$170+ Cheap flights from Hobby (HOU) 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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — SJU
Aug 27 — Sep 31
Round-trip
1 adult, Economy
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Find cheap flights from Hobby to Caribbean with Cheapflights
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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 Hobby to CaribbeanExplore the most affordable flight options available from Hobby to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 28, 2026.
Explore the most affordable flight options available from Hobby to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 28, 2026.
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/411:10 am
HOU
- SJU
1 stop10h 10m
Southwest
Thu 11/511:20 am
SJU
- HOU
1 stop10h 45m
Southwest
Deal found 7/23![Southwest logo]()
$371
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/243:45 pm
HOU
- SJU
1 stop6h 25m
Southwest
Sun 9/276:00 am
SJU
- HOU
1 stop6h 25m
Southwest
Deal found 7/27![Southwest logo]()
$376
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2611:20 am
HOU
- SJU
1 stop9h 40m
Southwest
Sat 8/295:55 am
SJU
- HOU
1 stop11h 15m
Southwest
Deal found 7/27![Southwest logo]()
$381
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/133:00 pm
HOU
- SJU
2 stops7h 55m
Southwest
Sat 11/216:00 pm
SJU
- HOU
Nonstop5h 00m
Southwest
Deal found 7/27![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:10 am
HOU
- SJU
1 stop11h 55m
Southwest
Fri 8/215:30 am
SJU
- HOU
2 stops15h 30m
Southwest
Deal found 7/24![Southwest logo]()
$386
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:00 am
HOU
- SJU
2 stops9h 10m
Southwest
Mon 9/285:30 am
SJU
- HOU
2 stops15h 30m
Southwest
Deal found 7/23![Southwest logo]()
$388
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/711:10 am
HOU
- SJU
Nonstop4h 10m
Southwest
Wed 11/116:15 am
SJU
- HOU
1 stop9h 45m
Southwest
Deal found 7/23![Southwest logo]()
$397
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1211:30 am
HOU
- SJU
2 stops9h 25m
Southwest
Mon 11/167:40 am
SJU
- HOU
2 stops10h 00m
Southwest
Deal found 7/23![Southwest logo]()
$400
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/89:50 pm
HOU
- SJU
1 stop10h 30m
Southwest
Mon 10/1210:50 pm
SJU
- HOU
1 stop12h 30m
Southwest
Deal found 7/22![Southwest logo]()
$401
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 9/266:04 am
HOU
- SJU
1 stop7h 41m
American Airlines
Tue 9/296:00 am
SJU
- HOU
2 stops12h 59m
American Airlines
Deal found 7/26![American Airlines logo]()
$411
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/165:25 am
HOU
- GCM
1 stop6h 10m
Southwest
Wed 1/201:50 pm
GCM
- HOU
1 stop9h 55m
Southwest
Deal found 7/23![Southwest logo]()
$459
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:00 pm
HOU
- SXM
2 stops19h 05m
Southwest
Thu 9/103:05 pm
SXM
- HOU
1 stop8h 20m
Southwest
Deal found 7/25![Southwest logo]()
$460
Best flights from Hobby to CaribbeanDiscover carefully curated flight deals from Hobby to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 28, 2026.
Discover carefully curated flight deals from Hobby to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 28, 2026.
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:15 pm
HOU
- SJU
1 stop8h 00m
Southwest
Tue 9/2911:50 am
SJU
- HOU
1 stop8h 30m
Southwest
Deal found 7/27![Southwest logo]()
$376
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 10/76:09 am
HOU
- SJU
1 stop6h 40m
Delta
Sat 10/107:15 am
SJU
- HOU
1 stop10h 17m
Delta
Deal found 7/26![Delta logo]()
$386
This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/119:33 am
HOU
- MBJ
1 stop6h 43m
American Airlines
Tue 9/152:09 pm
MBJ
- HOU
2 stops18h 47m
American Airlines
Deal found 7/27![American Airlines logo]()
$513
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/92:45 pm
HOU
- SJU
1 stop6h 20m
Southwest
Mon 9/146:30 am
SJU
- HOU
1 stop8h 40m
Southwest
Deal found 7/24![Southwest logo]()
$376
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/116:00 pm
HOU
- SJU
1 stop6h 25m
Southwest
Wed 10/145:05 am
SJU
- HOU
2 stops9h 35m
Southwest
Deal found 7/24![Southwest logo]()
$381
This Faresmojo deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/256:00 am
HOU
- SDQ
1 stop6h 35m
JetBlue
Thu 12/311:57 pm
SDQ
- HOU
1 stop9h 46m
JetBlue
Deal found 7/26![JetBlue logo]()
$895
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:45 pm
HOU
- SJU
2 stops8h 35m
Southwest
Sun 10/48:25 pm
SJU
- HOU
1 stop12h 45m
Southwest
Deal found 7/27![Southwest logo]()
$386
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 9/76:00 am
HOU
- SXM
1 stop6h 53m
Delta
Fri 9/113:18 pm
SXM
- HOU
1 stop8h 21m
Delta
Deal found 7/23![Delta logo]()
$495
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/268:00 am
HOU
- SJU
2 stops9h 10m
Southwest
Sat 8/298:20 am
SJU
- HOU
2 stops9h 30m
Southwest
Deal found 7/27![Southwest logo]()
$406
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:20 pm
HOU
- SJU
2 stops9h 30m
Southwest
Fri 8/215:30 am
SJU
- HOU
1 stop13h 15m
Southwest
Deal found 7/26![Southwest logo]()
$416
This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/116:19 pm
HOU
- PUJ
2 stops17h 18m
American Airlines
Fri 9/254:04 pm
PUJ
- HOU
2 stops19h 57m
American Airlines
Deal found 7/27![American Airlines logo]()
$611
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 9/196:00 am
HOU
- SXM
1 stop6h 53m
Delta
Sat 9/263:18 pm
SXM
- HOU
1 stop8h 21m
Delta
Deal found 7/24![Delta logo]()
$590
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/211:15 pm
HOU
- SJU
1 stop7h 55m
Southwest
Thu 8/276:30 am
SJU
- HOU
1 stop9h 10m
Southwest
Deal found 7/27![Southwest logo]()
$421
This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:06 pm
HOU
- STT
2 stops18h 52m
American Airlines
Fri 10/233:46 pm
STT
- HOU
2 stops18h 35m
American Airlines
Deal found 7/27![American Airlines logo]()
$636
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:40 am
HOU
- SJU
2 stops10h 30m
Southwest
Sat 9/1211:45 am
SJU
- HOU
1 stop8h 00m
Southwest
Deal found 7/23![Southwest logo]()
$421
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 1/186:00 am
HOU
- SXM
1 stop6h 40m
Delta
Mon 1/251:40 pm
SXM
- HOU
1 stop10h 03m
Delta
Deal found 7/25![Delta logo]()
$637
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:30 pm
HOU
- SJU
2 stops9h 20m
Southwest
Sun 8/239:25 pm
SJU
- HOU
1 stop12h 05m
Southwest
Deal found 7/24![Southwest logo]()
$426
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 10/306:00 am
HOU
- SDQ
1 stop6h 41m
Delta
Tue 11/33:56 pm
SDQ
- HOU
1 stop9h 13m
Delta
Deal found 7/23![Delta logo]()
$640
This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/108:24 pm
HOU
- PLS
2 stops16h 56m
American Airlines
Sat 10/171:05 pm
PLS
- HOU
2 stops11h 44m
American Airlines
Deal found 7/27![American Airlines logo]()
$745
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:00 am
HOU
- NAS
1 stop6h 53m
Delta
Tue 10/61:16 pm
NAS
- HOU
1 stop10h 53m
Delta
Deal found 7/23![Delta logo]()
$641
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/185:05 am
HOU
- SXM
1 stop7h 30m
Southwest
Mon 1/253:35 pm
SXM
- HOU
2 stops20h 40m
Southwest
Deal found 7/25![Southwest logo]()
$441
This American Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 9/46:14 pm
HOU
- PLS
2 stops17h 09m
American Airlines
Sun 9/63:18 pm
PLS
- HOU
2 stops9h 38m
American Airlines
Deal found 7/25![American Airlines logo]()
$750
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/93:45 pm
HOU
- SJU
2 stops8h 35m
Southwest
Mon 10/1210:50 pm
SJU
- HOU
1 stop12h 30m
Southwest
Deal found 7/23![Southwest logo]()
$446
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:09 am
HOU
- NAS
1 stop6h 45m
Delta
Mon 10/263:19 pm
NAS
- HOU
1 stop8h 44m
Delta
Deal found 7/25![Delta logo]()
$666
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:00 am
HOU
- NAS
1 stop4h 51m
Delta
Mon 9/283:18 pm
NAS
- HOU
1 stop8h 21m
Delta
Deal found 7/27![Delta logo]()
$666
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/165:25 am
HOU
- GCM
1 stop6h 10m
Southwest
Wed 1/201:50 pm
GCM
- HOU
1 stop9h 55m
Southwest
Deal found 7/23![Southwest logo]()
$459
This American Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/243:57 pm
HOU
- PLS
2 stops19h 08m
American Airlines
Thu 8/273:03 pm
PLS
- HOU
2 stops9h 53m
American Airlines
Deal found 7/24![American Airlines logo]()
$820
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 10/176:09 am
HOU
- STT
1 stop6h 28m
Delta
Thu 10/222:47 pm
STT
- HOU
1 stop9h 16m
Delta
Deal found 7/27![Delta logo]()
$670
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/72:50 pm
HOU
- SJU
2 stops7h 55m
Southwest
Sun 10/115:00 am
SJU
- HOU
2 stops9h 30m
Southwest
Deal found 7/25![Southwest logo]()
$466
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:00 am
HOU
- SXM
1 stop7h 05m
Southwest
Thu 9/103:05 pm
SXM
- HOU
1 stop8h 20m
Southwest
Deal found 7/26![Southwest logo]()
$472
Last-minute flights from Hobby to CaribbeanDiscover last-minute flight deals from Hobby to Caribbean. Data last updated July 28, 2026 and is based on user searches.
Discover last-minute flight deals from Hobby to Caribbean. Data last updated July 28, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 7/306:03 am
HOU
- NAS
1 stop7h 44m
American Airlines
Mon 8/36:05 pm
NAS
- HOU
1 stop6h 51m
American Airlines
Deal found 7/23![American Airlines logo]()
$474
This American Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 7/3110:18 am
HOU
- NAS
1 stop5h 47m
American Airlines
Sun 8/26:05 pm
NAS
- HOU
1 stop6h 51m
American Airlines
Deal found 7/23![American Airlines logo]()
$479
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:10 am
HOU
- SJU
1 stop11h 55m
Southwest
Fri 8/215:30 am
SJU
- HOU
2 stops15h 30m
Southwest
Deal found 7/24![Southwest logo]()
$386
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:15 pm
HOU
- SJU
1 stop9h 35m
Southwest
Fri 8/216:30 am
SJU
- HOU
1 stop9h 10m
Southwest
Deal found 7/26![Southwest logo]()
$416
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:15 pm
HOU
- SJU
1 stop7h 55m
Southwest
Tue 8/255:15 am
SJU
- HOU
1 stop7h 30m
Southwest
Deal found 7/27![Southwest logo]()
$426
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/211:15 pm
HOU
- SJU
1 stop7h 55m
Southwest
Tue 8/251:20 pm
SJU
- HOU
1 stop7h 30m
Southwest
Deal found 7/23![Southwest logo]()
$431
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/225:41 am
HOU
- SJU
2 stops10h 16m
American Airlines
Thu 8/273:44 pm
SJU
- HOU
1 stop9h 12m
American Airlines
Deal found 7/26![American Airlines logo]()
$411
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2310:30 am
HOU
- SJU
2 stops12h 20m
Southwest
Sat 8/296:25 am
SJU
- HOU
2 stops8h 20m
Southwest
Deal found 7/23![Southwest logo]()
$401
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/235:00 am
HOU
- SXM
1 stop8h 05m
Southwest
Thu 8/273:05 pm
SXM
- HOU
1 stop8h 15m
Southwest
Deal found 7/23![Southwest logo]()
$465
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2511:00 am
HOU
- SJU
2 stops9h 05m
Southwest
Tue 9/15:15 am
SJU
- HOU
2 stops9h 35m
Southwest
Deal found 7/27![Southwest logo]()
$376
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2611:20 am
HOU
- SJU
1 stop9h 40m
Southwest
Sat 8/295:55 am
SJU
- HOU
1 stop11h 15m
Southwest
Deal found 7/27![Southwest logo]()
$381
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:40 am
HOU
- SJU
2 stops10h 25m
Southwest
Tue 9/15:15 am
SJU
- HOU
2 stops9h 35m
Southwest
Deal found 7/24![Southwest logo]()
$421
One-way flights from Hobby to CaribbeanSearch for one-way flight options from Hobby to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 28, 2026.
Search for one-way flight options from Hobby to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 28, 2026.
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/189:00 pm
HOU
- SXM
2 stops15h 35m
Southwest
Deal found 7/25![Southwest logo]()
$170
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/268:00 am
HOU
- SJU
2 stops9h 10m
Southwest
Deal found 7/27![Southwest logo]()
$188
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/18:10 pm
HOU
- NAS
2 stops16h 05m
Southwest
Deal found 7/23![Southwest logo]()
$191
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 8/2810:50 am
HOU
- SJU
1 stop10h 39m
Delta
Deal found 7/27![Delta logo]()
$193
This American Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 11/211:35 am
HOU
- SJU
1 stop10h 41m
American Airlines
Deal found 7/23![American Airlines logo]()
$200
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 10/273:09 pm
HOU
- MBJ
2 stops20h 21m
Delta
Deal found 7/27![Delta logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 8/283:36 pm
HOU
- SJU
2 stops47h 35m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$206
This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/178:18 pm
HOU
- MBJ
2 stops16h 35m
American Airlines
Deal found 7/27![American Airlines logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 10/263:51 pm
HOU
- SJU
2 stops30h 47m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/148:03 pm
HOU
- NAS
2 stops35h 52m
Multiple Airlines
Deal found 7/24![Multiple Airlines logo]()
$210
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:25 am
HOU
- MBJ
1 stop5h 30m
Southwest
Deal found 7/27![Southwest logo]()
$210
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1510:40 am
HOU
- SJU
2 stops10h 15m
Southwest
Deal found 7/23![Southwest logo]()
$213
Find flight deals from Hobby to Caribbean
Keep the following information in mind while searching for Hobby to Caribbean flight deals. Data was last updated July 28, 2026.
Round-trip from | $371 (Southwest) |
|---|---|
One-way from | $170 (Southwest) |
Popular in | June |
Cheapest in | October |
Average price | $539 |
Good round-trip deal | $795 or less |
Good one-way deal | $314 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Hobby 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 July 28, 2026.
Use the filters below to find and compare flights from Houston Hobby Airport to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Thu 9/24
1:15 pm-10:15 pm
1 stop8h 00m
San Juan Luis Munoz Marin Intl
Tue 9/29
11:50 am-7:20 pm
1 stop8h 30m
$376
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Wed 9/9
2:45 pm-10:05 pm
1 stop6h 20m
San Juan Luis Munoz Marin Intl
Mon 9/14
6:30 am-2:10 pm
1 stop8h 40m
$376
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Sun 10/11
6:00 pm-1:25 am
1 stop6h 25m
San Juan Luis Munoz Marin Intl
Wed 10/14
5:05 am-1:40 pm
2 stops9h 35m
$381
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Wed 10/7
6:09 am-1:49 pm
1 stop6h 40m
San Juan Luis Munoz Marin Intl
Sat 10/10
7:15 am-4:32 pm
1 stop10h 17m
$386
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Thu 10/1
3:45 pm-1:20 am
2 stops8h 35m
San Juan Luis Munoz Marin Intl
Sun 10/4
8:25 pm-8:10 am
1 stop12h 45m
$386
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Wed 8/26
8:00 am-6:10 pm
2 stops9h 10m
San Juan Luis Munoz Marin Intl
Sat 8/29
8:20 am-4:50 pm
2 stops9h 30m
$406
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Thu 8/20
1:20 pm-11:50 pm
2 stops9h 30m
San Juan Luis Munoz Marin Intl
Fri 8/21
5:30 am-5:45 pm
1 stop13h 15m
$416
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Fri 8/21
1:15 pm-10:10 pm
1 stop7h 55m
San Juan Luis Munoz Marin Intl
Thu 8/27
6:30 am-2:40 pm
1 stop9h 10m
$421
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Sat 9/5
6:40 am-6:10 pm
2 stops10h 30m
San Juan Luis Munoz Marin Intl
Sat 9/12
11:45 am-6:45 pm
1 stop8h 00m
$421
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Thu 8/20
1:30 pm-11:50 pm
2 stops9h 20m
San Juan Luis Munoz Marin Intl
Sun 8/23
9:25 pm-8:30 am
1 stop12h 05m
$426
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Hobby to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Hobby with our price prediction graph.
HOU-SJU
HOU-MBJ
HOU-SDQ
HOU-SXM
HOU-PUJ
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Houston Hobby Airport to Caribbean
HOU-0CB
HOU-SJU
HOU-MBJ
HOU-SDQ
HOU-SXM
What is the cheapest month to book a flight from Houston Hobby Airport to Caribbean?
Currently, October is the cheapest month in which you can book a flight from Houston Hobby Airport to Caribbean (average of $463). Flying from Houston Hobby Airport to Caribbean in June is currently the most expensive (average of $708). 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.
What is the cheapest time of day to fly from HOU to CB?
Find hourly flight availability from Hobby to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 28, 2026.
A simple way to save on the total cost of your ticket is to fly from Houston Hobby Airport to Caribbean at noon. If you’re flexible enough to do this you can expect to save up to 18% on your trip compared to booking a flight in the morning.
How far ahead should I book a flight from Houston Hobby Airport to Caribbean?
The best time to book flights from Houston Hobby Airport to Caribbean is 3 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
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 July 28, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Houston Hobby Airport 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.
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Related info for your journey
Find useful and relevant information for your journey from Hobby 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 Hobby 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 Hobby to Caribbean by cabin class
Find flights from Hobby to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Hobby and Caribbean flights
Browse other Hobby and Caribbean flight options. Last updated on July 28, 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.
Hobby to Caribbean flights
Consider these flights traveling from Hobby to Caribbean.
Top 7 airlines flying from Hobby to Caribbean
Discover the top 7 airlines that operate flights from Hobby 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 July 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$646 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$178 | Average$433 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$200 | Average$661 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$222 | Average$629 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$244 | Average$537 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$312 | Average$685 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$376 | Average$652 | FlexibilityNo cancel fee | On-time63% |