$168 Find Cheap Flights from Chicago to the Cayman Islands

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 the Cayman Islands departing on 4/29. 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.
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Best Cayman Islands Flight Deals from Chicago

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

George Town
George Town1 stop$462

Cheap Flight Deals from Chicago to the Cayman Islands (CHI-KY0)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to the Cayman Islands 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.

Recent round-trip flight deals from Chicago to the Cayman Islands

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to the Cayman Islands.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
7:00 pm - 4:10 pmORD-GCM
21h 10m1 stop
8:50 am - 5:41 pmGCM-ORD
8h 51m1 stop
Tue, May 6 - Sat, May 10
3:11 pm - 11:40 amORD-GCM
20h 29m1 stop
8:50 am - 10:47 pmGCM-ORD
13h 57m1 stop
Sat, Sep 13 - Sat, Sep 20
5:50 am - 11:50 amMDW-GCM
6h 00m1 stop
12:45 pm - 8:15 pmGCM-MDW
7h 30m1 stop
$552Southwest
Find Deal
Fri, May 16 - Wed, May 21
4:15 pm - 11:50 amMDW-GCM
19h 35m2 stops
12:45 pm - 10:05 pmGCM-MDW
9h 20m1 stop
$566Southwest
Find Deal
Thu, May 15 - Tue, May 20
5:00 am - 1:10 pmORD-GCM
8h 10m1 stop
12:10 pm - 11:56 pmGCM-ORD
11h 46m1 stop
$596American Airlines
Find Deal
Wed, May 14 - Wed, May 21
5:00 am - 1:10 pmORD-GCM
8h 10m2 stops
12:25 pm - 9:43 pmGCM-ORD
9h 18m1 stop
$600American Airlines
Find Deal
Wed, May 14 - Wed, May 21
5:30 am - 11:20 amORD-GCM
5h 50m1 stop
12:35 pm - 9:20 pmGCM-ORD
8h 45m1 stop
$610Delta
Find Deal
Wed, May 14 - Wed, May 21
6:00 am - 11:20 amMDW-GCM
5h 20m1 stop
12:35 pm - 9:27 pmGCM-MDW
8h 52m1 stop
$610Delta
Find Deal
Wed, May 14 - Wed, May 21
8:10 pm - 12:30 pmORD-GCM
16h 20m1 stop
1:45 pm - 6:07 pmGCM-ORD
4h 22mnonstop
$625United Airlines
Find Deal
Mon, Jun 9 - Sat, Jun 14
9:26 am - 1:30 pmORD-GCM
4h 04mnonstop
1:35 pm - 11:12 pmGCM-ORD
9h 37m1 stop
$630United Airlines
Find Deal
Sat, May 17 - Fri, May 23

KAYAK's insights & trends for Chicago to the Cayman Islands flights

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

What is the cheapest Chicago to the Cayman Islands flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to the Cayman Islands.
The cheapest ticket to the Cayman Islands from Chicago found in the last 72 hours was to George Town, at $645 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 $645.

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

The average price for all round-trip flights from Chicago to the Cayman Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to the Cayman Islands is generally in the evening, when round-trip flights cost $507 on average. Morning departures are around 40% more expensive than evening flights, on average. The most expensive time of day to fly to the Cayman Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $712.

Can I save money by flying with a layover from Chicago to the Cayman Islands?

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 $849, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago to the Cayman Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to the Cayman Islands, 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 the Cayman Islands is September, when tickets cost $524 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $868 and $761 respectively.

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

The average price of all round-trip flights from Chicago to the Cayman Islands clicked on KAYAK for each day over the last 12 months.
For Chicago to Cayman Islands, Sunday is the cheapest day to fly on average and Friday is the most expensive. Flying from Cayman Islands back to Chicago, the best deals are generally found on Tuesday, with Friday being the most expensive.

How far in advance should I book a flight from Chicago to the Cayman Islands?

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 the Cayman Islands, 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 the Cayman Islands, you should book around 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low season

September

High season

March

Cheapest flight

$168
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 32% increase in price.
Flight from Chicago O'Hare Airport to George Town

FAQs - booking Cayman Islands flights

  • How does KAYAK find such low prices on flights from Chicago to the Cayman Islands?

    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 the Cayman Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to the Cayman Islands 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 the Cayman Islands?

    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 the Cayman Islands 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 the Cayman Islands?

    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 the Cayman Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 4 airlines serving from Chicago to the Cayman Islands

Need help choosing which airline to fly with from Chicago to the Cayman Islands? 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 4275 reviews
7.6Entertainment
8.2Boarding
8.1Comfort
7.1Food
8.7Crew
Airline reviews

1.5 hour delay, poor service, no compassion from the crew. Terrible experience

2.0 MediocreAndre, Mar 2025DEN - LIT
Read more Southwest reviews

1.5 hour delay, poor service, no compassion from the crew. Terrible experience

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

Short flight with plenty of open seats. Drinks and snacks were still provided even on such a short flight. <1 hr

I liked the crew member who gave flight instructions on "in case of a problem:. The seats are so small that only a young teenager could sit in middle seat.

Great experience flying Southwest. The crew was really kind and helpful, and very friendly with our toddler.

Very good. Sad to learn Southwest is going start to charge for bags

Our flight was diverted from being a non-stop to getting within 150 miles and requiring another plane. We heard 4 or 5 different versions from SW as to why we had to stop, then wait for a replacement plane. Five hour delay, weather did not come up as a single excuse.... communication was not clear and well explained. No one really took charge!

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

WiFi on the flight was not working. Thus, entertainment options were limited.

Great flight staff. Ease of boarding. Overall, very uneventful and easy trip.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

After a 5 hour delay waiting at the gate (3 delays adding up) with no clear reason provided, we finally boarded flew 3/4 of the way to Toronto then were turned back to New York. As we neared New York, the pilot declared that it was his fault, something to do with timing and him not being allowed into the country???? How could the airline let his happen? They had hours to prepare and make sure they had a crew available for the flight! We ended up in Toronto a day late with no sleep.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Terrible and im avoiding them in the future. My initial flight was delayed causing me to rebook my flight and when speaking with the representative to rebook I explained this is the second time my flights were delayed and they did nothing to help me. I wasn't booked to comfort plus or given a voucher or anything. I was almost late for my meeting that I needed to attend on Monday because of the games delta played delaying my flights even more and putting me in the very back of the plane next to an extremely intoxicated passenger

Friendly flight attendants, smooth 8-9 hours flight. Economy seats are small and uncomfortable as usual.

Flights on time. .Ride was as comfortable as can be expected in steerage. Luggage arrived at destination. Attendants were fairly friendly.

Great staff. Wifi is terrible. Signing up for skylines is a painstaking process. Had to call customer service just to get my flight itinerary and confirmation sent to me. Consistent delays. A well staffed company that is run so poorly. Upper management needs to be renewed.

The WiFi didn't seem as fast as it normally is

Bathrooms dirty sinks clogged. No one seemed to clean them. Plane very old

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

Fight was delayed an hour due to operational issues ,then further delayed due to ground control for a total of about 1.30 hours. Salad was completely frozen and flatware was so cold you could barely handle it. Crew was friendly and professional and the flight was smooth. The aircraft was clean and well-serviced.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

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

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

Everything you need to know for your flight from Chicago to the Cayman Islands

Cabin class types available on flights to the Cayman Islands

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

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