$142+ 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 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — SJU
Apr 11 — Apr 181
Round-trip
1 adult, Economy
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Find cheap flights from Hobby to Caribbean with Cheapflights
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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 March 12, 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 March 12, 2026.
This Southwest deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/41:30 pm
HOU
- SJU
2 stops9h 25m
Southwest
Sat 5/97:55 pm
SJU
- HOU
1 stop13h 05m
Southwest
Deal found 3/7![Southwest logo]()
$364
This Southwest deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 5/148:00 am
HOU
- SJU
1 stop11h 00m
Southwest
Sun 5/179:45 pm
SJU
- HOU
1 stop11h 50m
Southwest
Deal found 3/10![Southwest logo]()
$382
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:00 am
HOU
- SJU
1 stop6h 25m
Delta
Mon 5/46:15 am
SJU
- HOU
1 stop11h 13m
Delta
Deal found 3/10![Delta logo]()
$384
This American Airlines deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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 5/39:57 am
HOU
- SJU
1 stop12h 05m
American Airlines
Sat 5/1611:59 pm
SJU
- HOU
1 stop10h 27m
American Airlines
Deal found 3/11![American Airlines logo]()
$391
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/72:45 pm
HOU
- SJU
1 stop7h 40m
Southwest
Sun 5/1012:50 pm
SJU
- HOU
1 stop10h 00m
Southwest
Deal found 3/9![Southwest logo]()
$400
This Southwest deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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 5/82:45 pm
HOU
- SJU
1 stop7h 40m
Southwest
Sun 5/1012:50 pm
SJU
- HOU
1 stop10h 00m
Southwest
Deal found 3/11![Southwest logo]()
$402
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:50 am
HOU
- SJU
1 stop11h 15m
Southwest
Fri 4/176:50 am
SJU
- HOU
2 stops12h 45m
Southwest
Deal found 3/8![Southwest logo]()
$404
This American Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/18:21 pm
HOU
- SJU
1 stop7h 11m
American Airlines
Wed 9/303:45 pm
SJU
- HOU
1 stop8h 56m
American Airlines
Deal found 3/8![American Airlines logo]()
$405
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/32:35 pm
HOU
- SJU
2 stops8h 10m
Southwest
Sun 5/176:25 am
SJU
- HOU
2 stops10h 35m
Southwest
Deal found 3/9![Southwest logo]()
$406
This Southwest deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/145:50 am
HOU
- MBJ
1 stop5h 45m
Southwest
Thu 4/3012:15 pm
MBJ
- HOU
1 stop11h 15m
Southwest
Deal found 3/7![Southwest logo]()
$408
This American Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/204:18 pm
HOU
- SJU
1 stop11h 14m
American Airlines
Sat 4/2511:59 pm
SJU
- HOU
1 stop10h 27m
American Airlines
Deal found 3/9![American Airlines logo]()
$409
This American Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/112:18 pm
HOU
- SJU
1 stop9h 13m
American Airlines
Wed 4/811:59 pm
SJU
- HOU
1 stop10h 27m
American Airlines
Deal found 3/8![American Airlines logo]()
$410
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 March 12, 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 March 12, 2026.
This Southwest deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:05 pm
HOU
- SJU
1 stop13h 05m
Southwest
Sun 5/1712:50 pm
SJU
- HOU
1 stop10h 00m
Southwest
Deal found 3/7![Southwest logo]()
$382
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 5/296:00 am
HOU
- MBJ
1 stop9h 34m
Delta
Wed 6/32:21 pm
MBJ
- HOU
1 stop8h 05m
Delta
Deal found 3/10![Delta logo]()
$581
This American Airlines deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/94:19 pm
HOU
- CUR
2 stops20h 16m
American Airlines
Wed 5/134:49 pm
CUR
- HOU
2 stops17h 37m
American Airlines
Deal found 3/7![American Airlines logo]()
$623
This Southwest deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 5/32:35 pm
HOU
- SJU
2 stops8h 10m
Southwest
Sun 5/179:45 pm
SJU
- HOU
1 stop11h 50m
Southwest
Deal found 3/10![Southwest logo]()
$384
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/266:30 pm
HOU
- SJU
Nonstop4h 25m
Southwest
Sat 8/16:30 am
SJU
- HOU
1 stop9h 05m
Southwest
Deal found 3/8![Southwest logo]()
$442
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/27:00 pm
HOU
- SJU
Nonstop4h 25m
Southwest
Mon 7/610:20 pm
SJU
- HOU
2 stops12h 25m
Southwest
Deal found 3/8![Southwest logo]()
$442
This Delta deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:00 am
HOU
- MBJ
1 stop5h 53m
Delta
Tue 5/262:21 pm
MBJ
- HOU
1 stop8h 05m
Delta
Deal found 3/7![Delta logo]()
$585
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/2412:20 pm
HOU
- SJU
1 stop8h 10m
Southwest
Mon 7/278:15 pm
SJU
- HOU
2 stops14h 30m
Southwest
Deal found 3/8![Southwest logo]()
$446
This American Airlines deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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 4/184:18 pm
HOU
- CUR
2 stops20h 17m
American Airlines
Tue 4/214:49 pm
CUR
- HOU
2 stops17h 37m
American Airlines
Deal found 3/11![American Airlines logo]()
$643
This Southwest deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1911:20 am
HOU
- SJU
1 stop9h 40m
Southwest
Sun 8/236:00 am
SJU
- HOU
1 stop6h 25m
Southwest
Deal found 3/7![Southwest logo]()
$446
This Delta deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/76:00 am
HOU
- STT
1 stop7h 48m
Delta
Tue 4/143:05 pm
STT
- HOU
1 stop9h 03m
Delta
Deal found 3/8![Delta logo]()
$595
This American Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/168:21 pm
HOU
- CUR
2 stops17h 11m
American Airlines
Tue 4/214:49 pm
CUR
- HOU
2 stops17h 37m
American Airlines
Deal found 3/10![American Airlines logo]()
$643
This Southwest deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/27:30 am
HOU
- SJU
2 stops12h 45m
Southwest
Tue 7/77:00 am
SJU
- HOU
2 stops9h 15m
Southwest
Deal found 3/7![Southwest logo]()
$446
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 5/510:53 am
HOU
- NAS
1 stop4h 40m
Delta
Tue 5/121:16 pm
NAS
- HOU
1 stop10h 10m
Delta
Deal found 3/10![Delta logo]()
$596
This American Airlines deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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 8/198:25 pm
HOU
- CUR
2 stops17h 50m
American Airlines
Sun 8/302:15 pm
CUR
- HOU
2 stops19h 06m
American Airlines
Deal found 3/11![American Airlines logo]()
$653
This Southwest deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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 5/18:05 pm
HOU
- SJU
1 stop11h 50m
Southwest
Sat 5/95:45 am
SJU
- HOU
1 stop7h 10m
Southwest
Deal found 3/11![Southwest logo]()
$453
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:00 am
HOU
- PUJ
1 stop7h 51m
Delta
Tue 8/182:52 pm
PUJ
- HOU
1 stop7h 43m
Delta
Deal found 3/9![Delta logo]()
$619
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/910:25 am
HOU
- SJU
Nonstop4h 10m
Southwest
Wed 5/135:35 am
SJU
- HOU
1 stop11h 35m
Southwest
Deal found 3/9![Southwest logo]()
$456
This American Airlines deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:01 am
HOU
- AUA
2 stops9h 24m
American Airlines
Fri 5/155:25 pm
AUA
- HOU
2 stops17h 01m
American Airlines
Deal found 3/7![American Airlines logo]()
$681
This Southwest deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/145:50 am
HOU
- MBJ
1 stop5h 45m
Southwest
Thu 4/3012:35 pm
MBJ
- HOU
2 stops10h 55m
Southwest
Deal found 3/7![Southwest logo]()
$464
This American Airlines deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/44:18 pm
HOU
- CUR
2 stops20h 23m
American Airlines
Sat 5/94:49 pm
CUR
- HOU
2 stops17h 37m
American Airlines
Deal found 3/7![American Airlines logo]()
$703
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 4/186:00 am
HOU
- CUR
1 stop6h 41m
Delta
Sat 4/253:06 pm
CUR
- HOU
1 stop9h 01m
Delta
Deal found 3/10![Delta logo]()
$709
This Southwest deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 5/281:20 pm
HOU
- SJU
2 stops9h 05m
Southwest
Tue 6/25:35 am
SJU
- HOU
2 stops9h 25m
Southwest
Deal found 3/10![Southwest logo]()
$466
This Southwest deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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 8/411:20 am
HOU
- SJU
1 stop8h 45m
Southwest
Mon 8/105:30 am
SJU
- HOU
1 stop13h 15m
Southwest
Deal found 3/11![Southwest logo]()
$466
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 5/86:00 am
HOU
- AUA
1 stop7h 10m
Delta
Mon 5/111:15 pm
AUA
- HOU
1 stop10h 11m
Delta
Deal found 3/10![Delta logo]()
$766
This American Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 7/238:23 pm
HOU
- CUR
2 stops18h 23m
American Airlines
Mon 7/274:46 pm
CUR
- HOU
2 stops20h 30m
American Airlines
Deal found 3/10![American Airlines logo]()
$768
This Southwest deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 5/56:00 am
HOU
- PLS
2 stops7h 55m
Southwest
Tue 5/123:50 pm
PLS
- HOU
1 stop7h 55m
Southwest
Deal found 3/10![Southwest logo]()
$476
This Delta deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:00 am
HOU
- CUR
1 stop6h 41m
Delta
Sat 5/93:21 pm
CUR
- HOU
1 stop8h 05m
Delta
Deal found 3/7![Delta logo]()
$769
This American Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/318:23 pm
HOU
- CUR
2 stops18h 22m
American Airlines
Fri 6/54:46 pm
CUR
- HOU
2 stops20h 34m
American Airlines
Deal found 3/8![American Airlines logo]()
$803
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/135:50 am
HOU
- SXM
1 stop6h 40m
Southwest
Thu 5/212:25 pm
SXM
- HOU
1 stop10h 05m
Southwest
Deal found 3/8![Southwest logo]()
$501
Last-minute flights from Hobby to CaribbeanDiscover last-minute flight deals from Hobby to Caribbean. Data last updated March 12, 2026 and is based on user searches.
Discover last-minute flight deals from Hobby to Caribbean. Data last updated March 12, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/112:18 pm
HOU
- SJU
1 stop9h 13m
American Airlines
Wed 4/811:59 pm
SJU
- HOU
1 stop10h 27m
American Airlines
Deal found 3/8![American Airlines logo]()
$410
This Southwest deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 4/93:10 pm
HOU
- SJU
1 stop7h 45m
Southwest
Thu 4/161:00 pm
SJU
- HOU
1 stop9h 10m
Southwest
Deal found 3/10![Southwest logo]()
$406
This Southwest deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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 4/107:45 pm
HOU
- SJU
1 stop12h 10m
Southwest
Fri 4/172:00 pm
SJU
- HOU
1 stop10h 30m
Southwest
Deal found 3/11![Southwest logo]()
$402
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:50 am
HOU
- SJU
1 stop11h 15m
Southwest
Fri 4/176:50 am
SJU
- HOU
2 stops12h 45m
Southwest
Deal found 3/8![Southwest logo]()
$404
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1310:20 am
HOU
- SJU
2 stops12h 20m
Southwest
Thu 4/161:00 pm
SJU
- HOU
1 stop9h 10m
Southwest
Deal found 3/8![Southwest logo]()
$364
This Southwest deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/145:50 am
HOU
- MBJ
1 stop5h 45m
Southwest
Thu 4/3012:15 pm
MBJ
- HOU
1 stop11h 15m
Southwest
Deal found 3/7![Southwest logo]()
$408
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/181:20 pm
HOU
- SJU
1 stop8h 55m
Southwest
Fri 4/242:00 pm
SJU
- HOU
1 stop8h 00m
Southwest
Deal found 3/8![Southwest logo]()
$422
This American Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/204:18 pm
HOU
- SJU
1 stop11h 14m
American Airlines
Sat 4/2511:59 pm
SJU
- HOU
1 stop10h 27m
American Airlines
Deal found 3/9![American Airlines logo]()
$409
This Southwest deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 4/211:00 pm
HOU
- SJU
2 stops9h 40m
Southwest
Tue 4/285:35 am
SJU
- HOU
2 stops9h 25m
Southwest
Deal found 3/10![Southwest logo]()
$418
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2510:25 am
HOU
- SJU
Nonstop4h 10m
Southwest
Thu 4/302:00 pm
SJU
- HOU
1 stop10h 30m
Southwest
Deal found 3/8![Southwest logo]()
$400
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:00 am
HOU
- SJU
1 stop6h 25m
Delta
Mon 5/46:15 am
SJU
- HOU
1 stop11h 13m
Delta
Deal found 3/10![Delta logo]()
$384
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/273:10 pm
HOU
- SJU
1 stop7h 45m
Southwest
Fri 5/15:05 am
SJU
- HOU
2 stops10h 40m
Southwest
Deal found 3/8![Southwest logo]()
$382
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 March 12, 2026.
Search for one-way flight options from Hobby to Caribbean. Find affordable one-way fares based on user searches. Data last updated March 12, 2026.
This Mytrip deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:09 pm
HOU
- SJU
1 stop16h 41m
Avelo Airlines
Deal found 3/9![Avelo Airlines logo]()
$142
This Southwest deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/75:50 am
HOU
- GCM
1 stop6h 20m
Southwest
Deal found 3/7![Southwest logo]()
$171
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/145:50 am
HOU
- MBJ
1 stop5h 45m
Southwest
Deal found 3/9![Southwest logo]()
$180
This Southwest deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 5/32:35 pm
HOU
- SJU
2 stops8h 10m
Southwest
Deal found 3/10![Southwest logo]()
$182
This American Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:01 am
HOU
- MBJ
2 stops9h 36m
American Airlines
Deal found 3/9![American Airlines logo]()
$185
This American Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/138:21 pm
HOU
- MBJ
2 stops15h 03m
American Airlines
Deal found 3/9![American Airlines logo]()
$186
This American Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/68:21 pm
HOU
- SJU
1 stop7h 11m
American Airlines
Deal found 3/9![American Airlines logo]()
$187
This American Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:23 pm
HOU
- MBJ
2 stops16h 45m
American Airlines
Deal found 3/9![American Airlines logo]()
$191
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 5/111:06 pm
HOU
- SJU
1 stop8h 11m
Delta
Deal found 3/10![Delta logo]()
$192
This American Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/248:23 pm
HOU
- MBJ
1 stop19h 54m
American Airlines
Deal found 3/9![American Airlines logo]()
$192
This American Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/146:01 am
HOU
- PUJ
1 stop9h 24m
American Airlines
Deal found 3/9![American Airlines logo]()
$199
This Southwest deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 5/17:30 pm
HOU
- SJU
1 stop13h 55m
Southwest
Deal found 3/10![Southwest logo]()
$200
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 March 12, 2026.
Round-trip from | $364 (Southwest) |
|---|---|
One-way from | $142 (Mytrip) |
Popular in | December |
Cheapest in | April |
Average price | $403 |
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 March 12, 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
Wed 5/13
7:05 pm-9:10 am
1 stop13h 05m
San Juan Luis Munoz Marin Intl
Sun 5/17
12:50 pm-9:50 pm
1 stop10h 00m
$382
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Sun 5/3
2:35 pm-11:45 pm
2 stops8h 10m
San Juan Luis Munoz Marin Intl
Sun 5/17
9:45 pm-8:35 am
1 stop11h 50m
$384
Quickest round-trip
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Sun 7/26
6:30 pm-11:55 pm
Nonstop4h 25m
San Juan Luis Munoz Marin Intl
Sat 8/1
6:30 am-2:35 pm
1 stop9h 05m
$442
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Thu 7/2
7:00 pm-12:25 am
Nonstop4h 25m
San Juan Luis Munoz Marin Intl
Mon 7/6
10:20 pm-9:45 am
2 stops12h 25m
$442
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Fri 7/24
12:20 pm-9:30 pm
1 stop8h 10m
San Juan Luis Munoz Marin Intl
Mon 7/27
8:15 pm-9:45 am
2 stops14h 30m
$446
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Wed 8/19
11:20 am-10:00 pm
1 stop9h 40m
San Juan Luis Munoz Marin Intl
Sun 8/23
6:00 am-11:25 am
1 stop6h 25m
$446
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Thu 7/2
7:30 am-9:15 pm
2 stops12h 45m
San Juan Luis Munoz Marin Intl
Tue 7/7
7:00 am-3:15 pm
2 stops9h 15m
$446
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Fri 5/1
8:05 pm-8:55 am
1 stop11h 50m
San Juan Luis Munoz Marin Intl
Sat 5/9
5:45 am-11:55 am
1 stop7h 10m
$453
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Sat 5/9
10:25 am-3:35 pm
Nonstop4h 10m
San Juan Luis Munoz Marin Intl
Wed 5/13
5:35 am-4:10 pm
1 stop11h 35m
$456
HoustonMontego Bay
HOU - MBJ
HOUMBJ
Houston Hobby
Tue 4/14
5:50 am-11:35 am
1 stop5h 45m
Montego Bay Sangster Intl
Thu 4/30
12:35 pm-11:30 pm
2 stops10h 55m
$464
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-GCM
HOU-MBJ
HOU-PUJ
HOU-NAS
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-GCM
HOU-MBJ
HOU-PUJ
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 $95). Flying from Houston Hobby Airport to Caribbean in December is currently the most expensive (average of $151). 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 March 12, 2026.
A simple way to save on the total cost of your ticket is to fly from Houston Hobby Airport to Caribbean in the evening. If you’re flexible enough to do this you can expect to save up to 36% on your trip compared to booking a flight in the morning.
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 March 12, 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
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
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 March 12, 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 6 airlines flying from Hobby to Caribbean
Discover the top 6 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 March 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$104 | Average$377 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$108 | Average$573 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$137 | Average$431 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$165 | Average$681 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$170 | Average$636 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$203 | Average$653 | FlexibilityNo cancel fee | On-time69% |