$88+ 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 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — SJU
Jan 11 — Jan 181
1 adult, Economy
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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 December 12, 2025.
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 December 12, 2025.
This Southwest deal was found by Cheapflights users on 12/9. 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 12/1410:00 amHOU - SJU
2 stops13h 25mSouthwest
Tue 12/165:45 amSJU - HOU
1 stop10h 50mSouthwest
Deal found 12/9![Southwest logo]()
$255
This American Airlines deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/165:44 amHOU - SJU
1 stop7h 00mAmerican Airlines
Sat 12/201:30 amSJU - HOU
1 stop9h 02mAmerican Airlines
Deal found 12/10![American Airlines logo]()
$390
This American Airlines deal was found by Cheapflights users on 12/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/288:16 pmHOU - SJU
1 stop7h 18mAmerican Airlines
Tue 12/301:30 amSJU - HOU
1 stop9h 02mAmerican Airlines
Deal found 12/11![American Airlines logo]()
$395
This Southwest deal was found by Cheapflights users on 12/9. 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 12/161:25 pmHOU - SJU
2 stops9h 10mSouthwest
Sat 12/204:10 pmSJU - HOU
1 stop10h 45mSouthwest
Deal found 12/9![Southwest logo]()
$400
This Delta deal was found by Cheapflights users on 12/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/152:32 pmHOU - SJU
1 stop6h 48mDelta
Wed 12/171:57 pmSJU - HOU
1 stop10h 51mDelta
Deal found 12/11![Delta logo]()
$427
This Southwest deal was found by Cheapflights users on 12/9. 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 12/1410:00 amHOU - SJU
2 stops13h 25mSouthwest
Sun 12/215:35 amSJU - HOU
2 stops10h 10mSouthwest
Deal found 12/9![Southwest logo]()
$430
This Delta deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/132:32 pmHOU - SJU
1 stop6h 48mDelta
Sat 12/201:10 pmSJU - HOU
1 stop12h 01mDelta
Deal found 12/10![Delta logo]()
$440
This American Airlines deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/159:02 amHOU - SJU
1 stop10h 23mAmerican Airlines
Sun 12/211:30 amSJU - HOU
1 stop9h 02mAmerican Airlines
Deal found 12/10![American Airlines logo]()
$450
This American Airlines deal was found by Cheapflights users on 12/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:13 amHOU - SJU
1 stop11h 14mAmerican Airlines
Thu 1/83:54 pmSJU - HOU
1 stop8h 52mAmerican Airlines
Deal found 12/11![American Airlines logo]()
$460
This American Airlines deal was found by Cheapflights users on 12/8. 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 12/910:08 amHOU - SJU
1 stop9h 17mAmerican Airlines
Tue 12/167:00 amSJU - HOU
1 stop10h 53mAmerican Airlines
Deal found 12/8![American Airlines logo]()
$470
This Delta deal was found by Cheapflights users on 12/9. 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 12/132:32 pmHOU - SJU
1 stop6h 48mDelta
Mon 12/151:55 pmSJU - HOU
1 stop10h 53mDelta
Deal found 12/9![Delta logo]()
$471
This American Airlines deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/135:44 amHOU - SJU
2 stops10h 08mAmerican Airlines
Sat 12/206:44 amSJU - HOU
1 stop12h 53mAmerican Airlines
Deal found 12/10![American Airlines logo]()
$475
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 December 12, 2025.
Round-trip from | $340 (Southwest) |
|---|---|
One-way from | $88 (American Airlines) |
Popular in | December |
Cheapest in | April |
Average price | $492 |
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 December 12, 2025.
Use the filters below to find and compare flights from Houston Hobby Airport to Caribbean that are best for you.
Fly from
Hobby
Fly to
Caribbean
Route
Depart
Return
Price
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Tue 1/6
11:20 am-11:10 pm
1 stop9h 50m
San Juan Luis Munoz Marin Intl
Tue 1/13
5:40 am-11:55 am
1 stop8h 15m
$340
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Sun 2/1
5:45 am-5:17 pm
1 stop9h 32m
San Juan Luis Munoz Marin Intl
Thu 2/12
6:15 am-4:28 pm
1 stop12h 13m
$395
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Sat 1/17
3:00 pm-12:10 am
1 stop7h 10m
San Juan Luis Munoz Marin Intl
Sat 1/24
5:30 am-4:35 pm
1 stop13h 05m
$395
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Sat 5/2
10:05 am-8:06 pm
1 stop9h 01m
San Juan Luis Munoz Marin Intl
Sat 5/9
6:15 am-2:56 pm
1 stop9h 41m
$395
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Sun 2/1
4:25 pm-12:40 am
1 stop6h 15m
San Juan Luis Munoz Marin Intl
Thu 2/12
2:10 pm-9:15 pm
1 stop9h 05m
$395
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Thu 1/22
5:45 am-5:17 pm
1 stop9h 32m
San Juan Luis Munoz Marin Intl
Thu 1/29
2:15 pm-10:33 pm
1 stop10h 18m
$395
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Fri 2/27
7:00 pm-10:00 am
2 stops13h 00m
San Juan Luis Munoz Marin Intl
Wed 3/4
9:05 am-7:45 pm
1 stop12h 40m
$395
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Sat 5/2
5:15 am-12:55 pm
1 stop6h 40m
San Juan Luis Munoz Marin Intl
Sat 5/9
5:15 am-2:55 pm
2 stops10h 40m
$395
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Thu 1/22
2:55 pm-12:35 am
2 stops7h 40m
San Juan Luis Munoz Marin Intl
Thu 1/29
5:40 am-12:50 pm
2 stops9h 10m
$403
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Thu 1/8
1:35 pm-12:35 am
2 stops9h 00m
San Juan Luis Munoz Marin Intl
Thu 1/15
6:10 am-8:20 pm
2 stops16h 10m
$403
Showing 1-10 of 60 results
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.
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
What is the cheapest month to book a flight from Houston Hobby Airport to Caribbean?
Currently, April is the cheapest month in which you can book a flight from Houston Hobby Airport to Caribbean (average of $89). Flying from Houston Hobby Airport to Caribbean in January is currently the most expensive (average of $162). 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 December 12, 2025.
A simple way to save on the total cost of your ticket is to fly from Houston Hobby Airport to Caribbean in the evening. If you’re flexible enough to do this you can expect to save up to 38% on your trip compared to booking a flight in the afternoon.
What is the cheapest day to fly from Houston Hobby Airport to Caribbean?
Use this chart to determine the cheapest time to fly round-trip from Hobby to Caribbean. Price data was last updated on December 16, 2024.
Travelers seeking maximum savings on their Houston Hobby Airport to Caribbean flight should consider departing on Monday evenings when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
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 December 12, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United 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
Overall
7.9
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Overall
7.9
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Overall
7.9
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Overall
7.9
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Overall
7.9
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Overall
7.9
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Hobby to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
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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.
Top 6 airlines flying from Hobby to Caribbean
Discover the top 6 airlines that operate flights from Hobby to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$551 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$374 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$142 | Average$416 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$165 | Average$687 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$170 | Average$640 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$223 | Average$667 | FlexibilityNo cancel fee | On-time69% |