$154 Find Cheap Flights from Chicago to the Cayman Islands - Compare and Save

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Price, demand and travel trends for Chicago 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 to the Cayman Islands cheaper or more expensive than last year?

Fares from Chicago to the Cayman Islands are running about 9% lower than they were around this time last year, averaging $636 round-trip.

What are the cheapest fares from Chicago to the Cayman Islands right now?

The cheapest fare from Chicago to the Cayman Islands in the last week was $373 round-trip, to George Town Owen Roberts Intl (GCM).

What’s the cheapest month to fly from Chicago to the Cayman Islands?

February is the cheapest time of year to fly, with average fares of $570. Prices are highest in July, when average flight costs increase to around $776.

When is the best time to book flights from Chicago 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?

All flights from Chicago 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 to the Cayman Islands?

Wednesday tends to be the cheapest day to fly from Chicago 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 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 to the Cayman Islands flights

Low season

August

Cheapest flight

$165
Beat the crowds with an average 79% drop in travelers.
The most popular month to fly with an average 111% increase in travelers.
One-way flight from Chicago O'Hare Intl Airport to George Town

Your Chicago 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 to the Cayman Islands?

    Yes. Fares from Chicago 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 to the Cayman Islands?

    Over the past 12 months, round-trip fares from Chicago to the Cayman Islands have ranged from $528 to $775.

  • What airlines fly nonstop from Chicago 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?

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

  • Is it cheaper to fly with a layover from Chicago to the Cayman Islands?

    Yes. Nonstop flights from Chicago 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
    • Atlanta Hartsfield-Jackson (ATL) from $626

  • How long is a flight from Chicago to the Cayman Islands?

    Flights from Chicago to the Cayman Islands take 4h 05m on average.

  • Which cabin classes are available on flights from Chicago to the Cayman Islands?

    On flights from Chicago to the Cayman Islands you can book Economy Class or Business Class.

  • What are the earliest and latest flights from Chicago to the Cayman Islands?

    The earliest nonstop flight from Chicago 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 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 February 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 nonstop route from Chicago O'Hare Intl Airport to the Cayman Islands. If you'd rather save money, the route from Chicago O'Hare Intl Airport via Fort Lauderdale (FLL) is usually the cheapest.

Reviews of the top 3 airlines serving 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.
7.8
DeltaOverall score based on 8678 reviews
8.1Boarding
7.2Food
7.8Entertainment
7.8Comfort
8.5Crew
Airline reviews

No beverage/snack service without any explanation or reason. Late boarding and delayed flight.

4.0 OkayKathryn, Oct 2026
Read more Delta reviews

No beverage/snack service without any explanation or reason. Late boarding and delayed flight.

The cabin and bathroom experience was poor as the cabin and bathroom were dirty and showed signs of an older plane that had not been updated for Customer’s, comfort and health. There was gum on my seat when I arrived and dirt spots around the fan and light controls. The flight was almost entirely full, so there was no way I could be moved from my seat. Th bathroom had the peeling paint.

I'm 6' 2" and even in economy plenty of leg room

Horrible experience. Delta delayed the flight to 11pm which happens. Apparently the pilots were there but we were waiting for flight attendants to arrive from Detroit and they were delayed. They could have made arrangements but that’s fine. What was truly horrible was that at 10:50pm the pilot comes out and says the flight will be cancelled but hasn’t been cancelled yet in the system. It’s being cancelled because the pilots have timed out. As soon as that plane got delayed past 10:50pm delta knew it couldn’t fly. Yet they made us wait around for hours. When the flight finally got cancelled all the area hotels were booked and flights for the next day were unavailable until midday. All I wanted was to spend one day with my family before needing to fly abroad on another delta flight. That will be my last flight with them. I’ll take my 800k miles flown and annual spend to an airline that isn’t so thoughtless.

THI IS THE 3RD CONSECUTIVE FLIGHT FROM ORD TO MSP THAT HAS BEEN DELAYED 2+ HOURS. CRAZY

The plane was a rather tired 737-800, with old style small luggage bins. Poor air flow. USB charger in the infotainment system was not functioning. The flight was 2 hours late due to crew rest requirements (not their fault). On arrival in Seattle, waited on the tarmac for 30 minutes with very few updates from the crew.

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

The guy in front of me was talking constantly, even when the pilot was making announcements. I found this very disrespectful to the pilot and to others.

We left 1.5 hours late due to a “maintenance” issue. Very poor communication as to when we would board & depart. The crew in First Class was uncharacteristically not friendly). Delay into Brussels cost me my connection to Rome so lost the entire first day of vacation ( had a 10:30am flight to Rome - ended up on a 6:55pm flight).

Everything was OK except the meals, that was overpriced chicken meat.

Miss My connection I had to take a flight from Indianapolis to Denver , then to san fransisco , sleep in sans fransisco en the flight to Los Cabos the next morning

The TVs on the plane were all broken and inoperable. No snacks or food were served. Plane was very old and uncomfortable.

Takeoff delayed 2 hrs. Boarded on time to find we were missing part of the flight crew. Then informed that they had loaded too much fuel. Spent 1 1/2 hrs sitting there burning off the excess, which included a couple of laps around the runway until we were light enough to fly! Ridiculous!

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.

Crew were helpful, pilot kept us informed about turbulence, snack choice was awesome!

It was one of the worst I have ever had. The plane was over booked, and I did not have a seat. When I questioned why because I had booked this weeks in advance. I was brushed off to be advised they are trying to find someone to give up their seat. Only to be advised I would be boarding last. I had priority boarding in group 1-4. When I asked why I had to be last because that is not what I paid for I was advised it doesn't matter you will get a seat. The ticket person was very rude and unprofessional. The gate changed several times and it was going from one area to another area far away from where we were at. I feel like I should have been compensated in some kind of way because of the way I was treated. The ticket agent acted like it was my fault that the plane was over booked. Not one time was I apologized to for this inconvenience.

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

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