$155+ 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 8/17. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — SJU
May 24 — May 311
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 April 24, 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 April 24, 2026.
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 9/105:05 am
HOU
- SJU
1 stop10h 50m
Southwest
Mon 9/146:00 am
SJU
- HOU
1 stop6h 05m
Southwest
Deal found 4/21![Southwest logo]()
$310
This Southwest deal was found by Cheapflights users on 4/22. 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.
Tue 9/16:25 am
HOU
- SJU
1 stop9h 00m
Southwest
Sat 9/126:25 am
SJU
- HOU
1 stop7h 20m
Southwest
Deal found 4/22![Southwest logo]()
$350
This American Airlines deal was found by Cheapflights users on 4/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:41 am
HOU
- SJU
1 stop8h 13m
American Airlines
Sun 8/233:44 pm
SJU
- HOU
1 stop9h 11m
American Airlines
Deal found 4/22![American Airlines logo]()
$355
This Southwest deal was found by Cheapflights users on 4/23. 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 8/204:50 pm
HOU
- SJU
1 stop6h 00m
Southwest
Wed 8/261:20 pm
SJU
- HOU
1 stop7h 30m
Southwest
Deal found 4/23![Southwest logo]()
$368
This Southwest deal was found by Cheapflights users on 4/23. 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 9/41:15 pm
HOU
- SJU
1 stop8h 00m
Southwest
Wed 9/161:45 pm
SJU
- HOU
1 stop6h 35m
Southwest
Deal found 4/23![Southwest logo]()
$388
This American Airlines deal was found by Cheapflights users on 4/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/215:41 am
HOU
- SJU
1 stop8h 13m
American Airlines
Sat 8/296:00 am
SJU
- HOU
2 stops10h 28m
American Airlines
Deal found 4/22![American Airlines logo]()
$423
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 9/145:05 am
HOU
- SJU
1 stop10h 50m
Southwest
Mon 9/215:30 am
SJU
- HOU
1 stop13h 15m
Southwest
Deal found 4/21![Southwest logo]()
$426
This Delta deal was found by Cheapflights users on 4/23. 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.
Sun 8/1610:05 am
HOU
- SJU
1 stop11h 18m
Delta
Fri 8/211:06 pm
SJU
- HOU
1 stop9h 29m
Delta
Deal found 4/23![Delta logo]()
$428
This Delta deal was found by Cheapflights users on 4/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:00 am
HOU
- MBJ
1 stop9h 34m
Delta
Thu 9/104:59 pm
MBJ
- HOU
1 stop16h 16m
Delta
Deal found 4/22![Delta logo]()
$467
This Southwest deal was found by Cheapflights users on 4/22. 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.
Sun 9/65:00 am
HOU
- STT
1 stop7h 25m
Southwest
Thu 9/172:35 pm
STT
- HOU
2 stops18h 50m
Southwest
Deal found 4/22![Southwest logo]()
$468
This American Airlines deal was found by Cheapflights users on 4/23. 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 5/259:30 am
HOU
- MBJ
1 stop6h 47m
American Airlines
Thu 5/2812:47 pm
MBJ
- HOU
1 stop11h 12m
American Airlines
Deal found 4/23![American Airlines logo]()
$482
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 6/219:55 am
HOU
- MBJ
Nonstop3h 05m
Southwest
Thu 6/253:55 pm
MBJ
- HOU
Nonstop3h 10m
Southwest
Deal found 4/20![Southwest logo]()
$486
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 April 24, 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 April 24, 2026.
This Southwest deal was found by Cheapflights users on 4/23. 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 9/115:05 am
HOU
- SJU
1 stop7h 40m
Southwest
Tue 9/151:45 pm
SJU
- HOU
2 stops10h 00m
Southwest
Deal found 4/23![Southwest logo]()
$350
This Delta deal was found by Cheapflights users on 4/23. 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 5/81:06 pm
HOU
- SJU
1 stop6h 24m
Delta
Tue 5/127:30 am
SJU
- HOU
1 stop9h 39m
Delta
Deal found 4/23![Delta logo]()
$556
This American Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 6/238:23 pm
HOU
- SXM
2 stops16h 27m
American Airlines
Wed 7/12:53 pm
SXM
- HOU
2 stops19h 12m
American Airlines
Deal found 4/19![American Airlines logo]()
$670
This Southwest deal was found by Cheapflights users on 4/22. 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.
Fri 6/57:00 pm
HOU
- SJU
Nonstop4h 25m
Southwest
Fri 6/198:15 pm
SJU
- HOU
1 stop12h 30m
Southwest
Deal found 4/22![Southwest logo]()
$462
This Southwest deal was found by Cheapflights users on 4/23. 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 5/162:55 pm
HOU
- SJU
2 stops7h 50m
Southwest
Sat 5/232:10 pm
SJU
- HOU
1 stop8h 25m
Southwest
Deal found 4/23![Southwest logo]()
$466
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 8/192:45 pm
HOU
- SJU
1 stop6h 15m
Southwest
Wed 8/261:45 pm
SJU
- HOU
2 stops10h 00m
Southwest
Deal found 4/19![Southwest logo]()
$466
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 5/106:00 am
HOU
- MBJ
1 stop6h 56m
Delta
Fri 5/151:18 pm
MBJ
- HOU
1 stop9h 08m
Delta
Deal found 4/21![Delta logo]()
$576
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 7/222:00 pm
HOU
- SJU
2 stops8h 45m
Southwest
Mon 7/278:15 pm
SJU
- HOU
2 stops14h 30m
Southwest
Deal found 4/21![Southwest logo]()
$466
This Delta deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 7/296:00 am
HOU
- MBJ
1 stop9h 34m
Delta
Tue 8/41:17 pm
MBJ
- HOU
1 stop8h 34m
Delta
Deal found 4/19![Delta logo]()
$576
This American Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 7/78:23 pm
HOU
- SXM
2 stops16h 28m
American Airlines
Wed 7/154:46 pm
SXM
- HOU
2 stops17h 19m
American Airlines
Deal found 4/19![American Airlines logo]()
$670
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 6/215:35 am
HOU
- MBJ
1 stop9h 20m
Southwest
Thu 6/253:55 pm
MBJ
- HOU
Nonstop3h 10m
Southwest
Deal found 4/20![Southwest logo]()
$490
This American Airlines deal was found by Cheapflights users on 4/24. 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.
Sat 5/164:19 pm
HOU
- CUR
2 stops20h 19m
American Airlines
Sat 5/234:46 pm
CUR
- HOU
2 stops17h 11m
American Airlines
Deal found 4/24![American Airlines logo]()
$728
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/168:20 pm
HOU
- STT
2 stops15h 50m
Southwest
Wed 5/202:10 pm
STT
- HOU
2 stops9h 55m
Southwest
Deal found 4/20![Southwest logo]()
$503
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 6/276:00 am
HOU
- NAS
1 stop9h 37m
Delta
Mon 8/311:13 pm
NAS
- HOU
1 stop9h 22m
Delta
Deal found 4/20![Delta logo]()
$686
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 8/11:20 pm
HOU
- SJU
2 stops9h 20m
Southwest
Sat 8/86:25 am
SJU
- HOU
2 stops8h 20m
Southwest
Deal found 4/19![Southwest logo]()
$506
This Delta deal was found by Cheapflights users on 4/23. 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.
Wed 9/26:00 am
HOU
- STT
1 stop6h 52m
Delta
Sun 9/63:02 pm
STT
- HOU
1 stop7h 33m
Delta
Deal found 4/23![Delta logo]()
$698
This American Airlines deal was found by Cheapflights users on 4/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/148:21 pm
HOU
- CUR
2 stops18h 27m
American Airlines
Sun 5/173:32 pm
CUR
- HOU
2 stops18h 54m
American Airlines
Deal found 4/22![American Airlines logo]()
$778
This Southwest deal was found by Cheapflights users on 4/22. 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.
Fri 8/710:00 am
HOU
- SJU
2 stops11h 50m
Southwest
Sun 8/96:00 am
SJU
- HOU
1 stop6h 25m
Southwest
Deal found 4/22![Southwest logo]()
$506
This American Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 6/96:40 pm
HOU
- CUR
2 stops20h 05m
American Airlines
Sun 6/144:46 pm
CUR
- HOU
2 stops20h 34m
American Airlines
Deal found 4/19![American Airlines logo]()
$813
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 7/245:00 am
HOU
- MBJ
1 stop8h 55m
Southwest
Tue 7/283:55 pm
MBJ
- HOU
Nonstop3h 10m
Southwest
Deal found 4/20![Southwest logo]()
$515
This Delta deal was found by Cheapflights users on 4/23. 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 9/36:00 am
HOU
- STT
1 stop6h 52m
Delta
Sat 9/53:02 pm
STT
- HOU
1 stop7h 33m
Delta
Deal found 4/23![Delta logo]()
$760
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 7/217:20 pm
HOU
- SJU
Nonstop4h 25m
Southwest
Fri 7/2410:20 pm
SJU
- HOU
1 stop10h 25m
Southwest
Deal found 4/20![Southwest logo]()
$517
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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
- PUJ
1 stop7h 35m
Delta
Tue 5/261:05 pm
PUJ
- HOU
1 stop10h 21m
Delta
Deal found 4/20![Delta logo]()
$770
This American Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 6/38:23 pm
HOU
- CUR
2 stops18h 22m
American Airlines
Tue 6/94:46 pm
CUR
- HOU
2 stops17h 11m
American Airlines
Deal found 4/20![American Airlines logo]()
$873
This Southwest deal was found by Cheapflights users on 4/23. 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 9/35:05 am
HOU
- STT
1 stop7h 45m
Southwest
Sun 9/62:10 pm
STT
- HOU
2 stops9h 50m
Southwest
Deal found 4/23![Southwest logo]()
$520
This Delta deal was found by Cheapflights users on 4/23. 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 5/146:00 am
HOU
- PUJ
1 stop7h 35m
Delta
Tue 5/191:05 pm
PUJ
- HOU
1 stop10h 21m
Delta
Deal found 4/23![Delta logo]()
$776
This American Airlines deal was found by Cheapflights users on 4/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/188:23 pm
HOU
- CUR
2 stops18h 22m
American Airlines
Fri 6/264:46 pm
CUR
- HOU
2 stops17h 11m
American Airlines
Deal found 4/22![American Airlines logo]()
$883
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 6/206:00 am
HOU
- AUA
1 stop7h 10m
Delta
Sat 7/43:25 pm
AUA
- HOU
1 stop7h 28m
Delta
Deal found 4/20![Delta logo]()
$786
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 9/127:40 pm
HOU
- STT
2 stops16h 45m
Southwest
Sat 9/192:05 pm
STT
- HOU
1 stop7h 35m
Southwest
Deal found 4/21![Southwest logo]()
$538
This American Airlines deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 6/196:39 pm
HOU
- CUR
2 stops19h 00m
American Airlines
Thu 6/254:46 pm
CUR
- HOU
2 stops17h 11m
American Airlines
Deal found 4/21![American Airlines logo]()
$883
Last-minute flights from Hobby to CaribbeanDiscover last-minute flight deals from Hobby to Caribbean. Data last updated April 24, 2026 and is based on user searches.
Discover last-minute flight deals from Hobby to Caribbean. Data last updated April 24, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/81:30 pm
HOU
- SJU
2 stops9h 25m
Southwest
Sat 5/1610:00 am
SJU
- HOU
1 stop9h 45m
Southwest
Deal found 4/19![Southwest logo]()
$511
This Southwest deal was found by Cheapflights users on 4/22. 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.
Sat 5/910:25 am
HOU
- SJU
Nonstop4h 10m
Southwest
Wed 5/135:05 am
SJU
- HOU
1 stop11h 05m
Southwest
Deal found 4/22![Southwest logo]()
$507
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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
Mon 5/181:14 pm
SJU
- HOU
1 stop10h 12m
Delta
Deal found 4/20![Delta logo]()
$489
This American Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/1312:42 pm
HOU
- SJU
1 stop9h 21m
American Airlines
Sun 5/1711:59 pm
SJU
- HOU
1 stop10h 27m
American Airlines
Deal found 4/19![American Airlines logo]()
$471
This Southwest deal was found by Cheapflights users on 4/23. 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 5/165:40 am
HOU
- SJU
1 stop8h 10m
Southwest
Sat 5/233:30 pm
SJU
- HOU
Nonstop5h 05m
Southwest
Deal found 4/23![Southwest logo]()
$462
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/168:20 pm
HOU
- STT
2 stops15h 50m
Southwest
Wed 5/202:10 pm
STT
- HOU
2 stops9h 55m
Southwest
Deal found 4/20![Southwest logo]()
$503
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 5/176:45 am
HOU
- MBJ
1 stop6h 55m
Southwest
Wed 5/2012:15 pm
MBJ
- HOU
1 stop10h 30m
Southwest
Deal found 4/21![Southwest logo]()
$500
This American Airlines deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 5/178:21 pm
HOU
- MBJ
2 stops15h 03m
American Airlines
Wed 5/2012:25 pm
MBJ
- HOU
2 stops11h 29m
American Airlines
Deal found 4/21![American Airlines logo]()
$505
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 5/172:35 pm
HOU
- SJU
2 stops8h 10m
Southwest
Sun 5/247:50 pm
SJU
- HOU
1 stop13h 45m
Southwest
Deal found 4/21![Southwest logo]()
$506
This Southwest deal was found by Cheapflights users on 4/22. 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.
Mon 5/181:20 pm
HOU
- SJU
2 stops9h 05m
Southwest
Tue 5/195:35 am
SJU
- HOU
2 stops10h 25m
Southwest
Deal found 4/22![Southwest logo]()
$516
This American Airlines deal was found by Cheapflights users on 4/23. 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 5/259:30 am
HOU
- MBJ
1 stop6h 47m
American Airlines
Thu 5/2812:47 pm
MBJ
- HOU
1 stop11h 12m
American Airlines
Deal found 4/23![American Airlines logo]()
$482
This American Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/298:23 pm
HOU
- MBJ
1 stop19h 54m
American Airlines
Wed 6/312:47 pm
MBJ
- HOU
1 stop7h 04m
American Airlines
Deal found 4/19![American Airlines logo]()
$507
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 April 24, 2026.
Search for one-way flight options from Hobby to Caribbean. Find affordable one-way fares based on user searches. Data last updated April 24, 2026.
This Delta deal was found by Cheapflights users on 4/23. 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.
Sat 9/261:00 pm
HOU
- SJU
1 stop8h 00m
Delta
Deal found 4/23![Delta logo]()
$155
This Southwest deal was found by Cheapflights users on 4/23. 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 7/2210:10 am
HOU
- MBJ
Nonstop3h 10m
Southwest
Deal found 4/23![Southwest logo]()
$164
This Delta deal was found by Cheapflights users on 4/23. 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.
Sun 7/196:00 am
HOU
- MBJ
1 stop5h 52m
Delta
Deal found 4/23![Delta logo]()
$168
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Wed 7/228:23 pm
HOU
- MBJ
2 stops16h 46m
American Airlines
Deal found 4/23![American Airlines logo]()
$179
This American Airlines deal was found by Cheapflights users on 4/23. 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 6/228:23 pm
HOU
- MBJ
1 stop19h 54m
American Airlines
Deal found 4/23![American Airlines logo]()
$180
This Southwest deal was found by Cheapflights users on 4/23. 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.
Mon 8/171:20 pm
HOU
- SJU
2 stops9h 30m
Southwest
Deal found 4/23![Southwest logo]()
$195
This American Airlines deal was found by Cheapflights users on 4/23. 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 5/256:39 pm
HOU
- MBJ
2 stops16h 40m
American Airlines
Deal found 4/23![American Airlines logo]()
$203
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Tue 5/194:19 pm
HOU
- MBJ
2 stops21h 06m
American Airlines
Deal found 4/23![American Airlines logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/77:14 pm
HOU
- SJU
3 stops30h 32m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$213
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Sat 6/206:39 pm
HOU
- MBJ
1 stop21h 38m
American Airlines
Deal found 4/23![American Airlines logo]()
$216
This Southwest deal was found by Cheapflights users on 4/22. 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.
Sun 6/219:55 am
HOU
- MBJ
Nonstop3h 05m
Southwest
Deal found 4/22![Southwest logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 4/24. 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 6/197:44 pm
HOU
- SJU
2 stops43h 14m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$226
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 April 24, 2026.
Round-trip from | $310 (Delta) |
|---|---|
One-way from | $155 (Delta) |
Popular in | December |
Cheapest in | October |
Average price | $398 |
Good round-trip deal | $462 or less |
Good one-way deal | $228 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 April 24, 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
Fri 9/11
5:05 am-1:45 pm
1 stop7h 40m
San Juan Luis Munoz Marin Intl
Tue 9/15
1:45 pm-10:45 pm
2 stops10h 00m
$350
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Fri 6/5
7:00 pm-12:25 am
Nonstop4h 25m
San Juan Luis Munoz Marin Intl
Fri 6/19
8:15 pm-7:45 am
1 stop12h 30m
$462
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Sat 5/16
2:55 pm-11:45 pm
2 stops7h 50m
San Juan Luis Munoz Marin Intl
Sat 5/23
2:10 pm-9:35 pm
1 stop8h 25m
$466
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Wed 8/19
2:45 pm-10:00 pm
1 stop6h 15m
San Juan Luis Munoz Marin Intl
Wed 8/26
1:45 pm-10:45 pm
2 stops10h 00m
$466
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Wed 7/22
2:00 pm-11:45 pm
2 stops8h 45m
San Juan Luis Munoz Marin Intl
Mon 7/27
8:15 pm-9:45 am
2 stops14h 30m
$466
HoustonMontego Bay
HOU - MBJ
HOUMBJ
Houston Hobby
Sun 6/21
5:35 am-2:55 pm
1 stop9h 20m
Montego Bay Sangster Intl
Thu 6/25
3:55 pm-7:05 pm
Nonstop3h 10m
$490
HoustonSaint Thomas Island
HOU - STT
HOUSTT
Houston Hobby
Sat 5/16
8:20 pm-1:10 pm
2 stops15h 50m
Saint Thomas Island Cyril E King
Wed 5/20
2:10 pm-11:05 pm
2 stops9h 55m
$503
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Sat 8/1
1:20 pm-11:40 pm
2 stops9h 20m
San Juan Luis Munoz Marin Intl
Sat 8/8
6:25 am-1:45 pm
2 stops8h 20m
$506
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Fri 8/7
10:00 am-10:50 pm
2 stops11h 50m
San Juan Luis Munoz Marin Intl
Sun 8/9
6:00 am-11:25 am
1 stop6h 25m
$506
Quickest round-trip
HoustonMontego Bay
HOU - MBJ
HOUMBJ
Houston Hobby
Fri 7/24
5:00 am-1:55 pm
1 stop8h 55m
Montego Bay Sangster Intl
Tue 7/28
3:55 pm-7:05 pm
Nonstop3h 10m
$515
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-SXM
HOU-MBJ
HOU-CUR
HOU-STT
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-SXM
HOU-MBJ
HOU-CUR
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 2 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.
What is the cheapest month to book a flight from Houston Hobby Airport to Caribbean?
Currently, January is the cheapest month in which you can book a flight from Houston Hobby Airport to Caribbean (average of $58). Flying from Houston Hobby Airport to Caribbean in December is currently the most expensive (average of $1,103). 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 April 24, 2026.
A simple way to save on the total cost of your ticket is to fly from Houston Hobby Airport to Caribbean in the afternoon. If you’re flexible enough to do this you can expect to save up to 26% 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 April 24, 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.
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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 April 24, 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 April 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$572 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$108 | Average$379 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$147 | Average$414 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$165 | Average$685 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$165 | Average$634 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$229 | Average$657 | FlexibilityNo cancel fee | On-time69% |