$176 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 7/1. 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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Best Cayman Islands Flight Deals from O'Hare Intl

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
George Town
George Town1 stop$485
Cayman Brac
Cayman Brac3 stops$3,916
George Town
George Town1 stop$485
Cayman Brac
Cayman Brac3 stops$3,916

Cheap Flights from O'Hare Intl to the Cayman Islands

 
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

Tue, Jul 1 - Tue, Jul 8
 Logo
1:43 pm - 4:10 pmORD-GCM
26h 27m1 stop
 Logo
11:30 am - 4:11 pmGCM-ORD
28h 41m1 stop
Tue, Jul 29 - Tue, Aug 5
 Logo
8:09 am - 4:10 pmORD-GCM
8h 01m1 stop
 Logo
11:30 am - 4:11 pmGCM-ORD
28h 41m1 stop
Sat, Nov 1 - Wed, Nov 5
American Airlines Logo
8:45 pm - 12:00 pmORD-GCM
15h 15m1 stop
American Airlines Logo
2:20 pm - 10:15 pmGCM-ORD
8h 55m1 stop
$520American Airlines
Find Deal
Sat, Dec 6 - Sat, Dec 13
American Airlines Logo
6:45 pm - 11:46 amORD-GCM
16h 01m1 stop
American Airlines Logo
2:00 pm - 5:10 pmGCM-ORD
4h 10mnonstop
$535American Airlines
Find Deal
Sun, Oct 12 - Sun, Oct 19
Delta Logo
6:00 am - 11:42 amORD-GCM
5h 42m1 stop
Delta Logo
1:02 pm - 11:53 pmGCM-ORD
10h 51m1 stop
$545Delta
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Sat, Aug 23 - Thu, Aug 28
Delta Logo
5:45 am - 11:37 amORD-GCM
5h 52m1 stop
Delta Logo
12:50 pm - 10:37 pmGCM-ORD
9h 47m1 stop
$595Delta
Find Deal
Sat, Nov 29 - Thu, Dec 4
Air Canada Logo
3:35 pm - 12:20 pmORD-GCM
19h 45m2 stops
Air Canada Logo
1:35 pm - 10:39 amGCM-ORD
22h 04m2 stops
$609Air Canada
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Sat, Jul 12 - Sat, Jul 19
United Airlines Logo
9:26 am - 1:30 pmORD-GCM
4h 04mnonstop
United Airlines Logo
1:45 pm - 6:07 pmGCM-ORD
4h 22mnonstop
$690United Airlines
Find Deal
Sat, Jul 12 - Sat, Jul 19
United Airlines Logo
7:10 am - 3:35 pmORD-GCM
8h 25m1 stop
United Airlines Logo
1:45 pm - 6:07 pmGCM-ORD
4h 22mnonstop
$695United Airlines
Find Deal
Tue, Aug 26 - Mon, Sep 1
Air Canada Logo
6:06 pm - 11:55 amORD-GCM
41h 49m2 stops
Air Canada Logo
12:50 pm - 3:04 pmGCM-ORD
26h 14m1 stop
$696Air Canada
Find Deal
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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 $495 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 $495.

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 1 stop layover the cheapest option at $1,087 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 September, when tickets cost $565 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $865 and $828 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 Tuesday 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. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.


Good to know

Low seasonSeptember
High seasonMarch
Cheapest flight$176
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 27% 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 43% 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 $723.

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 7963 reviews
7.3Food
8.5Crew
7.9Entertainment
8.2Boarding
7.9Comfort
Airline reviews

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

4.0 OkayKoonj, Jun 2025MSP - AUS
Read more Delta reviews

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Overall, aside from the baggage issue, it was as good as one expects.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

I want to single out flight attendant Mitch who was in the Premium Economy section. When my wife’s hearing aide dropped through the cushion under the seat he was able to locate it and return it to her. Food was a different matter. Dinner was fine. Breakfast was another matter. They had a yogurt dish that the ran out of and the alternative was not very good according to those we talked to.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Flight was delayed long enough that I was misding my connecting flight. The agents could not get me on a comparable flight, nor could they get me s Main Cabin seat I had paid for, nor could they get me on a comparable connecting flight. The gate agent would not issue meal vouchers, even though I was delayed over six hours! I had to spend over an hour and 15 minutes with customer service on the phone to See if they could get me on a better flight and get a meal voucher. Customer service was not helpful enough in trying to find alternate flights and it Ended up taking me 24 hours for a 12 hour trip!! Delta does not provide upgrades NOR will they even give you a pass for a few hours to their lounge. They claim that they do not issue daily passes to their lounge anymore. I call BS since this would be no extra cost to them to provide excellent customer service and give you a few hours to relax in comfort when you’re sitting in a crowded airport and your flight has been screwed up for that many hours.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

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.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

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.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

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

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