$74 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 1/1. 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, Jan 18 - Thu, Jan 22
Spirit Airlines Logo
5:15 am - 1:53 pmORD-GCM
7h 38m1 stop
Spirit Airlines Logo
2:49 pm - 9:03 pmGCM-ORD
7h 14m1 stop
$271Spirit Airlines
Find Deal
Sun, Feb 1 - Sun, Feb 8
Spirit Airlines Logo
5:15 am - 1:53 pmORD-GCM
7h 38m1 stop
Spirit Airlines Logo
2:49 pm - 9:03 pmGCM-ORD
7h 14m1 stop
$291Spirit Airlines
Find Deal
Wed, Jan 7 - Sun, Jan 11
Spirit Airlines Logo
3:26 pm - 1:53 pmORD-GCM
21h 27m1 stop
Spirit Airlines Logo
2:49 pm - 11:22 amGCM-ORD
21h 33m1 stop
$295Spirit Airlines
Find Deal
Thu, Feb 5 - Mon, Feb 9
Multiple Airlines Logo
5:15 am - 1:53 pmORD-GCM
7h 38m1 stop
Multiple Airlines Logo
4:45 pm - 8:18 amGCM-ORD
16h 33m1 stop
$298Multiple Airlines
Find Deal
Mon, Jan 12 - Sat, Jan 17
Multiple Airlines Logo
9:23 am - 9:15 pmORD-GCM
10h 52m1 stop
Multiple Airlines Logo
2:34 pm - 9:03 pmGCM-ORD
7h 29m1 stop
$302Multiple Airlines
Find Deal
Sat, Jan 24 - Fri, Jan 30
Multiple Airlines Logo
5:15 am - 1:38 pmORD-GCM
7h 23m1 stop
Multiple Airlines Logo
4:45 pm - 8:18 amGCM-ORD
16h 33m1 stop
$303Multiple Airlines
Find Deal
Wed, Jan 7 - Sun, Jan 11
Multiple Airlines Logo
3:26 pm - 1:53 pmORD-GCM
21h 27m1 stop
Multiple Airlines Logo
2:49 pm - 11:35 amGCM-ORD
21h 46m2 stops
$312Multiple Airlines
Find Deal
Thu, Feb 5 - Mon, Feb 9
Multiple Airlines Logo
5:15 am - 1:53 pmORD-GCM
7h 38m1 stop
Multiple Airlines Logo
7:00 am - 6:16 pmGCM-ORD
12h 16m1 stop
$317Multiple Airlines
Find Deal
Sun, Jan 18 - Thu, Jan 22
Southwest Logo
5:00 am - 12:55 pmMDW-GCM
6h 55m1 stop
Southwest Logo
1:50 pm - 9:00 pmGCM-MDW
8h 10m1 stop
$406Southwest
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Sun, Jan 18 - Thu, Jan 22
Southwest Logo
5:00 am - 12:55 pmMDW-GCM
6h 55m1 stop
Southwest Logo
1:50 pm - 10:05 pmGCM-MDW
9h 15m2 stops
$411Southwest
Find Deal
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 $339 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 $339.

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 $427, 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 October, when tickets cost $537 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $803 and $781 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, Thursday 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 5 weeks before departure, which saves you about 20% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$74
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 17% 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.

  • 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 39% 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 $705.

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 4253 reviews
8.6Crew
7.0Food
8.1Boarding
7.5Entertainment
8.0Comfort
Airline reviews

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

10.0 ExcellentDavid, Nov 2025BUF - PHX
Read more Southwest reviews

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

It would’ve been nice for all that money to have a more substantial snack for free. I remember once upon a time getting a very nice turkey sandwich with Swiss cheese on whole wheat bread for no charge along with a drink. I guess those days are gone. it’s a little insulting being given a cookie or a bag of baked chips Going forward I’ll just bring my own.

Great. Seamless. Check in agent at kiosk international was amazing and extremely helpful.

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.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

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.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

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

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.