$168 Find Cheap Flights from Chicago to Cayman Islands - Compare and Save

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Cheap Flights from Chicago to the Cayman Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
George Town
George Town1 stop$435
Cayman Brac
Cayman Brac2 stops$786
George Town
George Town1 stop$435
Cayman Brac
Cayman Brac2 stops$786

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 $435 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's the cheapest time of day to fly from Chicago O'Hare Intl Airport to the Cayman Islands?

Data from the past 12 months shows it's cheapest to fly to the Cayman Islands during the evening with average prices of $464. The afternoon is the most expensive time to fly, with average prices of $756.

Key details for Chicago O'Hare Intl Airport to the Cayman Islands flights

Low season

August

Cheapest flight

$168
Beat the crowds with an average 78% drop in travelers.
The most popular month to fly with an average 114% increase in travelers.
One-way flight from Chicago O'Hare Intl Airport to George Town

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.

  • Is now a good time to book a flight from Chicago O'Hare Intl Airport to the Cayman Islands?

    Yes. Fares from Chicago O'Hare Intl Airport to the Cayman Islands are low right now. As a rule of thumb, a round-trip under $528 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Chicago O'Hare Intl Airport to the Cayman Islands?

    Over the past 12 months, round-trip fares from Chicago O'Hare Intl Airport to the Cayman Islands have ranged from $528 to $780.

  • What airlines fly nonstop from Chicago O'Hare Intl Airport to the Cayman Islands?

    Based on the flight schedule for the next 3 months, 2 airlines offer nonstop flights on this route:

    • United Airlines
    • American Airlines

  • Where in the Cayman Islands can I fly nonstop from Chicago O'Hare Intl Airport?

    Based on the flight schedule for the next 3 months, you can only fly nonstop from Chicago O'Hare Intl Airport to George Town.

  • Is it cheaper to fly with a layover from Chicago O'Hare Intl Airport to the Cayman Islands?

    Yes. Nonstop flights from Chicago O'Hare Intl Airport to the Cayman Islands average $647 over the past 12 months, but flights with a layover can cost less. The most affordable connecting airports are:

    • Fort Lauderdale (FLL) from $430
    • Toronto Pearson Intl (YYZ) from $436
    • Houston George Bush Intcntl (IAH) from $646

  • How long is a flight from Chicago O'Hare Intl Airport to the Cayman Islands?

    Flights from Chicago O'Hare Intl Airport to the Cayman Islands take 4h 05m on average.

  • Which cabin classes are available on flights from Chicago O'Hare Intl Airport to the Cayman Islands?

    On flights from Chicago O'Hare Intl Airport to the Cayman Islands you can book Economy Class or Business Class.

  • What are the earliest and latest flights from Chicago O'Hare Intl Airport to the Cayman Islands?

    The earliest nonstop flight from Chicago O'Hare Intl Airport to the Cayman Islands departs at 8:42 am and the latest departs at 11:38 am. Nonstop flights take about 4h 05m.

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.
  • If you can plan ahead, the sweet spot for booking your flight is 4 weeks before your trip. KAYAK data shows fares in this window are around 22% lower than last-minute bookings (made within 2 weeks of departure). Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • If your travel dates are flexible, book your trip for January when flights are typically cheapest and avoid July when prices are at their highest.
  • Flying on Wednesday is usually the cheapest. Flights on Saturday cost about 13% more on average, so being flexible with your travel dates could help you save.
  • Start your trip in George Town, which is the most popular destination in the Cayman Islands. From there, it's easy to continue on to other popular destinations such as West Bay, East End and North Side.
  • If you want the shortest trip, choose the Chicago O'Hare Intl Airport to the Cayman Islands nonstop route. If you'd rather save money, the route via Fort Lauderdale (FLL) is usually the cheapest.

Reviews of the top airlines flying from Chicago to the Cayman Islands

 
Need help choosing which airline to fly with from Chicago 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 10362 reviews
8.1Crew
7.7Boarding
6.7Food
7.3Comfort
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 from Chicago to the Cayman Islands

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