h 41m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$218
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 March 6, 2026.
Round-trip from | $319 (Kiwi.com) |
|---|---|
One-way from | $171 (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 March 6, 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
Tue 3/17
1:01 pm-11:10 am
1 stop22h 09m
San Juan Luis Munoz Marin Intl
Sat 3/21
7:54 pm-3:42 pm
2 stops19h 48m
$402
Key WestSan Juan
EYW - SJU
EYWSJU
Key West
Thu 8/13
7:09 pm-11:40 pm
1 stop4h 31m
San Juan Luis Munoz Marin Intl
Wed 8/19
1:35 pm-6:39 pm
1 stop5h 04m
$406
Key WestSan Juan
EYW - SJU
EYWSJU
Key West
Tue 3/17
1:01 pm-11:10 am
1 stop22h 09m
San Juan Luis Munoz Marin Intl
Fri 3/20
9:12 pm-10:21 am
2 stops37h 09m
$445
Key WestSan Juan
EYW - SJU
EYWSJU
Key West
Wed 4/1
12:25 pm-11:58 pm
3 stops35h 33m
San Juan Luis Munoz Marin Intl
Wed 4/8
7:54 pm-11:30 am
1 stop15h 36m
$458
Key WestSan Juan
EYW - SJU
EYWSJU
Key West
Thu 3/19
4:22 pm-10:10 am
1 stop17h 48m
San Juan Luis Munoz Marin Intl
Mon 3/23
7:54 pm-12:21 pm
2 stops16h 27m
$464
Key WestSan Juan
EYW - SJU
EYWSJU
Key West
Mon 3/23
2:35 pm-3:19 pm
3 stops24h 44m
San Juan Luis Munoz Marin Intl
Thu 3/26
8:47 pm-1:37 pm
2 stops16h 50m
$485
Key WestSan Juan
EYW - SJU
EYWSJU
Key West
Wed 4/1
7:42 pm-9:00 am
1 stop13h 18m
San Juan Luis Munoz Marin Intl
Wed 4/8
7:25 am-10:36 pm
1 stop15h 11m
$496
Key WestMarsh Harbour
EYW - MHH
EYWMHH
Key West
Wed 3/25
3:56 pm-3:30 pm
1 stop23h 34m
Marsh Harbour
Wed 4/1
1:04 pm-7:12 pm
1 stop6h 08m
$531
Key WestSan Juan
EYW - SJU
EYWSJU
Key West
Wed 4/8
2:29 pm-4:32 am
1 stop14h 03m
San Juan Luis Munoz Marin Intl
Fri 4/10
5:45 am-4:30 pm
1 stop10h 45m
$531
Key WestKingston
EYW - KIN
EYWKIN
Key West
Tue 3/31
12:25 pm-11:35 am
1 stop24h 10m
Kingston Norman Manley
Tue 4/7
12:32 pm-11:30 am
1 stop21h 58m
$533
Showing 1-10 of 48 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-MHH
EYW-KIN
EYW-FPO
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-MHH
EYW-KIN
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 March 6, 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.
Entertainment
6.9
Comfort
7.2
Crew
8.0
Overall
7.1
Food
6.4
Boarding
7.5
Reviews
1 / 20
2.0
MediocreAnonymous,Mar 2026
MIA - SFO
Entertainment
6.9
Comfort
7.2
Crew
8.0
Overall
7.1
Food
6.4
Boarding
7.5
Reviews
1 / 20
2.0
MediocreAnonymous,Mar 2026
MIA - SFO
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top countries
Top destinations
Alternative routes for Key West to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Key West to Caribbean by cabin class
Find flights from Key West to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Key West and Caribbean flights
Browse other Key West and Caribbean flight options. Last updated on March 6, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Key West to Caribbean flights
Consider these flights traveling from Key West to Caribbean.
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 March 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$390 | Average$495 | FlexibilityNo cancel fee | On-time71% |