$165+ 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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — SJU
Nov 30 — Dec 71
Round-trip
1 adult, Economy
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Find cheap flights from Hobby to Caribbean with Cheapflights
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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 October 31, 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 October 31, 2026.
This American Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/299:58 am -
1 stop6h 11m
Thu 12/31:26 pm -
1 stop10h 52m
Deal found 10/25![American Airlines logo]()
$449
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/211:05 am -
1 stop10h 20m
Mon 12/712:30 pm -
1 stop11h 00m
Deal found 10/28![Southwest logo]()
$480
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/22:45 pm -
2 stops8h 05m
Sat 12/53:50 pm -
Nonstop5h 05m
Deal found 10/29![Southwest logo]()
$499
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/257:25 am -
2 stops9h 30m
Wed 12/26:40 am -
2 stops15h 10m
Deal found 10/28![Southwest logo]()
$503
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/259:58 am -
1 stop12h 15m
Wed 12/24:59 pm -
1 stop8h 19m
Deal found 10/28![American Airlines logo]()
$508
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/55:00 am -
1 stop8h 00m
Sat 12/123:50 pm -
Nonstop5h 05m
Deal found 10/28![Southwest logo]()
$517
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/1911:05 am -
1 stop10h 20m
Fri 11/207:30 am -
2 stops8h 30m
Deal found 10/29![Southwest logo]()
$521
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/228:45 pm -
1 stop14h 45m
Tue 12/12:25 pm -
1 stop8h 30m
Deal found 10/28![Southwest logo]()
$526
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/295:20 am -
1 stop8h 30m
Thu 12/33:55 pm -
1 stop7h 35m
Deal found 10/29![Southwest logo]()
$534
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/88:10 am -
1 stop5h 35m
Wed 12/163:45 pm -
1 stop6h 45m
Deal found 10/27![Southwest logo]()
$539
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/221:30 pm -
2 stops9h 30m
Thu 11/266:45 am -
2 stops10h 55m
Deal found 10/27![Southwest logo]()
$544
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/161:00 pm -
2 stops9h 50m
Thu 11/196:40 am -
2 stops15h 10m
Deal found 10/29![Southwest logo]()
$548
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 October 31, 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 October 31, 2026.
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/810:00 am -
2 stops9h 55m
Tue 12/152:25 pm -
1 stop8h 30m
Deal found 10/26![Southwest logo]()
$480
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/286:00 am -
1 stop7h 30m
Sat 12/54:55 pm -
1 stop8h 36m
Deal found 10/29![Delta logo]()
$636
This American Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 11/286:00 am -
1 stop7h 50m
Wed 12/25:59 pm -
2 stops17h 29m
Deal found 10/30![American Airlines logo]()
$781
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 1/271:00 pm -
2 stops9h 35m
Tue 2/24:30 pm -
1 stop8h 10m
Deal found 10/28![Southwest logo]()
$480
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/16:20 am -
1 stop9h 00m
Fri 3/55:35 am -
2 stops9h 55m
Deal found 10/26![Southwest logo]()
$503
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 1/2312:05 pm -
1 stop9h 10m
Wed 1/275:35 am -
2 stops10h 15m
Deal found 10/26![Southwest logo]()
$503
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/76:12 am -
1 stop6h 16m
Wed 12/93:53 pm -
1 stop9h 38m
Deal found 10/26![Delta logo]()
$650
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 1/2211:25 am -
1 stop8h 20m
Tue 1/262:30 pm -
1 stop7h 10m
Deal found 10/26![Southwest logo]()
$503
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/236:00 am -
1 stop6h 28m
Tue 12/292:53 pm -
1 stop9h 22m
Deal found 10/29![Delta logo]()
$676
This Southwest deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 12/65:20 am -
1 stop7h 20m
Sun 12/66:40 pm -
1 stop6h 50m
Deal found 10/25![Southwest logo]()
$521
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 1/48:05 pm -
2 stops15h 12m
Sun 1/1012:59 pm -
2 stops11h 00m
Deal found 10/28![American Airlines logo]()
$810
This Southwest deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 1/3010:35 am -
Nonstop4h 10m
Sat 2/135:35 am -
1 stop11h 25m
Deal found 10/30![Southwest logo]()
$522
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/126:12 am -
1 stop7h 17m
Sat 12/193:40 pm -
1 stop9h 35m
Deal found 10/28![Delta logo]()
$695
This American Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 2/205:06 pm -
2 stops20h 47m
Sat 2/274:16 pm -
2 stops18h 09m
Deal found 10/30![American Airlines logo]()
$819
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/153:11 pm -
2 stops20h 15m
Fri 12/256:14 pm -
1 stop17h 27m
Deal found 10/28![Delta logo]()
$696
This Southwest deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 11/273:00 pm -
1 stop6h 35m
Fri 12/410:45 am -
1 stop10h 50m
Deal found 10/30![Southwest logo]()
$526
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/121:59 pm -
2 stops23h 19m
Sun 12/204:22 pm -
2 stops20h 43m
Deal found 10/28![American Airlines logo]()
$824
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/213:00 pm -
1 stop5h 47m
Mon 12/288:10 am -
1 stop7h 05m
Deal found 10/28![Delta logo]()
$701
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 1/22:35 pm -
1 stop7h 00m
Mon 1/117:25 am -
2 stops10h 20m
Deal found 10/28![Southwest logo]()
$548
This American Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 11/2610:50 am -
2 stops26h 35m
Thu 12/35:59 pm -
2 stops17h 29m
Deal found 10/30![American Airlines logo]()
$849
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 1/146:00 am -
1 stop6h 53m
Tue 1/194:03 pm -
1 stop8h 15m
Deal found 10/26![Delta logo]()
$710
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/138:45 pm -
2 stops16h 00m
Sun 12/202:40 pm -
1 stop10h 45m
Deal found 10/29![Southwest logo]()
$587
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 24m
Sat 2/63:49 pm -
1 stop8h 00m
Deal found 10/26![Delta logo]()
$720
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/305:05 am -
1 stop6h 10m
Thu 12/31:10 pm -
1 stop9h 20m
Deal found 10/28![Southwest logo]()
$588
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 1/126:00 am -
1 stop6h 24m
Wed 1/273:49 pm -
1 stop8h 29m
Deal found 10/28![Delta logo]()
$740
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/15:25 am -
1 stop5h 50m
Fri 12/41:10 pm -
1 stop9h 20m
Deal found 10/28![Southwest logo]()
$588
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/116:00 am -
1 stop6h 28m
Wed 11/183:53 pm -
1 stop9h 28m
Deal found 10/28![Delta logo]()
$740
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/46:55 pm -
2 stops18h 35m
Tue 12/81:50 pm -
2 stops10h 10m
Deal found 10/29![Southwest logo]()
$590
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 1/206:00 am -
2 stops12h 06m
Tue 1/263:49 pm -
1 stop8h 29m
Deal found 10/28![Delta logo]()
$745
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/95:25 am -
1 stop5h 50m
Wed 12/161:10 pm -
2 stops9h 45m
Deal found 10/26![Southwest logo]()
$593
Last-minute flights from Hobby to CaribbeanDiscover last-minute flight deals from Hobby to Caribbean. Data last updated October 31, 2026 and is based on user searches.
Discover last-minute flight deals from Hobby to Caribbean. Data last updated October 31, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 15m
Sun 11/225:35 am -
2 stops8h 55m
Deal found 10/27![Southwest logo]()
$567
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/161:20 pm -
2 stops9h 30m
Thu 11/192:25 pm -
1 stop8h 30m
Deal found 10/29![Southwest logo]()
$548
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/1911:05 am -
1 stop10h 20m
Fri 11/207:30 am -
2 stops8h 30m
Deal found 10/29![Southwest logo]()
$521
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/221:30 pm -
2 stops9h 30m
Thu 11/266:45 am -
2 stops10h 55m
Deal found 10/27![Southwest logo]()
$544
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/257:25 am -
2 stops9h 30m
Wed 12/26:40 am -
2 stops15h 10m
Deal found 10/28![Southwest logo]()
$503
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/259:58 am -
1 stop12h 15m
Wed 12/24:59 pm -
1 stop8h 19m
Deal found 10/28![American Airlines logo]()
$508
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/265:50 am -
1 stop10h 50m
Thu 12/312:30 pm -
1 stop9h 05m
Deal found 10/29![Southwest logo]()
$480
This Southwest deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 11/265:50 am -
1 stop10h 50m
Sat 12/53:50 pm -
Nonstop5h 05m
Deal found 10/30![Southwest logo]()
$522
This Southwest deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 11/276:00 am -
2 stops9h 50m
Fri 12/46:40 am -
1 stop14h 20m
Deal found 10/30![Southwest logo]()
$526
This American Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/299:58 am -
1 stop6h 11m
Thu 12/31:26 pm -
1 stop10h 52m
Deal found 10/25![American Airlines logo]()
$449
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/295:20 am -
1 stop8h 30m
Thu 12/33:55 pm -
1 stop7h 35m
Deal found 10/29![Southwest logo]()
$534
This Southwest deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/307:25 am -
1 stop6h 20m
Tue 12/81:00 pm -
1 stop8h 55m
Deal found 10/25![Southwest logo]()
$550
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 October 31, 2026.
Search for one-way flight options from Hobby to Caribbean. Find affordable one-way fares based on user searches. Data last updated October 31, 2026.
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 1/189:57 am -
1 stop6h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![American Airlines logo]()
$165
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/135:20 am -
1 stop5h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Southwest logo]()
$240
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/1510:00 am -
2 stops9h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Southwest logo]()
$240
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/306:00 am -
1 stop10h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![American Airlines logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 10/29![Multiple Airlines logo]()
$249
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/299:58 am -
1 stop12h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![American Airlines logo]()
$250
This Southwest deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 1/611:15 am -
1 stop10h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Southwest logo]()
$254
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 1/235:16 pm -
1 stop22h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![American Airlines logo]()
$258
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/511:10 am -
Nonstop4h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Southwest logo]()
$259
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 1/116:00 am -
1 stop7h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Delta logo]()
$259
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 2/286:00 am -
1 stop6h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![American Airlines logo]()
$260
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 1/87:18 pm -
2 stops17h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![American Airlines logo]()
$262
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 October 31, 2026.
Round-trip from | $480 (Southwest) |
|---|---|
One-way from | $165 (American Airlines) |
Popular in | June |
Cheapest in | January |
Average price | $462 |
Good round-trip deal | $540 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 7,457,451 searches. Data last updated October 31, 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
HoustonNassau
HOU Houston Hobby - NAS Nassau Intl
HOUNAS
Houston Hobby
Sun 12/13
6:00 pm-12:15 pm
2 stops17h 15m
Nassau Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$240
HoustonSan Juan
HOU Houston Hobby - SJU San Juan Luis Munoz Marin Intl
HOUSJU
Houston Hobby
Tue 1/26
11:30 am-9:55 pm
2 stops8h 25m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$240
HoustonSan Juan
HOU Houston Hobby - SJU San Juan Luis Munoz Marin Intl
HOUSJU
Houston Hobby
Tue 12/15
10:00 am-9:55 pm
2 stops9h 55m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$240
HoustonSan Juan
HOU Houston Hobby - SJU San Juan Luis Munoz Marin Intl
HOUSJU
Houston Hobby
Thu 12/10
2:40 pm-12:50 am
2 stops8h 10m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$240
HoustonSan Juan
HOU Houston Hobby - SJU San Juan Luis Munoz Marin Intl
HOUSJU
Houston Hobby
Wed 1/6
11:15 am-11:30 pm
1 stop10h 15m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$254
HoustonSan Juan
HOU Houston Hobby - SJU San Juan Luis Munoz Marin Intl
HOUSJU
Houston Hobby
Sat 12/5
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
$259
HoustonSan Juan
HOU Houston Hobby - SJU San Juan Luis Munoz Marin Intl
HOUSJU
Houston Hobby
Sun 12/6
5:20 am-5:50 pm
1 stop10h 30m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$263
HoustonSan Juan
HOU Houston Hobby - SJU San Juan Luis Munoz Marin Intl
HOUSJU
Houston Hobby
Fri 12/11
3:00 pm-1:00 am
2 stops8h 00m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$263
HoustonSan Juan
HOU Houston Hobby - SJU San Juan Luis Munoz Marin Intl
HOUSJU
Houston Hobby
Wed 11/25
8:30 pm-10:55 am
1 stop12h 25m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$263
HoustonSan Juan
HOU Houston Hobby - SJU San Juan Luis Munoz Marin Intl
HOUSJU
Houston Hobby
Sun 3/7
9:40 am-1:00 am
2 stops13h 20m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$263
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-MBJ
HOU-NAS
HOU-SJU
HOU-PUJ
HOU-SXM
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-MBJ
HOU-NAS
HOU-SJU
HOU-PUJ
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 $544). Flying from Houston Hobby Airport to Caribbean in June is currently the most expensive (average of $702). 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 October 31, 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 21% on your trip compared to booking a flight in the morning.
How often are flights from Houston to Caribbean delayed?
About 43% of weekly flights between Houston and Caribbean have experienced delays in the past year, with the average delay time being 139 minutes.
What is the most punctual flight time for Houston to Caribbean flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Saturday tends to have the lowest number of delays on this route, whereas Tuesday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Houston to Caribbean flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 43% of flights being delayed.
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 October 31, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andJetBlue 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
Crew
8.6
Food
7.0
Comfort
8.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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 October 31, 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 8 airlines flying from Hobby to Caribbean
Discover the top 8 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 October 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$177 | Average$459 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$244 | Average$578 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$256 | Average$656 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$273 | Average$702 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$370 | Average$700 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$390 | Average$685 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$501 | Average$629 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$506 | Average$576 | FlexibilityNo cancel fee | On-time67% |