
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
Cheap flights from Chicago with top airlines, updated regularly. Compare round-trip, one-way, direct and last-minute deals.
Price, demand and travel trends for Chicago O'Hare Intl Airport to the Cayman Islands flights
Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.
Are flights from Chicago O'Hare Intl Airport to the Cayman Islands cheaper or more expensive than last year?
Fares from Chicago O'Hare Intl Airport to the Cayman Islands are running about 10% lower than they were around this time last year, averaging $635 round-trip.
What are the cheapest fares from Chicago O'Hare Intl Airport to the Cayman Islands right now?
The cheapest fare from Chicago O'Hare Intl Airport to the Cayman Islands in the last week was $429 round-trip, to George Town Owen Roberts Intl (GCM).
What’s the cheapest month to fly from Chicago O'Hare Intl Airport to the Cayman Islands?
January is the cheapest time of year to fly, with average fares of $572. Prices are highest in July, when average flight costs increase to around $806.
When is the best time to book flights from Chicago O'Hare Intl Airport to the Cayman Islands?
Book your flights 4 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 22% compared to booking last-minute (within 2 weeks of departure).
Which airport in the Cayman Islands is the cheapest to fly to from Chicago O'Hare Intl Airport?
All flights from Chicago O'Hare Intl Airport to the Cayman Islands arrive at George Town Owen Roberts Intl (GCM). On average, round-trip fares are around $654.
What’s the cheapest day to fly from Chicago O'Hare Intl Airport to the Cayman Islands?
Wednesday tends to be the cheapest day to fly from Chicago O'Hare Intl Airport to the Cayman Islands, while Saturday is the most expensive. Fares run about 13% higher that day, based on the past 12 months of KAYAK data.
What are the cheapest airlines to fly with from Chicago O'Hare Intl Airport to the Cayman Islands?
Looking at KAYAK data from the last 12 months, the cheapest airlines to fly with from Chicago O'Hare Intl Airport to the Cayman Islands are:
• American Airlines from $330
• United Airlines from $339
• Air Canada from $366
• JetBlue from $508
• Delta from $574
What airlines fly the most from Chicago O'Hare Intl Airport to the Cayman Islands?
American Airlines operates the most nonstop flights from Chicago O'Hare Intl Airport to the Cayman Islands, with an average of 1 flight per week. United Airlines also flies regularly, averaging 1 flight per week.
How do nonstop and one-stop fares from Chicago O'Hare Intl Airport to the Cayman Islands compare?
Nonstop flights cost $647 on average, while one-stop flights average $674. If you are booking a connecting flight, the cheapest layover airport is generally Fort Lauderdale (FLL).
How many nonstop flights are there from Chicago O'Hare Intl Airport to the Cayman Islands across the week?
All 1 weekly nonstop flight from Chicago O'Hare Intl Airport to the Cayman Islands departs on Saturday.
What are the most popular flight destinations in the Cayman Islands?
George Town is the most popular flight destination in the Cayman Islands, based on KAYAK data from the past 3 months.
Key details for Chicago O'Hare Intl Airport to the Cayman Islands flights
Low season | August |
|---|---|
High season | February |
Cheapest flight | $165 |
Your Chicago O'Hare Intl Airport to the Cayman Islands flight questions, answered
Find helpful answers about this route, including flight times, airports, airlines and booking tips.
Your guide to booking Chicago O'Hare Intl Airport to the Cayman Islands flights
Get tips on when to book, when to fly and what to know before your trip.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.
I have posted the comments in the first flight leg.
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.