$242+ Cheap flights from Chattanooga (CHA) 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 12/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHA — SJU
Aug 21 — Aug 281
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chattanooga 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
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 Chattanooga to Caribbean Islands
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chattanooga to Caribbean IslandsExplore the most affordable flight options available from Chattanooga to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 22, 2026.
Explore the most affordable flight options available from Chattanooga to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/98:57 am
CHA
- SJU
1 stop7h 14m
Multiple Airlines
Sat 8/156:00 am
SJU
- CHA
1 stop26h 07m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 10/1810:09 am
CHA
- SJU
1 stop13h 29m
Multiple Airlines
Fri 10/234:39 pm
SJU
- CHA
2 stops40h 00m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 9/249:23 am
CHA
- SJU
1 stop14h 34m
Multiple Airlines
Sun 9/273:00 am
SJU
- CHA
1 stop11h 24m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$347
This Delta deal was found by Cheapflights users on 7/21. 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 9/1510:00 am
CHA
- SJU
1 stop6h 49m
Delta
Wed 9/237:00 am
SJU
- CHA
1 stop8h 22m
Delta
Deal found 7/21![Delta logo]()
$416
This American Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:08 pm
CHA
- STT
2 stops19h 50m
American Airlines
Sun 12/132:49 pm
STT
- CHA
2 stops18h 49m
American Airlines
Deal found 7/19![American Airlines logo]()
$418
This American Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/28:08 pm
CHA
- STT
2 stops19h 50m
American Airlines
Wed 12/94:22 pm
STT
- CHA
1 stop8h 39m
American Airlines
Deal found 7/19![American Airlines logo]()
$423
This Delta deal was found by Cheapflights users on 7/21. 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 9/162:32 pm
CHA
- SJU
1 stop7h 47m
Delta
Sat 9/267:00 am
SJU
- CHA
1 stop6h 47m
Delta
Deal found 7/21![Delta logo]()
$436
This Kiwi.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/238:59 am
CHA
- SJU
1 stop7h 06m
Multiple Airlines
Sat 7/256:00 am
SJU
- CHA
1 stop26h 09m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$442
This American Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/48:08 pm
CHA
- STT
2 stops16h 44m
American Airlines
Sun 12/132:49 pm
STT
- CHA
2 stops18h 49m
American Airlines
Deal found 7/19![American Airlines logo]()
$453
This Delta deal was found by Cheapflights users on 7/21. 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 9/244:09 pm
CHA
- SJU
1 stop6h 10m
Delta
Mon 9/285:59 pm
SJU
- CHA
1 stop5h 51m
Delta
Deal found 7/21![Delta logo]()
$456
This Delta deal was found by Cheapflights users on 7/21. 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 12/25:30 am
CHA
- SJU
1 stop6h 15m
Delta
Tue 12/87:00 am
SJU
- CHA
1 stop10h 06m
Delta
Deal found 7/21![Delta logo]()
$461
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 11/1210:09 am
CHA
- NAS
1 stop24h 21m
Multiple Airlines
Wed 11/184:00 pm
NAS
- CHA
1 stop26h 14m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$461
Best flights from Chattanooga to Caribbean IslandsDiscover carefully curated flight deals from Chattanooga to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 22, 2026.
Discover carefully curated flight deals from Chattanooga to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 22, 2026.
This Delta deal was found by Cheapflights users on 7/18. 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 9/1510:00 am
CHA
- SJU
1 stop6h 49m
Delta
Wed 9/237:00 am
SJU
- CHA
1 stop8h 22m
Delta
Deal found 7/18![Delta logo]()
$416
This American Airlines deal was found by Cheapflights users on 7/18. 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 12/38:08 pm
CHA
- STT
2 stops19h 50m
American Airlines
Sun 12/132:49 pm
STT
- CHA
2 stops18h 49m
American Airlines
Deal found 7/18![American Airlines logo]()
$418
This United Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:45 am
CHA
- MBJ
1 stop7h 03m
United Airlines
Thu 10/292:20 pm
MBJ
- CHA
2 stops18h 37m
United Airlines
Deal found 7/19![United Airlines logo]()
$582
This Delta deal was found by Cheapflights users on 7/21. 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 9/164:09 pm
CHA
- SJU
1 stop6h 10m
Delta
Sun 9/275:59 pm
SJU
- CHA
1 stop5h 51m
Delta
Deal found 7/21![Delta logo]()
$436
This American Airlines deal was found by Cheapflights users on 7/17. 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 12/28:08 pm
CHA
- STT
2 stops19h 50m
American Airlines
Wed 12/92:49 pm
STT
- CHA
2 stops18h 49m
American Airlines
Deal found 7/17![American Airlines logo]()
$458
This Delta deal was found by Cheapflights users on 7/17. 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.
Fri 10/94:00 pm
CHA
- SJU
1 stop5h 59m
Delta
Tue 10/137:30 am
SJU
- CHA
1 stop10h 08m
Delta
Deal found 7/17![Delta logo]()
$436
This American Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:12 pm
CHA
- SJU
2 stops15h 48m
American Airlines
Wed 9/236:00 am
SJU
- CHA
2 stops10h 48m
American Airlines
Deal found 7/20![American Airlines logo]()
$466
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1612:10 pm
CHA
- SJU
1 stop10h 09m
Delta
Sat 9/267:00 am
SJU
- CHA
1 stop6h 47m
Delta
Deal found 7/20![Delta logo]()
$436
This American Airlines deal was found by Cheapflights users on 7/21. 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 10/157:30 am
CHA
- MBJ
1 stop9h 42m
American Airlines
Mon 10/195:13 pm
MBJ
- CHA
2 stops15h 41m
American Airlines
Deal found 7/21![American Airlines logo]()
$467
This Delta deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/244:09 pm
CHA
- SJU
1 stop6h 10m
Delta
Mon 9/285:59 pm
SJU
- CHA
1 stop5h 51m
Delta
Deal found 7/19![Delta logo]()
$456
This American Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:12 pm
CHA
- MBJ
2 stops18h 41m
American Airlines
Fri 9/255:16 pm
MBJ
- CHA
2 stops17h 34m
American Airlines
Deal found 7/20![American Airlines logo]()
$501
This American Airlines deal was found by Cheapflights users on 7/22. 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 11/138:03 pm
CHA
- ELH
2 stops15h 16m
American Airlines
Wed 11/1811:59 am
ELH
- CHA
2 stops11h 05m
American Airlines
Deal found 7/22![American Airlines logo]()
$515
This Delta deal was found by Cheapflights users on 7/17. 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 10/155:35 am
CHA
- MBJ
1 stop10h 59m
Delta
Mon 10/194:49 pm
MBJ
- CHA
1 stop5h 55m
Delta
Deal found 7/17![Delta logo]()
$522
This Delta deal was found by Cheapflights users on 7/22. 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.
Fri 11/135:30 am
CHA
- ELH
1 stop6h 40m
Delta
Wed 11/181:05 pm
ELH
- CHA
1 stop9h 01m
Delta
Deal found 7/22![Delta logo]()
$538
This American Airlines deal was found by Cheapflights users on 7/17. 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 10/107:59 pm
CHA
- MBJ
1 stop16h 05m
American Airlines
Sun 10/185:13 pm
MBJ
- CHA
2 stops18h 33m
American Airlines
Deal found 7/17![American Airlines logo]()
$571
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:40 am
CHA
- STT
1 stop6h 59m
Delta
Thu 11/53:49 pm
STT
- CHA
1 stop5h 37m
Delta
Deal found 7/20![Delta logo]()
$560
This American Airlines deal was found by Cheapflights users on 7/22. 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 12/119:06 am
CHA
- NAS
1 stop4h 53m
American Airlines
Wed 12/161:13 pm
NAS
- CHA
1 stop10h 48m
American Airlines
Deal found 7/22![American Airlines logo]()
$583
This American Airlines deal was found by Cheapflights users on 7/21. 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 12/46:36 am
CHA
- STT
1 stop8h 06m
American Airlines
Sun 12/132:49 pm
STT
- CHA
2 stops18h 49m
American Airlines
Deal found 7/21![American Airlines logo]()
$583
This American Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/15:00 am
CHA
- NAS
1 stop8h 21m
American Airlines
Mon 12/73:00 pm
NAS
- CHA
1 stop7h 23m
American Airlines
Deal found 7/20![American Airlines logo]()
$597
This United Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/267:00 am
CHA
- STX
2 stops12h 38m
United Airlines
Sun 8/3010:25 am
STX
- CHA
2 stops12h 50m
United Airlines
Deal found 7/20![United Airlines logo]()
$1,340
This Delta deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/185:30 am
CHA
- AUA
1 stop8h 40m
Delta
Tue 11/243:10 pm
AUA
- CHA
2 stops24h 24m
Delta
Deal found 7/19![Delta logo]()
$704
This American Airlines deal was found by Cheapflights users on 7/21. 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 11/128:03 pm
CHA
- NAS
1 stop15h 15m
American Airlines
Wed 11/182:44 pm
NAS
- CHA
2 stops8h 40m
American Airlines
Deal found 7/21![American Airlines logo]()
$601
This Delta deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/185:30 am
CHA
- AUA
1 stop8h 40m
Delta
Mon 11/234:25 pm
AUA
- CHA
1 stop8h 26m
Delta
Deal found 7/19![Delta logo]()
$712
This American Airlines deal was found by Cheapflights users on 7/18. 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 10/167:59 pm
CHA
- AUA
2 stops19h 54m
American Airlines
Thu 10/224:16 pm
AUA
- CHA
1 stop16h 18m
American Airlines
Deal found 7/18![American Airlines logo]()
$613
This American Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/208:07 pm
CHA
- PUJ
2 stops16h 30m
American Airlines
Fri 9/2512:01 pm
PUJ
- CHA
2 stops21h 42m
American Airlines
Deal found 7/19![American Airlines logo]()
$631
This Delta deal was found by Cheapflights users on 7/18. 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.
Fri 10/165:35 am
CHA
- AUA
1 stop8h 35m
Delta
Thu 10/223:25 pm
AUA
- CHA
1 stop8h 19m
Delta
Deal found 7/18![Delta logo]()
$774
This American Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:02 pm
CHA
- PUJ
2 stops18h 37m
American Airlines
Tue 10/203:03 pm
PUJ
- CHA
1 stop8h 47m
American Airlines
Deal found 7/20![American Airlines logo]()
$631
This Delta deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:15 pm
CHA
- AUA
2 stops21h 40m
Delta
Mon 11/234:25 pm
AUA
- CHA
1 stop8h 26m
Delta
Deal found 7/19![Delta logo]()
$798
This American Airlines deal was found by Cheapflights users on 7/21. 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 1/26:13 pm
CHA
- STX
2 stops19h 27m
American Airlines
Sat 1/96:09 pm
STX
- CHA
2 stops16h 53m
American Airlines
Deal found 7/21![American Airlines logo]()
$655
This American Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:07 pm
CHA
- PUJ
1 stop18h 28m
American Airlines
Tue 10/203:03 pm
PUJ
- CHA
1 stop8h 47m
American Airlines
Deal found 7/20![American Airlines logo]()
$661
Last-minute flights from Chattanooga to Caribbean IslandsDiscover last-minute flight deals from Chattanooga to Caribbean Islands. Data last updated July 22, 2026 and is based on user searches.
Discover last-minute flight deals from Chattanooga to Caribbean Islands. Data last updated July 22, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 7/17. 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 7/216:04 am
CHA
- MBJ
1 stop11h 10m
American Airlines
Thu 7/232:09 pm
MBJ
- CHA
2 stops21h 45m
American Airlines
Deal found 7/17![American Airlines logo]()
$607
This Kiwi.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/238:59 am
CHA
- SJU
1 stop7h 06m
Multiple Airlines
Sat 7/256:00 am
SJU
- CHA
1 stop26h 09m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$442
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 7/268:59 am
CHA
- SJU
1 stop7h 06m
Multiple Airlines
Thu 7/306:09 pm
SJU
- CHA
1 stop26h 44m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$488
This American Airlines deal was found by Cheapflights users on 7/18. 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 8/67:18 pm
CHA
- SJU
2 stops14h 25m
American Airlines
Sat 8/157:05 am
SJU
- CHA
1 stop9h 48m
American Airlines
Deal found 7/18![American Airlines logo]()
$601
This Delta deal was found by Cheapflights users on 7/18. 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 8/81:22 pm
CHA
- SJU
1 stop9h 07m
Delta
Thu 8/132:59 pm
SJU
- CHA
1 stop5h 45m
Delta
Deal found 7/18![Delta logo]()
$526
This American Airlines deal was found by Cheapflights users on 7/18. 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 8/87:18 pm
CHA
- SJU
2 stops14h 25m
American Airlines
Thu 8/137:30 am
SJU
- CHA
1 stop13h 22m
American Airlines
Deal found 7/18![American Airlines logo]()
$546
This American Airlines deal was found by Cheapflights users on 7/18. 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 8/87:18 pm
CHA
- SJU
2 stops14h 25m
American Airlines
Fri 8/147:30 am
SJU
- CHA
1 stop15h 51m
American Airlines
Deal found 7/18![American Airlines logo]()
$551
This United Airlines deal was found by Cheapflights users on 7/18. 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 8/810:27 am
CHA
- SJU
1 stop10h 07m
United Airlines
Fri 8/142:20 pm
SJU
- CHA
1 stop8h 55m
United Airlines
Deal found 7/18![United Airlines logo]()
$573
This Kiwi.com deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/98:57 am
CHA
- SJU
1 stop7h 14m
Multiple Airlines
Sat 8/156:00 am
SJU
- CHA
1 stop26h 07m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$269
This United Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/187:00 am
CHA
- SJU
1 stop8h 42m
United Airlines
Mon 8/242:20 pm
SJU
- CHA
1 stop8h 55m
United Airlines
Deal found 7/20![United Airlines logo]()
$611
This United Airlines deal was found by Cheapflights users on 7/21. 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 8/256:15 am
CHA
- SJU
1 stop8h 29m
United Airlines
Fri 8/282:20 pm
SJU
- CHA
1 stop8h 55m
United Airlines
Deal found 7/21![United Airlines logo]()
$596
This American Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:18 pm
CHA
- STT
2 stops17h 35m
American Airlines
Sun 8/304:42 pm
STT
- CHA
2 stops17h 08m
American Airlines
Deal found 7/20![American Airlines logo]()
$418
One-way flights from Chattanooga to Caribbean IslandsSearch for one-way flight options from Chattanooga to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated July 22, 2026.
Search for one-way flight options from Chattanooga to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated July 22, 2026.
This American Airlines deal was found by Cheapflights users on 7/17. 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 12/256:03 pm
CHA
- MBJ
2 stops16h 04m
American Airlines
Deal found 7/17![American Airlines logo]()
$242
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/222:32 pm
CHA
- SJU
1 stop7h 47m
Delta
Deal found 7/20![Delta logo]()
$268
This American Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/225:30 am
CHA
- SJU
2 stops15h 17m
American Airlines
Deal found 7/20![American Airlines logo]()
$283
This Delta deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/52:44 pm
CHA
- SJU
1 stop7h 45m
Delta
Deal found 7/19![Delta logo]()
$313
This American Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:37 pm
CHA
- STT
2 stops18h 22m
American Airlines
Deal found 7/19![American Airlines logo]()
$320
This American Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/55:14 am
CHA
- SJU
2 stops13h 19m
American Airlines
Deal found 7/19![American Airlines logo]()
$324
This American Airlines deal was found by Cheapflights users on 7/17. 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 8/45:00 am
CHA
- ELH
1 stop6h 24m
American Airlines
Deal found 7/17![American Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 7/21. 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.
Sun 11/296:30 am
CHA
- SJU
1 stop5h 15m
Delta
Deal found 7/21![Delta logo]()
$403
This Delta deal was found by Cheapflights users on 7/17. 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.
Fri 12/255:30 am
CHA
- MBJ
1 stop5h 40m
Delta
Deal found 7/17![Delta logo]()
$427
This American Airlines deal was found by Cheapflights users on 7/21. 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 11/298:03 pm
CHA
- SJU
2 stops12h 35m
American Airlines
Deal found 7/21![American Airlines logo]()
$523
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 11/293:18 pm
CHA
- SJU
3 stops30h 32m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$653
This United Airlines deal was found by Cheapflights users on 7/21. 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 11/296:45 am
CHA
- SJU
1 stop7h 55m
United Airlines
Deal found 7/21![United Airlines logo]()
$750
Find flight deals from Chattanooga to Caribbean Islands
Keep the following information in mind while searching for Chattanooga to Caribbean Islands flight deals. Data was last updated July 22, 2026.
Round-trip from | $269 (Kiwi.com) |
|---|---|
One-way from | $242 (American Airlines) |
Popular in | March |
Cheapest in | October |
Average price | $605 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chattanooga 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 22, 2026.
Use the filters below to find and compare flights from Chattanooga to Caribbean Islands that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChattanoogaSan Juan
CHA - SJU
CHASJU
Chattanooga Lovell Field
Tue 9/15
10:00 am-4:49 pm
1 stop6h 49m
San Juan Luis Munoz Marin Intl
Wed 9/23
7:00 am-3:22 pm
1 stop8h 22m
$416
ChattanoogaSaint Thomas Island
CHA - STT
CHASTT
Chattanooga Lovell Field
Thu 12/3
8:08 pm-4:58 pm
2 stops19h 50m
Saint Thomas Island Cyril E King
Sun 12/13
2:49 pm-8:38 am
2 stops18h 49m
$418
Quickest round-trip
ChattanoogaSan Juan
CHA - SJU
CHASJU
Chattanooga Lovell Field
Wed 9/16
4:09 pm-10:19 pm
1 stop6h 10m
San Juan Luis Munoz Marin Intl
Sun 9/27
5:59 pm-11:50 pm
1 stop5h 51m
$436
ChattanoogaSan Juan
CHA - SJU
CHASJU
Chattanooga Lovell Field
Fri 10/9
4:00 pm-9:59 pm
1 stop5h 59m
San Juan Luis Munoz Marin Intl
Tue 10/13
7:30 am-5:38 pm
1 stop10h 08m
$436
ChattanoogaSan Juan
CHA - SJU
CHASJU
Chattanooga Lovell Field
Wed 9/16
12:10 pm-10:19 pm
1 stop10h 09m
San Juan Luis Munoz Marin Intl
Sat 9/26
7:00 am-1:47 pm
1 stop6h 47m
$436
ChattanoogaSan Juan
CHA - SJU
CHASJU
Chattanooga Lovell Field
Thu 9/24
4:09 pm-10:19 pm
1 stop6h 10m
San Juan Luis Munoz Marin Intl
Mon 9/28
5:59 pm-11:50 pm
1 stop5h 51m
$456
ChattanoogaSaint Thomas Island
CHA - STT
CHASTT
Chattanooga Lovell Field
Wed 12/2
8:08 pm-4:58 pm
2 stops19h 50m
Saint Thomas Island Cyril E King
Wed 12/9
2:49 pm-8:38 am
2 stops18h 49m
$458
ChattanoogaSan Juan
CHA - SJU
CHASJU
Chattanooga Lovell Field
Tue 9/15
7:12 pm-11:00 am
2 stops15h 48m
San Juan Luis Munoz Marin Intl
Wed 9/23
6:00 am-4:48 pm
2 stops10h 48m
$466
ChattanoogaMontego Bay
CHA - MBJ
CHAMBJ
Chattanooga Lovell Field
Thu 10/15
7:30 am-4:12 pm
1 stop9h 42m
Montego Bay Sangster Intl
Mon 10/19
5:13 pm-9:54 am
2 stops15h 41m
$467
ChattanoogaMontego Bay
CHA - MBJ
CHAMBJ
Chattanooga Lovell Field
Wed 9/23
7:12 pm-12:53 pm
2 stops18h 41m
Montego Bay Sangster Intl
Fri 9/25
5:16 pm-11:50 am
2 stops17h 34m
$501
Showing 1-10 of 42 resultsSorted by cheapest first
Best time to book a flight from Chattanooga to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Chattanooga with our price prediction graph.
CHA-MBJ
CHA-SJU
CHA-STT
CHA-ELH
CHA-NAS
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 Chattanooga to Caribbean Islands
CHA-zzEPX
CHA-MBJ
CHA-SJU
CHA-STT
CHA-ELH
What is the cheapest month to book a flight from Chattanooga to Caribbean Islands?
Currently, April is the cheapest month in which you can book a flight from Chattanooga to Caribbean Islands (average of $520). Flying from Chattanooga to Caribbean Islands in March is currently the most expensive (average of $797). 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 22, 2026.
Read through reviews of airlines operating flights from Chattanooga to Caribbean Islands, such as Delta and American Airlines. 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
8.5
Food
7.2
Comfort
7.8
Boarding
8.1
Overall
7.8
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Crew
8.5
Food
7.2
Comfort
7.8
Boarding
8.1
Overall
7.8
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Crew
8.5
Food
7.2
Comfort
7.8
Boarding
8.1
Overall
7.8
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Related info for your journey
Find useful and relevant information for your journey from Chattanooga to Caribbean Islands. 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 destinations
Alternative routes for Chattanooga to Caribbean Islands
See prices for flight routes from nearby airports that may be better suited for you.
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 Chattanooga to Caribbean Islands by cabin class
Find flights from Chattanooga to Caribbean Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chattanooga and Caribbean Islands flights
Browse other Chattanooga and Caribbean Islands flight options. Last updated on July 22, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chattanooga to Caribbean Islands flights
Consider these flights traveling from Chattanooga to Caribbean Islands.
Top 2 airlines flying from Chattanooga to Caribbean Islands
Discover the top 2 airlines that operate flights from Chattanooga 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 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$217 | Average$628 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$352 | Average$692 | FlexibilityNo cancel fee | On-time71% |