$162+ Cheap flights from Hobby (HOU) to Caribbean Islands
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/12. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — SJU
Mar 14 — Mar 211
1 adult, Economy
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Find cheap flights from Hobby to Caribbean Islands with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Hobby to Caribbean IslandsExplore the most affordable flight options available from Hobby to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 12, 2026.
Explore the most affordable flight options available from Hobby to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 12, 2026.
This Southwest deal was found by Cheapflights users on 2/10. 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 5/125:50 am
HOU
- GCM
1 stop6h 20m
Southwest
Tue 5/191:05 pm
GCM
- HOU
1 stop9h 40m
Southwest
Deal found 2/10![Southwest logo]()
$359
This Southwest deal was found by Cheapflights users on 2/11. 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.
Mon 4/2010:20 am
HOU
- SJU
2 stops12h 20m
Southwest
Thu 4/231:00 pm
SJU
- HOU
1 stop9h 10m
Southwest
Deal found 2/11![Southwest logo]()
$364
This Southwest deal was found by Cheapflights users on 2/11. 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.
Sat 5/210:25 am
HOU
- SJU
Nonstop4h 10m
Southwest
Wed 5/65:35 am
SJU
- HOU
1 stop11h 35m
Southwest
Deal found 2/11![Southwest logo]()
$365
This Delta deal was found by Cheapflights users on 2/9. 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 5/1410:12 am
HOU
- SJU
1 stop11h 05m
Delta
Mon 5/1812:50 pm
SJU
- HOU
1 stop11h 18m
Delta
Deal found 2/9![Delta logo]()
$374
This Southwest deal was found by Cheapflights users on 2/9. 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 5/710:20 am
HOU
- SJU
2 stops12h 20m
Southwest
Fri 5/86:50 am
SJU
- HOU
1 stop8h 10m
Southwest
Deal found 2/9![Southwest logo]()
$377
This Southwest deal was found by Cheapflights users on 2/9. 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 5/141:20 pm
HOU
- SJU
2 stops9h 05m
Southwest
Mon 5/188:40 pm
SJU
- HOU
1 stop12h 25m
Southwest
Deal found 2/9![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 2/10. 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 5/141:20 pm
HOU
- SJU
2 stops9h 05m
Southwest
Sun 5/179:45 pm
SJU
- HOU
1 stop13h 15m
Southwest
Deal found 2/10![Southwest logo]()
$387
This Southwest deal was found by Cheapflights users on 2/10. 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 4/125:05 am
HOU
- MBJ
1 stop9h 15m
Southwest
Fri 4/172:25 pm
MBJ
- HOU
1 stop9h 05m
Southwest
Deal found 2/10![Southwest logo]()
$388
This Southwest deal was found by Cheapflights users on 2/9. 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 3/1011:05 am
HOU
- SJU
2 stops10h 55m
Southwest
Mon 3/168:50 pm
SJU
- HOU
1 stop13h 20m
Southwest
Deal found 2/9![Southwest logo]()
$390
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Fri 4/248:21 pm
HOU
- MBJ
1 stop16h 49m
American Airlines
Mon 4/274:37 pm
MBJ
- HOU
2 stops16h 49m
American Airlines
Deal found 2/10![American Airlines logo]()
$393
This Southwest deal was found by Cheapflights users on 2/10. 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
Sun 5/312:50 pm
SJU
- HOU
1 stop10h 00m
Southwest
Deal found 2/10![Southwest logo]()
$400
This Southwest deal was found by Cheapflights users on 2/11. 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 4/285:50 am
HOU
- PUJ
1 stop6h 15m
Southwest
Thu 5/74:00 pm
PUJ
- HOU
1 stop9h 05m
Southwest
Deal found 2/11![Southwest logo]()
$401
Best flights from Hobby to Caribbean IslandsDiscover carefully curated flight deals from Hobby to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 12, 2026.
Discover carefully curated flight deals from Hobby to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 12, 2026.
This Southwest deal was found by Cheapflights users on 2/9. 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.
Wed 5/1312:50 pm
HOU
- SJU
2 stops9h 50m
Southwest
Sun 5/179:45 pm
SJU
- HOU
1 stop13h 15m
Southwest
Deal found 2/9![Southwest logo]()
$364
This American Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:21 pm
HOU
- MBJ
1 stop16h 49m
American Airlines
Tue 4/144:37 pm
MBJ
- HOU
2 stops16h 49m
American Airlines
Deal found 2/9![American Airlines logo]()
$393
This Delta deal was found by Cheapflights users on 2/9. 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.
Tue 3/176:00 am
HOU
- NAS
1 stop9h 45m
Delta
Wed 3/253:05 pm
NAS
- HOU
1 stop8h 37m
Delta
Deal found 2/9![Delta logo]()
$516
This Southwest deal was found by Cheapflights users on 2/11. 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.
Mon 4/2010:20 am
HOU
- SJU
2 stops12h 20m
Southwest
Thu 4/231:00 pm
SJU
- HOU
1 stop9h 10m
Southwest
Deal found 2/11![Southwest logo]()
$364
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Mon 4/138:21 pm
HOU
- MBJ
2 stops15h 03m
American Airlines
Fri 4/174:37 pm
MBJ
- HOU
2 stops16h 49m
American Airlines
Deal found 2/10![American Airlines logo]()
$393
This Southwest deal was found by Cheapflights users on 2/11. 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 5/510:25 am
HOU
- SJU
2 stops9h 40m
Southwest
Tue 5/125:05 am
SJU
- HOU
1 stop10h 55m
Southwest
Deal found 2/11![Southwest logo]()
$364
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Fri 4/248:21 pm
HOU
- MBJ
1 stop16h 49m
American Airlines
Mon 4/274:37 pm
MBJ
- HOU
2 stops16h 49m
American Airlines
Deal found 2/10![American Airlines logo]()
$393
This Southwest deal was found by Cheapflights users on 2/11. 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.
Sat 5/210:25 am
HOU
- SJU
Nonstop4h 10m
Southwest
Tue 5/52:00 pm
SJU
- HOU
1 stop6h 45m
Southwest
Deal found 2/11![Southwest logo]()
$365
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Sat 4/258:21 pm
HOU
- MBJ
2 stops15h 03m
American Airlines
Wed 4/2912:25 pm
MBJ
- HOU
2 stops11h 22m
American Airlines
Deal found 2/10![American Airlines logo]()
$393
This Southwest deal was found by Cheapflights users on 2/11. 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.
Sat 5/210:25 am
HOU
- SJU
Nonstop4h 10m
Southwest
Wed 5/65:35 am
SJU
- HOU
1 stop11h 35m
Southwest
Deal found 2/11![Southwest logo]()
$365
This Delta deal was found by Cheapflights users on 2/9. 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.
Tue 5/56:00 am
HOU
- NAS
1 stop7h 03m
Delta
Tue 5/121:12 pm
NAS
- HOU
1 stop10h 56m
Delta
Deal found 2/9![Delta logo]()
$516
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 4/286:01 am
HOU
- PUJ
1 stop9h 24m
American Airlines
Thu 5/73:34 pm
PUJ
- HOU
1 stop18h 52m
American Airlines
Deal found 2/10![American Airlines logo]()
$401
This Southwest deal was found by Cheapflights users on 2/11. 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.
Sat 4/255:40 am
HOU
- SJU
1 stop8h 10m
Southwest
Wed 4/295:05 am
SJU
- HOU
1 stop15h 05m
Southwest
Deal found 2/11![Southwest logo]()
$369
This Delta deal was found by Cheapflights users on 2/9. 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.
Tue 3/106:00 am
HOU
- NAS
1 stop4h 53m
Delta
Tue 3/171:15 pm
NAS
- HOU
2 stops10h 27m
Delta
Deal found 2/9![Delta logo]()
$520
This Southwest deal was found by Cheapflights users on 2/10. 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.
Mon 5/111:30 pm
HOU
- SJU
2 stops8h 55m
Southwest
Sun 5/179:45 pm
SJU
- HOU
1 stop11h 50m
Southwest
Deal found 2/10![Southwest logo]()
$369
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 5/56:01 am
HOU
- PUJ
1 stop9h 24m
American Airlines
Mon 5/113:34 pm
PUJ
- HOU
1 stop9h 13m
American Airlines
Deal found 2/10![American Airlines logo]()
$411
This Delta deal was found by Cheapflights users on 2/10. 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 8/46:00 am
HOU
- UVF
1 stop7h 13m
Delta
Thu 8/133:28 pm
UVF
- HOU
1 stop18h 47m
Delta
Deal found 2/10![Delta logo]()
$538
This American Airlines deal was found by Cheapflights users on 2/9. 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.
Thu 3/56:00 am
HOU
- MBJ
1 stop7h 53m
American Airlines
Mon 3/163:04 pm
MBJ
- HOU
1 stop8h 54m
American Airlines
Deal found 2/9![American Airlines logo]()
$414
This Southwest deal was found by Cheapflights users on 2/10. 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 4/125:05 am
HOU
- MBJ
1 stop9h 15m
Southwest
Fri 4/172:25 pm
MBJ
- HOU
1 stop9h 05m
Southwest
Deal found 2/10![Southwest logo]()
$388
This Delta deal was found by Cheapflights users on 2/8. 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 3/176:00 am
HOU
- SDQ
1 stop6h 10m
Delta
Tue 3/242:35 pm
SDQ
- HOU
1 stop9h 07m
Delta
Deal found 2/8![Delta logo]()
$539
This Southwest deal was found by Cheapflights users on 2/11. 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.
Sun 5/35:05 am
HOU
- PUJ
1 stop9h 10m
Southwest
Wed 5/62:05 pm
PUJ
- HOU
1 stop9h 40m
Southwest
Deal found 2/11![Southwest logo]()
$401
This Delta deal was found by Cheapflights users on 2/10. 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 3/216:00 am
HOU
- NAS
1 stop9h 45m
Delta
Wed 3/251:18 pm
NAS
- HOU
1 stop10h 24m
Delta
Deal found 2/10![Delta logo]()
$541
This Southwest deal was found by Cheapflights users on 2/10. 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 4/285:50 am
HOU
- PUJ
1 stop6h 15m
Southwest
Thu 5/71:40 pm
PUJ
- HOU
1 stop11h 25m
Southwest
Deal found 2/10![Southwest logo]()
$401
This Delta deal was found by Cheapflights users on 2/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:00 am
HOU
- NAS
1 stop9h 33m
Delta
Wed 4/293:28 pm
NAS
- HOU
1 stop8h 37m
Delta
Deal found 2/11![Delta logo]()
$541
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/285:50 am
HOU
- PUJ
1 stop6h 15m
Southwest
Tue 5/52:05 pm
PUJ
- HOU
1 stop9h 40m
Southwest
Deal found 2/12![Southwest logo]()
$401
This Delta deal was found by Cheapflights users on 2/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/16:00 am
HOU
- NAS
1 stop9h 45m
Delta
Sun 4/53:05 pm
NAS
- HOU
1 stop8h 37m
Delta
Deal found 2/11![Delta logo]()
$541
This American Airlines deal was found by Cheapflights users on 2/8. 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.
Tue 3/1712:18 pm
HOU
- SDQ
2 stops9h 35m
American Airlines
Tue 3/246:00 am
SDQ
- HOU
2 stops10h 50m
American Airlines
Deal found 2/8![American Airlines logo]()
$543
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 8/46:23 pm
HOU
- UVF
2 stops18h 52m
American Airlines
Thu 8/133:15 pm
UVF
- HOU
2 stops19h 30m
American Airlines
Deal found 2/10![American Airlines logo]()
$543
This Southwest deal was found by Cheapflights users on 2/9. 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.
Mon 3/98:55 pm
HOU
- MBJ
2 stops17h 35m
Southwest
Fri 3/132:50 pm
MBJ
- HOU
Nonstop3h 30m
Southwest
Deal found 2/9![Southwest logo]()
$414
This Delta deal was found by Cheapflights users on 2/9. 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.
Wed 3/186:00 am
HOU
- SDQ
1 stop6h 10m
Delta
Mon 3/232:35 pm
SDQ
- HOU
1 stop9h 07m
Delta
Deal found 2/9![Delta logo]()
$569
Last-minute flights from Hobby to Caribbean IslandsDiscover last-minute flight deals from Hobby to Caribbean Islands. Data last updated February 12, 2026 and is based on user searches.
Discover last-minute flight deals from Hobby to Caribbean Islands. Data last updated February 12, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 2/9. 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.
Wed 3/45:25 am
HOU
- SJU
1 stop10h 02m
Delta
Tue 3/176:15 am
SJU
- HOU
1 stop11h 21m
Delta
Deal found 2/9![Delta logo]()
$400
This Southwest deal was found by Cheapflights users on 2/10. 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.
Wed 3/46:00 am
HOU
- MBJ
1 stop7h 10m
Southwest
Tue 3/101:00 pm
MBJ
- HOU
2 stops11h 05m
Southwest
Deal found 2/10![Southwest logo]()
$418
This American Airlines deal was found by Cheapflights users on 2/9. 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.
Thu 3/56:00 am
HOU
- MBJ
1 stop7h 53m
American Airlines
Mon 3/163:04 pm
MBJ
- HOU
1 stop8h 54m
American Airlines
Deal found 2/9![American Airlines logo]()
$414
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 3/58:20 pm
HOU
- MBJ
1 stop17h 33m
American Airlines
Tue 3/173:04 pm
MBJ
- HOU
1 stop18h 39m
American Airlines
Deal found 2/12![American Airlines logo]()
$427
This Southwest deal was found by Cheapflights users on 2/9. 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 3/102:45 pm
HOU
- SJU
1 stop6h 30m
Southwest
Mon 3/168:50 pm
SJU
- HOU
1 stop13h 20m
Southwest
Deal found 2/9![Southwest logo]()
$390
This Southwest deal was found by Cheapflights users on 2/10. 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 3/1011:05 am
HOU
- SJU
2 stops10h 55m
Southwest
Tue 3/1710:10 am
SJU
- HOU
2 stops10h 25m
Southwest
Deal found 2/10![Southwest logo]()
$395
This Southwest deal was found by Cheapflights users on 2/8. 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 3/1110:15 am
HOU
- SJU
1 stop11h 45m
Southwest
Tue 3/178:20 pm
SJU
- HOU
1 stop13h 50m
Southwest
Deal found 2/8![Southwest logo]()
$416
This Delta deal was found by Cheapflights users on 2/10. 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.
Wed 3/112:13 pm
HOU
- SJU
1 stop8h 02m
Delta
Tue 3/176:15 am
SJU
- HOU
1 stop11h 21m
Delta
Deal found 2/10![Delta logo]()
$421
This Southwest deal was found by Cheapflights users on 2/9. 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.
Wed 3/1110:15 am
HOU
- SJU
1 stop11h 45m
Southwest
Wed 3/185:15 am
SJU
- HOU
1 stop11h 55m
Southwest
Deal found 2/9![Southwest logo]()
$430
This Southwest deal was found by Cheapflights users on 2/9. 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 3/122:45 pm
HOU
- SJU
1 stop7h 10m
Southwest
Mon 3/168:50 pm
SJU
- HOU
1 stop13h 20m
Southwest
Deal found 2/9![Southwest logo]()
$408
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/155:00 am
HOU
- MBJ
1 stop9h 55m
Southwest
Fri 3/202:50 pm
MBJ
- HOU
Nonstop3h 30m
Southwest
Deal found 2/12![Southwest logo]()
$430
This Southwest deal was found by Cheapflights users on 2/11. 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.
Wed 3/182:40 pm
HOU
- SJU
2 stops8h 35m
Southwest
Wed 3/255:55 am
SJU
- HOU
2 stops8h 45m
Southwest
Deal found 2/11![Southwest logo]()
$426
One-way flights from Hobby to Caribbean IslandsSearch for one-way flight options from Hobby to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated February 12, 2026.
Search for one-way flight options from Hobby to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated February 12, 2026.
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/126:45 am
HOU
- NAS
1 stop5h 35m
Southwest
Deal found 2/12![Southwest logo]()
$162
This Mytrip deal was found by Cheapflights users on 2/9. 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 2/9![Avelo Airlines logo]()
$169
This Southwest deal was found by Cheapflights users on 2/9. 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 4/126:45 am
HOU
- MBJ
1 stop6h 55m
Southwest
Deal found 2/9![Southwest logo]()
$170
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Sat 4/188:21 pm
HOU
- MBJ
2 stops15h 03m
American Airlines
Deal found 2/10![American Airlines logo]()
$176
This Southwest deal was found by Cheapflights users on 2/9. 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 3/1011:05 am
HOU
- SJU
2 stops10h 55m
Southwest
Deal found 2/9![Southwest logo]()
$182
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 3/98:20 pm
HOU
- MBJ
1 stop17h 44m
American Airlines
Deal found 2/12![American Airlines logo]()
$182
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/210:25 am
HOU
- SJU
Nonstop4h 10m
Southwest
Deal found 2/12![Southwest logo]()
$183
This Delta deal was found by Cheapflights users on 2/10. 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 5/910:12 am
HOU
- SJU
1 stop11h 05m
Delta
Deal found 2/10![Delta logo]()
$187
This Southwest deal was found by Cheapflights users on 2/11. 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.
Sun 4/126:35 pm
HOU
- PUJ
2 stops17h 05m
Southwest
Deal found 2/11![Southwest logo]()
$189
This American Airlines deal was found by Cheapflights users on 2/11. 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.
Mon 4/138:21 pm
HOU
- PUJ
2 stops15h 41m
American Airlines
Deal found 2/11![American Airlines logo]()
$194
This Mytrip deal was found by Cheapflights users on 2/9. 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 3/16:32 pm
HOU
- SJU
1 stop16h 48m
Avelo Airlines
Deal found 2/9![Avelo Airlines logo]()
$195
This Southwest deal was found by Cheapflights users on 2/9. 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.
Wed 5/66:00 am
HOU
- MBJ
1 stop7h 55m
Southwest
Deal found 2/9![Southwest logo]()
$195
Find flight deals from Hobby to Caribbean Islands
Keep the following information in mind while searching for Hobby to Caribbean Islands flight deals. Data was last updated February 12, 2026.
Round-trip from | $359 (Southwest) |
|---|---|
One-way from | $162 (Southwest) |
Popular in | December |
Cheapest in | April |
Average price | $387 |
Cheapflights Fare Finder
Customize your flight search to find flights from Hobby to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 12, 2026.
Use the filters below to find and compare flights from Houston Hobby Airport to Caribbean Islands that are best for you.
Fly from
Hobby
Fly to
Caribbean Islands
Route
Depart
Return
Price
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Wed 5/13
12:50 pm-11:40 pm
2 stops9h 50m
San Juan Luis Munoz Marin Intl
Sun 5/17
9:45 pm-10:00 am
1 stop13h 15m
$364
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Mon 4/20
10:20 am-11:40 pm
2 stops12h 20m
San Juan Luis Munoz Marin Intl
Thu 4/23
1:00 pm-9:10 pm
1 stop9h 10m
$364
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Tue 5/5
10:25 am-9:05 pm
2 stops9h 40m
San Juan Luis Munoz Marin Intl
Tue 5/12
5:05 am-3:00 pm
1 stop10h 55m
$364
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Sat 5/2
10:25 am-3:35 pm
Nonstop4h 10m
San Juan Luis Munoz Marin Intl
Tue 5/5
2:00 pm-7:45 pm
1 stop6h 45m
$365
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Sat 5/2
10:25 am-3:35 pm
Nonstop4h 10m
San Juan Luis Munoz Marin Intl
Wed 5/6
5:35 am-4:10 pm
1 stop11h 35m
$365
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Sat 4/25
5:40 am-2:50 pm
1 stop8h 10m
San Juan Luis Munoz Marin Intl
Wed 4/29
5:05 am-7:10 pm
1 stop15h 05m
$369
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Mon 5/11
1:30 pm-11:25 pm
2 stops8h 55m
San Juan Luis Munoz Marin Intl
Sun 5/17
9:45 pm-8:35 am
1 stop11h 50m
$369
HoustonMontego Bay
HOU - MBJ
HOUMBJ
Houston Hobby
Sun 4/12
5:05 am-2:20 pm
1 stop9h 15m
Montego Bay Sangster Intl
Fri 4/17
2:25 pm-11:30 pm
1 stop9h 05m
$388
HoustonMontego Bay
HOU - MBJ
HOUMBJ
Houston Hobby
Fri 4/10
8:21 pm-1:10 pm
1 stop16h 49m
Montego Bay Sangster Intl
Tue 4/14
4:37 pm-9:26 am
2 stops16h 49m
$393
HoustonMontego Bay
HOU - MBJ
HOUMBJ
Houston Hobby
Mon 4/13
8:21 pm-11:24 am
2 stops15h 03m
Montego Bay Sangster Intl
Fri 4/17
4:37 pm-9:26 am
2 stops16h 49m
$393
Showing 1-10 of 60 results
Best time to book a flight from Hobby to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Hobby with our price prediction graph.
HOU-NAS
HOU-SJU
HOU-MBJ
HOU-PUJ
HOU-UVF
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 Islands
HOU-zzEPX
HOU-NAS
HOU-SJU
HOU-MBJ
HOU-PUJ
What is the cheapest month to book a flight from Houston Hobby Airport to Caribbean Islands?
Currently, April is the cheapest month in which you can book a flight from Houston Hobby Airport to Caribbean Islands (average of $91). Flying from Houston Hobby Airport to Caribbean Islands 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 EPX?
Find hourly flight availability from Hobby to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 12, 2026.
It’s typically best to fly out from Houston Hobby Airport to Caribbean Islands in the evening. Doing so could potentially save you 37% on the flight price compared to flying in the morning, which is usually more expensive.
Reviews of airlines servicing Caribbean Islands
Get insights into the airlines that provide service to Caribbean Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean Islands. Reviews last updated February 12, 2026.
Read through reviews of airlines operating flights from Houston Hobby Airport to Caribbean Islands, such as Southwest, Delta, and United Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Hobby to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Hobby to Caribbean Islands
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean Islands by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Hobby to Caribbean Islands by cabin class
Find flights from Hobby to Caribbean Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Hobby and Caribbean Islands flights
Browse other Hobby and Caribbean Islands flight options. Last updated on February 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Hobby to Caribbean Islands flights
Consider these flights traveling from Hobby to Caribbean Islands.
Top 6 airlines flying from Hobby to Caribbean Islands
Discover the top 6 airlines that operate flights from Hobby to Caribbean Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$102 | Average$363 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$108 | Average$552 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$134 | Average$423 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$165 | Average$689 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$170 | Average$622 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$192 | Average$672 | FlexibilityNo cancel fee | On-time69% |