$236+ Cheap flights from Chattanooga (CHA) to Caribbean Islands
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHA — SJU
Oct 17 — Oct 241
Round-trip
1 adult, Economy
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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
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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 September 17, 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 September 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/298:59 am -
1 stop27h 47m
Wed 11/48:45 am -
1 stop25h 34m
Deal found 9/14![Multiple Airlines logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 11/19:29 am -
1 stop26h 56m
Wed 11/48:45 am -
1 stop25h 34m
Deal found 9/15![Multiple Airlines logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/298:59 am -
1 stop27h 47m
Sat 11/73:20 pm -
1 stop18h 49m
Deal found 9/14![Multiple Airlines logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 11/510:09 am -
1 stop26h 16m
Sat 11/73:20 pm -
1 stop18h 49m
Deal found 9/15![Multiple Airlines logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 11/19:29 am -
1 stop26h 56m
Sat 11/73:20 pm -
1 stop18h 49m
Deal found 9/14![Multiple Airlines logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 -
1 stop27h 41m
Sat 10/244:00 pm -
1 stop16h 39m
Deal found 9/14![Multiple Airlines logo]()
$442
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 12/27:08 pm -
2 stops16h 09m
Wed 12/91:07 pm -
2 stops11h 35m
Deal found 9/15![American Airlines logo]()
$443
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/159:04 am -
1 stop4h 46m
Sat 10/244:00 pm -
1 stop16h 39m
Deal found 9/14![Multiple Airlines logo]()
$451
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 -
1 stop27h 41m
Wed 10/214:00 pm -
1 stop16h 09m
Deal found 9/14![Multiple Airlines logo]()
$468
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Thu 12/35:05 pm -
2 stops18h 12m
Sun 12/131:07 pm -
2 stops21h 42m
Deal found 9/17![American Airlines logo]()
$472
This American Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 12/46:08 pm -
2 stops17h 09m
Sun 12/131:07 pm -
2 stops21h 42m
Deal found 9/16![American Airlines logo]()
$473
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/159:04 am -
1 stop4h 46m
Wed 10/214:00 pm -
1 stop16h 09m
Deal found 9/14![Multiple Airlines logo]()
$476
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 September 17, 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 September 17, 2026.
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/317:19 am -
1 stop9h 29m
Tue 11/33:59 pm -
1 stop5h 36m
Deal found 9/14![Delta logo]()
$436
This American Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/68:03 pm -
1 stop16h 10m
Wed 12/91:07 pm -
2 stops20h 25m
Deal found 9/12![American Airlines logo]()
$502
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 11/17:00 am -
1 stop8h 36m
Tue 11/108:25 am -
1 stop9h 45m
Deal found 9/15![United Airlines logo]()
$506
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/302:50 pm -
1 stop7h 28m
Tue 11/33:59 pm -
1 stop5h 36m
Deal found 9/14![Delta logo]()
$436
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 2/41:30 pm -
1 stop9h 20m
Mon 2/86:15 am -
1 stop7h 51m
Deal found 9/16![Delta logo]()
$456
This American Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 2/47:14 pm -
2 stops13h 24m
Mon 2/82:04 pm -
1 stop10h 26m
Deal found 9/16![American Airlines logo]()
$516
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/178:20 am -
1 stop8h 28m
Sat 10/242:59 pm -
1 stop7h 48m
Deal found 9/16![Delta logo]()
$456
This United Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/286:50 am -
1 stop6h 58m
Wed 11/42:54 pm -
1 stop22h 20m
Deal found 9/13![United Airlines logo]()
$599
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Thu 11/58:03 pm -
2 stops12h 39m
Mon 11/93:53 pm -
1 stop8h 50m
Deal found 9/17![American Airlines logo]()
$566
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 12/35:05 pm -
2 stops20h 18m
Sun 12/131:07 pm -
2 stops21h 42m
Deal found 9/14![American Airlines logo]()
$576
This American Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 12/26:05 am -
1 stop6h 08m
Wed 12/93:15 pm -
2 stops22h 30m
Deal found 9/12![American Airlines logo]()
$581
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/145:35 am -
1 stop8h 19m
Tue 10/203:19 pm -
1 stop8h 20m
Deal found 9/14![Delta logo]()
$608
This United Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 2/76:45 am -
1 stop8h 35m
Tue 2/93:00 pm -
1 stop27h 58m
Deal found 9/12![United Airlines logo]()
$757
This American Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 3/18:15 pm -
1 stop18h 09m
Fri 3/54:53 pm -
1 stop16h 50m
Deal found 9/12![American Airlines logo]()
$584
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 1/137:15 am -
1 stop6h 15m
Sun 1/176:10 pm -
1 stop14h 56m
Deal found 9/16![Delta logo]()
$611
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 2/16:46 pm -
1 stop16h 03m
Fri 2/512:55 pm -
1 stop30h 03m
Deal found 9/14![United Airlines logo]()
$762
This American Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 12/116:20 am -
1 stop4h 58m
Wed 12/162:18 pm -
1 stop9h 21m
Deal found 9/16![American Airlines logo]()
$598
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 1/137:00 am -
1 stop8h 15m
Sat 1/166:10 pm -
1 stop14h 56m
Deal found 9/16![Delta logo]()
$611
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 2/16:46 pm -
1 stop17h 27m
Fri 2/52:54 pm -
1 stop26h 04m
Deal found 9/16![United Airlines logo]()
$767
This American Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 12/16:20 am -
1 stop5h 01m
Mon 12/711:45 am -
1 stop4h 58m
Deal found 9/16![American Airlines logo]()
$612
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 1/86:00 am -
2 stops9h 15m
Tue 1/121:20 pm -
2 stops19h 46m
Deal found 9/16![Delta logo]()
$615
This United Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 12/66:45 pm -
1 stop19h 15m
Thu 12/104:10 pm -
1 stop27h 00m
Deal found 9/13![United Airlines logo]()
$770
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 1/76:00 am -
2 stops9h 15m
Tue 1/121:20 pm -
2 stops19h 46m
Deal found 9/16![Delta logo]()
$615
This American Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:08 pm -
2 stops20h 39m
Sat 11/145:59 pm -
2 stops19h 46m
Deal found 9/13![American Airlines logo]()
$620
This United Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 2/16:46 pm -
1 stop18h 31m
Fri 2/52:23 pm -
1 stop27h 35m
Deal found 9/12![United Airlines logo]()
$795
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 1/106:00 am -
2 stops9h 15m
Sat 1/166:10 pm -
1 stop14h 56m
Deal found 9/16![Delta logo]()
$615
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 2/225:00 am -
1 stop7h 24m
Mon 3/111:17 am -
1 stop11h 38m
Deal found 9/15![American Airlines logo]()
$651
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 2/26:46 pm -
1 stop16h 03m
Fri 2/512:55 pm -
1 stop30h 03m
Deal found 9/16![United Airlines logo]()
$802
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/305:00 am -
1 stop8h 31m
Fri 11/63:07 pm -
1 stop10h 13m
Deal found 9/15![American Airlines logo]()
$655
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/316:50 am -
1 stop7h 05m
Sat 11/72:23 pm -
1 stop26h 57m
Deal found 9/16![United Airlines logo]()
$816
Last-minute flights from Chattanooga to Caribbean IslandsDiscover last-minute flight deals from Chattanooga to Caribbean Islands. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chattanooga to Caribbean Islands. Data last updated September 17, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/19:04 am -
1 stop28h 38m
Mon 10/511:44 am -
2 stops45h 55m
Deal found 9/16![Multiple Airlines logo]()
$508
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/89:04 am -
1 stop28h 27m
Thu 10/152:51 pm -
2 stops48h 47m
Deal found 9/13![Multiple Airlines logo]()
$401
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/159:04 am -
1 stop4h 46m
Sat 10/244:00 pm -
1 stop16h 39m
Deal found 9/14![Multiple Airlines logo]()
$451
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/159:04 am -
1 stop4h 46m
Wed 10/214:00 pm -
1 stop16h 09m
Deal found 9/14![Multiple Airlines logo]()
$476
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/178:20 am -
1 stop8h 28m
Sat 10/242:59 pm -
1 stop7h 48m
Deal found 9/16![Delta logo]()
$456
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 -
1 stop27h 41m
Sat 10/244:00 pm -
1 stop16h 39m
Deal found 9/14![Multiple Airlines logo]()
$442
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 -
1 stop27h 41m
Wed 10/214:00 pm -
1 stop16h 09m
Deal found 9/14![Multiple Airlines logo]()
$468
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/298:59 am -
1 stop27h 47m
Wed 11/48:45 am -
1 stop25h 34m
Deal found 9/14![Multiple Airlines logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/298:59 am -
1 stop27h 47m
Sat 11/73:20 pm -
1 stop18h 49m
Deal found 9/14![Multiple Airlines logo]()
$256
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/302:50 pm -
1 stop7h 28m
Tue 11/33:59 pm -
1 stop5h 36m
Deal found 9/14![Delta logo]()
$436
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/304:00 pm -
1 stop6h 18m
Tue 11/106:55 pm -
1 stop5h 59m
Deal found 9/15![Delta logo]()
$446
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/304:00 pm -
1 stop6h 18m
Sun 11/86:59 pm -
1 stop5h 40m
Deal found 9/15![Delta logo]()
$501
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 September 17, 2026.
Search for one-way flight options from Chattanooga to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
This American Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/86:00 am -
1 stop6h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![American Airlines logo]()
$274
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/127:59 pm -
2 stops19h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![American Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/123:13 pm -
1 stop25h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Multiple Airlines logo]()
$362
This Justfly.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/236:34 am -
2 stops9h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![WestJet logo]()
$1,956
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 September 17, 2026.
Round-trip from | $236 (Kiwi.com) |
|---|---|
One-way from | $130 (Kiwi.com) |
Popular in | March |
Cheapest in | October |
Average price | $596 |
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 7,457,451 searches. Data last updated September 17, 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
Quickest round-trip
ChattanoogaSan Juan
CHA Chattanooga Lovell Field - SJU San Juan Luis Munoz Marin Intl
CHASJU
Chattanooga Lovell Field
Fri 1/8
6:00 am-1:13 pm
1 stop6h 13m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$274
ChattanoogaPunta Cana
CHA Chattanooga Lovell Field - PUJ Punta Cana
CHAPUJ
Chattanooga Lovell Field
Mon 10/12
7:59 pm-3:04 pm
2 stops19h 05m
Punta Cana
Wed 12/31
12:00 am-11:30 pm
Nonstop0h 00m
$334
ChattanoogaPunta Cana
CHA Chattanooga Lovell Field - PUJ Punta Cana
CHAPUJ
Chattanooga Lovell Field
Mon 10/12
3:13 pm-4:40 pm
1 stop25h 27m
Punta Cana
Wed 12/31
12:00 am-11:30 pm
Nonstop0h 00m
$362
ChattanoogaSan Juan
CHA Chattanooga Lovell Field - SJU San Juan Luis Munoz Marin Intl
CHASJU
Chattanooga Lovell Field
Sat 10/31
7:19 am-4:48 pm
1 stop9h 29m
San Juan Luis Munoz Marin Intl
Tue 11/3
3:59 pm-8:35 pm
1 stop5h 36m
$436
ChattanoogaSan Juan
CHA Chattanooga Lovell Field - SJU San Juan Luis Munoz Marin Intl
CHASJU
Chattanooga Lovell Field
Fri 10/30
2:50 pm-10:18 pm
1 stop7h 28m
San Juan Luis Munoz Marin Intl
Tue 11/3
3:59 pm-8:35 pm
1 stop5h 36m
$436
ChattanoogaSan Juan
CHA Chattanooga Lovell Field - SJU San Juan Luis Munoz Marin Intl
CHASJU
Chattanooga Lovell Field
Thu 2/4
1:30 pm-11:50 pm
1 stop9h 20m
San Juan Luis Munoz Marin Intl
Mon 2/8
6:15 am-1:06 pm
1 stop7h 51m
$456
ChattanoogaSan Juan
CHA Chattanooga Lovell Field - SJU San Juan Luis Munoz Marin Intl
CHASJU
Chattanooga Lovell Field
Sat 10/17
8:20 am-4:48 pm
1 stop8h 28m
San Juan Luis Munoz Marin Intl
Sat 10/24
2:59 pm-10:47 pm
1 stop7h 48m
$456
ChattanoogaSaint Thomas Island
CHA Chattanooga Lovell Field - STT Saint Thomas Island Cyril E King
CHASTT
Chattanooga Lovell Field
Sun 12/6
8:03 pm-1:13 pm
1 stop16h 10m
Saint Thomas Island Cyril E King
Wed 12/9
1:07 pm-8:32 am
2 stops20h 25m
$502
ChattanoogaSan Juan
CHA Chattanooga Lovell Field - SJU San Juan Luis Munoz Marin Intl
CHASJU
Chattanooga Lovell Field
Sun 11/1
7:00 am-4:36 pm
1 stop8h 36m
San Juan Luis Munoz Marin Intl
Tue 11/10
8:25 am-5:10 pm
1 stop9h 45m
$506
ChattanoogaSan Juan
CHA Chattanooga Lovell Field - SJU San Juan Luis Munoz Marin Intl
CHASJU
Chattanooga Lovell Field
Thu 2/4
7:14 pm-9:38 am
2 stops13h 24m
San Juan Luis Munoz Marin Intl
Mon 2/8
2:04 pm-11:30 pm
1 stop10h 26m
$516
Showing 1-10 of 34 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-SJU
CHA-NAS
CHA-STT
CHA-PUJ
CHA-MBJ
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-SJU
CHA-NAS
CHA-STT
CHA-PUJ
What is the cheapest month to book a flight from Chattanooga to Caribbean Islands?
Currently, July is the cheapest month in which you can book a flight from Chattanooga to Caribbean Islands (average of $622). Flying from Chattanooga to Caribbean Islands in October is currently the most expensive (average of $810). 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 September 17, 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
Overall
7.8
Comfort
7.8
Entertainment
7.8
Food
7.2
Boarding
8.1
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Crew
8.5
Overall
7.8
Comfort
7.8
Entertainment
7.8
Food
7.2
Boarding
8.1
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Crew
8.5
Overall
7.8
Comfort
7.8
Entertainment
7.8
Food
7.2
Boarding
8.1
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
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.
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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 September 17, 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 7,457,451 searches. Data last updated September 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$217 | Average$680 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$352 | Average$702 | FlexibilityNo cancel fee | On-time71% |