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1 adult, Economy, 0 bags

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

Get data-powered insights and trends into flights from O'Hare Intl to Grand Cayman 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 Grand Cayman?

The cheapest time of day to fly to Grand Cayman is generally in the morning, when round-trip flights cost $656 on average. The most expensive time of day to fly to Grand Cayman is generally in the morning, which is peak travel time and where the average cost of a ticket is $656.

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

No, with an average price for the route of $532, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Grand Cayman?

The cheapest month for flights from Chicago O'Hare Intl Airport to Grand Cayman is April, when tickets cost $600 (return) on average. On the other hand, the most expensive months are July and November, when the average cost of round-trip tickets is $806 and $786 respectively.

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

If your flying dates are flexible, you should consider flying to Grand Cayman on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Chicago O'Hare Airport to Grand Cayman. For your return ticket, we recommend flying on a Thursday and avoiding Fridays for the best deals.

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

To get a below average price on the flight from Chicago O'Hare Intl Airport to Grand Cayman, you should book around 2 weeks before departure, which saves you about 21% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low season

September
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 10% increase in price.

FAQs - booking Grand Cayman flights

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

    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 Grand Cayman.

  • 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 Grand Cayman?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago O'Hare Airport to Grand Cayman 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 Grand Cayman?

    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 Grand Cayman 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 Grand Cayman?

    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 Grand Cayman up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many flights are there between Chicago O'Hare Intl Airport and Grand Cayman per day?

    There is a maximum of 1 nonstop flight a day that takes off from Chicago O'Hare Intl Airport and lands in Grand Cayman, with an average flight time of 4h 03m. The most common departure time is 8:00 am and most flights take off in the morning. Each week, there are 1 flights.

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

 
Need help choosing which airline to fly with from O'Hare Intl to Grand Cayman? 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 10362 reviews
6.7Food
7.3Comfort
8.1Crew
7.7Boarding
7.1Entertainment
Airline reviews

I especially enjoyed having a lightly packed flight which enabled me and my wife to occupy a three seat area with nobody in the middle seat.

10.0 ExcellentAJ, Oct 2026
Read more United Airlines reviews

I especially enjoyed having a lightly packed flight which enabled me and my wife to occupy a three seat area with nobody in the middle seat.

The seats are very small, that is all the staff did a good job.

It was great. The staff is always helpful and polite. The app is great and makes the whole trip and process so easy. They even offer a step to step guide to your correct terminal. And they keep all the information you'll need updated. Anything you can think of! Great experience.

Perfect. On time and the weather was perfect so we came in a few minutes early.

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

We did not fly on American Airlines from Chicago to London. We were rebooked on British Airways (by American Airlines) and our luggage was left behind. A full day delay and lost luggage.

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.

More options for your flight to Grand Cayman

Complete your trip to Grand Cayman with a hotel stay or car rental