$129 Find Cheap Flights from Chicago O'Hare Airport to Grand Cayman - 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 O'Hare Intl to Grand Cayman departing on 9/16. 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, 0 bags

Save 20% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
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

Fri, Sep 11 - Thu, Sep 17
Air Canada Logo
8:40 pm - 9:45 am
ORD
-
GCM
13h 05m
1 stop
Air Canada Logo
12:25 pm - 8:00 am
GCM
-
ORD
19h 35m
1 stop
$352Air Canada
Sun, Oct 18 - Sat, Oct 24
Air Canada Logo
9:50 am - 11:30 am
ORD
-
GCM
25h 40m
1 stop
Air Canada Logo
12:25 pm - 1:13 pm
GCM
-
ORD
24h 48m
1 stop
$357Air Canada
Sun, Oct 18 - Sat, Oct 24
Air Canada Logo
8:45 am - 11:30 am
ORD
-
GCM
26h 45m
2 stops
Air Canada Logo
12:25 pm - 3:38 pm
GCM
-
ORD
27h 13m
1 stop
$360Air Canada
Wed, Oct 21 - Sat, Oct 24
Air Canada Logo
5:53 pm - 11:30 am
ORD
-
GCM
17h 37m
1 stop
Air Canada Logo
12:25 pm - 9:23 am
GCM
-
ORD
20h 58m
1 stop
$362Air Canada
Sun, Jan 3 - Wed, Jan 13
United Airlines Logo
8:42 am - 1:42 pm
ORD
-
GCM
4h 00mnonstop
United Airlines Logo
2:55 pm - 6:13 pm
GCM
-
ORD
4h 18mnonstop
$617United Airlines
Sun, Jan 17 - Fri, Jan 22
United Airlines Logo
8:45 am - 1:45 pm
ORD
-
GCM
4h 00mnonstop
United Airlines Logo
2:50 pm - 6:04 pm
GCM
-
ORD
4h 14mnonstop
$617United Airlines
Sun, Jan 3 - Fri, Jan 8
United Airlines Logo
8:42 am - 1:42 pm
ORD
-
GCM
4h 00mnonstop
United Airlines Logo
2:50 pm - 6:04 pm
GCM
-
ORD
4h 14mnonstop
$617United Airlines
Sun, Jan 3 - Wed, Jan 13
American Airlines Logo
8:55 pm - 11:57 am
ORD
-
GCM
14h 02m
1 stop
American Airlines Logo
3:25 pm - 6:49 pm
GCM
-
ORD
4h 24mnonstop
$621American Airlines
Sun, Jan 3 - Wed, Jan 13
American Airlines Logo
7:37 pm - 12:15 pm
ORD
-
GCM
15h 38m
1 stop
American Airlines Logo
3:25 pm - 6:49 pm
GCM
-
ORD
4h 24mnonstop
$621American Airlines
Sun, Jan 3 - Wed, Jan 13
American Airlines Logo
6:40 pm - 11:57 am
ORD
-
GCM
16h 17m
1 stop
American Airlines Logo
12:55 pm - 7:51 pm
GCM
-
ORD
7h 56m
1 stop
$631American Airlines
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 $634 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 $634.

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 $490, 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 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 $938 and $764 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 Thursday, 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 Saturday 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 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

$129
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 6% 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 10061 reviews
8.1Crew
7.7Boarding
7.1Entertainment
7.3Comfort
6.6Food
Airline reviews

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.

8.0 ExcellentArmedrest, Jul 2026
ORD - PAH
Read more United Airlines reviews

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

The kid in the middle seat kicked me almost the whole flight, almost kicked my hot tea off my tray. The flight was delayed due to the first plane not being able to be de-iced in July! We had to get a new plane. Now I drive 3 hours back to Edmonton because direct flights from PVR were way to expensive

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

Agents at gate were not immediately available to solve problems and once they did they didn’t fix all the fight connections

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.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

Everything you need to know for your flight to Grand Cayman

Information on your arrival and departure airports