$187+ Cheap flights from Hobby (HOU) to Caribbean
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — SJU
Oct 9 — Oct 161
Round-trip
1 adult, Economy
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Find cheap flights from Hobby to Caribbean 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 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 September 9, 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 September 9, 2026.
This Southwest deal was found by Cheapflights users on 9/6. 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 10/68:50 am -
2 stops12h 05m
Tue 10/133:35 pm -
1 stop7h 40m
Deal found 9/6![Southwest logo]()
$450
This Southwest deal was found by Cheapflights users on 9/5. 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.
Thu 10/293:05 pm -
1 stop5h 50m
Fri 10/305:00 am -
1 stop6h 25m
Deal found 9/5![Southwest logo]()
$453
This American Airlines deal was found by Cheapflights users on 9/6. 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 11/58:09 pm -
1 stop20h 00m
Wed 11/111:21 pm -
1 stop10h 55m
Deal found 9/6![American Airlines logo]()
$455
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1411:10 am -
Nonstop4h 10m
Sat 11/216:00 pm -
Nonstop5h 00m
Deal found 9/9![Southwest logo]()
$457
This Southwest deal was found by Cheapflights users on 9/6. 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.
Mon 10/195:10 am -
1 stop5h 45m
Fri 10/236:30 am -
1 stop8h 50m
Deal found 9/6![Southwest logo]()
$458
This Southwest deal was found by Cheapflights users on 9/6. 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.
Sat 10/32:10 pm -
1 stop6h 20m
Sun 10/46:00 am -
1 stop8h 25m
Deal found 9/6![Southwest logo]()
$461
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3011:00 am -
1 stop10h 19m
Wed 10/142:59 pm -
1 stop9h 04m
Deal found 9/7![Delta logo]()
$466
This American Airlines deal was found by Cheapflights users on 9/8. 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 10/209:51 am -
2 stops11h 18m
Tue 10/276:00 am -
1 stop8h 33m
Deal found 9/8![American Airlines logo]()
$467
This American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:04 am -
2 stops13h 43m
Wed 10/146:00 am -
1 stop8h 33m
Deal found 9/9![American Airlines logo]()
$471
This Southwest deal was found by Cheapflights users on 9/6. 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 10/89:35 pm -
1 stop13h 40m
Tue 10/132:25 pm -
1 stop6h 30m
Deal found 9/6![Southwest logo]()
$475
This Southwest deal was found by Cheapflights users on 9/9. 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 10/89:50 pm -
1 stop10h 30m
Sun 10/188:25 pm -
1 stop12h 45m
Deal found 9/9![Southwest logo]()
$483
This Southwest deal was found by Cheapflights users on 9/6. 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 12/28:40 pm -
2 stops14h 55m
Wed 12/91:30 pm -
1 stop8h 55m
Deal found 9/6![Southwest logo]()
$484
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 September 9, 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 September 9, 2026.
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/54:20 pm -
1 stop6h 35m
Mon 11/99:35 pm -
1 stop12h 15m
Deal found 9/8![Southwest logo]()
$450
This Delta deal was found by Cheapflights users on 9/5. 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.
Thu 12/176:08 am -
1 stop9h 30m
Mon 12/213:30 pm -
1 stop9h 45m
Deal found 9/5![Delta logo]()
$466
This American Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 10/128:24 pm -
2 stops16h 44m
Thu 10/155:13 pm -
2 stops16h 08m
Deal found 9/4![American Airlines logo]()
$513
This Southwest deal was found by Cheapflights users on 9/9. 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 10/304:00 pm -
2 stops8h 25m
Mon 11/24:00 pm -
2 stops9h 35m
Deal found 9/9![Southwest logo]()
$458
This Southwest deal was found by Cheapflights users on 9/5. 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 10/165:10 am -
1 stop9h 10m
Tue 10/202:25 pm -
1 stop6h 30m
Deal found 9/5![Southwest logo]()
$458
This Delta deal was found by Cheapflights users on 9/9. 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.
Mon 9/282:25 pm -
1 stop6h 54m
Fri 10/232:59 pm -
1 stop9h 04m
Deal found 9/9![Delta logo]()
$511
This Delta deal was found by Cheapflights users on 9/9. 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 9/292:25 pm -
1 stop6h 54m
Fri 10/2312:50 pm -
1 stop11h 13m
Deal found 9/9![Delta logo]()
$511
This Southwest deal was found by Cheapflights users on 9/6. 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 12/28:40 pm -
2 stops14h 55m
Wed 12/91:30 pm -
2 stops9h 55m
Deal found 9/6![Southwest logo]()
$484
This Southwest deal was found by Cheapflights users on 9/7. 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.
Sun 11/155:20 am -
1 stop7h 25m
Thu 11/192:40 pm -
2 stops18h 15m
Deal found 9/7![Southwest logo]()
$488
This American Airlines deal was found by Cheapflights users on 9/8. 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 1/197:18 pm -
2 stops18h 56m
Tue 1/265:14 pm -
2 stops19h 47m
Deal found 9/8![American Airlines logo]()
$663
This Southwest deal was found by Cheapflights users on 9/5. 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 11/26:00 am -
2 stops7h 45m
Fri 11/61:00 pm -
1 stop10h 40m
Deal found 9/5![Southwest logo]()
$493
This American Airlines deal was found by Cheapflights users on 9/6. 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.
Sat 10/245:06 pm -
2 stops19h 40m
Wed 10/284:13 pm -
2 stops19h 58m
Deal found 9/6![American Airlines logo]()
$663
This Delta deal was found by Cheapflights users on 9/6. 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 11/66:09 am -
1 stop6h 23m
Tue 11/103:57 pm -
1 stop9h 24m
Deal found 9/6![Delta logo]()
$640
This American Airlines deal was found by Cheapflights users on 9/5. 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 1/315:05 pm -
2 stops18h 59m
Wed 2/105:14 pm -
2 stops18h 11m
Deal found 9/5![American Airlines logo]()
$663
This Southwest deal was found by Cheapflights users on 9/7. 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.
Sun 10/112:40 pm -
2 stops8h 05m
Fri 10/165:00 am -
2 stops9h 10m
Deal found 9/7![Southwest logo]()
$506
This Delta deal was found by Cheapflights users on 9/8. 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.
Sat 1/306:00 am -
1 stop6h 15m
Sat 2/63:40 pm -
1 stop8h 03m
Deal found 9/8![Delta logo]()
$660
This American Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/205:05 pm -
2 stops18h 59m
Tue 1/265:14 pm -
2 stops19h 47m
Deal found 9/8![American Airlines logo]()
$668
This Southwest deal was found by Cheapflights users on 9/6. 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.
Sat 10/108:30 am -
2 stops9h 35m
Sat 10/175:00 am -
2 stops9h 15m
Deal found 9/6![Southwest logo]()
$506
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:09 am -
1 stop6h 45m
Mon 11/93:15 pm -
1 stop9h 06m
Deal found 9/7![Delta logo]()
$666
This Southwest deal was found by Cheapflights users on 9/5. 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 10/232:45 pm -
2 stops8h 40m
Sun 10/255:00 am -
2 stops9h 35m
Deal found 9/5![Southwest logo]()
$506
This American Airlines deal was found by Cheapflights users on 9/6. 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 10/228:24 pm -
2 stops14h 36m
Thu 10/298:00 am -
2 stops8h 36m
Deal found 9/6![American Airlines logo]()
$741
This Southwest deal was found by Cheapflights users on 9/5. 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.
Thu 9/241:30 pm -
2 stops8h 40m
Sun 9/276:00 am -
1 stop6h 25m
Deal found 9/5![Southwest logo]()
$511
This Delta deal was found by Cheapflights users on 9/6. 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.
Sun 10/256:09 am -
1 stop7h 31m
Sun 11/15:05 pm -
1 stop7h 58m
Deal found 9/6![Delta logo]()
$700
This American Airlines deal was found by Cheapflights users on 9/6. 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.
Tue 11/37:18 pm -
2 stops18h 06m
Sun 11/81:01 pm -
2 stops11h 15m
Deal found 9/6![American Airlines logo]()
$750
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/262:45 pm -
2 stops20h 15m
Fri 11/61:50 pm -
2 stops8h 55m
Deal found 9/7![Southwest logo]()
$513
This Delta deal was found by Cheapflights users on 9/6. 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.
Mon 10/196:09 am -
1 stop7h 31m
Tue 10/202:55 pm -
1 stop9h 08m
Deal found 9/6![Delta logo]()
$700
This Southwest deal was found by Cheapflights users on 9/5. 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 11/25:20 am -
1 stop6h 15m
Tue 11/101:30 pm -
2 stops9h 55m
Deal found 9/5![Southwest logo]()
$514
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Thu 10/16:19 pm -
2 stops17h 08m
Mon 10/52:10 pm -
2 stops9h 39m
Deal found 9/5![American Airlines logo]()
$784
This Delta deal was found by Cheapflights users on 9/6. 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.
Sun 12/65:27 pm -
2 stops18h 28m
Tue 12/153:10 pm -
2 stops20h 26m
Deal found 9/6![Delta logo]()
$721
This Southwest deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 12/65:55 am -
1 stop7h 30m
Sat 12/122:15 pm -
Nonstop3h 25m
Deal found 9/4![Southwest logo]()
$528
Last-minute flights from Hobby to CaribbeanDiscover last-minute flight deals from Hobby to Caribbean. Data last updated September 9, 2026 and is based on user searches.
Discover last-minute flight deals from Hobby to Caribbean. Data last updated September 9, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3011:00 am -
1 stop10h 19m
Wed 10/142:59 pm -
1 stop9h 04m
Deal found 9/7![Delta logo]()
$466
This American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:04 am -
2 stops13h 43m
Wed 10/146:00 am -
1 stop8h 33m
Deal found 9/9![American Airlines logo]()
$471
This Southwest deal was found by Cheapflights users on 9/6. 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.
Sat 10/32:10 pm -
1 stop6h 20m
Sun 10/46:00 am -
1 stop8h 25m
Deal found 9/6![Southwest logo]()
$461
This Southwest deal was found by Cheapflights users on 9/7. 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 10/67:10 am -
2 stops12h 25m
Tue 10/1310:00 am -
2 stops8h 40m
Deal found 9/7![Southwest logo]()
$450
This Southwest deal was found by Cheapflights users on 9/6. 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 10/89:35 pm -
1 stop13h 40m
Tue 10/132:25 pm -
1 stop6h 30m
Deal found 9/6![Southwest logo]()
$475
This Southwest deal was found by Cheapflights users on 9/9. 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 10/89:50 pm -
1 stop10h 30m
Sun 10/188:25 pm -
1 stop12h 45m
Deal found 9/9![Southwest logo]()
$483
This Southwest deal was found by Cheapflights users on 9/6. 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.
Sat 10/108:30 am -
2 stops9h 35m
Wed 10/1410:00 am -
2 stops8h 40m
Deal found 9/6![Southwest logo]()
$498
This Southwest deal was found by Cheapflights users on 9/8. 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 10/121:15 pm -
2 stops9h 55m
Thu 10/1512:35 pm -
2 stops10h 05m
Deal found 9/8![Southwest logo]()
$488
This American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1211:41 am -
1 stop10h 39m
Fri 10/166:00 am -
1 stop8h 26m
Deal found 9/9![American Airlines logo]()
$496
This Southwest deal was found by Cheapflights users on 9/6. 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.
Mon 10/1912:00 pm -
2 stops8h 55m
Fri 10/2312:35 pm -
2 stops10h 05m
Deal found 9/6![Southwest logo]()
$458
This American Airlines deal was found by Cheapflights users on 9/8. 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 10/209:51 am -
2 stops11h 18m
Tue 10/276:00 am -
1 stop8h 33m
Deal found 9/8![American Airlines logo]()
$467
This Southwest deal was found by Cheapflights users on 9/5. 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.
Thu 10/293:05 pm -
1 stop5h 50m
Fri 10/305:00 am -
1 stop6h 25m
Deal found 9/5![Southwest logo]()
$453
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 September 9, 2026.
Search for one-way flight options from Hobby to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 9, 2026.
This Southwest deal was found by Cheapflights users on 9/9. 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 11/45:25 am -
1 stop6h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 9/5. 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.
Tue 9/296:25 am -
1 stop4h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Southwest logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/95:09 pm -
2 stops44h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$212
This Southwest deal was found by Cheapflights users on 9/8. 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 12/18:30 pm -
2 stops15h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 12/65:55 am -
1 stop7h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Southwest logo]()
$220
This Southwest deal was found by Cheapflights users on 9/5. 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 10/58:30 pm -
1 stop11h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Southwest logo]()
$225
This Southwest deal was found by Cheapflights users on 9/7. 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 11/145:00 am -
1 stop8h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Southwest logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 10/168:35 pm -
2 stops24h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Multiple Airlines logo]()
$230
This Southwest deal was found by Cheapflights users on 9/5. 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.
Sun 11/16:00 am -
2 stops7h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Southwest logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:19 pm -
2 stops42h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$231
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:00 am -
1 stop9h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Delta logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 9/6. 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.
Mon 11/23:51 pm -
2 stops45h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Multiple Airlines logo]()
$235
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 September 9, 2026.
Round-trip from | $450 (Southwest) |
|---|---|
One-way from | $187 (Southwest) |
Popular in | June |
Cheapest in | January |
Average price | $458 |
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 7,457,451 searches. Data last updated September 9, 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
HoustonGeorge Town
HOU Houston Hobby - GCM George Town Owen Roberts Intl
HOUGCM
Houston Hobby
Tue 12/1
5:25 am-12:35 pm
1 stop6h 10m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$187
HoustonGeorge Town
HOU Houston Hobby - GCM George Town Owen Roberts Intl
HOUGCM
Houston Hobby
Wed 11/4
5:25 am-12:35 pm
1 stop6h 10m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$187
Quickest round-trip
HoustonNassau
HOU Houston Hobby - NAS Nassau Intl
HOUNAS
Houston Hobby
Tue 9/29
6:25 am-12:15 pm
1 stop4h 50m
Nassau Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$199
HoustonSan Juan
HOU Houston Hobby - SJU San Juan Luis Munoz Marin Intl
HOUSJU
Houston Hobby
Wed 11/4
2:40 pm-10:20 pm
1 stop5h 40m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$225
HoustonSan Juan
HOU Houston Hobby - SJU San Juan Luis Munoz Marin Intl
HOUSJU
Houston Hobby
Tue 12/8
2:40 pm-10:20 pm
1 stop5h 40m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$225
HoustonSan Juan
HOU Houston Hobby - SJU San Juan Luis Munoz Marin Intl
HOUSJU
Houston Hobby
Mon 10/5
8:30 pm-9:10 am
1 stop11h 40m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$225
HoustonSan Juan
HOU Houston Hobby - SJU San Juan Luis Munoz Marin Intl
HOUSJU
Houston Hobby
Wed 10/7
10:55 am-11:10 pm
1 stop11h 15m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$225
HoustonSan Juan
HOU Houston Hobby - SJU San Juan Luis Munoz Marin Intl
HOUSJU
Houston Hobby
Tue 10/6
7:35 am-5:45 pm
2 stops9h 10m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$225
HoustonMontego Bay
HOU Houston Hobby - MBJ Montego Bay Sangster Intl
HOUMBJ
Houston Hobby
Sun 12/6
10:40 pm-2:45 pm
2 stops15h 05m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$226
HoustonSan Juan
HOU Houston Hobby - SJU San Juan Luis Munoz Marin Intl
HOUSJU
Houston Hobby
Sat 11/7
5:00 am-3:00 pm
1 stop8h 00m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$229
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Hobby to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Hobby with our price prediction graph.
HOU-SJU
HOU-MBJ
HOU-GCM
HOU-PLS
HOU-CUR
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Houston Hobby Airport to Caribbean
HOU-0CB
HOU-SJU
HOU-MBJ
HOU-GCM
HOU-PLS
What is the cheapest month to book a flight from Houston Hobby Airport to Caribbean?
Currently, October is the cheapest month in which you can book a flight from Houston Hobby Airport to Caribbean (average of $506). Flying from Houston Hobby Airport to Caribbean in June is currently the most expensive (average of $708). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from HOU to CB?
Find hourly flight availability from Hobby to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 9, 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 19% on your trip compared to booking a flight in the morning.
How far ahead should I book a flight from Houston Hobby Airport to Caribbean?
The best time to book flights from Houston Hobby Airport to Caribbean is 3 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated September 9, 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.
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Related info for your journey
Find useful and relevant information for your journey from Hobby to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Hobby to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Hobby to Caribbean by cabin class
Find flights from Hobby to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Hobby and Caribbean flights
Browse other Hobby and Caribbean flight options. Last updated on September 9, 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.
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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 7,457,451 searches. Data last updated September 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$177 | Average$432 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$244 | Average$582 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$273 | Average$696 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$323 | Average$648 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$355 | Average$676 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$390 | Average$666 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$501 | Average$642 | FlexibilityNo cancel fee | On-time71% |