$123 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 6/5. 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

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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Flight Deals

Book Cheap O'Hare Intl to Grand Cayman 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 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, Jun 10 - Sat, Jun 13
Air Canada Logo
1:55 pm - 11:25 am
ORD
-
GCM
21h 30m
2 stops
Air Canada Logo
10:55 am - 9:00 am
GCM
-
ORD
22h 05m
1 stop
$350Air Canada
Sat, Jun 6 - Sat, Jun 13
Air Canada Logo
6:22 pm - 11:25 am
ORD
-
GCM
41h 03m
2 stops
Air Canada Logo
10:55 am - 9:00 am
GCM
-
ORD
22h 05m
1 stop
$355Air Canada
Fri, Jun 5 - Mon, Jun 8
Air Canada Logo
8:20 pm - 10:00 am
ORD
-
GCM
13h 40m
1 stop
Air Canada Logo
12:25 pm - 1:25 pm
GCM
-
ORD
25h 00m
1 stop
$365Air Canada
Fri, Jun 5 - Mon, Jun 8
Air Canada Logo
8:20 pm - 10:00 am
ORD
-
GCM
13h 40m
1 stop
Air Canada Logo
12:25 pm - 10:18 am
GCM
-
ORD
21h 53m
2 stops
$368Air Canada
Wed, Jun 10 - Sat, Jun 13
Air Canada Logo
1:55 pm - 11:25 am
ORD
-
GCM
21h 30m
2 stops
Air Canada Logo
10:55 am - 9:00 am
GCM
-
ORD
22h 05m
1 stop
$370Air Canada
Fri, Jun 5 - Mon, Jun 8
Air Canada Logo
10:41 am - 10:00 am
ORD
-
GCM
23h 19m
2 stops
Air Canada Logo
12:25 pm - 12:11 pm
GCM
-
ORD
23h 46m
2 stops
$375Air Canada
Sat, May 30 - Sat, Jun 6
Air Canada Logo
8:45 am - 11:25 am
ORD
-
GCM
50h 40m
2 stops
Air Canada Logo
10:55 am - 9:00 am
GCM
-
ORD
22h 05m
1 stop
$386Air Canada
Sat, May 30 - Sat, Jun 6
Air Canada Logo
8:45 am - 11:25 am
ORD
-
GCM
50h 40m
2 stops
Air Canada Logo
10:55 am - 10:18 am
GCM
-
ORD
47h 23m
2 stops
$389Air Canada
Tue, Jun 9 - Sat, Jun 20
Air Canada Logo
6:22 pm - 11:25 am
ORD
-
GCM
41h 03m
2 stops
Air Canada Logo
10:55 am - 1:22 pm
GCM
-
ORD
26h 27m
1 stop
$405Air Canada
Sun, May 17 - Thu, May 21
Air Canada Logo
9:55 am - 11:25 am
ORD
-
GCM
25h 30m
1 stop
Air Canada Logo
12:25 pm - 2:55 pm
GCM
-
ORD
26h 30m
1 stop
$406Air Canada
Booking Insights

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.

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

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

The cheapest time of day to fly to Grand Cayman is generally in the morning, when round-trip flights cost $633 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 $633.

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 $459, 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 January, when tickets cost $498 (return) on average. On the other hand, the most expensive months are November and March, when the average cost of round-trip tickets is $935 and $752 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 Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday 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 Fridays 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, 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 seasonSeptember
Cheapest flight$123
Most popular time to fly with an average 12% 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.

Reviews of the top airlines flying 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.
7.4
United AirlinesOverall score based on 9562 reviews
7.7Boarding
8.1Crew
7.1Entertainment
7.3Comfort
6.6Food
Airline reviews

Poor communication, flight was delayed for preventable reasons. I missed my connection.

2.0 MediocreAaron, Apr 2026
ORD - BNA
Read more United Airlines reviews

Poor communication, flight was delayed for preventable reasons. I missed my connection.

The boarding timing needs to be improved. The flight was delayed again because it took way too long to board. I was already exhausted from sleeping at the airport and spending all day there due to delay from my previous flight that connected in Chicago.

Great until we got to FRA. The next trip leg we were put in Business Class where seats had minimal padding!!!! They were awful and United Airlines needs to have their Lufthansa partner up their game or I won’t fly with them again!!

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

Awful. No counter attendants. No dinner offered due to delays.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

Everything you need to know for your flight to Grand Cayman

Information on your arrival and departure airports