$177 Find Cheap Flights from Houston Hobby Airport to Cayman Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Hobby to the Cayman Islands departing on 12/15. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Book Cheap Hobby to the Cayman Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Hobby to the Cayman Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Hobby to the Cayman Islands

Tue, Nov 3 - Mon, Nov 9
Southwest Logo
5:25 am - 12:35 pm
HOU
-
GCM
6h 10m
1 stop
Southwest Logo
1:30 pm - 9:45 pm
GCM
-
HOU
9h 15m
2 stops
$431Southwest
Tue, Nov 3 - Mon, Nov 9
Southwest Logo
5:25 am - 12:35 pm
HOU
-
GCM
6h 10m
1 stop
Southwest Logo
1:30 pm - 8:05 pm
GCM
-
HOU
7h 35m
1 stop
$458Southwest
Tue, Nov 3 - Mon, Nov 9
Southwest Logo
8:30 pm - 12:35 pm
HOU
-
GCM
15h 05m
2 stops
Southwest Logo
1:30 pm - 11:15 pm
GCM
-
HOU
10h 45m
2 stops
$495Southwest
Mon, Jul 20 - Wed, Jul 22
Southwest Logo
5:05 am - 11:55 am
HOU
-
GCM
6h 50m
1 stop
Southwest Logo
12:50 pm - 8:30 pm
GCM
-
HOU
7h 40m
1 stop
$496Southwest
Mon, Jul 20 - Wed, Jul 22
Southwest Logo
5:05 am - 11:55 am
HOU
-
GCM
6h 50m
1 stop
Southwest Logo
12:50 pm - 11:45 pm
GCM
-
HOU
10h 55m
2 stops
$562Southwest
Wed, Jul 8 - Sat, Jul 11
Southwest Logo
5:00 am - 11:55 am
HOU
-
GCM
6h 55m
1 stop
Southwest Logo
1:05 pm - 12:10 am
GCM
-
HOU
11h 05m
1 stop
$623Southwest
Mon, Jul 20 - Wed, Jul 22
Southwest Logo
8:35 pm - 11:55 am
HOU
-
GCM
15h 20m
2 stops
Southwest Logo
12:50 pm - 11:45 pm
GCM
-
HOU
10h 55m
2 stops
$626Southwest
Wed, Jul 8 - Sat, Jul 11
Southwest Logo
5:00 am - 11:55 am
HOU
-
GCM
6h 55m
1 stop
Southwest Logo
11:25 am - 9:25 pm
GCM
-
HOU
10h 00m
2 stops
$628Southwest
Mon, Jul 13 - Mon, Jul 20
Southwest Logo
5:05 am - 11:55 am
HOU
-
GCM
6h 50m
1 stop
Southwest Logo
12:50 pm - 11:50 pm
GCM
-
HOU
11h 00m
1 stop
$665Southwest
Mon, Jul 13 - Mon, Jul 20
Southwest Logo
8:35 pm - 11:55 am
HOU
-
GCM
15h 20m
2 stops
Southwest Logo
12:50 pm - 11:50 pm
GCM
-
HOU
11h 00m
1 stop
$682Southwest
Booking Insights

KAYAK's insights & trends for Hobby to the Cayman Islands flights

Get data-powered insights and trends into flights from Hobby to the Cayman Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest time of day to fly to the Cayman Islands?

The average price for all round-trip flights from Houston Hobby Airport to the Cayman Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to the Cayman Islands is generally in the morning, when round-trip flights cost $805 on average. The most expensive time of day to fly to the Cayman Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $805.

What is the cheapest month to fly from Houston Hobby Airport to the Cayman Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Houston Hobby Airport to the Cayman Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Houston Hobby Airport to the Cayman Islands is March, when tickets cost $240 (return) on average. On the other hand, the most expensive months are February and August, when the average cost of round-trip tickets is $654 and $644 respectively.

What’s the cheapest day of the week to fly from Houston Hobby Airport to Cayman Islands?

The average price of all round-trip flights from Houston Hobby Airport to the Cayman Islands clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Cayman Islands on a Wednesday and more expensive on a Tuesday. On your return trip to Houston Hobby Airport, you should consider flying back on a Monday, and avoid Wednesdays for better deals.

Good to know

Low seasonSeptember
Cheapest flight$177
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Houston Hobby Airport to George Town

FAQs - booking Cayman Islands flights

  • How does KAYAK find such low prices on flights from Houston Hobby Airport to Cayman Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Houston Hobby Airport to Cayman Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Houston Hobby Airport to Cayman Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Houston Hobby Airport to Cayman Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Houston Hobby Airport to Cayman Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Houston Hobby Airport to Cayman Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Houston Hobby Airport to Cayman Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Houston Hobby Airport to Cayman Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Hobby to the Cayman Islands

 
Need help choosing which airline to fly with from Hobby to the Cayman Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
SouthwestOverall score based on 4246 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
7.0Food
8.6Crew
Airline reviews

Flight was constantly delayed with significant changes in time, it was supposed to get to Colorado Springs at 8:30 PM but it got there after midnight.

2.0 MediocreMarcela, Jun 2026
DAL - COS
Read more Southwest reviews

Flight was constantly delayed with significant changes in time, it was supposed to get to Colorado Springs at 8:30 PM but it got there after midnight.

I don't know why flying out of Sarasota requires two plane changes.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

My experience was find with Southwest. The only issue I have is...at the exact time for me to check in...I don't understand how I always end up in C.

Very helpful, convenient, nice crew members, no extra fees, helped us saving 4 hrs of travel by booking is on an earlier flight

Our first flight was so delayed that we had 10 mins to board the next one. We requested if the flight attendant could allow us off there plane first and they denied our request even though I have seen this done before. Luck was on our side that we didn’t miss our next flight.

It was a very good experience. No major issues at all.

For the expense of first class, the seats could have been nicer and higher tier snacks would have been nice.

They delayed the flight 3 hours because it wasn't full they moved us to 5 different gates probably the worst airline ever not even spirit is this bad.

Packed flight, which makes it tough on crew and boarding staff (and the customers of course). But this was great boarding, clear instructions, etc. Traveling on the weekends are always fraught with danger as you have families and less frequent flyers thus more confusion. But this flight went as planned.

Boarded early, left early, arrived 40 mins early! A win win for me!

I felt scammed. The priced advertised was different than what I paid. I paid the whole some online. I then got a call 20 minutes later saying I need to paid 70 more person. She said the price online is not the guaranteed price.

We had a delay, but thankfully I made it to my connection. Overall it went smooth

Left an hour and a half after the listed time. Up side was it had TV screens on the seat.

It's a long flight and I would have liked better snacks between lunch and the arrival meal. It's fine to have fruit and nuts but I really don't like ramen because it's salty junk soup. I'd suggest sandwiches. They're not expensive nor are they hard to store for a long flight. The FA's had a couple of big services and they were super busy preparing, executing and then cleaning up. Then they disappeared.

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

I've been flying American mostly, and it's been very frustrating. This united flight makes me realize maybe the issue isn't flying, but the airline. United was a significantly better experience. The plane was more comfortable, with a normal amount of leg room (vs the ridiculous reductions AA has made), more comfortable seats, screens to watch movies. It was a much better experience!

Forced to check bags. Crew uninterested in collecting trash. Unclean seats.

There's nothing I liked about it. For first off I scheduled this trip two weeks in advance then they delayed my flight which messed up my whole trip. So I scheduled it for the following weekend thinking there won't be a delay and guess what as soon as I got to the airport we said in the airplane on the tarmac for an hour and a half. Not only was it delayed I missed my connecting flight meaning I had to stay the night at Dallas-Fort Worth airport sleeping on the floor. I will tell you this I will never fly American airlines ever again I have had nothing but horrible experience with them and I just throw money at them

They changed my seat from one that I had paid for as an upgrade to a regular seat at the last minute.

Very aggressive and unhelpful ground crew. Wanted to check my hand luggage for 3 flights. I had lots of delicate items and computer equipment. So the silly lady wanted to rebook 3 international flights because of a carry on. What nonsense. The baggage handler suggested I put it under my seat - so I did. And this was during the rebooking chaos of the Microsoft crash. She was the most arrogant annoying and aggressive ground staff member I’ve met in 20yrs. (AA flight out of Houston).

Left from gate 30 minutes before flight. Never been late to a flight ever. It says 15 minutes before explicitly on the ticket.

Was as expected. Good leg room on planes - much appreciated.

I know that there is nothing than can be done about rude customers. I did find a couple of them were very rude and inconsiderate In my case the guy who was sitting in the same row as I was in, was trying to watch a movie with no headphones, a crew member did ask him to turn it down or off (thumbs up for that.) Another thing, as we were about to land another young man must have taken his phone off airplane mode was talking with his friends and using fowl language which I found inappropriate to the ppl who were sitting in the same row as him and other ppl around him. I understand how no one wanted to address this person and not get involved. We all just wanted to get home safely with out any incident.

The food service was limited and not good. For a seven hour flight they could do better.

Left 40 mins late; we were fine on our connection but many on our flight were not.

Pros: "The crew member who is close to my seat did not even offer to help with my luggage which was very unprofessional."
Cons: "The crew members needs to be helpful, and customer service to their passengers!"

Everything you need to know for your flight from Hobby to the Cayman Islands

Information on your arrival and departure airports