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Cayman Islands

$227+ Cheap flights from Hobby (HOU) to the Cayman Islands

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 12/1. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — GCM
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Cheap flight deals from Hobby to Cayman Islands

Keep the following information in mind while searching for Hobby to Cayman Islands flight deals. Data was last updated October 28, 2025.

Round-trip from

$484
(Southwest)

One-way from

$227
(Southwest)

Popular in

November

Cheapest in

January

Average price

$719
From Houston Hobby to Cayman Islands
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One-way flight from Houston Hobby to Cayman Islands
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Highest demand for flights based on searches. 10% potential increase in price ($89 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($27 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 Cayman Islands

Cheapest flights from Hobby to Cayman Islands
Explore the most affordable flight options available from Hobby to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 28, 2025.

This Southwest deal was found by Cheapflights users on 10/28. 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 12/75:00 amHOU - GCM
1 stop6h 35mSouthwest
Tue 12/91:30 pmGCM - HOU
1 stop6h 30mSouthwest
Deal found 10/28$484
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/166:40 amHOU - GCM
1 stop4h 55mSouthwest
Tue 12/231:30 pmGCM - HOU
2 stops9h 05mSouthwest
Deal found 10/27$521
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.
Wed 12/106:36 pmHOU - GCM
2 stops16h 34mAmerican Airlines
Wed 12/173:45 pmGCM - HOU
2 stops17h 47mAmerican Airlines
Deal found 10/26$650
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.
Fri 12/126:36 pmHOU - GCM
1 stop19h 46mAmerican Airlines
Fri 12/194:30 pmGCM - HOU
1 stop8h 16mAmerican Airlines
Deal found 10/27$663
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 12/106:00 amHOU - GCM
1 stop5h 35mDelta
Wed 12/171:50 pmGCM - HOU
1 stop9h 58mDelta
Deal found 10/26$665
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 11/166:00 amHOU - GCM
1 stop5h 35mDelta
Sun 11/231:50 pmGCM - HOU
1 stop10h 17mDelta
Deal found 10/26$1,209
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.
Fri 11/219:05 amHOU - GCM
2 stops10h 23mAmerican Airlines
Fri 11/289:00 amGCM - HOU
2 stops11h 50mAmerican Airlines
Deal found 10/27$1,320
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.
Thu 11/276:00 amHOU - GCM
2 stops13h 28mAmerican Airlines
Sun 11/309:00 amGCM - HOU
2 stops9h 52mAmerican Airlines
Deal found 10/27$1,759

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hobby to Cayman Islands 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 28, 2025.
Use the filters below to find and compare flights from Houston Hobby Airport to the Cayman Islands that are best for you.

Fly from

Hobby

Fly to

Cayman Islands

Route

Depart

Return

Price

HoustonGeorge Town

HOU - GCM

HOUGCM

Houston Hobby

Sun 12/7

7:25 pm-12:35 pm

2 stops16h 10m

George Town Owen Roberts Intl

Tue 12/9

1:30 pm-7:00 pm

1 stop6h 30m

$489

HoustonGeorge Town

HOU - GCM

HOUGCM

Houston Hobby

Tue 12/16

6:40 am-12:35 pm

1 stop4h 55m

George Town Owen Roberts Intl

Tue 12/23

1:30 pm-9:35 pm

2 stops9h 05m

$521

HoustonGeorge Town

HOU - GCM

HOUGCM

Houston Hobby

Wed 12/10

6:36 pm-12:10 pm

2 stops16h 34m

George Town Owen Roberts Intl

Wed 12/17

3:45 pm-8:32 am

2 stops17h 47m

$650

HoustonGeorge Town

HOU - GCM

HOUGCM

Houston Hobby

Fri 3/27

6:06 am-1:19 pm

1 stop7h 13m

George Town Owen Roberts Intl

Mon 3/30

3:35 pm-11:43 pm

1 stop8h 08m

$655

HoustonGeorge Town

HOU - GCM

HOUGCM

Houston Hobby

Sat 1/3

5:40 am-3:26 pm

1 stop8h 46m

George Town Owen Roberts Intl

Sat 1/10

4:25 pm-10:46 pm

1 stop7h 21m

$655

HoustonGeorge Town

HOU - GCM

HOUGCM

Houston Hobby

Fri 12/12

6:36 pm-3:22 pm

1 stop19h 46m

George Town Owen Roberts Intl

Fri 12/19

4:30 pm-11:46 pm

1 stop8h 16m

$663

HoustonGeorge Town

HOU - GCM

HOUGCM

Houston Hobby

Wed 12/10

6:00 am-12:35 pm

1 stop5h 35m

George Town Owen Roberts Intl

Wed 12/17

1:50 pm-10:48 pm

1 stop9h 58m

$665

HoustonGeorge Town

HOU - GCM

HOUGCM

Houston Hobby

Sat 1/3

6:00 am-12:40 pm

1 stop5h 40m

George Town Owen Roberts Intl

Sat 1/10

12:45 pm-10:35 pm

2 stops10h 50m

$720

HoustonGeorge Town

HOU - GCM

HOUGCM

Houston Hobby

Mon 1/5

5:40 am-3:25 pm

1 stop8h 45m

George Town Owen Roberts Intl

Sat 1/10

4:25 pm-10:46 pm

1 stop7h 21m

$730

HoustonGeorge Town

HOU - GCM

HOUGCM

Houston Hobby

Mon 12/1

8:20 pm-12:35 pm

2 stops15h 15m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 17 results
1
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Best time to book a flight from Hobby to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands 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 the Cayman Islands

What is the cheapest month to book a flight from Houston Hobby Airport to Cayman Islands?

Currently, October is the cheapest month in which you can book a flight from Houston Hobby Airport to Cayman Islands (average of $338). Flying from Houston Hobby Airport to Cayman Islands in March is currently the most expensive (average of $694). 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.

Reviews of airlines servicing Cayman Islands

Get insights into the airlines that provide service to Cayman Islands. 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 Cayman Islands. Reviews last updated October 28, 2025.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and American Airlines from Houston Hobby Airport to the Cayman Islands to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

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
9,001 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

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
11,032 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

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 Cayman Islands. 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 Cayman Islands?

    Airlines like Southwest fly from Houston Hobby Airport to Cayman Islands in about 16h 10m. The time it takes to get you to your destination can typically vary by up to . Airlines will cover a distance of 1128 mi.

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

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

  • How can I find direct flights from Hobby to Cayman Islands?

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

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

    Yes. Cheapflights offers flight deals from Hobby to Cayman Islands 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 Cayman Islands?

    Currently, October is the cheapest month in which you can book a flight from Houston Hobby Airport to Cayman Islands (average of $338). Flying from Houston Hobby Airport to Cayman Islands in March is currently the most expensive (average of $694). 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

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See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Hobby to Cayman Islands

Discover the top 3 airlines that operate flights from Hobby to Cayman Islands. 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 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$338Average$739FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$540Average$690FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$654Average$757FlexibilityNo cancel feeOn-time69%

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