$190 Find Cheap Flights from Chicago O'Hare Airport to Grand Cayman

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 Grand Cayman departing on 8/16. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Grand Cayman

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Grand Cayman, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Grand Cayman, as well as popular online travel agencies
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Best Grand Cayman 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$443
George Town
George Town1 stop$443

Cheap Flights from O'Hare Intl to Grand Cayman

 
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 Grand Cayman 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 Grand Cayman

Wed, Jul 30 - Sat, Aug 2
 Logo
8:09 am - 4:10 pmORD-GCM
8h 01m1 stop
 Logo
8:50 am - 4:11 pmGCM-ORD
7h 21m1 stop
Wed, Jul 23 - Sat, Aug 2
 Logo
8:09 am - 4:10 pmORD-GCM
8h 01m1 stop
 Logo
8:50 am - 4:11 pmGCM-ORD
7h 21m1 stop
Tue, Aug 12 - Tue, Aug 19
 Logo
8:09 am - 4:10 pmORD-GCM
8h 01m1 stop
 Logo
11:30 am - 9:22 amGCM-ORD
21h 52m1 stop
Wed, Aug 13 - Wed, Aug 20
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10:27 am - 11:40 amORD-GCM
25h 13m1 stop
 Logo
11:30 am - 9:22 amGCM-ORD
21h 52m1 stop
Tue, Aug 12 - Tue, Aug 19
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8:09 am - 4:10 pmORD-GCM
8h 01m1 stop
 Logo
11:30 am - 9:22 amGCM-ORD
21h 52m1 stop
Sun, Oct 19 - Sun, Oct 26
Air Canada Logo
9:55 am - 11:55 amORD-GCM
26h 00m1 stop
Air Canada Logo
12:30 pm - 1:01 pmGCM-ORD
24h 31m1 stop
$499Air Canada
Find Deal
Sun, Oct 5 - Thu, Oct 9
Delta Logo
9:10 am - 11:42 amORD-GCM
26h 32m2 stops
Delta Logo
1:02 pm - 7:26 amGCM-ORD
18h 24m2 stops
$524Delta
Find Deal
Wed, Dec 24 - Tue, Dec 30
American Airlines Logo
8:10 am - 12:56 pmORD-GCM
3h 46mnonstop
American Airlines Logo
2:00 pm - 5:10 pmGCM-ORD
4h 10mnonstop
$530American Airlines
Find Deal
Wed, Dec 24 - Tue, Dec 30
American Airlines Logo
8:10 am - 12:56 pmORD-GCM
3h 46mnonstop
American Airlines Logo
4:40 pm - 11:09 pmGCM-ORD
7h 29m1 stop
$540American Airlines
Find Deal
Sat, Oct 4 - Thu, Oct 9
Delta Logo
7:10 am - 11:36 amORD-GCM
28h 26m2 stops
Delta Logo
1:02 pm - 9:25 amGCM-ORD
20h 23m2 stops
$549Delta
Find Deal
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KAYAK's insights & trends for O'Hare Intl to Grand Cayman flights

Get data-powered insights and trends into flights from O'Hare Intl to Grand Cayman to help you find the cheapest flights, the best time to fly and much more.

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

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 $958, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Grand Cayman?

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 Grand Cayman, 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 Grand Cayman 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 $866 and $833 respectively.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to Grand Cayman?

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

If your flying dates are flexible, you should consider flying to Grand Cayman on a Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Friday is the most expensive day to fly from Chicago O'Hare Airport to Grand Cayman. For your return ticket, we recommend flying on a Sunday and avoiding Wednesdays for the best deals.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Grand Cayman?

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 Grand Cayman, 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 Grand Cayman, 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$190
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 26% increase in price.
Flight from Chicago O'Hare Airport to George Town

FAQs - booking Grand Cayman flights

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport to Grand Cayman?

    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 Grand Cayman.

  • 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 Grand Cayman?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago O'Hare Airport to Grand Cayman 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 Grand Cayman?

    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 Grand Cayman 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 Grand Cayman?

    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 Grand Cayman 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 Grand Cayman?

    The cheapest time of day to fly to Grand Cayman 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 Grand Cayman is generally in the morning, which is peak travel time and where the average cost of a ticket is $726.

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

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Grand Cayman. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from O'Hare Intl to Grand Cayman? 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 7969 reviews
7.3Food
7.9Comfort
7.9Entertainment
8.2Boarding
8.5Crew
Airline reviews

Crew was excellent. Comfort seats not as nice as other kinds of planes.

10.0 ExcellentMary, Jun 2025SAN - ATL
Read more Delta reviews

Crew was excellent. Comfort seats not as nice as other kinds of planes.

Not a "Delta" issue, but a JFK issue: We booked a connecting flight with 3 1/2 hours between to clearn immigration and customs. Our inbound flight (BCN to JFK) was on the taxiway 45 minutes which ate into our layover time. Immigtration was insanely quick with the CBP MPC app; however, clearing TSA (again, after we were ALREADY cleared in Spain on the inbound international flight) took over 95 minutes. This left us with 10 minutes before boarding the connecting flight (JFK to SAN) to walk to the far end of Terminal 4 and try to find food. We didn't find any food that could promise to serve us in under 10 minutes so we boarded the Delta flight after coming off a plance and an 8-hour flight knowing that we wouldn't be served any food on the next 5 1/2 hour flight. I feel like Delta needs to put pressure on the JFK TSA to open more screening stations (by our count, we saw only 5 scanners open and a line of - as we said - over 90 minutes. The insult is that we WERE ALREADY SCREENED through TSA, but as you come off one flight into the USA, you have to go through the whole process again. It seems like if you have a connecting flight, there should be a way to pass through immigration and customs without needing to return through TSA.

It was a great flight and the stewards and stewardess were all kind and accommodating!! The seats were comfortable and entertainment screen excellent!

There are 4 flights in consecutive gates with about the same departure time. Two flights were boarding at the same time. One was delayed or boarding would be happening at the same time. I am not sure what Delta and LAX need to do to have a better layout at the end of Terminal 2

Flight was an hour late, who knows why. It was OK, nothing outstanding.

Only not having an assigned seat was an issue. Rest was great

There was a security issue at the airport and we were unable to land. We circled endlessly and then landed at another airfield for fuel. We then circled the airport again, almost landed but didn’t fully touch down before circling again. I am thankful to the crew for keeping us safe- the issue was the airline and staff at the airport getting us seats on our connecting flights. That part was hours of searching for someone and getting in double my steps.

Boarding was organised and relaxed. Crew were fantastic! Seats were lacking padding causing butt pain and stiffness.

I like for how they process during check in. It was very smoothly.

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.

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.

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

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.

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

Everything you need to know for your flight to Grand Cayman

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