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Caribbean

$101+ Cheap flights from Houston 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 5/10. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — SJU
May 17 — May 241
Sun 5/17
Sun 5/24
1 adult, Economy
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Cheap flight deals from Houston to Caribbean

Cheapest flights from Houston to Caribbean
Explore the most affordable flight options available from Houston to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2026.

This CheapOair deal was found by Cheapflights users on 4/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/88:29 am
IAH
-
SJU
1 stop7h 47m
Frontier
Mon 5/113:03 am
SJU
-
IAH
1 stop16h 46m
Frontier
Deal found 4/14$222
This Kiwi.com deal was found by Cheapflights users on 4/12. 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.
Tue 5/126:05 am
IAH
-
SJU
1 stop7h 02m
Frontier
Sat 5/166:41 pm
SJU
-
IAH
1 stop14h 37m
Frontier
Deal found 4/12$223
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 5/41:58 pm
IAH
-
SJU
1 stop8h 31m
Frontier
Sat 5/96:30 am
SJU
-
IAH
2 stops17h 20m
Frontier
Deal found 4/13$224
This Kiwi.com deal was found by Cheapflights users on 4/15. 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.
Tue 5/59:45 am
IAH
-
SJU
1 stop15h 23m
Multiple Airlines
Thu 5/145:47 pm
SJU
-
IAH
1 stop15h 31m
Multiple Airlines
Deal found 4/15$225
This Frontier deal was found by Cheapflights users on 4/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/252:01 pm
IAH
-
SJU
1 stop7h 47m
Frontier
Sat 5/23:21 am
SJU
-
IAH
1 stop7h 33m
Frontier
Deal found 4/14$226
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 4/206:00 pm
IAH
-
SJU
1 stop22h 59m
Multiple Airlines
Wed 4/2911:30 am
SJU
-
IAH
1 stop21h 53m
Multiple Airlines
Deal found 4/13$227
This Kiwi.com deal was found by Cheapflights users on 4/13. 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.
Sun 5/178:29 am
IAH
-
SJU
1 stop7h 47m
Frontier
Tue 5/269:00 am
SJU
-
IAH
1 stop28h 34m
Frontier
Deal found 4/13$228
This CheapOair deal was found by Cheapflights users on 4/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/79:03 am
IAH
-
SJU
1 stop29h 46m
Frontier
Mon 5/117:20 am
SJU
-
IAH
1 stop14h 12m
Frontier
Deal found 4/14$229
This Kiwi.com deal was found by Cheapflights users on 4/15. 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.
Sat 5/22:01 pm
IAH
-
SJU
1 stop11h 00m
Frontier
Tue 5/58:30 am
SJU
-
IAH
2 stops31h 43m
Frontier
Deal found 4/15$230
This Frontier deal was found by Cheapflights users on 4/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/197:00 am
IAH
-
SJU
1 stop14h 19m
Frontier
Sat 5/23:21 am
SJU
-
IAH
1 stop7h 33m
Frontier
Deal found 4/16$231
This Kiwi.com deal was found by Cheapflights users on 4/14. 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.
Thu 4/304:39 pm
IAH
-
SJU
1 stop8h 22m
Frontier
Mon 5/46:30 am
SJU
-
IAH
2 stops33h 28m
Frontier
Deal found 4/14$232
This Kiwi.com deal was found by Cheapflights users on 4/14. 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.
Thu 4/303:42 pm
IAH
-
SJU
1 stop7h 17m
Multiple Airlines
Mon 5/45:47 pm
SJU
-
IAH
1 stop23h 29m
Multiple Airlines
Deal found 4/14$233

Find flight deals from Houston to Caribbean

Keep the following information in mind while searching for Houston to Caribbean flight deals. Data was last updated April 17, 2026.

Round-trip from

$222
(CheapOair)

One-way from

$101
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$398
From Houston to Caribbean
Search Deals
One-way flight from Houston to Caribbean
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Houston 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 April 17, 2026.
Use the filters below to find and compare flights from Houston to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Mon 5/18

1:20 pm-11:25 pm

2 stops9h 05m

San Juan Luis Munoz Marin Intl

Sat 5/23

6:25 am-1:40 pm

1 stop8h 15m

$446

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Thu 7/30

7:00 pm-12:25 am

Nonstop4h 25m

San Juan Luis Munoz Marin Intl

Mon 8/3

10:20 pm-8:45 am

1 stop11h 25m

$462

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Wed 8/26

6:00 am-1:30 pm

1 stop6h 30m

San Juan Luis Munoz Marin Intl

Wed 9/2

1:06 pm-9:35 pm

1 stop9h 29m

$466

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Thu 7/23

6:05 pm-1:20 am

1 stop6h 15m

San Juan Luis Munoz Marin Intl

Wed 8/5

1:20 pm-7:50 pm

1 stop7h 30m

$466

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Sat 8/29

6:00 am-4:40 pm

2 stops9h 40m

San Juan Luis Munoz Marin Intl

Tue 9/8

11:50 am-8:05 pm

2 stops9h 15m

$466

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Tue 6/2

10:25 am-9:05 pm

2 stops9h 40m

San Juan Luis Munoz Marin Intl

Mon 6/22

8:15 pm-7:50 am

1 stop12h 35m

$466

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Thu 9/24

10:00 am-10:50 pm

2 stops11h 50m

San Juan Luis Munoz Marin Intl

Sun 9/27

5:30 am-7:40 pm

2 stops15h 10m

$466

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Fri 5/15

1:30 pm-11:55 pm

2 stops9h 25m

San Juan Luis Munoz Marin Intl

Mon 5/18

8:40 pm-8:05 am

1 stop12h 25m

$468

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Sat 8/8

10:30 am-6:15 pm

1 stop6h 45m

San Juan Luis Munoz Marin Intl

Mon 8/10

5:30 am-5:45 pm

1 stop13h 15m

$476
Quickest round-trip

HoustonMontego Bay

IAH - MBJ

IAHMBJ

Houston George Bush Intcntl

Wed 7/1

10:05 am-1:30 pm

Nonstop3h 25m

Montego Bay Sangster Intl

Wed 7/8

2:40 pm-6:08 pm

Nonstop3h 28m

$486

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/13

Showing 1-10 of 60 resultsSorted by cheapest first
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6

Best time to book a flight from Houston to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Houston 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 to Caribbean

What is the cheapest month to book a flight from Houston to Caribbean?

Currently, October is the cheapest month in which you can book a flight from Houston to Caribbean (average of $468). Flying from Houston to Caribbean in May is currently the most expensive (average of $698). 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 Houston 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 April 17, 2026.

A simple way to save on the total cost of your ticket is to fly from Houston to Caribbean at noon. If you’re flexible enough to do this you can expect to save up to 36% on your trip compared to booking a flight in the morning.

What is the cheapest day to fly from Houston to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from Houston to Caribbean. Price data was last updated on April 11, 2026.

Travelers seeking maximum savings on their Houston to Caribbean flight should consider departing on Tuesday at noon 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 April 17, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican Airlines from Houston to Caribbean have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,328 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,328 reviews
Southwest
8.0
Very good
4,328 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,602 reviews
Southwest
8.0
Very good
4,328 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,593 reviews
Southwest
8.0
Very good
4,328 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Spirit Airlines
6.3
Okay
8,618 reviews
Southwest
8.0
Very good
4,328 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
2,986 reviews
Southwest
8.0
Very good
4,328 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Houston 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 to Caribbean?

    For as low as $462, United Airlines can have you in Caribbean from Houston in 4h 32m. There are 2004 mi between Houston and Caribbean. Both multi-stop and nonstop flights can be found to your destination and back.

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

    $69 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on American Airlines and Southwest, with prices starting from $72 and $72, respectively.

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

    When deciding which route to take from Houston to Caribbean consider Houston Hobby - San Juan Luis Munoz Marin Intl, Houston George Bush Intcntl - San Juan Luis Munoz Marin Intl or Houston Hobby - Punta Cana as they are the most popular.

  • What are the cheapest flights from Houston to Caribbean?

    On average you can expect to pay $373 for a flight from Houston to Caribbean. The cheapest flight overall is $228 while the most popular route, (Houston Hobby - San Juan Luis Munoz Marin Intl) is currently priced at $176.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Houston 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 to Caribbean?

    Currently, October is the cheapest month in which you can book a flight from Houston to Caribbean (average of $468). Flying from Houston to Caribbean in May is currently the most expensive (average of $698). 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 Houston 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 Houston to Caribbean

Discover the top 6 airlines that operate flights from Houston 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 April 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$78Average$390FlexibilityNo cancel feeOn-time65%
DeltaCheapest$108Average$551FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$109Average$454FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$165Average$659FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$165Average$624FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$194Average$656FlexibilityNo cancel feeOn-time69%

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