$147+ 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 6/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHA — SJU
May 9 — May 161
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 April 9, 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 April 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/74:11 pm
CHA
- SJU
1 stop26h 48m
Multiple Airlines
Sat 5/168:04 pm
SJU
- CHA
1 stop25h 08m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/104:11 pm
CHA
- SJU
1 stop26h 48m
Multiple Airlines
Sat 5/168:04 pm
SJU
- CHA
1 stop25h 08m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/74:11 pm
CHA
- SJU
1 stop26h 48m
Multiple Airlines
Thu 5/1411:00 am
SJU
- CHA
1 stop10h 12m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/248:57 am
CHA
- SJU
1 stop10h 02m
Multiple Airlines
Sat 5/306:00 am
SJU
- CHA
1 stop26h 07m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/104:11 pm
CHA
- SJU
1 stop26h 48m
Multiple Airlines
Thu 5/1411:00 am
SJU
- CHA
1 stop10h 12m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/83:29 pm
CHA
- SJU
1 stop18h 49m
Multiple Airlines
Sat 5/168:04 pm
SJU
- CHA
1 stop25h 08m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/43:29 pm
CHA
- SJU
2 stops25h 14m
Multiple Airlines
Sat 5/168:04 pm
SJU
- CHA
1 stop25h 08m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 4/233:29 pm
CHA
- STT
1 stop24h 46m
Multiple Airlines
Sun 4/2612:25 pm
STT
- CHA
1 stop8h 05m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 4/238:04 pm
CHA
- STT
2 stops17h 11m
American Airlines
Mon 4/272:30 pm
STT
- CHA
1 stop7h 15m
American Airlines
Deal found 4/8![American Airlines logo]()
$390
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/178:04 pm
CHA
- MBJ
2 stops16h 47m
American Airlines
Sat 5/232:08 pm
MBJ
- CHA
1 stop8h 51m
American Airlines
Deal found 4/6![American Airlines logo]()
$392
This American Airlines deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 7/255:52 pm
CHA
- MBJ
1 stop20h 31m
American Airlines
Sat 8/12:25 pm
MBJ
- CHA
1 stop8h 34m
American Airlines
Deal found 4/9![American Airlines logo]()
$394
This American Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:09 pm
CHA
- STT
2 stops19h 06m
American Airlines
Mon 4/275:05 pm
STT
- CHA
2 stops19h 22m
American Airlines
Deal found 4/7![American Airlines logo]()
$395
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 April 9, 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 April 9, 2026.
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/178:04 pm
CHA
- MBJ
2 stops16h 47m
American Airlines
Sat 5/232:08 pm
MBJ
- CHA
1 stop8h 51m
American Airlines
Deal found 4/6![American Airlines logo]()
$392
This Delta deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 6/165:35 am
CHA
- SJU
1 stop6h 09m
Delta
Thu 6/186:00 am
SJU
- CHA
1 stop9h 20m
Delta
Deal found 4/8![Delta logo]()
$436
This United Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/210:42 am
CHA
- SJU
1 stop9h 52m
United Airlines
Tue 5/57:00 am
SJU
- CHA
1 stop8h 43m
United Airlines
Deal found 4/8![United Airlines logo]()
$446
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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
- SJU
1 stop6h 58m
Multiple Airlines
Wed 5/276:00 am
SJU
- CHA
1 stop26h 07m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$475
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/188:04 pm
CHA
- MBJ
2 stops16h 47m
American Airlines
Sat 5/2312:47 pm
MBJ
- CHA
1 stop9h 12m
American Airlines
Deal found 4/6![American Airlines logo]()
$392
This American Airlines deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 7/255:52 pm
CHA
- MBJ
1 stop20h 31m
American Airlines
Sat 8/12:25 pm
MBJ
- CHA
1 stop8h 34m
American Airlines
Deal found 4/9![American Airlines logo]()
$394
This Delta deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 8/15:35 am
CHA
- STX
1 stop8h 22m
Delta
Sat 8/292:30 pm
STX
- CHA
1 stop9h 21m
Delta
Deal found 4/8![Delta logo]()
$446
This United Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:30 am
CHA
- STT
1 stop9h 01m
United Airlines
Thu 4/232:10 pm
STT
- CHA
1 stop10h 13m
United Airlines
Deal found 4/5![United Airlines logo]()
$460
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/69:43 pm
CHA
- NAS
2 stops17h 02m
Multiple Airlines
Sat 7/114:00 pm
NAS
- CHA
1 stop16h 09m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$502
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 6/108:17 am
CHA
- SJU
1 stop8h 29m
Delta
Tue 6/306:00 am
SJU
- CHA
1 stop8h 05m
Delta
Deal found 4/6![Delta logo]()
$461
This American Airlines deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/258:11 pm
CHA
- SJU
2 stops13h 28m
American Airlines
Fri 5/295:30 am
SJU
- CHA
1 stop17h 29m
American Airlines
Deal found 4/4![American Airlines logo]()
$436
This United Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:30 am
CHA
- STT
1 stop9h 01m
United Airlines
Thu 4/301:22 pm
STT
- CHA
1 stop9h 41m
United Airlines
Deal found 4/7![United Airlines logo]()
$480
This United Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/187:15 am
CHA
- MBJ
1 stop7h 15m
United Airlines
Sat 5/232:40 pm
MBJ
- CHA
1 stop7h 26m
United Airlines
Deal found 4/6![United Airlines logo]()
$493
This American Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 8/16:15 am
CHA
- STX
2 stops14h 40m
American Airlines
Mon 8/311:37 pm
STX
- CHA
2 stops20h 57m
American Airlines
Deal found 4/8![American Airlines logo]()
$450
This American Airlines deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:09 pm
CHA
- STX
2 stops19h 06m
American Airlines
Mon 5/45:14 pm
STX
- CHA
2 stops20h 43m
American Airlines
Deal found 4/9![American Airlines logo]()
$450
This United Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:30 am
CHA
- SJU
1 stop8h 14m
United Airlines
Fri 4/243:56 pm
SJU
- CHA
1 stop8h 27m
United Airlines
Deal found 4/5![United Airlines logo]()
$516
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/308:11 pm
CHA
- SJU
2 stops13h 28m
American Airlines
Tue 6/211:55 am
SJU
- CHA
2 stops12h 24m
American Airlines
Deal found 4/6![American Airlines logo]()
$496
This United Airlines deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2610:50 am
CHA
- SJU
1 stop9h 44m
United Airlines
Thu 4/302:55 pm
SJU
- CHA
1 stop8h 08m
United Airlines
Deal found 4/4![United Airlines logo]()
$571
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 6/108:11 pm
CHA
- SJU
2 stops13h 28m
American Airlines
Mon 6/2912:44 am
SJU
- CHA
1 stop11h 07m
American Airlines
Deal found 4/6![American Airlines logo]()
$501
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/85:40 am
CHA
- BGI
1 stop8h 40m
Delta
Mon 5/113:30 pm
BGI
- CHA
1 stop8h 23m
Delta
Deal found 4/7![Delta logo]()
$752
This American Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 5/38:04 pm
CHA
- MBJ
2 stops16h 47m
American Airlines
Mon 5/1110:17 am
MBJ
- CHA
2 stops11h 20m
American Airlines
Deal found 4/8![American Airlines logo]()
$510
This United Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/36:00 am
CHA
- NAS
1 stop8h 57m
United Airlines
Thu 8/62:53 pm
NAS
- CHA
1 stop8h 13m
United Airlines
Deal found 4/8![United Airlines logo]()
$636
This American Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 4/238:04 pm
CHA
- STT
1 stop14h 43m
American Airlines
Mon 4/272:30 pm
STT
- CHA
1 stop7h 15m
American Airlines
Deal found 4/8![American Airlines logo]()
$511
This American Airlines deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/287:00 am
CHA
- STT
1 stop7h 50m
American Airlines
Sat 5/25:05 pm
STT
- CHA
1 stop6h 54m
American Airlines
Deal found 4/4![American Airlines logo]()
$523
This United Airlines deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/106:30 am
CHA
- PUJ
1 stop8h 42m
United Airlines
Thu 5/142:20 pm
PUJ
- CHA
1 stop8h 43m
United Airlines
Deal found 4/4![United Airlines logo]()
$746
This American Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/95:00 am
CHA
- SJU
2 stops9h 52m
American Airlines
Sat 5/163:44 pm
SJU
- CHA
1 stop8h 15m
American Airlines
Deal found 4/7![American Airlines logo]()
$546
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 10/35:30 am
CHA
- BGI
1 stop8h 50m
Delta
Sat 10/103:30 pm
BGI
- CHA
1 stop8h 21m
Delta
Deal found 4/9![Delta logo]()
$1,088
This American Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 8/16:15 am
CHA
- STX
1 stop14h 40m
American Airlines
Sat 8/291:37 pm
STX
- CHA
2 stops20h 57m
American Airlines
Deal found 4/8![American Airlines logo]()
$547
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/295:00 am
CHA
- NAS
2 stops8h 54m
American Airlines
Wed 6/312:16 pm
NAS
- CHA
1 stop9h 39m
American Airlines
Deal found 4/6![American Airlines logo]()
$575
This American Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:36 pm
CHA
- STX
2 stops20h 24m
American Airlines
Sat 8/13:50 pm
STX
- CHA
2 stops21h 04m
American Airlines
Deal found 4/5![American Airlines logo]()
$577
Last-minute flights from Chattanooga to Caribbean IslandsDiscover last-minute flight deals from Chattanooga to Caribbean Islands. Data last updated April 9, 2026 and is based on user searches.
Discover last-minute flight deals from Chattanooga to Caribbean Islands. Data last updated April 9, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:09 pm
CHA
- STT
2 stops19h 06m
American Airlines
Mon 4/275:05 pm
STT
- CHA
2 stops19h 22m
American Airlines
Deal found 4/7![American Airlines logo]()
$395
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 4/233:29 pm
CHA
- STT
1 stop24h 46m
Multiple Airlines
Sun 4/2612:25 pm
STT
- CHA
1 stop8h 05m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 4/238:04 pm
CHA
- STT
2 stops17h 11m
American Airlines
Mon 4/272:30 pm
STT
- CHA
1 stop7h 15m
American Airlines
Deal found 4/8![American Airlines logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/43:29 pm
CHA
- SJU
2 stops25h 14m
Multiple Airlines
Sat 5/168:04 pm
SJU
- CHA
1 stop25h 08m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/74:11 pm
CHA
- SJU
1 stop26h 48m
Multiple Airlines
Sat 5/168:04 pm
SJU
- CHA
1 stop25h 08m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/74:11 pm
CHA
- SJU
1 stop26h 48m
Multiple Airlines
Thu 5/1411:00 am
SJU
- CHA
1 stop10h 12m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/83:29 pm
CHA
- SJU
1 stop18h 49m
Multiple Airlines
Sat 5/168:04 pm
SJU
- CHA
1 stop25h 08m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/104:11 pm
CHA
- SJU
1 stop26h 48m
Multiple Airlines
Sat 5/168:04 pm
SJU
- CHA
1 stop25h 08m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/104:11 pm
CHA
- SJU
1 stop26h 48m
Multiple Airlines
Thu 5/1411:00 am
SJU
- CHA
1 stop10h 12m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$276
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/178:04 pm
CHA
- MBJ
2 stops16h 47m
American Airlines
Sat 5/232:08 pm
MBJ
- CHA
1 stop8h 51m
American Airlines
Deal found 4/6![American Airlines logo]()
$392
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/248:57 am
CHA
- SJU
1 stop10h 02m
Multiple Airlines
Sat 5/306:00 am
SJU
- CHA
1 stop26h 07m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/248:57 am
CHA
- PUJ
1 stop28h 33m
Multiple Airlines
Fri 5/291:10 pm
PUJ
- CHA
1 stop8h 05m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$441
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 April 9, 2026.
Search for one-way flight options from Chattanooga to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated April 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 6/288:59 am
CHA
- SJU
1 stop30h 59m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/248:57 am
CHA
- NAS
1 stop5h 48m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$162
This Delta deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 6/268:17 am
CHA
- SJU
1 stop8h 29m
Delta
Deal found 4/8![Delta logo]()
$298
This American Airlines deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/1910:18 am
CHA
- NAS
1 stop6h 10m
American Airlines
Deal found 4/9![American Airlines logo]()
$298
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 8/18:10 pm
CHA
- STT
2 stops16h 40m
American Airlines
Deal found 4/6![American Airlines logo]()
$311
This American Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 6/274:18 pm
CHA
- SJU
1 stop12h 07m
American Airlines
Deal found 4/7![American Airlines logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 6/2610:04 pm
CHA
- SJU
3 stops41h 54m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 6/268:11 pm
CHA
- SJU
2 stops13h 28m
American Airlines
Deal found 4/8![American Airlines logo]()
$435
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 April 9, 2026.
Round-trip from | $249 (Kiwi.com) |
|---|---|
One-way from | $147 (Kiwi.com) |
Popular in | February |
Cheapest in | October |
Average price | $615 |
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 April 9, 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
ChattanoogaMontego Bay
CHA - MBJ
CHAMBJ
Chattanooga Lovell Field
Sun 5/17
8:04 pm-11:51 am
2 stops16h 47m
Montego Bay Sangster Intl
Sat 5/23
2:08 pm-11:59 pm
1 stop8h 51m
$392
ChattanoogaMontego Bay
CHA - MBJ
CHAMBJ
Chattanooga Lovell Field
Mon 5/18
8:04 pm-11:51 am
2 stops16h 47m
Montego Bay Sangster Intl
Sat 5/23
12:47 pm-10:59 pm
1 stop9h 12m
$392
ChattanoogaMontego Bay
CHA - MBJ
CHAMBJ
Chattanooga Lovell Field
Sat 7/25
5:52 pm-1:23 pm
1 stop20h 31m
Montego Bay Sangster Intl
Sat 8/1
2:25 pm-11:59 pm
1 stop8h 34m
$394
ChattanoogaSan Juan
CHA - SJU
CHASJU
Chattanooga Lovell Field
Tue 6/16
5:35 am-11:44 am
1 stop6h 09m
San Juan Luis Munoz Marin Intl
Thu 6/18
6:00 am-3:20 pm
1 stop9h 20m
$436
ChattanoogaSan Juan
CHA - SJU
CHASJU
Chattanooga Lovell Field
Mon 5/25
8:11 pm-9:39 am
2 stops13h 28m
San Juan Luis Munoz Marin Intl
Fri 5/29
5:30 am-10:59 pm
1 stop17h 29m
$436
ChattanoogaSan Juan
CHA - SJU
CHASJU
Chattanooga Lovell Field
Sat 5/2
10:42 am-8:34 pm
1 stop9h 52m
San Juan Luis Munoz Marin Intl
Tue 5/5
7:00 am-3:43 pm
1 stop8h 43m
$446
ChattanoogaChristiansted
CHA - STX
CHASTX
Chattanooga Lovell Field
Sat 8/1
5:35 am-1:57 pm
1 stop8h 22m
Christiansted Henry Rohlsen
Sat 8/29
2:30 pm-11:51 pm
1 stop9h 21m
$446
ChattanoogaChristiansted
CHA - STX
CHASTX
Chattanooga Lovell Field
Sat 8/1
6:15 am-8:55 pm
2 stops14h 40m
Christiansted Henry Rohlsen
Mon 8/31
1:37 pm-10:34 am
2 stops20h 57m
$450
ChattanoogaChristiansted
CHA - STX
CHASTX
Chattanooga Lovell Field
Fri 5/1
6:09 pm-1:15 pm
2 stops19h 06m
Christiansted Henry Rohlsen
Mon 5/4
5:14 pm-1:57 pm
2 stops20h 43m
$450
ChattanoogaSaint Thomas Island
CHA - STT
CHASTT
Chattanooga Lovell Field
Mon 4/20
6:30 am-3:31 pm
1 stop9h 01m
Saint Thomas Island Cyril E King
Thu 4/23
2:10 pm-12:23 am
1 stop10h 13m
$460
Showing 1-10 of 38 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-NAS
CHA-SJU
CHA-STT
CHA-MBJ
CHA-STX
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-NAS
CHA-SJU
CHA-STT
CHA-MBJ
What is the cheapest month to book a flight from Chattanooga to Caribbean Islands?
Currently, August is the cheapest month in which you can book a flight from Chattanooga to Caribbean Islands (average of $86). Flying from Chattanooga to Caribbean Islands in March is currently the most expensive (average of $419). 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 April 9, 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
Entertainment
7.8
Overall
7.9
Boarding
8.1
Comfort
7.9
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Entertainment
7.8
Overall
7.9
Boarding
8.1
Comfort
7.9
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Entertainment
7.8
Overall
7.9
Boarding
8.1
Comfort
7.9
Food
7.2
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 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 April 9, 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 April 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$396 | Average$574 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$421 | Average$705 | FlexibilityNo cancel fee | On-time71% |