$126 Find Cheap Flights from Chicago to Cayman Islands - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to the Cayman Islands departing on 9/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to the Cayman Islands from Chicago O'Hare Intl Airport found in the last 5 days was to George Town, at $641 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 $641.

What is the cheapest time of day to fly to the Cayman Islands?

The average price for all round-trip flights from Chicago O'Hare Intl Airport to the Cayman Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to the Cayman Islands is generally in the morning, when round-trip flights cost $632 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 $632.

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

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

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?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to the Cayman Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to the Cayman Islands is February, when tickets cost $530 (return) on average. On the other hand, the most expensive months are November and July, when the average cost of round-trip tickets is $972 and $806 respectively.

What’s the cheapest day of the week to fly from Chicago to Cayman Islands?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to the Cayman Islands clicked on KAYAK for each day over the last 12 months.

When flying from Chicago to Cayman Islands, you should consider leaving on a Thursday and avoid Sundays 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 calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to the Cayman Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

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 15 weeks before departure.

Good to know

Low season

September

Cheapest flight

$126
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from Chicago O'Hare Airport to George Town

FAQs - booking Cayman Islands flights

  • How does KAYAK find such low prices on flights from Chicago to Cayman Islands?

    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 to Cayman Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Cayman Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Cayman Islands 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 to Cayman Islands?

    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 to Cayman Islands 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 to Cayman Islands?

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

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 10113 reviews
8.1Crew
7.1Entertainment
6.7Food
7.3Comfort
7.7Boarding
Airline reviews

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.

6.0 GoodHeather, Aug 2026
Read more United Airlines reviews

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.

It was a good experience, unfortunately my checked baggages were come late and not arrived on time.

Very stressful to locate United Airline boarding area, delayed flight, changing boarding area again to another location with all tiredness 😩. But flying was fine.

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

It was extremely hot in the cabin the entire flight, vent air was worn

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

We were forced to eat vegetarian food because non veg food ran out. The breakfast was mediocre.

My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well

Couldn't make the flight because connecting flight was canceled.

gate crew was courteous and helpful, flight attendant was nice and friendly once we got going. But we pushed off from the gate relatively on time, then sat there like 10 ft away, for an hour, with no announcement or explanation. Taxiing then took forever, and I get that there was runway congestion, but would be helpful to keep us posted on whats going on

The power outlets were not working for my row. Also felt like the seats have gotten smaller. I was in the window seat and felt like suffocated, as the two passengers next to me were tall and wide.

Terrible. The flight I booked had a convenient departure time. Quick layover. And an arrival timed that worked for the people who had to pick me up. Thanks to delays and rebooking I got none of those things

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

Long delays to board due to mechanical issues with plane.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Everything you need to know for your flight from Chicago to the Cayman Islands

Information on your arrival and departure airports