
Cheap Flights from Chicago to the Cayman Islands
Cheapest round-trip prices found by our users on KAYAK in the last 5 daysBook Cheap Chicago to the Cayman Islands Plane Tickets
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KAYAK's insights & trends for Chicago to the Cayman Islands flights
Get data-powered insights and trends into flights from Chicago 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?
The cheapest ticket to the Cayman Islands from Chicago O'Hare Intl Airport found in the last 5 days was to George Town, at $616 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 5 days was $616.
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 morning, when round-trip flights cost $651 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 $651.
Can I save money by flying with a layover from Chicago O'Hare Intl Airport to the Cayman Islands?
Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $681 on average.
What is the cheapest month to fly from Chicago O'Hare Intl Airport to the Cayman Islands?
The cheapest month for flights from Chicago O'Hare Intl Airport to the Cayman Islands is January, when tickets cost $568 (return) on average. On the other hand, the most expensive months are November and July, when the average cost of round-trip tickets is $905 and $806 respectively.
What’s the cheapest day of the week to fly from Chicago to Cayman Islands?
When flying from Chicago to Cayman Islands, you should consider leaving on a Wednesday and avoid Mondays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Saturdays 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 get a below average price on the flight from Chicago O'Hare Intl Airport to the Cayman Islands, you should book around 2 weeks before departure, which saves you about 16% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.
Which airlines fly non-stop between Chicago O'Hare Intl Airport and Cayman Islands?
There are 2 airlines that fly nonstop from Chicago O'Hare Intl Airport to the Cayman Islands. They are American Airlines and United Airlines. The cheapest airline for this route is United Airlines, with the best round-trip deal found costing $341 and arriving in George Town (GCM). On average, United Airlines offers the best prices for nonstop flights between Chicago O'Hare Intl Airport and Cayman Islands.
Which airlines provide the cheapest flights from Chicago O'Hare Intl Airport to the Cayman Islands?
In the past 5 days, the cheapest round-trip tickets from Chicago O'Hare Intl Airport to the Cayman Islands were found on United Airlines ($598) and Delta ($602).
How long does a flight from Chicago O'Hare Intl Airport to the Cayman Islands take?
The duration of a flight to the Cayman Islands depends on your arrival airport. The shortest routes to the Cayman Islands from Chicago O'Hare Intl Airport are to George Town, which takes 4h 00m, and Cayman Brac, which takes 17h 35m.
Which cabin class options are there for flights between Chicago O'Hare Intl Airport and Cayman Islands?
There are 3 cabin class options for the route. These are Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.
What’s the earliest departure time from Chicago O'Hare Intl Airport to the Cayman Islands?
The earliest flight from Chicago O'Hare Intl Airport to the Cayman Islands departs at 8:42 am, landing in George Town at 12:45 pm.
What’s the latest departure time from Chicago O'Hare Intl Airport to the Cayman Islands?
If you prefer to fly at night, the latest flight from Chicago O'Hare Intl Airport to the Cayman Islands jets off at 8:42 am and lands in George Town at 12:45 pm.
Good to know
Low season | September |
|---|---|
High season | March |
Cheapest flight | $148 |
FAQs - booking Cayman Islands flights
Reviews of the top airlines flying from Chicago to the Cayman Islands
On time. Carry on and personal bag was accommodated on the plane. Entertainment was accessible without bringing own device. Whole can of juice was provided rather than a pour.
On time. Carry on and personal bag was accommodated on the plane. Entertainment was accessible without bringing own device. Whole can of juice was provided rather than a pour.
Price was crazy watch it if you Chan he your flight
On time, easy boarding. Anytime you sit in an economy seat, it’s uncomfortable. New plane and the bathrooms were in the galley at the back of the plane which seemed odd.
Terrible service - they don’t want to be there and bad food. Entertainment system in economy from the 2000s
No drink service but there was no N/A as an option to choose. Seats were extremely tight. I am under 5.5 and I bumped my knees have no idea how taller people could manage.
Flight delayed, last seat on the plane, no arrival Gate available due to the plane departing late
Kayak booked this flight with only 1h 20min layover in Chicago. This made it impossible for me and several other passengers to reach this flight. Moreover, the gate closed boarding in spite of several passengers still on their way without waiting even one more minute. However, the plane departed with 20min (!) delay, i.e., there would have been at least 15 min time to let the delayed passengers board without causing any delays. I complained and as a "thank you" the attendent booked us on the last (!) flight to Indianapolis ~7h later! Thankfully, I caught the spitefulness and the United customer line rebooked the flight to an earlier flight. Although I can't grade this particular flight since I never had a chance to take it, Kayak made the mistake of a too short layover and the crew at the gate was awful.
Flight did not have wifi service. It was experiencing technical difficulties. Definitely and old plane that needs updating.
This flight has a history of leaving late, however, I was pleasantly surprised that it was not delayed this day. The flight went smooth, except I was in a window seat and the wall and my feet were freezing. I found it difficult to sleep due to being so cold, I also was using 2 provided UAL blankets and could not get my feet warm. This was annoying, but I still made it there on time and safe.
Old 757 with poor entertainment system. United no longer partners with United for free text and email. O'Hara an absolute disaster! Limited gates clauses two hour delay. Unfortunately this appears to be the norm.
First class snacks - stewardess gave out multiples to everyone until there was almost no selection left when she got back to me last in first class cabin. Nothing left that I would eat.
My feedback from the trip to Columbia to Chicago was meant for Chicago to Denver.
The WiFi was out gr entire flight. Had to Diane for almost 1 hour to wait for a gate to open up for plane to dock. Very bad experience.
After boarding, the AC was shut off on the flight. At business class, I really could not breathe. I was absolutely dripping sweat. I was told by the FA that there was nothing they could do but I could stand by the door until departure. So, that's what I did. I was clearly in the way while the FAs were trying to do their work, but I had to be able to breathe. After that, of course, I had sweated up a lot so was very uncomfortable for the six hour flight.
DELAYED AGAIN and AGAIN and AGAIN - not only that, you delay in 20 minute increments for hours and hours instead of having an accurate delay understanding.
AA was fine....the overall experience was subpar, but not due to the airline due to broader issues
No ground air conditioner for the plane. Very hot and humid prior to take off which was an uncomfortable period of time.
Check-in process was poor, very poor, only one person to check-in all passengers, so if one passenger had a check-in issue, all other passengers were delayed. All check-ins should have two airline staff to check-in passengers.
The flight up was great no issues. The flight back home was a cluster. I was told the plane I was waiting on was giving to another flight which caused me to miss my connection flight. Granted the airline did great with getting hotel and vouchr for food.
Flight was delayed and so much of inconvenience related to the gate change.