$94 Find Cheap Flights from Chicago 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 Chicago to Grand Cayman departing on 4/5. 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 Chicago 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 Chicago 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 Chicago to Grand Cayman

Sun, Apr 26 - Wed, May 27
Multiple Airlines Logo
3:57 pm - 11:35 am
ORD
-
GCM
19h 38m
1 stop
Multiple Airlines Logo
11:30 am - 1:05 pm
GCM
-
ORD
25h 35m
1 stop
$486Multiple Airlines
Tue, Apr 7 - Sun, Apr 12
Multiple Airlines Logo
4:51 pm - 4:05 pm
ORD
-
GCM
23h 14m
1 stop
Multiple Airlines Logo
1:52 pm - 11:17 am
GCM
-
ORD
21h 25m
1 stop
$487Multiple Airlines
Tue, May 19 - Wed, May 27
Multiple Airlines Logo
6:55 am - 4:05 pm
ORD
-
GCM
33h 10m
2 stops
Multiple Airlines Logo
11:30 am - 1:05 pm
GCM
-
ORD
25h 35m
1 stop
$488Multiple Airlines
Sun, May 3 - Thu, May 7
Air Canada Logo
8:20 pm - 11:25 am
ORD
-
GCM
15h 05m
1 stop
Air Canada Logo
12:25 pm - 2:55 pm
GCM
-
ORD
26h 30m
1 stop
$489Air Canada
Sun, May 3 - Thu, May 7
Air Canada Logo
8:45 am - 11:25 am
ORD
-
GCM
26h 40m
2 stops
Air Canada Logo
12:25 pm - 4:59 pm
GCM
-
ORD
28h 34m
1 stop
$493Air Canada
Sun, May 24 - Sat, May 30
Air Canada Logo
6:22 pm - 11:25 am
ORD
-
GCM
17h 03m
2 stops
Air Canada Logo
10:55 am - 7:25 pm
GCM
-
ORD
8h 30m
1 stop
$494Air Canada
Mon, May 11 - Fri, May 15
Southwest Logo
5:35 am - 12:10 pm
MDW
-
GCM
6h 35m
1 stop
Southwest Logo
1:05 pm - 12:05 am
GCM
-
MDW
11h 00m
1 stop
$498Southwest
Mon, May 25 - Fri, May 29
Southwest Logo
9:25 pm - 12:10 pm
MDW
-
GCM
14h 45m
2 stops
Southwest Logo
1:05 pm - 12:05 am
GCM
-
MDW
11h 00m
1 stop
$528Southwest
Sun, May 3 - Thu, May 7
Southwest Logo
5:05 am - 11:55 am
MDW
-
GCM
6h 50m
1 stop
Southwest Logo
1:05 pm - 12:05 am
GCM
-
MDW
11h 00m
1 stop
$529Southwest
Sun, May 3 - Thu, May 7
Southwest Logo
5:05 am - 11:55 am
MDW
-
GCM
6h 50m
1 stop
Southwest Logo
1:05 pm - 10:20 pm
GCM
-
MDW
9h 15m
2 stops
$534Southwest
Booking Insights

KAYAK's insights & trends for Chicago to Grand Cayman flights

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

What is the cheapest Chicago to Grand Cayman flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Grand Cayman from Chicago found in the last 72 hours was to George Town, at $485 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 $485.

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

The average price for all round-trip flights from Chicago 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 $626 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 $626.

Can I save money by flying with a layover from Chicago 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 $424, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago 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 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 to Grand Cayman is February, when tickets cost $527 (return) on average. On the other hand, the most expensive months are December and August, when the average cost of round-trip tickets is $775 and $712 respectively.

What’s the cheapest day of the week to fly from Chicago to Grand Cayman?

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

For Chicago to Grand Cayman, Wednesday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Grand Cayman back to Chicago, the best deals are generally found on Sunday, with Wednesday being the most expensive.

How far in advance should I book a flight from Chicago 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 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 to Grand Cayman, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 1 week before departure.

Good to know

Low seasonSeptember
Cheapest flight$94
Best time to beat the crowds with an average 8% 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 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 to Grand Cayman.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Grand Cayman?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago 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 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 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 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 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 4 airlines serving from Chicago 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 Chicago 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
SouthwestOverall score based on 4324 reviews
7.5Entertainment
8.6Crew
8.0Comfort
7.0Food
8.1Boarding
Airline reviews

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

10.0 ExcellentMartie, Mar 2026
LGB - BNA
Read more Southwest reviews

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Entertainment is ok! Boarding and seat with zone is terrible. I paid for the seats but you didn’t give me what I paid for which is exit isles.

the crew cancel the morning service due to the weather. Then the flight got deverted to Nashville . we were on the ground for over two hours the only gave us water once... no food or any snacks.... the crew should have handled better and offered something to passengers.

My recent experience was excellent on Delta! I flew with Delta Comfort and I was really comfortable in my seat. I enjoyed the in-flight service. The flight attendants were so friendly and hospitable. I love the snack on the flight as well. This was my first time flying on Delta and I will definitely consider flying with them again.

My flight was cencaled due with the bad weather on Sunday the crew was poorly mistaken my luggage supposed depart with my flight instead I didn’t have my luggage for almost 3 days the website is poorly respond to my complain until I have someone to do it my connection smooth their not even respon or email me even the have my luggage

Delta needs to step its game up get a more reliable internet service. Internet service was non-existent for this flight.

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

This was a Latam operated flight. Seats seemed a bit narrow in business class. Older aircraft.

I had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.

NEVER MADE THE FLIGHT BECAUSE DELTA SAID THEY CAN NOT

THEY FAILED ME AND I NEVER GOT ON THE FLIGHT BECAUSE IT WAS SO DELAYED! I ENDED UP HAVING TO PAY OUT OF POCKET FOR A HOTEL AND STAY IN NASHVILLE TO CATCH A FLIGHT FOR THE FOLLOWING DAY. DELTA IS POOR CUSTOMER SERVICE>

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.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

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. :/

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.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

Everything you need to know for your flight to Grand Cayman

Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.