$213+ Cheap flights from Tallahassee (TLH) to Caribbean Islands
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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — SJU
Aug 30 — Sep 61
Round-trip
1 adult, Economy
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Find cheap flights from Tallahassee to Caribbean Islands 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 Tallahassee to Caribbean IslandsExplore the most affordable flight options available from Tallahassee to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2026.
Explore the most affordable flight options available from Tallahassee to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2026.
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 9/241:07 pm
TLH
- SJU
1 stop24h 27m
Multiple Airlines
Mon 9/287:00 am
SJU
- TLH
1 stop27h 30m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$259
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.
Thu 11/51:07 pm
TLH
- SJU
1 stop10h 31m
Multiple Airlines
Wed 11/116:12 pm
SJU
- TLH
1 stop14h 33m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$266
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.
Thu 9/241:07 pm
TLH
- SJU
1 stop24h 27m
Multiple Airlines
Thu 10/85:12 pm
SJU
- TLH
1 stop16h 18m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$284
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 8/238:08 am
TLH
- SJU
1 stop15h 51m
Multiple Airlines
Sat 8/296:35 am
SJU
- TLH
1 stop24h 53m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$286
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 8/238:08 am
TLH
- SJU
1 stop15h 51m
Multiple Airlines
Wed 8/266:35 am
SJU
- TLH
1 stop24h 53m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$297
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.
Thu 9/178:25 am
TLH
- SJU
2 stops15h 33m
Multiple Airlines
Mon 9/217:00 am
SJU
- TLH
1 stop27h 30m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$313
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.
Tue 8/252:17 pm
TLH
- SJU
2 stops19h 02m
Multiple Airlines
Sat 8/296:35 am
SJU
- TLH
1 stop24h 53m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$332
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.
Sat 11/76:44 pm
TLH
- STT
2 stops16h 33m
American Airlines
Mon 11/163:15 pm
STT
- TLH
2 stops20h 06m
American Airlines
Deal found 7/27![American Airlines logo]()
$418
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.
Fri 10/910:10 am
TLH
- NAS
1 stop4h 25m
Multiple Airlines
Sun 10/114:00 pm
NAS
- TLH
1 stop17h 30m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$443
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.
Thu 8/276:52 pm
TLH
- STT
2 stops18h 01m
American Airlines
Thu 9/31:48 pm
STT
- TLH
2 stops20h 27m
American Airlines
Deal found 7/28![American Airlines logo]()
$443
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.
Sat 11/74:32 pm
TLH
- STT
2 stops18h 45m
American Airlines
Sat 11/142:40 pm
STT
- TLH
2 stops19h 31m
American Airlines
Deal found 7/27![American Airlines logo]()
$453
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 9/106:54 pm
TLH
- MBJ
2 stops17h 09m
American Airlines
Thu 9/175:16 pm
MBJ
- TLH
2 stops19h 44m
American Airlines
Deal found 7/27![American Airlines logo]()
$467
Best flights from Tallahassee to Caribbean IslandsDiscover carefully curated flight deals from Tallahassee to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 31, 2026.
Discover carefully curated flight deals from Tallahassee to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 31, 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.
Thu 9/241:07 pm
TLH
- SJU
1 stop24h 27m
Multiple Airlines
Mon 9/286:42 pm
SJU
- TLH
2 stops20h 30m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$338
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.
Sat 11/78:23 pm
TLH
- STT
1 stop14h 54m
American Airlines
Mon 11/161:07 pm
STT
- TLH
1 stop5h 44m
American Airlines
Deal found 7/27![American Airlines logo]()
$418
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 8/276:00 am
TLH
- STT
1 stop7h 34m
Delta
Thu 9/32:49 pm
STT
- TLH
1 stop6h 02m
Delta
Deal found 7/28![Delta logo]()
$521
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.
Fri 10/910:10 am
TLH
- NAS
1 stop4h 25m
Multiple Airlines
Sun 10/114:00 pm
NAS
- TLH
1 stop17h 30m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$443
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.
Thu 8/276:52 pm
TLH
- STT
2 stops18h 01m
American Airlines
Thu 9/31:48 pm
STT
- TLH
2 stops20h 27m
American Airlines
Deal found 7/28![American Airlines logo]()
$443
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 11/78:23 pm
TLH
- STT
1 stop14h 54m
American Airlines
Sat 11/142:40 pm
STT
- TLH
2 stops19h 31m
American Airlines
Deal found 7/28![American Airlines logo]()
$453
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 11/18:25 am
TLH
- SJU
2 stops23h 33m
Multiple Airlines
Mon 11/234:18 pm
SJU
- TLH
1 stop28h 17m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$468
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.
Tue 8/253:49 pm
TLH
- SJU
1 stop6h 40m
Delta
Thu 8/277:00 am
SJU
- TLH
1 stop10h 11m
Delta
Deal found 7/30![Delta logo]()
$546
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 10/77:33 pm
TLH
- SJU
2 stops14h 13m
American Airlines
Thu 10/83:51 pm
SJU
- TLH
1 stop17h 03m
American Airlines
Deal found 7/28![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.
Sat 8/296:52 pm
TLH
- MBJ
2 stops19h 57m
American Airlines
Tue 9/112:38 pm
MBJ
- TLH
2 stops19h 37m
American Airlines
Deal found 7/28![American Airlines logo]()
$467
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.
Thu 8/273:49 pm
TLH
- SJU
1 stop6h 40m
Delta
Sat 8/292:59 pm
SJU
- TLH
1 stop8h 04m
Delta
Deal found 7/30![Delta logo]()
$576
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.
Thu 9/106:54 pm
TLH
- MBJ
2 stops17h 09m
American Airlines
Thu 9/175:16 pm
MBJ
- TLH
2 stops19h 44m
American Airlines
Deal found 7/30![American Airlines logo]()
$467
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 8/2412:05 pm
TLH
- SJU
1 stop10h 24m
Delta
Sat 8/2912:56 pm
SJU
- TLH
1 stop10h 07m
Delta
Deal found 7/30![Delta logo]()
$581
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.
Tue 12/17:45 pm
TLH
- MBJ
2 stops17h 15m
American Airlines
Fri 12/44:23 pm
MBJ
- TLH
1 stop7h 36m
American Airlines
Deal found 7/29![American Airlines logo]()
$467
This WestJet 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:00 am
TLH
- NAS
2 stops33h 40m
WestJet
Sat 10/314:50 pm
NAS
- TLH
2 stops26h 41m
WestJet
Deal found 7/29![WestJet logo]()
$1,530
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.
Wed 1/276:00 am
TLH
- SJU
2 stops11h 22m
American Airlines
Wed 2/32:52 pm
SJU
- TLH
1 stop6h 18m
American Airlines
Deal found 7/29![American Airlines logo]()
$471
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:00 am
TLH
- GCM
1 stop6h 39m
Delta
Tue 8/251:04 pm
GCM
- TLH
1 stop6h 05m
Delta
Deal found 7/29![Delta logo]()
$681
This American Airlines deal was found by Cheapflights users on 7/26. 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 9/3010:56 am
TLH
- STT
2 stops25h 55m
American Airlines
Thu 10/81:48 pm
STT
- TLH
2 stops19h 06m
American Airlines
Deal found 7/26![American Airlines logo]()
$474
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 am
TLH
- GCM
1 stop6h 39m
Delta
Tue 8/251:04 pm
GCM
- TLH
1 stop6h 05m
Delta
Deal found 7/29![Delta logo]()
$706
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.
Tue 11/106:00 am
TLH
- MHH
1 stop5h 27m
American Airlines
Tue 12/1512:10 pm
MHH
- TLH
1 stop8h 01m
American Airlines
Deal found 7/30![American Airlines logo]()
$499
This 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:00 am
TLH
- GCM
1 stop6h 39m
Delta
Tue 8/251:04 pm
GCM
- TLH
1 stop8h 59m
Delta
Deal found 7/31![Delta logo]()
$731
This American Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:05 am
TLH
- SJU
1 stop10h 06m
American Airlines
Fri 8/285:10 pm
SJU
- TLH
1 stop16h 05m
American Airlines
Deal found 7/28![American Airlines logo]()
$527
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.
Wed 11/410:38 am
TLH
- MHH
1 stop4h 42m
American Airlines
Sun 11/812:07 pm
MHH
- TLH
1 stop5h 44m
American Airlines
Deal found 7/30![American Airlines logo]()
$534
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.
Tue 8/186:00 am
TLH
- SJU
2 stops12h 33m
American Airlines
Tue 8/257:30 am
SJU
- TLH
1 stop8h 03m
American Airlines
Deal found 7/27![American Airlines logo]()
$536
This WestJet 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:00 am
TLH
- NAS
2 stops33h 40m
WestJet
Thu 12/311:20 am
NAS
- TLH
2 stops24h 02m
WestJet
Deal found 7/30![WestJet logo]()
$1,536
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/228:05 am
TLH
- GCM
1 stop4h 34m
Delta
Sun 8/231:04 pm
GCM
- TLH
1 stop6h 47m
Delta
Deal found 7/29![Delta logo]()
$916
This WestJet 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/53:32 pm
TLH
- NAS
2 stops19h 38m
WestJet
Wed 10/712:00 pm
NAS
- TLH
2 stops30h 27m
WestJet
Deal found 7/27![WestJet logo]()
$1,552
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.
Sat 10/248:49 pm
TLH
- NAS
1 stop12h 38m
American Airlines
Sat 10/312:08 pm
NAS
- TLH
1 stop6h 11m
American Airlines
Deal found 7/29![American Airlines logo]()
$587
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.
Thu 9/36:52 pm
TLH
- STT
2 stops21h 00m
American Airlines
Tue 9/81:49 pm
STT
- TLH
2 stops20h 38m
American Airlines
Deal found 7/29![American Airlines logo]()
$618
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.
Fri 1/226:00 am
TLH
- CUR
1 stop7h 47m
American Airlines
Fri 1/295:45 pm
CUR
- TLH
2 stops20h 59m
American Airlines
Deal found 7/30![American Airlines logo]()
$634
Last-minute flights from Tallahassee to Caribbean IslandsDiscover last-minute flight deals from Tallahassee to Caribbean Islands. Data last updated July 31, 2026 and is based on user searches.
Discover last-minute flight deals from Tallahassee to Caribbean Islands. Data last updated July 31, 2026 and is based on user searches.
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.
Thu 8/138:08 am
TLH
- SJU
1 stop15h 59m
Multiple Airlines
Wed 8/198:57 pm
SJU
- TLH
2 stops15h 10m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$428
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.
Thu 8/138:08 am
TLH
- SJU
1 stop15h 59m
Multiple Airlines
Mon 8/176:00 am
SJU
- TLH
1 stop26h 58m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$434
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 8/168:08 am
TLH
- SJU
1 stop15h 59m
Multiple Airlines
Wed 8/198:57 pm
SJU
- TLH
2 stops15h 10m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$424
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 8/168:08 am
TLH
- SJU
1 stop15h 59m
Multiple Airlines
Mon 8/176:00 am
SJU
- TLH
1 stop26h 58m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$430
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 8/238:08 am
TLH
- SJU
1 stop15h 51m
Multiple Airlines
Sat 8/296:35 am
SJU
- TLH
1 stop24h 53m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$286
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 8/238:08 am
TLH
- SJU
1 stop15h 51m
Multiple Airlines
Wed 8/266:35 am
SJU
- TLH
1 stop24h 53m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$297
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 8/238:08 am
TLH
- SJU
1 stop15h 51m
Multiple Airlines
Mon 8/243:10 am
SJU
- TLH
2 stops10h 27m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$341
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 8/238:08 am
TLH
- SJU
1 stop15h 51m
Multiple Airlines
Sun 8/307:55 pm
SJU
- TLH
2 stops37h 03m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$401
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.
Tue 8/252:17 pm
TLH
- SJU
2 stops19h 02m
Multiple Airlines
Sat 8/296:35 am
SJU
- TLH
1 stop24h 53m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$332
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.
Tue 8/252:17 pm
TLH
- SJU
1 stop25h 54m
Multiple Airlines
Sun 8/307:55 pm
SJU
- TLH
2 stops37h 03m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$408
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.
Thu 8/276:52 pm
TLH
- STT
2 stops18h 01m
American Airlines
Thu 9/31:48 pm
STT
- TLH
2 stops20h 27m
American Airlines
Deal found 7/28![American Airlines logo]()
$443
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 8/297:05 am
TLH
- MBJ
1 stop10h 03m
American Airlines
Tue 9/12:37 pm
MBJ
- TLH
2 stops25h 24m
American Airlines
Deal found 7/28![American Airlines logo]()
$467
One-way flights from Tallahassee to Caribbean IslandsSearch for one-way flight options from Tallahassee to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated July 31, 2026.
Search for one-way flight options from Tallahassee to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated July 31, 2026.
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.
Tue 8/257:04 pm
TLH
- MBJ
2 stops17h 33m
American Airlines
Deal found 7/30![American Airlines logo]()
$213
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.
Tue 8/256:00 am
TLH
- MBJ
1 stop8h 01m
Delta
Deal found 7/30![Delta logo]()
$267
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 8/106:00 am
TLH
- STT
2 stops9h 52m
American Airlines
Deal found 7/30![American Airlines logo]()
$320
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 12/271:07 pm
TLH
- SJU
1 stop23h 55m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$375
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 12/279:42 am
TLH
- SJU
1 stop12h 57m
American Airlines
Deal found 7/28![American Airlines logo]()
$413
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 8/138:08 am
TLH
- STT
3 stops23h 42m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$507
Find flight deals from Tallahassee to Caribbean Islands
Keep the following information in mind while searching for Tallahassee to Caribbean Islands flight deals. Data was last updated July 31, 2026.
Round-trip from | $259 (Kiwi.com) |
|---|---|
One-way from | $213 (American Airlines) |
Popular in | June |
Cheapest in | January |
Average price | $661 |
Cheapflights Fare Finder
Customize your flight search to find flights from Tallahassee to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 31, 2026.
Use the filters below to find and compare flights from Tallahassee to Caribbean Islands that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
TallahasseeSan Juan
TLH - SJU
TLHSJU
Tallahassee
Thu 9/24
1:07 pm-1:34 pm
1 stop24h 27m
San Juan Luis Munoz Marin Intl
Mon 9/28
6:42 pm-3:12 pm
2 stops20h 30m
$338
TallahasseeSaint Thomas Island
TLH - STT
TLHSTT
Tallahassee
Sat 11/7
8:23 pm-12:17 pm
1 stop14h 54m
Saint Thomas Island Cyril E King
Mon 11/16
1:07 pm-5:51 pm
1 stop5h 44m
$418
TallahasseeNassau
TLH - NAS
TLHNAS
Tallahassee
Fri 10/9
10:10 am-2:35 pm
1 stop4h 25m
Nassau Intl
Sun 10/11
4:00 pm-9:30 am
1 stop17h 30m
$443
TallahasseeSaint Thomas Island
TLH - STT
TLHSTT
Tallahassee
Thu 8/27
6:52 pm-12:53 pm
2 stops18h 01m
Saint Thomas Island Cyril E King
Thu 9/3
1:48 pm-10:15 am
2 stops20h 27m
$443
TallahasseeSaint Thomas Island
TLH - STT
TLHSTT
Tallahassee
Sat 11/7
8:23 pm-12:17 pm
1 stop14h 54m
Saint Thomas Island Cyril E King
Sat 11/14
2:40 pm-9:11 am
2 stops19h 31m
$453
TallahasseeSan Juan
TLH - SJU
TLHSJU
Tallahassee
Wed 10/7
7:33 pm-9:46 am
2 stops14h 13m
San Juan Luis Munoz Marin Intl
Thu 10/8
3:51 pm-8:54 am
1 stop17h 03m
$466
TallahasseeMontego Bay
TLH - MBJ
TLHMBJ
Tallahassee
Sat 8/29
6:52 pm-1:49 pm
2 stops19h 57m
Montego Bay Sangster Intl
Tue 9/1
12:38 pm-9:15 am
2 stops19h 37m
$467
TallahasseeMontego Bay
TLH - MBJ
TLHMBJ
Tallahassee
Thu 9/10
6:54 pm-11:03 am
2 stops17h 09m
Montego Bay Sangster Intl
Thu 9/17
5:16 pm-2:00 pm
2 stops19h 44m
$467
TallahasseeMontego Bay
TLH - MBJ
TLHMBJ
Tallahassee
Tue 12/1
7:45 pm-1:00 pm
2 stops17h 15m
Montego Bay Sangster Intl
Fri 12/4
4:23 pm-11:59 pm
1 stop7h 36m
$467
TallahasseeSan Juan
TLH - SJU
TLHSJU
Tallahassee
Sun 11/1
8:25 am-8:58 am
2 stops23h 33m
San Juan Luis Munoz Marin Intl
Mon 11/23
4:18 pm-7:35 pm
1 stop28h 17m
$468
Showing 1-10 of 37 resultsSorted by cheapest first
Best time to book a flight from Tallahassee to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Tallahassee with our price prediction graph.
TLH-SJU
TLH-STT
TLH-MBJ
TLH-NAS
TLH-GCM
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 Tallahassee to Caribbean Islands
TLH-zzEPX
TLH-SJU
TLH-STT
TLH-MBJ
TLH-NAS
What is the cheapest month to book a flight from Tallahassee to Caribbean Islands?
Currently, February is the cheapest month in which you can book a flight from Tallahassee to Caribbean Islands (average of $529). Flying from Tallahassee to Caribbean Islands in October is currently the most expensive (average of $859). 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.
Reviews of airlines servicing Caribbean Islands
Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated July 31, 2026.
Get a feel of what it's like to fly with American Airlines from Tallahassee to Caribbean Islands by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
7.5
Food
6.4
Crew
7.9
Entertainment
6.8
Comfort
7.2
Overall
7.1
Reviews
1 / 20
8.0
ExcellentOlwin,Jul 2026
MCO - DCA
Boarding
7.5
Food
6.4
Crew
7.9
Entertainment
6.8
Comfort
7.2
Overall
7.1
Reviews
1 / 20
8.0
ExcellentOlwin,Jul 2026
MCO - DCA
Related info for your journey
Find useful and relevant information for your journey from Tallahassee to Caribbean Islands. 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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Complete your trip
Complete your trip to Caribbean Islands by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Tallahassee to Caribbean Islands by cabin class
Find flights from Tallahassee to Caribbean Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Tallahassee and Caribbean Islands flights
Browse other Tallahassee and Caribbean Islands flight options. Last updated on July 31, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Tallahassee to Caribbean Islands flights
Consider these flights traveling from Tallahassee to Caribbean Islands.
Top 2 airlines flying from Tallahassee to Caribbean Islands
Discover the top 2 airlines that operate flights from Tallahassee to Caribbean Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$247 | Average$701 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$441 | Average$610 | FlexibilityNo cancel fee | On-timeN/A |