$123+ 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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — SJU
Jul 10 — Jul 171
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 June 10, 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 June 10, 2026.
This Southwest deal was found by Cheapflights users on 6/9. 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 10/295:05 am
HOU
- SJU
1 stop10h 25m
Southwest
Thu 10/299:45 pm
SJU
- HOU
1 stop12h 40m
Southwest
Deal found 6/9![Southwest logo]()
$371
This Southwest deal was found by Cheapflights users on 6/9. 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 10/295:05 am
HOU
- SJU
1 stop10h 25m
Southwest
Tue 11/36:45 am
SJU
- HOU
1 stop14h 05m
Southwest
Deal found 6/9![Southwest logo]()
$376
This Southwest deal was found by Cheapflights users on 6/8. 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 7/195:00 am
HOU
- SXM
1 stop9h 30m
Southwest
Wed 7/223:00 pm
SXM
- HOU
1 stop9h 15m
Southwest
Deal found 6/8![Southwest logo]()
$389
This Southwest deal was found by Cheapflights users on 6/9. 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 8/315:05 am
HOU
- STT
1 stop7h 45m
Southwest
Fri 9/42:35 pm
STT
- HOU
2 stops19h 35m
Southwest
Deal found 6/9![Southwest logo]()
$402
This Southwest deal was found by Cheapflights users on 6/9. 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 7/155:00 am
HOU
- GCM
1 stop6h 55m
Southwest
Wed 7/2212:50 pm
GCM
- HOU
1 stop7h 40m
Southwest
Deal found 6/9![Southwest logo]()
$406
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 8/215:05 am
HOU
- SXM
1 stop8h 00m
Southwest
Sun 8/233:05 pm
SXM
- HOU
1 stop9h 10m
Southwest
Deal found 6/6![Southwest logo]()
$415
This Southwest deal was found by Cheapflights users on 6/8. 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 9/145:05 am
HOU
- AUA
1 stop6h 40m
Southwest
Thu 9/171:45 pm
AUA
- HOU
1 stop9h 35m
Southwest
Deal found 6/8![Southwest logo]()
$421
This Southwest deal was found by Cheapflights users on 6/8. 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 8/156:40 am
HOU
- SJU
1 stop6h 20m
Southwest
Wed 8/198:20 am
SJU
- HOU
1 stop9h 35m
Southwest
Deal found 6/8![Southwest logo]()
$426
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/2712:20 pm
HOU
- NAS
1 stop5h 15m
Southwest
Thu 7/308:45 am
NAS
- HOU
1 stop6h 05m
Southwest
Deal found 6/5![Southwest logo]()
$435
This Southwest deal was found by Cheapflights users on 6/9. 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 8/315:05 am
HOU
- STT
1 stop7h 45m
Southwest
Sat 9/52:05 pm
STT
- HOU
1 stop7h 35m
Southwest
Deal found 6/9![Southwest logo]()
$437
This Southwest deal was found by Cheapflights users on 6/8. 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 8/145:05 am
HOU
- SXM
1 stop8h 00m
Southwest
Mon 8/173:05 pm
SXM
- HOU
1 stop8h 15m
Southwest
Deal found 6/8![Southwest logo]()
$442
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 7/1410:25 am
HOU
- NAS
1 stop7h 10m
Southwest
Thu 7/162:10 pm
NAS
- HOU
1 stop7h 55m
Southwest
Deal found 6/6![Southwest logo]()
$448
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 June 10, 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 June 10, 2026.
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/2712:20 pm
HOU
- NAS
1 stop5h 15m
Southwest
Thu 7/308:45 am
NAS
- HOU
1 stop6h 05m
Southwest
Deal found 6/5![Southwest logo]()
$435
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 8/106:00 am
HOU
- SJU
1 stop9h 38m
Delta
Fri 8/142:59 pm
SJU
- HOU
1 stop8h 06m
Delta
Deal found 6/5![Delta logo]()
$521
This American Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 10/256:19 pm
HOU
- CUR
2 stops19h 46m
American Airlines
Sun 11/15:40 pm
CUR
- HOU
2 stops18h 00m
American Airlines
Deal found 6/6![American Airlines logo]()
$678
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 9/135:00 am
HOU
- STT
1 stop7h 25m
Southwest
Sat 9/192:05 pm
STT
- HOU
1 stop7h 35m
Southwest
Deal found 6/6![Southwest logo]()
$464
This Southwest deal was found by Cheapflights users on 6/8. 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 6/207:10 am
HOU
- SXM
1 stop6h 55m
Southwest
Wed 6/243:00 pm
SXM
- HOU
1 stop9h 10m
Southwest
Deal found 6/8![Southwest logo]()
$468
This Southwest deal was found by Cheapflights users on 6/8. 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.
Tue 7/287:20 pm
HOU
- SJU
Nonstop4h 30m
Southwest
Thu 7/308:15 pm
SJU
- HOU
1 stop13h 10m
Southwest
Deal found 6/8![Southwest logo]()
$472
This Delta deal was found by Cheapflights users on 6/8. 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.
Mon 8/106:00 am
HOU
- PUJ
1 stop7h 39m
Delta
Tue 8/182:50 pm
PUJ
- HOU
1 stop8h 15m
Delta
Deal found 6/8![Delta logo]()
$590
This Southwest deal was found by Cheapflights users on 6/9. 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 7/58:40 pm
HOU
- SJU
1 stop13h 05m
Southwest
Thu 7/910:20 pm
SJU
- HOU
1 stop12h 15m
Southwest
Deal found 6/9![Southwest logo]()
$476
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:00 am
HOU
- PUJ
1 stop6h 22m
Delta
Tue 8/251:10 pm
PUJ
- HOU
1 stop9h 55m
Delta
Deal found 6/6![Delta logo]()
$600
This American Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:18 pm
HOU
- CUR
2 stops18h 13m
American Airlines
Sun 9/274:57 pm
CUR
- HOU
2 stops19h 17m
American Airlines
Deal found 6/6![American Airlines logo]()
$678
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/115:35 pm
HOU
- SJU
1 stop6h 45m
Southwest
Wed 7/158:35 pm
SJU
- HOU
1 stop12h 50m
Southwest
Deal found 6/5![Southwest logo]()
$476
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 39m
Delta
Thu 8/202:50 pm
PUJ
- HOU
1 stop8h 15m
Delta
Deal found 6/6![Delta logo]()
$600
This Southwest deal was found by Cheapflights users on 6/8. 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 7/66:05 pm
HOU
- SJU
1 stop6h 20m
Southwest
Fri 7/1010:20 pm
SJU
- HOU
1 stop12h 20m
Southwest
Deal found 6/8![Southwest logo]()
$476
This American Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/18:23 pm
HOU
- CUR
2 stops18h 17m
American Airlines
Sat 7/184:40 pm
CUR
- HOU
2 stops18h 08m
American Airlines
Deal found 6/5![American Airlines logo]()
$723
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 10/315:35 pm
HOU
- GCM
2 stops19h 00m
Southwest
Tue 11/31:30 pm
GCM
- HOU
2 stops10h 20m
Southwest
Deal found 6/5![Southwest logo]()
$490
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:00 am
HOU
- PUJ
1 stop6h 25m
Delta
Mon 8/172:50 pm
PUJ
- HOU
1 stop8h 15m
Delta
Deal found 6/6![Delta logo]()
$655
This American Airlines deal was found by Cheapflights users on 6/7. 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.
Wed 7/18:23 pm
HOU
- CUR
2 stops18h 17m
American Airlines
Tue 7/74:40 pm
CUR
- HOU
2 stops20h 36m
American Airlines
Deal found 6/7![American Airlines logo]()
$723
This Southwest deal was found by Cheapflights users on 6/8. 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 8/286:10 pm
HOU
- STT
2 stops18h 10m
Southwest
Thu 9/32:35 pm
STT
- HOU
1 stop6h 25m
Southwest
Deal found 6/8![Southwest logo]()
$499
This Delta deal was found by Cheapflights users on 6/9. 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.
Sat 8/296:00 am
HOU
- STT
1 stop6h 34m
Delta
Fri 9/42:49 pm
STT
- HOU
1 stop8h 16m
Delta
Deal found 6/9![Delta logo]()
$670
This American Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 11/16:22 pm
HOU
- CUR
2 stops18h 03m
American Airlines
Sat 11/75:40 pm
CUR
- HOU
2 stops18h 00m
American Airlines
Deal found 6/6![American Airlines logo]()
$753
This Southwest deal was found by Cheapflights users on 6/9. 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 7/912:20 pm
HOU
- NAS
1 stop5h 15m
Southwest
Thu 7/168:45 am
NAS
- HOU
2 stops8h 10m
Southwest
Deal found 6/9![Southwest logo]()
$504
This American Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:19 pm
HOU
- CUR
2 stops20h 12m
American Airlines
Mon 9/212:41 pm
CUR
- HOU
2 stops19h 15m
American Airlines
Deal found 6/5![American Airlines logo]()
$758
This Delta deal was found by Cheapflights users on 6/9. 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.
Sat 8/296:00 am
HOU
- STT
1 stop8h 02m
Delta
Mon 8/312:49 pm
STT
- HOU
1 stop8h 16m
Delta
Deal found 6/9![Delta logo]()
$695
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/47:00 am
HOU
- SXM
1 stop7h 05m
Southwest
Thu 7/92:25 pm
SXM
- HOU
1 stop10h 25m
Southwest
Deal found 6/5![Southwest logo]()
$507
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/76:00 am
HOU
- PUJ
1 stop6h 25m
Delta
Mon 9/143:59 pm
PUJ
- HOU
1 stop7h 36m
Delta
Deal found 6/5![Delta logo]()
$700
This American Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 8/308:14 pm
HOU
- CUR
2 stops18h 25m
American Airlines
Sat 9/54:39 pm
CUR
- HOU
2 stops20h 48m
American Airlines
Deal found 6/5![American Airlines logo]()
$798
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 7/147:20 pm
HOU
- SJU
Nonstop4h 30m
Southwest
Sat 7/184:40 pm
SJU
- HOU
1 stop7h 45m
Southwest
Deal found 6/6![Southwest logo]()
$512
This American Airlines deal was found by Cheapflights users on 6/7. 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 6/228:23 pm
HOU
- CUR
2 stops18h 12m
American Airlines
Sun 6/284:46 pm
CUR
- HOU
2 stops20h 34m
American Airlines
Deal found 6/7![American Airlines logo]()
$813
This Delta deal was found by Cheapflights users on 6/9. 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 9/16:00 am
HOU
- GCM
1 stop5h 39m
Delta
Tue 9/812:56 pm
GCM
- HOU
1 stop8h 39m
Delta
Deal found 6/9![Delta logo]()
$746
This Southwest deal was found by Cheapflights users on 6/7. 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.
Sat 7/411:00 am
HOU
- SJU
1 stop7h 45m
Southwest
Tue 7/75:00 am
SJU
- HOU
1 stop12h 30m
Southwest
Deal found 6/7![Southwest logo]()
$516
Last-minute flights from Hobby to CaribbeanDiscover last-minute flight deals from Hobby to Caribbean. Data last updated June 10, 2026 and is based on user searches.
Discover last-minute flight deals from Hobby to Caribbean. Data last updated June 10, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/8. 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 6/207:10 am
HOU
- SXM
1 stop6h 55m
Southwest
Wed 6/243:00 pm
SXM
- HOU
1 stop9h 10m
Southwest
Deal found 6/8![Southwest logo]()
$468
This Southwest deal was found by Cheapflights users on 6/9. 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 7/67:05 pm
HOU
- SJU
Nonstop4h 30m
Southwest
Tue 7/148:35 pm
SJU
- HOU
1 stop12h 25m
Southwest
Deal found 6/9![Southwest logo]()
$472
This Southwest deal was found by Cheapflights users on 6/9. 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 7/912:20 pm
HOU
- NAS
1 stop5h 15m
Southwest
Thu 7/162:10 pm
NAS
- HOU
1 stop7h 55m
Southwest
Deal found 6/9![Southwest logo]()
$453
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 7/912:20 pm
HOU
- NAS
1 stop5h 15m
Southwest
Tue 7/148:45 am
NAS
- HOU
1 stop5h 10m
Southwest
Deal found 6/6![Southwest logo]()
$477
This Southwest deal was found by Cheapflights users on 6/7. 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 7/912:20 pm
HOU
- NAS
1 stop5h 15m
Southwest
Mon 7/138:45 am
NAS
- HOU
1 stop10h 30m
Southwest
Deal found 6/7![Southwest logo]()
$481
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 7/1410:25 am
HOU
- NAS
1 stop7h 10m
Southwest
Thu 7/162:10 pm
NAS
- HOU
1 stop7h 55m
Southwest
Deal found 6/6![Southwest logo]()
$448
This Southwest deal was found by Cheapflights users on 6/9. 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 7/155:00 am
HOU
- GCM
1 stop6h 55m
Southwest
Wed 7/2212:50 pm
GCM
- HOU
1 stop7h 40m
Southwest
Deal found 6/9![Southwest logo]()
$406
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/1712:20 pm
HOU
- NAS
1 stop5h 15m
Southwest
Wed 7/228:45 am
NAS
- HOU
1 stop11h 25m
Southwest
Deal found 6/5![Southwest logo]()
$495
This Southwest deal was found by Cheapflights users on 6/8. 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 7/195:00 am
HOU
- SXM
1 stop9h 30m
Southwest
Wed 7/223:00 pm
SXM
- HOU
1 stop9h 15m
Southwest
Deal found 6/8![Southwest logo]()
$389
This Southwest deal was found by Cheapflights users on 6/7. 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 7/212:50 pm
HOU
- SJU
1 stop8h 30m
Southwest
Tue 7/287:20 pm
SJU
- HOU
2 stops15h 25m
Southwest
Deal found 6/7![Southwest logo]()
$476
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/2712:20 pm
HOU
- NAS
1 stop5h 15m
Southwest
Thu 7/308:45 am
NAS
- HOU
1 stop6h 05m
Southwest
Deal found 6/5![Southwest logo]()
$435
This Southwest deal was found by Cheapflights users on 6/8. 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 7/297:40 pm
HOU
- SJU
1 stop12h 20m
Southwest
Thu 7/308:15 pm
SJU
- HOU
2 stops14h 30m
Southwest
Deal found 6/8![Southwest logo]()
$471
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 June 10, 2026.
Search for one-way flight options from Hobby to Caribbean. Find affordable one-way fares based on user searches. Data last updated June 10, 2026.
This Southwest deal was found by Cheapflights users on 6/7. 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.
Sat 8/296:40 am
HOU
- GCM
1 stop5h 25m
Southwest
Deal found 6/7![Southwest logo]()
$123
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 7/1510:25 am
HOU
- NAS
1 stop7h 10m
Southwest
Deal found 6/6![Southwest logo]()
$132
This Southwest deal was found by Cheapflights users on 6/10. 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 8/215:05 am
HOU
- SXM
1 stop8h 00m
Southwest
Deal found 6/10![Southwest logo]()
$150
This Southwest deal was found by Cheapflights users on 6/9. 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 8/315:05 am
HOU
- STT
1 stop7h 45m
Southwest
Deal found 6/9![Southwest logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/97:11 pm
HOU
- SJU
2 stops44h 00m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$178
This Southwest deal was found by Cheapflights users on 6/9. 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 8/305:00 am
HOU
- STT
1 stop7h 25m
Southwest
Deal found 6/9![Southwest logo]()
$188
This Southwest deal was found by Cheapflights users on 6/8. 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 10/247:50 pm
HOU
- SXM
2 stops17h 10m
Southwest
Deal found 6/8![Southwest logo]()
$203
This Southwest deal was found by Cheapflights users on 6/9. 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.
Fri 7/248:35 pm
HOU
- SXM
2 stops17h 30m
Southwest
Deal found 6/9![Southwest logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/148:03 pm
HOU
- SJU
2 stops43h 08m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/78:03 pm
HOU
- SJU
2 stops43h 08m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 6/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:32 pm
HOU
- SJU
2 stops44h 26m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$219
This Southwest deal was found by Cheapflights users on 6/9. 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 7/77:35 am
HOU
- NAS
2 stops10h 00m
Southwest
Deal found 6/9![Southwest logo]()
$220
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 June 10, 2026.
Round-trip from | $371 (Southwest) |
|---|---|
One-way from | $123 (Southwest) |
Popular in | June |
Cheapest in | October |
Average price | $542 |
Good round-trip deal | $562 or less |
Good one-way deal | $298 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 June 10, 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
Quickest round-trip
HoustonNassau
HOU - NAS
HOUNAS
Houston Hobby
Mon 7/27
12:20 pm-6:35 pm
1 stop5h 15m
Nassau Intl
Thu 7/30
8:45 am-1:50 pm
1 stop6h 05m
$435
HoustonSaint Thomas Island
HOU - STT
HOUSTT
Houston Hobby
Sun 9/13
5:00 am-1:25 pm
1 stop7h 25m
Saint Thomas Island Cyril E King
Sat 9/19
2:05 pm-8:40 pm
1 stop7h 35m
$464
HoustonSimpson Bay
HOU - SXM
HOUSXM
Houston Hobby
Sat 6/20
7:10 am-3:05 pm
1 stop6h 55m
Simpson Bay Princess Juliana
Wed 6/24
3:00 pm-11:10 pm
1 stop9h 10m
$468
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Tue 7/28
7:20 pm-12:50 am
Nonstop4h 30m
San Juan Luis Munoz Marin Intl
Thu 7/30
8:15 pm-8:25 am
1 stop13h 10m
$472
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Sun 7/5
8:40 pm-10:45 am
1 stop13h 05m
San Juan Luis Munoz Marin Intl
Thu 7/9
10:20 pm-9:35 am
1 stop12h 15m
$476
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Sat 7/11
5:35 pm-1:20 am
1 stop6h 45m
San Juan Luis Munoz Marin Intl
Wed 7/15
8:35 pm-8:25 am
1 stop12h 50m
$476
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Mon 7/6
6:05 pm-1:25 am
1 stop6h 20m
San Juan Luis Munoz Marin Intl
Fri 7/10
10:20 pm-9:40 am
1 stop12h 20m
$476
HoustonGeorge Town
HOU - GCM
HOUGCM
Houston Hobby
Sat 10/31
5:35 pm-12:35 pm
2 stops19h 00m
George Town Owen Roberts Intl
Tue 11/3
1:30 pm-10:50 pm
2 stops10h 20m
$490
HoustonSaint Thomas Island
HOU - STT
HOUSTT
Houston Hobby
Fri 8/28
6:10 pm-1:20 pm
2 stops18h 10m
Saint Thomas Island Cyril E King
Thu 9/3
2:35 pm-8:00 pm
1 stop6h 25m
$499
HoustonNassau
HOU - NAS
HOUNAS
Houston Hobby
Thu 7/9
12:20 pm-6:35 pm
1 stop5h 15m
Nassau Intl
Thu 7/16
8:45 am-3:55 pm
2 stops8h 10m
$504
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-STT
HOU-GCM
HOU-AUA
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-STT
HOU-GCM
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 $1,198). 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 June 10, 2026.
A simple way to save on the total cost of your ticket is to fly from Houston Hobby Airport to Caribbean at noon. If you’re flexible enough to do this you can expect to save up to 16% on your trip compared to booking a flight in the morning.
How far ahead should I book a flight from Houston Hobby Airport to Caribbean?
The best time to book flights from Houston Hobby Airport to Caribbean is 74 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated June 10, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited 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.
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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 June 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Hobby to Caribbean flights
Consider these flights traveling from Hobby to Caribbean.
Top 7 airlines flying from Hobby to Caribbean
Discover the top 7 airlines that operate flights from Hobby to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$599 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$165 | Average$663 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$169 | Average$427 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$170 | Average$669 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$222 | Average$629 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$254 | Average$675 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$263 | Average$548 | FlexibilityNo cancel fee | On-time62% |