$121+ Cheap flights from Charlottesville (CHO) 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — SJU
Mar 18 — Mar 251
1 adult, Economy
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Find cheap flights from Charlottesville 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
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Cheapest flights from Charlottesville to CaribbeanExplore the most affordable flight options available from Charlottesville to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 16, 2026.
Explore the most affordable flight options available from Charlottesville to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 16, 2026.
This United Airlines deal was found by Cheapflights users on 2/15. 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.
Mon 4/136:20 am
CHO
- SJU
1 stop6h 14m
United Airlines
Wed 4/151:00 am
SJU
- CHO
2 stops8h 58m
United Airlines
Deal found 2/15![United Airlines logo]()
$260
This American Airlines deal was found by Cheapflights users on 2/14. 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.
Wed 3/44:55 pm
CHO
- STT
2 stops18h 17m
American Airlines
Wed 3/114:42 pm
STT
- CHO
1 stop15h 45m
American Airlines
Deal found 2/14![American Airlines logo]()
$260
This United Airlines deal was found by Cheapflights users on 2/14. 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.
Thu 3/56:45 am
CHO
- STT
1 stop8h 33m
United Airlines
Wed 3/1112:02 pm
STT
- CHO
1 stop7h 40m
United Airlines
Deal found 2/14![United Airlines logo]()
$296
This American Airlines deal was found by Cheapflights users on 2/12. 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.
Thu 3/54:20 pm
CHO
- GCM
2 stops19h 45m
American Airlines
Mon 3/92:35 pm
GCM
- CHO
2 stops22h 04m
American Airlines
Deal found 2/12![American Airlines logo]()
$312
This American Airlines deal was found by Cheapflights users on 2/15. 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 3/97:57 pm
CHO
- MBJ
2 stops17h 30m
American Airlines
Fri 3/1310:07 am
MBJ
- CHO
2 stops21h 20m
American Airlines
Deal found 2/15![American Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 2/14. 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.
Wed 4/226:07 pm
CHO
- MBJ
2 stops18h 44m
American Airlines
Sun 4/2612:56 pm
MBJ
- CHO
2 stops18h 43m
American Airlines
Deal found 2/14![American Airlines logo]()
$322
This United Airlines deal was found by Cheapflights users on 2/15. 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.
Thu 3/58:29 pm
CHO
- GCM
2 stops16h 46m
United Airlines
Mon 3/91:25 pm
GCM
- CHO
2 stops19h 27m
United Airlines
Deal found 2/15![United Airlines logo]()
$328
This American Airlines deal was found by Cheapflights users on 2/12. 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.
Sat 2/217:57 pm
CHO
- PUJ
1 stop14h 37m
American Airlines
Tue 3/35:41 pm
PUJ
- CHO
1 stop17h 06m
American Airlines
Deal found 2/12![American Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 2/12. 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.
Sat 4/116:20 am
CHO
- NAS
1 stop5h 35m
United Airlines
Wed 4/153:59 pm
NAS
- CHO
1 stop8h 37m
United Airlines
Deal found 2/12![United Airlines logo]()
$336
This American Airlines deal was found by Cheapflights users on 2/12. 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.
Sat 4/118:03 pm
CHO
- NAS
2 stops14h 56m
American Airlines
Wed 4/155:26 pm
NAS
- CHO
2 stops15h 13m
American Airlines
Deal found 2/12![American Airlines logo]()
$340
This American Airlines deal was found by Cheapflights users on 2/12. 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.
Tue 5/268:00 pm
CHO
- NAS
1 stop14h 03m
American Airlines
Tue 6/22:18 pm
NAS
- CHO
1 stop18h 15m
American Airlines
Deal found 2/12![American Airlines logo]()
$343
This American Airlines deal was found by Cheapflights users on 2/15. 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 4/138:03 pm
CHO
- SJU
1 stop16h 00m
American Airlines
Thu 4/164:30 pm
SJU
- CHO
1 stop7h 24m
American Airlines
Deal found 2/15![American Airlines logo]()
$348
Best flights from Charlottesville to CaribbeanDiscover carefully curated flight deals from Charlottesville to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 16, 2026.
Discover carefully curated flight deals from Charlottesville to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 16, 2026.
This United Airlines deal was found by Cheapflights users on 2/15. 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.
Mon 4/136:20 am
CHO
- SJU
1 stop6h 14m
United Airlines
Wed 4/151:00 am
SJU
- CHO
2 stops8h 58m
United Airlines
Deal found 2/15![United Airlines logo]()
$260
This American Airlines deal was found by Cheapflights users on 2/14. 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.
Wed 3/44:55 pm
CHO
- STT
2 stops18h 17m
American Airlines
Wed 3/114:42 pm
STT
- CHO
1 stop15h 45m
American Airlines
Deal found 2/14![American Airlines logo]()
$260
This Delta deal was found by Cheapflights users on 2/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:45 am
CHO
- NAS
1 stop8h 05m
Delta
Thu 4/304:00 pm
NAS
- CHO
1 stop7h 05m
Delta
Deal found 2/12![Delta logo]()
$336
This United Airlines deal was found by Cheapflights users on 2/14. 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.
Thu 3/56:45 am
CHO
- STT
1 stop8h 33m
United Airlines
Wed 3/1112:02 pm
STT
- CHO
1 stop7h 40m
United Airlines
Deal found 2/14![United Airlines logo]()
$296
This American Airlines deal was found by Cheapflights users on 2/12. 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.
Thu 3/54:20 pm
CHO
- GCM
2 stops19h 45m
American Airlines
Mon 3/92:35 pm
GCM
- CHO
2 stops22h 04m
American Airlines
Deal found 2/12![American Airlines logo]()
$312
This American Airlines deal was found by Cheapflights users on 2/15. 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 3/97:57 pm
CHO
- MBJ
1 stop15h 24m
American Airlines
Fri 3/1310:07 am
MBJ
- CHO
2 stops21h 20m
American Airlines
Deal found 2/15![American Airlines logo]()
$317
This United Airlines deal was found by Cheapflights users on 2/15. 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.
Thu 3/58:29 pm
CHO
- GCM
2 stops16h 46m
United Airlines
Mon 3/91:25 pm
GCM
- CHO
2 stops19h 27m
United Airlines
Deal found 2/15![United Airlines logo]()
$328
This Delta deal was found by Cheapflights users on 2/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:00 am
CHO
- GCM
1 stop6h 29m
Delta
Mon 3/91:12 pm
GCM
- CHO
1 stop8h 36m
Delta
Deal found 2/12![Delta logo]()
$387
This American Airlines deal was found by Cheapflights users on 2/12. 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 3/297:57 pm
CHO
- MBJ
2 stops17h 30m
American Airlines
Sun 4/51:27 pm
MBJ
- CHO
2 stops18h 00m
American Airlines
Deal found 2/12![American Airlines logo]()
$322
This United Airlines deal was found by Cheapflights users on 2/12. 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.
Sat 4/116:20 am
CHO
- NAS
1 stop5h 35m
United Airlines
Wed 4/153:59 pm
NAS
- CHO
1 stop8h 37m
United Airlines
Deal found 2/12![United Airlines logo]()
$336
This American Airlines deal was found by Cheapflights users on 2/14. 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.
Wed 4/228:03 pm
CHO
- MBJ
1 stop14h 10m
American Airlines
Sun 4/2612:56 pm
MBJ
- CHO
2 stops18h 43m
American Airlines
Deal found 2/14![American Airlines logo]()
$322
This Delta deal was found by Cheapflights users on 2/14. 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.
Tue 3/106:00 am
CHO
- SJU
1 stop10h 18m
Delta
Tue 3/176:15 am
SJU
- CHO
1 stop7h 31m
Delta
Deal found 2/14![Delta logo]()
$405
This United Airlines deal was found by Cheapflights users on 2/13. 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.
Fri 3/68:29 pm
CHO
- MBJ
2 stops17h 17m
United Airlines
Fri 3/272:20 pm
MBJ
- CHO
2 stops18h 32m
United Airlines
Deal found 2/13![United Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 2/15. 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 3/25:00 pm
CHO
- PUJ
2 stops18h 01m
American Airlines
Fri 3/612:50 pm
PUJ
- CHO
2 stops20h 37m
American Airlines
Deal found 2/15![American Airlines logo]()
$333
This Delta deal was found by Cheapflights users on 2/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2511:53 am
CHO
- SJU
1 stop11h 05m
Delta
Tue 3/36:15 am
SJU
- CHO
1 stop11h 31m
Delta
Deal found 2/12![Delta logo]()
$421
This American Airlines deal was found by Cheapflights users on 2/12. 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 4/208:03 pm
CHO
- PUJ
2 stops18h 31m
American Airlines
Thu 4/231:39 pm
PUJ
- CHO
2 stops19h 00m
American Airlines
Deal found 2/12![American Airlines logo]()
$333
This American Airlines deal was found by Cheapflights users on 2/12. 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.
Sat 4/118:03 pm
CHO
- NAS
2 stops14h 56m
American Airlines
Wed 4/156:03 pm
NAS
- CHO
1 stop14h 36m
American Airlines
Deal found 2/12![American Airlines logo]()
$340
This United Airlines deal was found by Cheapflights users on 2/12. 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.
Sat 5/3010:30 am
CHO
- SJU
2 stops13h 20m
United Airlines
Mon 6/11:00 am
SJU
- CHO
2 stops8h 26m
United Airlines
Deal found 2/12![United Airlines logo]()
$422
This Delta deal was found by Cheapflights users on 2/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/155:48 am
CHO
- STT
1 stop9h 33m
Delta
Wed 5/201:20 pm
STT
- CHO
1 stop10h 15m
Delta
Deal found 2/12![Delta logo]()
$472
This American Airlines deal was found by Cheapflights users on 2/12. 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.
Tue 5/268:00 pm
CHO
- NAS
1 stop14h 03m
American Airlines
Tue 6/22:18 pm
NAS
- CHO
1 stop18h 15m
American Airlines
Deal found 2/12![American Airlines logo]()
$343
This Delta deal was found by Cheapflights users on 2/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:48 am
CHO
- STT
1 stop9h 33m
Delta
Wed 5/203:00 pm
STT
- CHO
1 stop8h 35m
Delta
Deal found 2/12![Delta logo]()
$472
This United Airlines deal was found by Cheapflights users on 2/12. 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.
Wed 3/45:38 pm
CHO
- GCM
2 stops22h 52m
United Airlines
Sun 3/81:50 pm
GCM
- CHO
2 stops28h 52m
United Airlines
Deal found 2/12![United Airlines logo]()
$440
This American Airlines deal was found by Cheapflights users on 2/15. 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 4/138:03 pm
CHO
- SJU
1 stop16h 00m
American Airlines
Thu 4/164:30 pm
SJU
- CHO
1 stop7h 24m
American Airlines
Deal found 2/15![American Airlines logo]()
$348
This Delta deal was found by Cheapflights users on 2/14. 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 2/2511:53 am
CHO
- SJU
1 stop8h 19m
Delta
Mon 3/27:30 am
SJU
- CHO
1 stop7h 16m
Delta
Deal found 2/14![Delta logo]()
$492
This United Airlines deal was found by Cheapflights users on 2/15. 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.
Mon 3/96:45 am
CHO
- MBJ
1 stop7h 01m
United Airlines
Fri 3/131:48 pm
MBJ
- CHO
1 stop19h 21m
United Airlines
Deal found 2/15![United Airlines logo]()
$448
This American Airlines deal was found by Cheapflights users on 2/14. 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.
Tue 3/317:17 pm
CHO
- SXM
2 stops18h 04m
American Airlines
Tue 4/712:41 pm
SXM
- CHO
2 stops19h 58m
American Airlines
Deal found 2/14![American Airlines logo]()
$350
This United Airlines deal was found by Cheapflights users on 2/14. 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.
Tue 5/196:20 am
CHO
- MBJ
2 stops32h 10m
United Airlines
Sun 5/244:33 pm
MBJ
- CHO
2 stops30h 54m
United Airlines
Deal found 2/14![United Airlines logo]()
$448
This Delta deal was found by Cheapflights users on 2/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/16:08 pm
CHO
- PUJ
2 stops18h 00m
Delta
Tue 4/73:18 pm
PUJ
- CHO
2 stops22h 17m
Delta
Deal found 2/12![Delta logo]()
$493
This American Airlines deal was found by Cheapflights users on 2/13. 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.
Fri 4/175:05 am
CHO
- STT
1 stop9h 44m
American Airlines
Fri 4/245:05 pm
STT
- CHO
2 stops19h 11m
American Airlines
Deal found 2/13![American Airlines logo]()
$374
This United Airlines deal was found by Cheapflights users on 2/15. 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.
Tue 3/2410:45 am
CHO
- SJU
2 stops12h 51m
United Airlines
Sun 3/291:00 am
SJU
- CHO
2 stops8h 58m
United Airlines
Deal found 2/15![United Airlines logo]()
$461
Last-minute flights from Charlottesville to CaribbeanDiscover last-minute flight deals from Charlottesville to Caribbean. Data last updated February 16, 2026 and is based on user searches.
Discover last-minute flight deals from Charlottesville to Caribbean. Data last updated February 16, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 2/12. 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.
Sat 2/217:57 pm
CHO
- PUJ
1 stop14h 37m
American Airlines
Tue 3/35:41 pm
PUJ
- CHO
1 stop17h 06m
American Airlines
Deal found 2/12![American Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 2/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2411:53 am
CHO
- SJU
1 stop11h 05m
Delta
Wed 3/47:30 am
SJU
- CHO
1 stop7h 16m
Delta
Deal found 2/12![Delta logo]()
$360
This American Airlines deal was found by Cheapflights users on 2/14. 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.
Wed 3/44:55 pm
CHO
- STT
2 stops18h 17m
American Airlines
Wed 3/114:42 pm
STT
- CHO
1 stop15h 45m
American Airlines
Deal found 2/14![American Airlines logo]()
$260
This United Airlines deal was found by Cheapflights users on 2/14. 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.
Thu 3/56:45 am
CHO
- STT
1 stop8h 33m
United Airlines
Wed 3/1112:02 pm
STT
- CHO
1 stop7h 40m
United Airlines
Deal found 2/14![United Airlines logo]()
$296
This American Airlines deal was found by Cheapflights users on 2/12. 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.
Thu 3/54:20 pm
CHO
- GCM
2 stops19h 45m
American Airlines
Mon 3/92:35 pm
GCM
- CHO
2 stops22h 04m
American Airlines
Deal found 2/12![American Airlines logo]()
$312
This United Airlines deal was found by Cheapflights users on 2/15. 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.
Thu 3/58:29 pm
CHO
- GCM
2 stops16h 46m
United Airlines
Mon 3/91:25 pm
GCM
- CHO
2 stops19h 27m
United Airlines
Deal found 2/15![United Airlines logo]()
$328
This United Airlines deal was found by Cheapflights users on 2/13. 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.
Fri 3/68:29 pm
CHO
- MBJ
2 stops17h 17m
United Airlines
Fri 3/272:20 pm
MBJ
- CHO
2 stops18h 32m
United Airlines
Deal found 2/13![United Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 2/13. 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.
Fri 3/67:57 pm
CHO
- MBJ
2 stops17h 29m
American Airlines
Mon 3/91:27 pm
MBJ
- CHO
2 stops19h 20m
American Airlines
Deal found 2/13![American Airlines logo]()
$374
This American Airlines deal was found by Cheapflights users on 2/15. 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 3/97:57 pm
CHO
- MBJ
2 stops17h 30m
American Airlines
Fri 3/1310:07 am
MBJ
- CHO
2 stops21h 20m
American Airlines
Deal found 2/15![American Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 2/13. 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.
Mon 3/237:57 pm
CHO
- STT
1 stop16h 08m
American Airlines
Fri 3/274:42 pm
STT
- CHO
1 stop15h 45m
American Airlines
Deal found 2/13![American Airlines logo]()
$377
This American Airlines deal was found by Cheapflights users on 2/12. 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 3/297:57 pm
CHO
- MBJ
2 stops17h 30m
American Airlines
Sun 4/51:27 pm
MBJ
- CHO
2 stops18h 00m
American Airlines
Deal found 2/12![American Airlines logo]()
$322
This American Airlines deal was found by Cheapflights users on 2/14. 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.
Tue 3/317:17 pm
CHO
- SXM
2 stops18h 04m
American Airlines
Tue 4/712:41 pm
SXM
- CHO
2 stops19h 58m
American Airlines
Deal found 2/14![American Airlines logo]()
$350
One-way flights from Charlottesville to CaribbeanSearch for one-way flight options from Charlottesville to Caribbean. Find affordable one-way fares based on user searches. Data last updated February 16, 2026.
Search for one-way flight options from Charlottesville to Caribbean. Find affordable one-way fares based on user searches. Data last updated February 16, 2026.
This United Airlines deal was found by Cheapflights users on 2/13. 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.
Tue 5/52:40 pm
CHO
- SJU
1 stop6h 44m
United Airlines
Deal found 2/13![United Airlines logo]()
$121
This Delta deal was found by Cheapflights users on 2/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/62:30 pm
CHO
- SJU
1 stop8h 43m
Delta
Deal found 2/13![Delta logo]()
$157
This Delta deal was found by Cheapflights users on 2/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2411:53 am
CHO
- SJU
1 stop8h 19m
Delta
Deal found 2/12![Delta logo]()
$194
This American Airlines deal was found by Cheapflights users on 2/12. 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 3/25:00 pm
CHO
- SJU
2 stops16h 00m
American Airlines
Deal found 2/12![American Airlines logo]()
$214
This Delta deal was found by Cheapflights users on 2/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/42:30 pm
CHO
- SJU
1 stop8h 43m
Delta
Deal found 2/13![Delta logo]()
$225
This American Airlines deal was found by Cheapflights users on 2/13. 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.
Sun 5/38:03 pm
CHO
- SJU
1 stop14h 45m
American Airlines
Deal found 2/13![American Airlines logo]()
$227
This United Airlines deal was found by Cheapflights users on 2/12. 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.
Tue 2/246:45 am
CHO
- SJU
2 stops13h 41m
United Airlines
Deal found 2/12![United Airlines logo]()
$239
This United Airlines deal was found by Cheapflights users on 2/12. 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 3/15:38 pm
CHO
- SJU
2 stops11h 33m
United Airlines
Deal found 2/12![United Airlines logo]()
$251
This United Airlines deal was found by Cheapflights users on 2/13. 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 5/36:20 am
CHO
- SJU
2 stops14h 14m
United Airlines
Deal found 2/13![United Airlines logo]()
$258
This American Airlines deal was found by Cheapflights users on 2/12. 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 5/175:05 am
CHO
- SJU
1 stop5h 43m
American Airlines
Deal found 2/12![American Airlines logo]()
$265
This United Airlines deal was found by Cheapflights users on 2/13. 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.
Sat 5/96:49 am
CHO
- SJU
2 stops13h 49m
United Airlines
Deal found 2/13![United Airlines logo]()
$286
This American Airlines deal was found by Cheapflights users on 2/12. 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 3/48:02 am
CHO
- ELH
2 stops7h 21m
American Airlines
Deal found 2/12![American Airlines logo]()
$334
Find flight deals from Charlottesville to Caribbean
Keep the following information in mind while searching for Charlottesville to Caribbean flight deals. Data was last updated February 16, 2026.
Round-trip from | $260 (United Airlines) |
|---|---|
One-way from | $121 (United Airlines) |
Popular in | August |
Cheapest in | May |
Average price | $482 |
Cheapflights Fare Finder
Customize your flight search to find flights from Charlottesville 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 16, 2026.
Use the filters below to find and compare flights from Charlottesville to Caribbean that are best for you.
Fly from
Charlottesville
Fly to
Caribbean
Route
Depart
Return
Price
CharlottesvilleSan Juan
CHO - SJU
CHOSJU
Charlottesville Albemarle
Mon 4/13
6:20 am-12:34 pm
1 stop6h 14m
San Juan Luis Munoz Marin Intl
Wed 4/15
1:00 am-9:58 am
2 stops8h 58m
$260
CharlottesvilleSaint Thomas Island
CHO - STT
CHOSTT
Charlottesville Albemarle
Wed 3/4
4:55 pm-12:12 pm
2 stops18h 17m
Saint Thomas Island Cyril E King
Wed 3/11
4:42 pm-8:27 am
1 stop15h 45m
$260
CharlottesvilleSaint Thomas Island
CHO - STT
CHOSTT
Charlottesville Albemarle
Thu 3/5
6:45 am-4:18 pm
1 stop8h 33m
Saint Thomas Island Cyril E King
Wed 3/11
12:02 pm-7:42 pm
1 stop7h 40m
$296
CharlottesvilleGeorge Town
CHO - GCM
CHOGCM
Charlottesville Albemarle
Thu 3/5
4:20 pm-12:05 pm
2 stops19h 45m
George Town Owen Roberts Intl
Mon 3/9
2:35 pm-1:39 pm
2 stops22h 04m
$312
CharlottesvilleMontego Bay
CHO - MBJ
CHOMBJ
Charlottesville Albemarle
Mon 3/9
7:57 pm-10:21 am
1 stop15h 24m
Montego Bay Sangster Intl
Fri 3/13
10:07 am-8:27 am
2 stops21h 20m
$317
CharlottesvilleMontego Bay
CHO - MBJ
CHOMBJ
Charlottesville Albemarle
Sun 3/29
7:57 pm-12:27 pm
2 stops17h 30m
Montego Bay Sangster Intl
Sun 4/5
1:27 pm-8:27 am
2 stops18h 00m
$322
CharlottesvilleMontego Bay
CHO - MBJ
CHOMBJ
Charlottesville Albemarle
Wed 4/22
8:03 pm-9:13 am
1 stop14h 10m
Montego Bay Sangster Intl
Sun 4/26
12:56 pm-8:39 am
2 stops18h 43m
$322
CharlottesvilleGeorge Town
CHO - GCM
CHOGCM
Charlottesville Albemarle
Thu 3/5
8:29 pm-1:15 pm
2 stops16h 46m
George Town Owen Roberts Intl
Mon 3/9
1:25 pm-9:52 am
2 stops19h 27m
$328
CharlottesvillePunta Cana
CHO - PUJ
CHOPUJ
Charlottesville Albemarle
Mon 3/2
5:00 pm-12:01 pm
2 stops18h 01m
Punta Cana
Fri 3/6
12:50 pm-8:27 am
2 stops20h 37m
$333
CharlottesvillePunta Cana
CHO - PUJ
CHOPUJ
Charlottesville Albemarle
Mon 4/20
8:03 pm-2:34 pm
2 stops18h 31m
Punta Cana
Thu 4/23
1:39 pm-8:39 am
2 stops19h 00m
$333
Showing 1-10 of 46 results
Best time to book a flight from Charlottesville to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Charlottesville with our price prediction graph.
CHO-SJU
CHO-ELH
CHO-STT
CHO-GCM
CHO-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 Charlottesville to Caribbean
CHO-0CB
CHO-SJU
CHO-ELH
CHO-STT
CHO-GCM
What is the cheapest month to book a flight from Charlottesville to Caribbean?
Currently, January is the cheapest month in which you can book a flight from Charlottesville to Caribbean (average of $73). Flying from Charlottesville to Caribbean in December is currently the most expensive (average of $163). 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 16, 2026.
Get a feel of what it's like to fly with United Airlines and American Airlines from Charlottesville to Caribbean by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.3
Food
6.6
Overall
7.4
Entertainment
7.1
Boarding
7.7
Crew
8.1
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Comfort
7.3
Food
6.6
Overall
7.4
Entertainment
7.1
Boarding
7.7
Crew
8.1
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Comfort
7.3
Food
6.6
Overall
7.4
Entertainment
7.1
Boarding
7.7
Crew
8.1
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Related info for your journey
Find useful and relevant information for your journey from Charlottesville to Caribbean. 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 Charlottesville to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Charlottesville to Caribbean by cabin class
Find flights from Charlottesville to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Charlottesville and Caribbean flights
Browse other Charlottesville and Caribbean flight options. Last updated on February 16, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Charlottesville to Caribbean flights
Consider these flights traveling from Charlottesville to Caribbean.
Top 2 airlines flying from Charlottesville to Caribbean
Discover the top 2 airlines that operate flights from Charlottesville 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 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$315 | Average$711 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$368 | Average$615 | FlexibilityNo cancel fee | On-time69% |