$174 Find Cheap Flights from Chicago O'Hare Airport to Cayman Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to the Cayman Islands departing on 8/31. 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

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Cheap Flights from O'Hare Intl to the Cayman Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
George Town
George Town1 stop$448
Cayman Brac
Cayman Brac1 stop$560
George Town
George Town1 stop$448
Cayman Brac
Cayman Brac1 stop$560

Book Cheap O'Hare Intl to the Cayman Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl to the Cayman Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from O'Hare Intl to the Cayman Islands

Mon, Jan 12 - Wed, Jan 21
Southwest Logo
6:05 am - 12:55 pmORD-GCM
5h 50m1 stop
Southwest Logo
1:50 pm - 9:50 pmGCM-ORD
9h 00m1 stop
$448Southwest
Find Deal
Wed, Oct 15 - Mon, Oct 20
Air Canada Logo
8:25 pm - 11:55 amORD-GCM
15h 30m1 stop
Air Canada Logo
12:50 pm - 9:51 amGCM-ORD
21h 01m2 stops
$451Air Canada
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Sat, Aug 30 - Thu, Sep 4
American Airlines Logo
6:30 pm - 11:25 amORD-GCM
16h 55m1 stop
American Airlines Logo
12:25 pm - 8:27 pmGCM-ORD
8h 02m1 stop
$452American Airlines
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Sat, Aug 30 - Thu, Sep 4
American Airlines Logo
9:11 pm - 11:10 amORD-GCM
13h 59m2 stops
American Airlines Logo
12:10 pm - 9:22 pmGCM-ORD
9h 12m1 stop
$456American Airlines
Find Deal
Fri, Sep 12 - Fri, Sep 19
 Logo
10:27 am - 9:20 pmORD-GCM
10h 53m1 stop
 Logo
4:45 pm - 9:18 amGCM-ORD
16h 33m1 stop
Sat, Nov 22 - Thu, Nov 27
Air Canada Logo
2:00 pm - 12:20 pmORD-GCM
21h 20m1 stop
Air Canada Logo
1:30 pm - 1:01 pmGCM-ORD
24h 31m1 stop
$462Air Canada
Find Deal
Thu, Sep 25 - Mon, Sep 29
 Logo
10:27 am - 9:20 pmORD-GCM
10h 53m1 stop
 Logo
4:45 pm - 9:18 amGCM-ORD
16h 33m1 stop
Sun, Dec 14 - Fri, Dec 19
United Airlines Logo
7:35 am - 4:30 pmORD-GCM
7h 55m1 stop
United Airlines Logo
2:50 pm - 6:04 pmGCM-ORD
4h 14mnonstop
$510United Airlines
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Mon, Dec 22 - Tue, Dec 30
Delta Logo
7:59 pm - 12:30 pmORD-GCM
15h 31m1 stop
Delta Logo
1:55 pm - 11:58 pmGCM-ORD
11h 03m1 stop
$520Delta
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Mon, Dec 22 - Sat, Dec 27
Delta Logo
7:59 pm - 12:30 pmORD-GCM
15h 31m1 stop
Delta Logo
4:10 pm - 9:09 amGCM-ORD
17h 59m1 stop
$545Delta
Find Deal
Booking Insights

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

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

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago O'Hare Intl Airport to the Cayman Islands.

The cheapest ticket to the Cayman Islands from Chicago O'Hare Intl Airport found in the last 72 hours was to George Town, at $429 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 72 hours was $429.

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.

No, with an average price for the route of $1,568, prices are generally cheapest when you fly direct.

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 August, when tickets cost $599 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $868 and $829 respectively.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport 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 O'Hare Airport to Cayman Islands, you should consider leaving on a Monday and avoid Fridays if you are looking for the best rates. For your return to Chicago O'Hare Airport, you’ll find the best rates on Sundays and the most expensive ones on Wednesdays.

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 3 weeks before departure, which saves you about 10% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.


Good to know

Low seasonSeptember
Cheapest flight$174
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 25% 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 O'Hare Airport 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 O'Hare Airport to Cayman Islands.

  • 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 Cayman Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport to Cayman Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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

    The cheapest time of day to fly to the Cayman Islands is generally in the evening, when round-trip flights cost $507 on average. Morning departures are around 44% more expensive than evening flights, 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 $732.

Reviews of the top 3 airlines serving from O'Hare Intl to the Cayman Islands

 
Need help choosing which airline to fly with from O'Hare Intl 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.
8.0
DeltaOverall score based on 7980 reviews
7.9Comfort
8.2Boarding
7.3Food
8.5Crew
7.9Entertainment
Airline reviews

Delayed and took off even later than the scheduled delay time

8.0 ExcellentAnonymous, Jul 2025DTW - SEA
Read more Delta reviews

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Only issue was with seating. The economy fare we purchased did say there was no guarantee the three people in our party would be seated together, and we were not. At the gate, the agent told us more specifically, the fare we purchased meant we would be seated in middle seats only. This should just be made more obvious.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

Everything you need to know for your flight from O'Hare Intl to the Cayman Islands

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