$127+ 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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — SJU
Feb 25 — Mar 41
1 adult, Economy
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Hobby to Caribbean
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 January 26, 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 January 26, 2026.
This Southwest deal was found by Cheapflights users on 1/26. 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 2/241:35 pm
HOU
- SJU
2 stops9h 00m
Southwest
Tue 3/35:40 am
SJU
- HOU
2 stops9h 10m
Southwest
Deal found 1/26![Southwest logo]()
$364
This Southwest deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/147:45 pm
HOU
- SJU
1 stop12h 25m
Southwest
Mon 5/181:00 pm
SJU
- HOU
1 stop9h 10m
Southwest
Deal found 1/24![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 1/25. 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.
Sat 2/2110:15 am
HOU
- SJU
Nonstop4h 10m
Southwest
Wed 2/256:10 am
SJU
- HOU
2 stops15h 30m
Southwest
Deal found 1/25![Southwest logo]()
$386
This Southwest deal was found by Cheapflights users on 1/25. 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.
Fri 5/1512:50 pm
HOU
- SJU
2 stops9h 50m
Southwest
Sun 5/179:45 pm
SJU
- HOU
1 stop11h 50m
Southwest
Deal found 1/25![Southwest logo]()
$390
This Southwest deal was found by Cheapflights users on 1/26. 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.
Thu 2/265:00 am
HOU
- SJU
1 stop9h 55m
Southwest
Thu 3/58:00 am
SJU
- HOU
1 stop8h 00m
Southwest
Deal found 1/26![Southwest logo]()
$404
This Southwest deal was found by Cheapflights users on 1/25. 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 7/67:00 pm
HOU
- SJU
Nonstop4h 25m
Southwest
Tue 7/146:30 am
SJU
- HOU
Nonstop4h 35m
Southwest
Deal found 1/25![Southwest logo]()
$407
This Southwest deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/71:00 pm
HOU
- SJU
2 stops9h 40m
Southwest
Mon 4/134:25 pm
SJU
- HOU
1 stop8h 40m
Southwest
Deal found 1/24![Southwest logo]()
$408
This Southwest deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:00 am
HOU
- GCM
1 stop7h 10m
Southwest
Thu 4/161:05 pm
GCM
- HOU
1 stop10h 25m
Southwest
Deal found 1/24![Southwest logo]()
$409
This Southwest deal was found by Cheapflights users on 1/25. 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.
Sat 6/61:20 pm
HOU
- SJU
2 stops9h 20m
Southwest
Thu 6/116:00 am
SJU
- HOU
Nonstop4h 35m
Southwest
Deal found 1/25![Southwest logo]()
$412
This Southwest deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2910:20 am
HOU
- SJU
2 stops12h 20m
Southwest
Wed 6/35:35 am
SJU
- HOU
1 stop11h 35m
Southwest
Deal found 1/24![Southwest logo]()
$416
This Southwest deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/710:20 am
HOU
- SJU
2 stops12h 20m
Southwest
Mon 5/112:00 pm
SJU
- HOU
2 stops10h 55m
Southwest
Deal found 1/24![Southwest logo]()
$418
This Southwest deal was found by Cheapflights users on 1/26. 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 5/231:20 pm
HOU
- SJU
1 stop8h 55m
Southwest
Mon 5/254:25 pm
SJU
- HOU
1 stop8h 40m
Southwest
Deal found 1/26![Southwest logo]()
$430
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 January 26, 2026.
Round-trip from | $364 (Southwest) |
|---|---|
One-way from | $127 (Southwest) |
Popular in | December |
Cheapest in | April |
Average price | $314 |
Good round-trip deal | $465 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Hobby to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 26, 2026.
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 2/24
2:55 pm-12:35 am
2 stops7h 40m
San Juan Luis Munoz Marin Intl
Tue 3/3
10:20 am-5:10 pm
1 stop8h 50m
$364
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Sun 3/1
5:00 am-4:55 pm
1 stop9h 55m
San Juan Luis Munoz Marin Intl
Wed 3/4
9:05 am-7:45 pm
1 stop12h 40m
$364
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Sat 2/21
10:15 am-4:25 pm
Nonstop4h 10m
San Juan Luis Munoz Marin Intl
Wed 2/25
6:10 am-7:40 pm
2 stops15h 30m
$386
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Wed 4/1
2:55 pm-12:15 am
1 stop8h 20m
San Juan Luis Munoz Marin Intl
Tue 4/14
11:25 am-7:55 pm
1 stop9h 30m
$390
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Mon 2/16
4:50 pm-1:35 am
1 stop6h 45m
San Juan Luis Munoz Marin Intl
Tue 2/24
10:20 am-8:10 pm
1 stop11h 50m
$390
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Wed 3/11
2:40 pm-12:15 am
2 stops8h 35m
San Juan Luis Munoz Marin Intl
Tue 3/17
6:40 am-3:50 pm
2 stops10h 10m
$390
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Fri 4/24
8:00 am-8:00 pm
1 stop11h 00m
San Juan Luis Munoz Marin Intl
Tue 4/28
5:35 am-2:00 pm
2 stops9h 25m
$390
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Thu 2/26
4:50 pm-1:35 am
1 stop6h 45m
San Juan Luis Munoz Marin Intl
Thu 3/5
6:30 am-1:25 pm
2 stops8h 55m
$404
HoustonSan Juan
HOU - SJU
HOUSJU
Houston Hobby
Fri 4/10
10:20 am-11:40 pm
2 stops12h 20m
San Juan Luis Munoz Marin Intl
Mon 4/13
4:25 pm-12:05 am
1 stop8h 40m
$408
HoustonGeorge Town
HOU - GCM
HOUGCM
Houston Hobby
Mon 4/13
5:00 am-12:10 pm
1 stop7h 10m
George Town Owen Roberts Intl
Thu 4/16
1:05 pm-11:30 pm
1 stop10h 25m
$409
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 $101). Flying from Houston Hobby Airport to Caribbean in December is currently the most expensive (average of $151). 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 January 26, 2026.
When flying from Houston Hobby Airport to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
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 January 26, 2026.
Get a feel of what it's like to fly with Southwest, United Airlines, and American 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.
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
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 January 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$102 | Average$372 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$108 | Average$546 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$134 | Average$420 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$165 | Average$694 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$170 | Average$633 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$191 | Average$658 | FlexibilityNo cancel fee | On-time69% |