$179 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 7/29. 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.
1 adult
1 adult, Economy

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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$467
George Town
George Town1 stop$467

Cheap Flights from Chicago to the Cayman Islands

 
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.
Discover the best prices for you by selecting your travel dates on KAYAK.

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

Tue, Jul 8 - Mon, Jul 14
 Logo
1:43 pm - 4:10 pmORD-GCM
26h 27m1 stop
 Logo
4:45 pm - 4:11 pmGCM-ORD
23h 26m1 stop
Tue, Jul 29 - Mon, Aug 4
 Logo
8:09 am - 4:10 pmORD-GCM
8h 01m1 stop
 Logo
4:45 pm - 4:11 pmGCM-ORD
23h 26m1 stop
Sat, Nov 1 - Thu, Nov 6
Southwest Logo
5:15 pm - 12:35 pmMDW-GCM
19h 20m2 stops
Southwest Logo
1:30 pm - 12:10 amGCM-MDW
11h 40m2 stops
$489Southwest
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Mon, Oct 20 - Fri, Oct 24
Delta Logo
6:00 am - 11:42 amORD-GCM
5h 42m1 stop
Delta Logo
1:02 pm - 9:12 pmGCM-ORD
8h 10m1 stop
$520Delta
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Sun, Oct 19 - Thu, Oct 30
Delta Logo
6:00 am - 11:42 amMDW-GCM
5h 42m1 stop
Delta Logo
1:02 pm - 9:44 pmGCM-MDW
8h 42m1 stop
$520Delta
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Sun, Sep 14 - Fri, Sep 19
American Airlines Logo
8:44 pm - 11:10 amORD-GCM
14h 26m2 stops
American Airlines Logo
12:10 pm - 11:12 pmGCM-ORD
11h 02m2 stops
$524American Airlines
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Sat, Nov 1 - Thu, Nov 6
Southwest Logo
5:05 am - 12:10 pmMDW-GCM
7h 05m1 stop
Southwest Logo
1:30 pm - 6:55 pmGCM-MDW
6h 25m1 stop
$529Southwest
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Sat, Dec 6 - Sat, Dec 13
American Airlines Logo
6:35 pm - 12:05 pmORD-GCM
16h 30m1 stop
American Airlines Logo
2:00 pm - 5:10 pmGCM-ORD
4h 10mnonstop
$535American Airlines
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Sun, Oct 19 - Wed, Oct 29
United Airlines Logo
6:00 am - 12:30 pmORD-GCM
6h 30m1 stop
United Airlines Logo
4:40 pm - 12:15 amGCM-ORD
7h 35m1 stop
$610United Airlines
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Sat, Aug 2 - Sat, Aug 9
United Airlines Logo
6:00 am - 3:35 pmORD-GCM
9h 35m1 stop
United Airlines Logo
1:45 pm - 6:07 pmGCM-ORD
4h 22mnonstop
$697United Airlines
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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 $495 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 $495.

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $1,533 on average.

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 $523 (return) on average. On the other hand, the most expensive months are March and February, when the average cost of round-trip tickets is $868 and $706 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, Tuesday 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 Sunday, with Wednesday 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 14 weeks before departure.


Good to know

Low seasonSeptember
High seasonMarch
Cheapest flight$179
Best time to beat the crowds with an average 21% 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.

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

    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 43% 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 $723.

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 4287 reviews
8.2Boarding
8.0Comfort
7.6Entertainment
7.1Food
8.6Crew
Airline reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Great flight! Only complaint I had was that I didn’t get breakfast that morning because I don’t eat eggs for breakfast.. I ate an energy bar I bought in the airport which I had never done before. Otherwise, another great Delta flight!

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

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

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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