$72 Find Cheap Flights from Chicago O'Hare 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 O'Hare Intl to the Cayman Islands departing on 1/15. 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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Cheap Flights from O'Hare Intl to the Cayman Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
George Town
George Town1 stop$333
Cayman Brac
Cayman Brac2 stops$648
George Town
George Town1 stop$333
Cayman Brac
Cayman Brac2 stops$648

Book Cheap O'Hare Intl 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 O'Hare Intl 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 O'Hare Intl to the Cayman Islands

Thu, Feb 26 - Sun, Mar 1
Multiple Airlines Logo
5:15 am - 1:43 pm
ORD
-
GCM
7h 28m1 stop
Multiple Airlines Logo
2:49 pm - 5:23 pm
GCM
-
ORD
27h 34m2 stops
$333Multiple Airlines
Sun, Feb 1 - Sun, Feb 8
Spirit Airlines Logo
5:15 am - 1:53 pm
ORD
-
GCM
7h 38m1 stop
Spirit Airlines Logo
2:49 pm - 9:12 am
GCM
-
ORD
19h 23m2 stops
$335Spirit Airlines
Fri, Jan 16 - Thu, Jan 22
Multiple Airlines Logo
6:57 pm - 2:50 pm
ORD
-
GCM
18h 53m2 stops
Multiple Airlines Logo
2:49 pm - 10:36 pm
GCM
-
ORD
8h 47m1 stop
$336Multiple Airlines
Thu, Jan 15 - Sun, Jan 18
Multiple Airlines Logo
5:15 am - 1:53 pm
ORD
-
GCM
7h 38m1 stop
Multiple Airlines Logo
2:49 pm - 11:43 pm
GCM
-
ORD
33h 54m2 stops
$340Multiple Airlines
Sat, Jan 10 - Sat, Jan 17
Spirit Airlines Logo
5:15 am - 1:38 pm
ORD
-
GCM
7h 23m1 stop
Spirit Airlines Logo
2:34 pm - 11:22 am
GCM
-
ORD
21h 48m1 stop
$341Spirit Airlines
Fri, Jan 9 - Mon, Jan 12
Multiple Airlines Logo
6:57 pm - 2:50 pm
ORD
-
GCM
18h 53m2 stops
Multiple Airlines Logo
4:45 pm - 8:18 am
GCM
-
ORD
16h 33m1 stop
$342Multiple Airlines
Thu, Jan 15 - Mon, Jan 19
Multiple Airlines Logo
5:15 am - 1:53 pm
ORD
-
GCM
7h 38m1 stop
Multiple Airlines Logo
4:45 pm - 6:27 pm
GCM
-
ORD
26h 42m2 stops
$345Multiple Airlines
Fri, Jan 16 - Mon, Jan 19
Multiple Airlines Logo
8:43 pm - 1:38 pm
ORD
-
GCM
15h 55m1 stop
Multiple Airlines Logo
1:30 pm - 4:40 pm
GCM
-
ORD
28h 10m1 stop
$347Multiple Airlines
Sat, Jan 10 - Wed, Jan 14
Multiple Airlines Logo
5:15 am - 1:38 pm
ORD
-
GCM
7h 23m1 stop
Multiple Airlines Logo
11:30 am - 3:27 pm
GCM
-
ORD
28h 57m2 stops
$349Multiple Airlines
Thu, Jan 22 - Sun, Feb 1
Spirit Airlines Logo
5:15 am - 1:53 pm
ORD
-
GCM
7h 38m1 stop
Spirit Airlines Logo
2:49 pm - 11:47 pm
GCM
-
ORD
9h 58m1 stop
$351Spirit Airlines
Booking Insights

KAYAK's insights & trends for O'Hare Intl to the Cayman Islands flights

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

What is the cheapest Chicago O'Hare Intl Airport to the Cayman Islands flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to the Cayman Islands from Chicago O'Hare Intl Airport found in the last 72 hours was to George Town, at $339 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to George Town (GCM), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $339.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to the Cayman Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $534 on average.

What is the cheapest month to fly from Chicago O'Hare Intl 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 Chicago O'Hare Intl 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 Chicago O'Hare Intl Airport to the Cayman Islands is February, when tickets cost $539 (return) on average. On the other hand, the most expensive months are November and March, when the average cost of round-trip tickets is $935 and $840 respectively.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to Cayman Islands?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to the Cayman Islands clicked on KAYAK for each day over the last 12 months.

When flying from Chicago O'Hare Airport to Cayman Islands, you should consider leaving on a Thursday and avoid Sundays if you are looking for the best rates. For your return to Chicago O'Hare Airport, you’ll find the best rates on Sundays and the most expensive ones on Wednesdays.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to the Cayman Islands?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to the Cayman Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago O'Hare Intl Airport to the Cayman Islands, you should book around 5 weeks before departure, which saves you about 24% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$72
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 20% increase in price.
Flight from Chicago O'Hare Airport to George Town

FAQs - booking Cayman Islands flights

  • How does KAYAK find such low prices on flights from Chicago O'Hare 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 Chicago O'Hare Airport to Cayman Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago O'Hare 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 Chicago O'Hare 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 Chicago O'Hare 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 Chicago O'Hare 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 Chicago O'Hare Airport to Cayman Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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

    The cheapest time of day to fly to the Cayman Islands is generally in the evening, when round-trip flights cost $507 on average. Morning departures are around 37% more expensive than evening flights, 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 $694.

Reviews of the top airlines flying from O'Hare Intl to the Cayman Islands

 
Need help choosing which airline to fly with from O'Hare Intl 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.
7.4
United AirlinesOverall score based on 9091 reviews
7.7Boarding
7.3Comfort
6.6Food
8.1Crew
7.1Entertainment
Airline reviews

The movies offered were great. Staff were very pleasant and very efficient.

10.0 ExcellentAnonymous, Dec 2025
ORD - HND
Read more United Airlines reviews

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Everything you need to know for your flight from O'Hare Intl to the Cayman Islands

Information on your arrival and departure airports