Caribbean

$112+ Cheap flights from Houston to Caribbean

HOU — SJU
Dec 5 — Dec 121
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Cheap flight deals from Houston to Caribbean

Cheapest flights from Houston to Caribbean

Mon 11/305:26 pm -
1 stop25h 11m
Mon 12/711:40 am -
1 stop13h 24m
Deal found 11/2$300
Wed 12/301:19 pm -
1 stop11h 30m
Fri 1/89:14 pm -
Nonstop5h 10m
Deal found 11/3$301
Sat 11/78:18 am -
1 stop27h 07m
Sat 11/144:52 pm -
1 stop22h 55m
Deal found 11/2$303
Thu 12/39:41 am -
2 stops14h 17m
Sat 12/52:49 am -
2 stops15h 17m
Deal found 11/1$304
Thu 12/314:37 pm -
1 stop18h 00m
Wed 1/69:14 pm -
Nonstop5h 10m
Deal found 11/2$305
Sat 11/78:18 am -
1 stop27h 07m
Mon 11/97:00 am -
1 stop9h 44m
Deal found 11/1$306
Mon 11/92:32 pm -
1 stop7h 06m
Thu 11/126:00 am -
1 stop9h 47m
Deal found 11/2$308
Thu 12/109:41 am -
2 stops14h 17m
Mon 12/149:52 pm -
2 stops20h 14m
Deal found 10/31$309
Tue 11/178:18 am -
2 stops14h 41m
Mon 11/237:31 am -
2 stops13h 53m
Deal found 11/1$310
Wed 12/304:52 pm -
1 stop18h 00m
Wed 1/63:09 am -
1 stop9h 20m
Deal found 11/1$311
Mon 11/98:18 am -
2 stops14h 41m
Fri 11/136:00 am -
1 stop9h 47m
Deal found 11/2$312
Wed 12/25:01 pm -
2 stops15h 24m
Wed 12/911:00 am -
1 stop6h 06m
Deal found 11/4$385

Find flight deals from Houston to Caribbean

Round-trip from

$277
(Kiwi.com)

One-way from

$112
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$493
From Houston to Caribbean
One-way flight from Houston to Caribbean
Highest demand for flights based on searches. 9% potential increase in price ($47 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Average for round-trip flights in November 2026

Cheapflights Fare Finder

 
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

IAH Houston George Bush Intcntl - SJU San Juan Luis Munoz Marin Intl

IAHSJU

Houston George Bush Intcntl

Sun 12/13

10:57 am-1:58 am

1 stop13h 01m

San Juan Luis Munoz Marin Intl

Wed 12/31

12:00 am-10:00 pm

Nonstop0h 00m

$154

HoustonNassau

IAH Houston George Bush Intcntl - NAS Nassau Intl

IAHNAS

Houston George Bush Intcntl

Wed 2/3

3:50 pm-10:30 am

2 stops17h 40m

Nassau Intl

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$156

HoustonNassau

IAH Houston George Bush Intcntl - NAS Nassau Intl

IAHNAS

Houston George Bush Intcntl

Sun 1/31

11:37 am-8:45 pm

2 stops32h 08m

Nassau Intl

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$162

HoustonNassau

IAH Houston George Bush Intcntl - NAS Nassau Intl

IAHNAS

Houston George Bush Intcntl

Tue 11/17

8:18 am-2:45 pm

1 stop5h 27m

Nassau Intl

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$182

HoustonSan Juan

IAH Houston George Bush Intcntl - SJU San Juan Luis Munoz Marin Intl

IAHSJU

Houston George Bush Intcntl

Fri 1/8

5:01 am-11:21 am

Nonstop4h 20m

San Juan Luis Munoz Marin Intl

Wed 12/31

12:00 am-10:00 pm

Nonstop0h 00m

$190

HoustonNassau

IAH Houston George Bush Intcntl - NAS Nassau Intl

IAHNAS

Houston George Bush Intcntl

Mon 11/16

7:25 am-11:00 am

2 stops26h 35m

Nassau Intl

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$200

HoustonSanto Domingo

IAH Houston George Bush Intcntl - SDQ Santo Domingo Las Americas

IAHSDQ

Houston George Bush Intcntl

Mon 1/11

6:44 pm-4:29 pm

2 stops43h 45m

Santo Domingo Las Americas

Wed 12/31

12:00 am-10:30 pm

Nonstop0h 00m

$201

HoustonNassau

IAH Houston George Bush Intcntl - NAS Nassau Intl

IAHNAS

Houston George Bush Intcntl

Wed 11/18

8:21 pm-8:45 pm

2 stops23h 24m

Nassau Intl

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$213

HoustonOranjestad

IAH Houston George Bush Intcntl - AUA Oranjestad Reina Beatrix

IAHAUA

Houston George Bush Intcntl

Tue 11/10

11:55 am-4:25 pm

1 stop26h 30m

Oranjestad Reina Beatrix

Wed 12/31

12:00 am-10:00 pm

Nonstop0h 00m

$219

HoustonOranjestad

IAH Houston George Bush Intcntl - AUA Oranjestad Reina Beatrix

IAHAUA

Houston George Bush Intcntl

Sat 12/12

11:55 am-2:25 pm

2 stops24h 30m

Oranjestad Reina Beatrix

Wed 12/31

12:00 am-10:00 pm

Nonstop0h 00m

$222

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 60 resultsSorted by cheapest first
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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

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, January is the cheapest month in which you can book a flight from Houston to Caribbean (average of $559). Flying from Houston to Caribbean in June is currently the most expensive (average of $699). 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?

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 40% on your trip compared to booking a flight in the afternoon.

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 to Caribbean?

The best time to book flights from Houston to Caribbean is 14 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.

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

Travelers seeking maximum savings on their Houston to Caribbean flight should consider departing on Thursday at noon when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Caribbean

See what other customers who have flown with Southwest,United Airlines, andJetBlue 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.

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Related info for your journey

  • How long is the flight from Houston to Caribbean?

    For as low as $471, United Airlines can have you in Caribbean from Houston in 4h 19m. 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?

    $72 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on JetBlue and Frontier, with prices starting from $88 and $101, respectively.

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

  • 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, January is the cheapest month in which you can book a flight from Houston to Caribbean (average of $559). Flying from Houston to Caribbean in June is currently the most expensive (average of $699). 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Houston to Caribbean

Top 8 airlines flying from Houston to Caribbean

AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$175Average$473FlexibilityNo cancel feeOn-time62%
DeltaCheapest$213Average$651FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$223Average$567FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$276Average$698FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$354Average$748FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$390Average$686FlexibilityNo cancel feeOn-time63%
AviancaCheapest$501Average$653FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$506Average$576FlexibilityNo cancel feeOn-time67%

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