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Caribbean

$103+ 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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — SJU
Nov 26 — Dec 31
Wed 11/26
Wed 12/3
1 adult, Economy
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Cheap 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 27, 2025.

Round-trip from

$209
(American Airlines)

One-way from

$103
(American Airlines)

Popular in

December

Cheapest in

April

Average price

$316
From Houston Hobby to Caribbean
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One-way flight from Houston Hobby to Caribbean
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Hobby to Caribbean

Cheapest flights from Hobby to Caribbean
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 27, 2025.

This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/39:07 amHOU - SJU
1 stop10h 28mAmerican Airlines
Thu 11/63:51 pmSJU - HOU
1 stop10h 06mAmerican Airlines
Deal found 10/26$209
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.
Wed 10/296:00 amHOU - SJU
1 stop9h 33mDelta
Fri 10/312:31 pmSJU - HOU
1 stop9h 29mDelta
Deal found 10/26$215
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.
Sun 11/25:00 amHOU - SJU
1 stop9h 33mDelta
Thu 11/61:46 pmSJU - HOU
1 stop11h 14mDelta
Deal found 10/26$264
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 12/211:15 amHOU - SJU
1 stop10h 05mSouthwest
Sat 12/610:50 amSJU - HOU
1 stop10h 20mSouthwest
Deal found 10/26$270
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.
Thu 11/278:50 amHOU - SJU
1 stop5h 40mSouthwest
Sat 12/610:50 amSJU - HOU
1 stop10h 20mSouthwest
Deal found 10/26$280
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/306:00 amHOU - SJU
2 stops8h 54mAmerican Airlines
Mon 11/311:13 amSJU - HOU
2 stops8h 41mAmerican Airlines
Deal found 10/26$301
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 12/51:40 pmHOU - SJU
2 stops8h 55mSouthwest
Tue 12/98:55 amSJU - HOU
2 stops10h 50mSouthwest
Deal found 10/26$302
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.
Mon 11/106:00 amHOU - SJU
1 stop7h 01mAmerican Airlines
Sat 12/136:54 amSJU - HOU
1 stop15h 24mAmerican Airlines
Deal found 10/25$305
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 11/16:00 amHOU - SJU
1 stop6h 21mDelta
Thu 11/61:46 pmSJU - HOU
1 stop11h 14mDelta
Deal found 10/26$313
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/306:00 amHOU - SJU
2 stops8h 54mAmerican Airlines
Sat 11/13:34 pmSJU - HOU
1 stop7h 40mAmerican Airlines
Deal found 10/26$319
This American Airlines deal was found by Cheapflights users on 10/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/286:00 amHOU - SJU
1 stop7h 25mAmerican Airlines
Thu 10/307:05 amSJU - HOU
2 stops10h 06mAmerican Airlines
Deal found 10/24$334
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 12/85:44 amHOU - MBJ
1 stop8h 12mAmerican Airlines
Tue 12/233:45 pmMBJ - HOU
1 stop9h 01mAmerican Airlines
Deal found 10/27$429

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 October 27, 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

Sun 11/2

5:00 am-4:33 pm

1 stop9h 33m

San Juan Luis Munoz Marin Intl

Thu 11/6

1:46 pm-11:00 pm

1 stop11h 14m

$264

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Fri 1/23

11:15 am-11:10 pm

2 stops9h 55m

San Juan Luis Munoz Marin Intl

Fri 1/30

6:10 am-7:40 pm

2 stops15h 30m

$270

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Sun 12/7

10:00 am-1:25 am

1 stop13h 25m

San Juan Luis Munoz Marin Intl

Sat 12/13

8:20 am-2:40 pm

1 stop8h 20m

$270

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Tue 12/2

1:25 pm-12:35 am

2 stops9h 10m

San Juan Luis Munoz Marin Intl

Sat 12/6

10:50 am-7:10 pm

1 stop10h 20m

$270

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Sat 11/1

6:00 am-1:21 pm

1 stop6h 21m

San Juan Luis Munoz Marin Intl

Thu 11/6

1:46 pm-11:00 pm

1 stop11h 14m

$313

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Sat 11/1

6:00 am-1:21 pm

1 stop6h 21m

San Juan Luis Munoz Marin Intl

Wed 11/5

3:36 pm-11:00 pm

1 stop9h 24m

$362

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Fri 11/28

5:30 pm-10:25 am

2 stops14h 55m

San Juan Luis Munoz Marin Intl

Tue 12/2

5:45 am-11:10 am

1 stop7h 25m

$395

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Wed 12/10

1:40 pm-12:35 am

2 stops8h 55m

San Juan Luis Munoz Marin Intl

Mon 12/15

9:40 am-7:35 pm

1 stop11h 55m

$395

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Thu 11/20

11:15 am-11:20 pm

1 stop10h 05m

San Juan Luis Munoz Marin Intl

Tue 11/25

6:05 am-1:15 pm

2 stops9h 10m

$415

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Fri 1/16

4:55 pm-10:10 am

2 stops16h 15m

Montego Bay Sangster Intl

Wed 1/21

11:32 am-10:46 pm

2 stops12h 14m

$419

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/25

Showing 1-10 of 60 results
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2
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6

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, October is the cheapest month in which you can book a flight from Houston Hobby Airport to Caribbean (average of $95). Flying from Houston Hobby Airport to Caribbean in December is currently the most expensive (average of $179). 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 27, 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 33% 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. Friday 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 October 27, 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.
Southwest
8.0
Very good
4,236 reviews

Overall

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,236 reviews
Southwest
8.0
Very good
4,236 reviews

Overall

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,996 reviews
Southwest
8.0
Very good
4,236 reviews

Overall

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,997 reviews
Southwest
8.0
Very good
4,236 reviews

Overall

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,033 reviews
Southwest
8.0
Very good
4,236 reviews

Overall

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,110 reviews
Southwest
8.0
Very good
4,236 reviews

Overall

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Houston Hobby Airport to Caribbean?

    A quick flight from Houston Hobby Airport to Caribbean can take about 9h 33m. Delta provides one of the quickest options available for as low as $264. Houston Hobby Airport and Caribbean are separated by a distance of 1994 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Houston Hobby Airport to Caribbean one-way?

    $108 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on American Airlines and Southwest, with prices starting from $137 and $171, respectively.

  • What are the most popular routes from Houston Hobby Airport to Caribbean?

    Most travelers choose Houston Hobby - San Juan Luis Munoz Marin Intl, Houston Hobby - Montego Bay Sangster Intl or Houston Hobby - Punta Cana when deciding on the best route from Houston Hobby Airport to Caribbean.

  • Can I find deals for flights from Hobby to Caribbean that include hotel bookings?

    Yes. In addition to deals on Hobby to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Hobby to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Hobby to Caribbean.

  • Can I find deals for business class flights from Hobby to Caribbean?

    Yes. Cheapflights offers flight deals from Hobby to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • 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 $95). Flying from Houston Hobby Airport to Caribbean in December is currently the most expensive (average of $179). 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.

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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.
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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 October 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$108Average$559FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$120Average$389FlexibilityNo cancel feeOn-time65%
FrontierCheapest$138Average$416FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$165Average$690FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$175Average$640FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$224Average$670FlexibilityNo cancel feeOn-time69%

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