$133 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 6/24. 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$365
Cayman Brac
Cayman Brac2 stops$664
George Town
George Town1 stop$365
Cayman Brac
Cayman Brac2 stops$664

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

Sun, Jun 7 - Thu, Jun 11
Air Canada Logo
9:55 am - 11:25 am
ORD
-
GCM
25h 30m
1 stop
Air Canada Logo
12:25 pm - 9:00 am
GCM
-
ORD
20h 35m
1 stop
$365Air Canada
Wed, Jun 10 - Mon, Jun 15
Air Canada Logo
1:55 pm - 11:25 am
ORD
-
GCM
21h 30m
2 stops
Air Canada Logo
12:25 pm - 9:00 am
GCM
-
ORD
20h 35m
1 stop
$370Air Canada
Wed, Jun 10 - Mon, Jun 15
Air Canada Logo
1:55 pm - 11:25 am
ORD
-
GCM
21h 30m
2 stops
Air Canada Logo
12:25 pm - 12:11 pm
GCM
-
ORD
23h 46m
2 stops
$375Air Canada
Sat, Jun 6 - Mon, Jun 15
Air Canada Logo
6:22 pm - 11:25 am
ORD
-
GCM
41h 03m
2 stops
Air Canada Logo
12:25 pm - 11:20 am
GCM
-
ORD
46h 55m
2 stops
$379Air Canada
Fri, Jun 12 - Mon, Jun 22
Air Canada Logo
8:20 pm - 10:00 am
ORD
-
GCM
13h 40m
1 stop
Air Canada Logo
12:25 pm - 8:00 am
GCM
-
ORD
19h 35m
1 stop
$390Air Canada
Sat, Jun 6 - Sat, Jun 13
Air Canada Logo
6:22 pm - 11:25 am
ORD
-
GCM
41h 03m
2 stops
Air Canada Logo
10:55 am - 9:00 am
GCM
-
ORD
22h 05m
1 stop
$395Air Canada
Sun, Jun 7 - Fri, Jun 12
Multiple Airlines Logo
9:55 am - 11:25 am
ORD
-
GCM
25h 30m
1 stop
Multiple Airlines Logo
7:00 am - 9:00 am
GCM
-
ORD
26h 00m
2 stops
$402Multiple Airlines
Sun, Sep 13 - Sat, Sep 19
Air Canada Logo
8:40 pm - 11:30 am
ORD
-
GCM
14h 50m
1 stop
Air Canada Logo
12:25 pm - 9:00 am
GCM
-
ORD
20h 35m
1 stop
$413Air Canada
Wed, Jun 10 - Mon, Jun 15
Multiple Airlines Logo
7:09 am - 11:25 am
ORD
-
GCM
28h 16m
1 stop
Multiple Airlines Logo
7:00 am - 9:00 am
GCM
-
ORD
26h 00m
2 stops
$417Multiple Airlines
Sun, Sep 13 - Sat, Sep 19
Air Canada Logo
3:40 pm - 11:30 am
ORD
-
GCM
19h 50m
2 stops
Air Canada Logo
12:25 pm - 7:44 am
GCM
-
ORD
19h 19m
2 stops
$422Air Canada
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 $640 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 $640.

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

The average price for all round-trip flights from Chicago O'Hare Intl 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 $631 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 $631.

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.

No, with an average price for the route of $580, prices are generally cheapest when you fly direct.

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 December, when tickets cost $174 (return) on average. On the other hand, the most expensive months are September and August, when the average cost of round-trip tickets is $659 and $577 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 Wednesday 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 Fridays.

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 3 weeks before departure, which saves you about 16% 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$133
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 11% 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.

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 9675 reviews
7.1Entertainment
7.7Boarding
7.3Comfort
8.1Crew
6.6Food
Airline reviews

A long delay. Don't travel late in the day.

8.0 ExcellentTimothy, Apr 2026
ORD - CID
Read more United Airlines reviews

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

The boarding timing needs to be improved. The flight was delayed again because it took way too long to board. I was already exhausted from sleeping at the airport and spending all day there due to delay from my previous flight that connected in Chicago.

Great until we got to FRA. The next trip leg we were put in Business Class where seats had minimal padding!!!! They were awful and United Airlines needs to have their Lufthansa partner up their game or I won’t fly with them again!!

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

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

Information on your arrival and departure airports