$140+ Cheap flights from Chattanooga (CHA) 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 4/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHA — SJU
Mar 4 — Mar 111
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chattanooga 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 Chattanooga to Caribbean
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chattanooga to CaribbeanExplore the most affordable flight options available from Chattanooga to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 2, 2026.
Explore the most affordable flight options available from Chattanooga to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/19:23 pm
CHA
- SJU
1 stop17h 08m
Multiple Airlines
Wed 3/44:06 pm
SJU
- CHA
2 stops26h 32m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/86:28 pm
CHA
- SJU
1 stop20h 03m
Multiple Airlines
Wed 3/113:22 pm
SJU
- CHA
2 stops25h 14m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/29:56 pm
CHA
- SJU
1 stop16h 30m
Multiple Airlines
Thu 2/54:40 pm
SJU
- CHA
2 stops29h 26m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/19:23 pm
CHA
- SJU
1 stop17h 08m
Multiple Airlines
Fri 3/69:11 pm
SJU
- CHA
2 stops44h 27m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/229:36 pm
CHA
- SJU
1 stop14h 13m
Multiple Airlines
Wed 3/251:45 am
SJU
- CHA
2 stops19h 01m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$336
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/33:03 pm
CHA
- SJU
1 stop17h 50m
Multiple Airlines
Sat 4/118:47 pm
SJU
- CHA
1 stop24h 19m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/86:28 pm
CHA
- SJU
1 stop20h 03m
Multiple Airlines
Wed 3/113:08 am
SJU
- CHA
2 stops13h 28m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$356
This American Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/268:06 pm
CHA
- STX
2 stops20h 21m
American Airlines
Thu 4/25:17 pm
STX
- CHA
2 stops20h 24m
American Airlines
Deal found 1/31![American Airlines logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/163:29 pm
CHA
- AUA
1 stop24h 41m
Multiple Airlines
Wed 4/293:41 pm
AUA
- CHA
1 stop29h 31m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/163:29 pm
CHA
- AUA
1 stop24h 41m
Multiple Airlines
Sat 4/253:41 pm
AUA
- CHA
1 stop28h 49m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$389
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/263:29 pm
CHA
- AUA
1 stop23h 04m
Multiple Airlines
Sat 5/23:41 pm
AUA
- CHA
1 stop29h 31m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/94:43 pm
CHA
- MBJ
1 stop19h 22m
Multiple Airlines
Thu 4/1612:00 pm
MBJ
- CHA
1 stop7h 30m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$410
Best flights from Chattanooga to CaribbeanDiscover carefully curated flight deals from Chattanooga to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 2, 2026.
Discover carefully curated flight deals from Chattanooga to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/19:23 pm
CHA
- SJU
1 stop17h 08m
Multiple Airlines
Fri 3/69:11 pm
SJU
- CHA
2 stops44h 27m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$324
This American Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/268:06 pm
CHA
- STX
2 stops20h 21m
American Airlines
Thu 4/25:17 pm
STX
- CHA
2 stops20h 24m
American Airlines
Deal found 1/31![American Airlines logo]()
$360
This Delta deal was found by Cheapflights users on 1/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/411:42 am
CHA
- SJU
1 stop8h 30m
Delta
Fri 3/66:42 pm
SJU
- CHA
1 stop5h 39m
Delta
Deal found 1/31![Delta logo]()
$426
This United Airlines deal was found by Cheapflights users on 1/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:30 am
CHA
- NAS
1 stop8h 33m
United Airlines
Wed 2/253:35 pm
NAS
- CHA
1 stop20h 41m
United Airlines
Deal found 1/30![United Airlines logo]()
$630
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Sun 3/229:36 pm
CHA
- SJU
1 stop14h 13m
Multiple Airlines
Thu 3/2612:55 pm
SJU
- CHA
1 stop7h 51m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$366
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/86:28 pm
CHA
- SJU
1 stop20h 03m
Multiple Airlines
Wed 3/113:36 pm
SJU
- CHA
1 stop25h 00m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 1/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/43:03 pm
CHA
- SJU
1 stop5h 09m
Delta
Tue 3/106:15 am
SJU
- CHA
1 stop8h 09m
Delta
Deal found 1/31![Delta logo]()
$426
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Sat 3/216:07 pm
CHA
- SJU
1 stop16h 33m
American Airlines
Tue 3/241:30 am
SJU
- CHA
1 stop10h 16m
American Airlines
Deal found 2/1![American Airlines logo]()
$456
This Delta deal was found by Cheapflights users on 1/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/411:42 am
CHA
- SJU
1 stop8h 30m
Delta
Sat 3/77:30 am
SJU
- CHA
1 stop7h 34m
Delta
Deal found 1/31![Delta logo]()
$451
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Sun 3/229:36 pm
CHA
- SJU
1 stop14h 13m
Multiple Airlines
Sat 3/283:08 am
SJU
- CHA
2 stops17h 38m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$418
This American Airlines deal was found by Cheapflights users on 2/1. 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 3/228:06 pm
CHA
- SJU
1 stop14h 34m
American Airlines
Thu 3/264:18 pm
SJU
- CHA
1 stop16h 25m
American Airlines
Deal found 2/1![American Airlines logo]()
$476
This Delta deal was found by Cheapflights users on 1/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/411:42 am
CHA
- SJU
1 stop8h 30m
Delta
Fri 3/136:15 am
SJU
- CHA
1 stop6h 55m
Delta
Deal found 1/31![Delta logo]()
$486
This American Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/197:14 pm
CHA
- STX
2 stops20h 53m
American Airlines
Thu 5/283:39 pm
STX
- CHA
2 stops21h 08m
American Airlines
Deal found 1/31![American Airlines logo]()
$500
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/309:44 am
CHA
- PUJ
1 stop5h 56m
Delta
Tue 3/315:05 pm
PUJ
- CHA
1 stop15h 54m
Delta
Deal found 2/1![Delta logo]()
$495
This American Airlines deal was found by Cheapflights users on 2/1. 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 3/189:08 am
CHA
- NAS
1 stop4h 50m
American Airlines
Wed 3/251:56 pm
NAS
- CHA
1 stop7h 55m
American Airlines
Deal found 2/1![American Airlines logo]()
$511
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/309:44 am
CHA
- PUJ
1 stop5h 56m
Delta
Wed 4/13:18 pm
PUJ
- CHA
2 stops19h 43m
Delta
Deal found 2/1![Delta logo]()
$499
This American Airlines deal was found by Cheapflights users on 1/30. 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 6/18:02 pm
CHA
- PLS
1 stop16h 25m
American Airlines
Thu 6/43:20 pm
PLS
- CHA
1 stop9h 00m
American Airlines
Deal found 1/30![American Airlines logo]()
$515
This United Airlines deal was found by Cheapflights users on 1/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/155:22 pm
CHA
- PLS
1 stop20h 33m
United Airlines
Wed 3/182:23 pm
PLS
- CHA
1 stop19h 49m
United Airlines
Deal found 1/31![United Airlines logo]()
$769
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/218:57 am
CHA
- NAS
1 stop4h 53m
Multiple Airlines
Tue 5/265:30 pm
NAS
- CHA
2 stops38h 37m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$593
This Delta deal was found by Cheapflights users on 1/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:15 am
CHA
- PLS
1 stop5h 25m
Delta
Tue 5/192:00 pm
PLS
- CHA
1 stop6h 21m
Delta
Deal found 1/31![Delta logo]()
$515
This American Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/135:00 am
CHA
- PLS
1 stop7h 00m
American Airlines
Tue 5/193:23 pm
PLS
- CHA
2 stops17h 15m
American Airlines
Deal found 1/31![American Airlines logo]()
$520
This American Airlines deal was found by Cheapflights users on 1/30. 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 3/175:35 pm
CHA
- PUJ
1 stop17h 00m
American Airlines
Tue 3/244:01 pm
PUJ
- CHA
1 stop16h 42m
American Airlines
Deal found 1/30![American Airlines logo]()
$522
This Delta deal was found by Cheapflights users on 1/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/77:05 am
CHA
- MBJ
1 stop9h 23m
Delta
Wed 4/154:32 pm
MBJ
- CHA
1 stop15h 32m
Delta
Deal found 1/31![Delta logo]()
$532
This Delta deal was found by Cheapflights users on 1/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/89:44 am
CHA
- MBJ
1 stop6h 44m
Delta
Wed 4/154:32 pm
MBJ
- CHA
1 stop15h 32m
Delta
Deal found 1/31![Delta logo]()
$532
This American Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:02 pm
CHA
- PUJ
1 stop16h 49m
American Airlines
Mon 6/14:49 pm
PUJ
- CHA
1 stop7h 31m
American Airlines
Deal found 1/31![American Airlines logo]()
$545
This Delta deal was found by Cheapflights users on 1/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/811:46 am
CHA
- MBJ
1 stop4h 42m
Delta
Thu 4/1612:44 pm
MBJ
- CHA
1 stop7h 32m
Delta
Deal found 1/31![Delta logo]()
$532
This American Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/307:51 am
CHA
- PUJ
1 stop7h 32m
American Airlines
Sun 5/312:06 pm
PUJ
- CHA
1 stop10h 12m
American Airlines
Deal found 1/31![American Airlines logo]()
$550
This Delta deal was found by Cheapflights users on 1/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/129:44 am
CHA
- MBJ
1 stop6h 44m
Delta
Wed 4/154:32 pm
MBJ
- CHA
1 stop15h 32m
Delta
Deal found 1/31![Delta logo]()
$532
This American Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/185:00 am
CHA
- PUJ
2 stops8h 30m
American Airlines
Tue 3/242:20 pm
PUJ
- CHA
2 stops18h 23m
American Airlines
Deal found 1/31![American Airlines logo]()
$559
This Delta deal was found by Cheapflights users on 1/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/75:50 am
CHA
- MBJ
1 stop10h 38m
Delta
Thu 4/1612:44 pm
MBJ
- CHA
1 stop7h 32m
Delta
Deal found 1/31![Delta logo]()
$532
Last-minute flights from Chattanooga to CaribbeanDiscover last-minute flight deals from Chattanooga to Caribbean. Data last updated February 2, 2026 and is based on user searches.
Discover last-minute flight deals from Chattanooga to Caribbean. Data last updated February 2, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/29:56 pm
CHA
- SJU
1 stop16h 30m
Multiple Airlines
Thu 2/54:40 pm
SJU
- CHA
2 stops29h 26m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/29:56 pm
CHA
- SJU
1 stop10h 51m
Multiple Airlines
Sat 2/711:49 am
SJU
- CHA
2 stops33h 49m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$372
This American Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/27:20 pm
CHA
- SJU
1 stop16h 48m
American Airlines
Sat 2/71:58 pm
SJU
- CHA
1 stop8h 49m
American Airlines
Deal found 1/31![American Airlines logo]()
$671
This Delta deal was found by Cheapflights users on 1/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/35:30 am
CHA
- SJU
1 stop8h 01m
Delta
Sat 2/77:30 am
SJU
- CHA
1 stop6h 40m
Delta
Deal found 1/31![Delta logo]()
$651
This American Airlines deal was found by Cheapflights users on 2/1. 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 2/48:00 am
CHA
- SJU
1 stop11h 50m
American Airlines
Mon 2/97:07 am
SJU
- CHA
1 stop14h 26m
American Airlines
Deal found 2/1![American Airlines logo]()
$626
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/85:30 am
CHA
- SJU
1 stop8h 01m
Delta
Fri 2/136:15 am
SJU
- CHA
1 stop7h 49m
Delta
Deal found 2/1![Delta logo]()
$586
This Delta deal was found by Cheapflights users on 1/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/169:41 am
CHA
- SJU
1 stop6h 46m
Delta
Fri 2/206:15 am
SJU
- CHA
1 stop5h 40m
Delta
Deal found 1/31![Delta logo]()
$546
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/193:33 pm
CHA
- SJU
1 stop22h 58m
Multiple Airlines
Fri 2/277:44 pm
SJU
- CHA
2 stops49h 49m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$365
This American Airlines deal was found by Cheapflights users on 2/1. 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 2/198:07 pm
CHA
- SJU
1 stop16h 46m
American Airlines
Fri 2/2712:30 pm
SJU
- CHA
1 stop12h 25m
American Airlines
Deal found 2/1![American Airlines logo]()
$556
This United Airlines deal was found by Cheapflights users on 1/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:30 am
CHA
- NAS
1 stop8h 33m
United Airlines
Wed 2/253:35 pm
NAS
- CHA
1 stop25h 12m
United Airlines
Deal found 1/31![United Airlines logo]()
$630
This American Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/235:00 am
CHA
- BGI
1 stop8h 50m
American Airlines
Fri 2/273:50 pm
BGI
- CHA
1 stop9h 05m
American Airlines
Deal found 1/31![American Airlines logo]()
$682
This American Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/255:15 am
CHA
- BGI
2 stops15h 59m
American Airlines
Sun 3/13:50 pm
BGI
- CHA
2 stops20h 56m
American Airlines
Deal found 1/31![American Airlines logo]()
$672
One-way flights from Chattanooga to CaribbeanSearch for one-way flight options from Chattanooga to Caribbean. Find affordable one-way fares based on user searches. Data last updated February 2, 2026.
Search for one-way flight options from Chattanooga to Caribbean. Find affordable one-way fares based on user searches. Data last updated February 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 4/304:11 pm
CHA
- SJU
1 stop20h 22m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Sun 2/810:52 am
CHA
- SJU
3 stops45h 55m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$216
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/31:49 pm
CHA
- SJU
1 stop6h 23m
Delta
Deal found 2/1![Delta logo]()
$243
This American Airlines deal was found by Cheapflights users on 2/1. 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 3/410:19 am
CHA
- SJU
2 stops12h 15m
American Airlines
Deal found 2/1![American Airlines logo]()
$283
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/85:30 am
CHA
- SJU
1 stop6h 36m
Delta
Deal found 2/1![Delta logo]()
$293
This American Airlines deal was found by Cheapflights users on 2/1. 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 3/29:08 am
CHA
- SJU
2 stops11h 26m
American Airlines
Deal found 2/1![American Airlines logo]()
$323
This American Airlines deal was found by Cheapflights users on 2/2. 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.
Sat 3/219:08 am
CHA
- SJU
2 stops11h 42m
American Airlines
Deal found 2/2![American Airlines logo]()
$418
Find flight deals from Chattanooga to Caribbean
Keep the following information in mind while searching for Chattanooga to Caribbean flight deals. Data was last updated February 2, 2026.
Round-trip from | $289 (Kiwi.com) |
|---|---|
One-way from | $140 (Kiwi.com) |
Popular in | April |
Cheapest in | October |
Average price | $668 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chattanooga to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 2, 2026.
Use the filters below to find and compare flights from Chattanooga to Caribbean that are best for you.
Fly from
Chattanooga
Fly to
Caribbean
Route
Depart
Return
Price
ChattanoogaSan Juan
CHA - SJU
CHASJU
Chattanooga Lovell Field
Sun 3/1
9:23 pm-3:31 pm
1 stop17h 08m
San Juan Luis Munoz Marin Intl
Fri 3/6
9:11 pm-4:38 pm
2 stops44h 27m
$324
ChattanoogaChristiansted
CHA - STX
CHASTX
Chattanooga Lovell Field
Thu 3/26
8:06 pm-4:27 pm
2 stops20h 21m
Christiansted Henry Rohlsen
Thu 4/2
5:17 pm-1:41 pm
2 stops20h 24m
$360
ChattanoogaSan Juan
CHA - SJU
CHASJU
Chattanooga Lovell Field
Sun 3/22
9:36 pm-11:49 am
1 stop14h 13m
San Juan Luis Munoz Marin Intl
Thu 3/26
12:55 pm-8:46 pm
1 stop7h 51m
$366
ChattanoogaSan Juan
CHA - SJU
CHASJU
Chattanooga Lovell Field
Sun 3/8
6:28 pm-2:31 pm
1 stop20h 03m
San Juan Luis Munoz Marin Intl
Wed 3/11
3:36 pm-4:36 pm
1 stop25h 00m
$367
ChattanoogaSan Juan
CHA - SJU
CHASJU
Chattanooga Lovell Field
Sun 3/22
9:36 pm-11:49 am
1 stop14h 13m
San Juan Luis Munoz Marin Intl
Sat 3/28
3:08 am-8:46 pm
2 stops17h 38m
$418
ChattanoogaSan Juan
CHA - SJU
CHASJU
Chattanooga Lovell Field
Wed 3/4
11:42 am-9:12 pm
1 stop8h 30m
San Juan Luis Munoz Marin Intl
Fri 3/6
6:42 pm-11:21 pm
1 stop5h 39m
$426
ChattanoogaSan Juan
CHA - SJU
CHASJU
Chattanooga Lovell Field
Wed 3/4
3:03 pm-9:12 pm
1 stop5h 09m
San Juan Luis Munoz Marin Intl
Tue 3/10
6:15 am-2:24 pm
1 stop8h 09m
$426
ChattanoogaSan Juan
CHA - SJU
CHASJU
Chattanooga Lovell Field
Wed 3/4
11:42 am-9:12 pm
1 stop8h 30m
San Juan Luis Munoz Marin Intl
Sat 3/7
7:30 am-2:04 pm
1 stop7h 34m
$451
ChattanoogaSan Juan
CHA - SJU
CHASJU
Chattanooga Lovell Field
Sat 3/21
6:07 pm-10:40 am
1 stop16h 33m
San Juan Luis Munoz Marin Intl
Tue 3/24
1:30 am-11:46 am
1 stop10h 16m
$456
ChattanoogaSan Juan
CHA - SJU
CHASJU
Chattanooga Lovell Field
Sun 3/22
8:06 pm-10:40 am
1 stop14h 34m
San Juan Luis Munoz Marin Intl
Thu 3/26
4:18 pm-8:43 am
1 stop16h 25m
$476
Showing 1-10 of 39 results
Best time to book a flight from Chattanooga to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Chattanooga with our price prediction graph.
CHA-SJU
CHA-NAS
CHA-BGI
CHA-STX
CHA-PUJ
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
CHA-0CB
CHA-SJU
CHA-NAS
CHA-BGI
CHA-STX
What is the cheapest month to book a flight from Chattanooga to Caribbean?
Currently, August is the cheapest month in which you can book a flight from Chattanooga to Caribbean (average of $86). Flying from Chattanooga to Caribbean in May is currently the most expensive (average of $385). 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
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated February 2, 2026.
Peruse reviews from past customers who have flown with Delta and American Airlines from Chattanooga to Caribbean to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.2
Comfort
7.9
Overall
7.9
Crew
8.5
Entertainment
7.8
Boarding
8.1
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Food
7.2
Comfort
7.9
Overall
7.9
Crew
8.5
Entertainment
7.8
Boarding
8.1
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Food
7.2
Comfort
7.9
Overall
7.9
Crew
8.5
Entertainment
7.8
Boarding
8.1
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Related info for your journey
Find useful and relevant information for your journey from Chattanooga 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 for Chattanooga to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Top 2 airlines flying from Chattanooga to Caribbean
Discover the top 2 airlines that operate flights from Chattanooga to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$335 | Average$632 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$401 | Average$686 | FlexibilityNo cancel fee | On-time71% |