$58 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 2/28. 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

Sat, Feb 28 - Mon, Mar 2
Multiple Airlines Logo
8:16 pm - 1:43 pm
ORD
-
GCM
16h 27m
1 stop
Multiple Airlines Logo
3:40 pm - 11:49 am
GCM
-
ORD
21h 09m
1 stop
$346Multiple Airlines
Sat, Feb 21 - Wed, Feb 25
Multiple Airlines Logo
12:06 pm - 1:43 pm
ORD
-
GCM
24h 37m
1 stop
Multiple Airlines Logo
11:30 am - 9:39 am
GCM
-
ORD
23h 09m
1 stop
$355Multiple Airlines
Thu, Feb 26 - Mon, Mar 2
Multiple Airlines Logo
5:15 am - 1:43 pm
ORD
-
GCM
7h 28m
1 stop
Multiple Airlines Logo
4:45 pm - 4:52 pm
GCM
-
ORD
25h 07m
2 stops
$356Multiple Airlines
Wed, Mar 4 - Sat, Mar 7
Multiple Airlines Logo
8:16 pm - 1:43 pm
ORD
-
GCM
16h 27m
1 stop
Multiple Airlines Logo
8:50 am - 12:21 am
GCM
-
ORD
16h 31m
2 stops
$358Multiple Airlines
Sun, Mar 8 - Thu, Mar 12
Multiple Airlines Logo
5:15 am - 12:43 pm
ORD
-
GCM
7h 28m
1 stop
Multiple Airlines Logo
1:52 pm - 11:38 pm
GCM
-
ORD
9h 46m
2 stops
$361Multiple Airlines
Sun, Feb 8 - Thu, Feb 12
Spirit Airlines Logo
5:15 am - 1:53 pm
ORD
-
GCM
7h 38m
1 stop
Spirit Airlines Logo
2:49 pm - 7:54 am
GCM
-
ORD
18h 05m
2 stops
$363Spirit Airlines
Wed, Mar 11 - Wed, Mar 18
Multiple Airlines Logo
8:42 pm - 12:57 pm
ORD
-
GCM
16h 15m
2 stops
Multiple Airlines Logo
11:30 am - 6:35 pm
GCM
-
ORD
7h 05m
1 stop
$365Multiple Airlines
Sat, Apr 11 - Wed, Apr 15
Multiple Airlines Logo
8:55 pm - 12:57 pm
ORD
-
GCM
16h 02m
2 stops
Multiple Airlines Logo
11:30 am - 6:15 pm
GCM
-
ORD
6h 45m
1 stop
$366Multiple Airlines
Wed, Feb 25 - Wed, Mar 4
Multiple Airlines Logo
8:16 pm - 1:43 pm
ORD
-
GCM
16h 27m
1 stop
Multiple Airlines Logo
11:30 am - 7:54 am
GCM
-
ORD
21h 24m
2 stops
$368Multiple Airlines
Thu, Feb 26 - Thu, Mar 5
Spirit Airlines Logo
5:15 am - 1:43 pm
ORD
-
GCM
7h 28m
1 stop
Spirit Airlines Logo
2:49 pm - 12:40 am
GCM
-
ORD
10h 51m
2 stops
$369Spirit 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.

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 $425, 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 $775 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 Tuesdays 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 15% 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$58
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 14% 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 morning, when round-trip flights cost $645 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 $645.

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 9215 reviews
8.1Crew
7.7Boarding
6.6Food
7.1Entertainment
7.3Comfort
Airline reviews

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

8.0 ExcellentAnonymous, Jan 2026
ORD - TPA
Read more United Airlines reviews

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

Everything you need to know for your flight to Grand Cayman

Information on your arrival and departure airports