$126 Find Cheap Flights from Chicago to Cayman Islands - Compare and Save
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 9/9. 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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1 adult
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0 bags
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1 adult, Economy, 0 bags
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Book Cheap Chicago to the Cayman Islands 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 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.
Round-trip
One-way
Last minute
Direct
Recent round-trip flight deals from Chicago to the Cayman Islands
Fri, Sep 11 - Thu, Sep 17
5:35 pm - 9:45 amORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
16h 10m1 stop Toronto Pearson Intl
12:25 pm - 2:50 pmGCM George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
26h 25m1 stop Toronto Pearson Intl
$329Air Canada
Fri, Sep 11 - Thu, Sep 17
5:35 pm - 9:45 amORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
16h 10m1 stop Toronto Pearson Intl
12:25 pm - 2:50 pmGCM George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
26h 25m1 stop Toronto Pearson Intl
$335Air Canada
Fri, Oct 16 - Sun, Oct 25
3:45 pm - 11:30 amORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
19h 45m1 stop Toronto Pearson Intl
12:10 pm - 8:13 pmGCM George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
8h 03m1 stop Toronto Pearson Intl
$346Air Canada
Fri, Oct 16 - Sun, Oct 25
5:35 pm - 11:30 amORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
17h 55m1 stop Toronto Pearson Intl
12:10 pm - 11:07 amGCM George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
22h 57m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
$349Air Canada
Tue, Feb 2 - Wed, Feb 10
9:31 am - 2:35 pmORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 04mnonstop
3:25 pm - 6:49 pmGCM George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 24mnonstop
$597American Airlines
Mon, Feb 1 - Tue, Feb 9
9:31 am - 2:35 pmORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 04mnonstop
3:25 pm - 6:49 pmGCM George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 24mnonstop
$597American Airlines
Tue, Feb 2 - Wed, Feb 10
6:59 am - 8:23 pmORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
12h 24m1 stop Miami
3:25 pm - 6:49 pmGCM George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 24mnonstop
$601American Airlines
Mon, Feb 8 - Fri, Feb 12
8:45 am - 1:45 pmORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 00mnonstop
2:50 pm - 6:04 pmGCM George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 14mnonstop
$617United Airlines
Wed, Jan 27 - Wed, Feb 3
8:42 am - 1:45 pmORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 03mnonstop
2:55 pm - 6:13 pmGCM George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 18mnonstop
$617United Airlines
Sun, Feb 7 - Fri, Feb 12
8:45 am - 1:45 pmORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 00mnonstop
2:50 pm - 6:04 pmGCM George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 14mnonstop
$617United Airlines
Recent one-way flight deals from Chicago to the Cayman Islands
Wed, Sep 9
9:55 am - 11:25 amORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
25h 30m1 stop Toronto Pearson Intl
$126Air Canada
Tue, Sep 8
8:45 am - 11:25 amORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
50h 40m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
$129Air Canada
Tue, Sep 29
3:40 pm - 11:30 amORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
43h 50m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
$129Air Canada
Wed, Sep 9
8:45 am - 11:25 amORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
26h 40m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
$129Air Canada
Sat, Nov 7
8:42 am - 1:45 pmORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 03mnonstop
$324United Airlines
Mon, Feb 8
8:45 am - 1:45 pmORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 00mnonstop
$324United Airlines
Tue, Feb 9
9:31 am - 2:35 pmORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 04mnonstop
$324American Airlines
Thu, Sep 10
9:01 pm - 11:27 amORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
14h 26m1 stop Charlotte Douglas
$328American Airlines
Sat, Oct 10
9:38 pm - 12:30 pmORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
14h 52m1 stop Houston George Bush Intcntl
$328United Airlines
Tue, Sep 8
6:59 am - 1:10 pmORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
6h 11m1 stop Miami
$328American Airlines
Recent last minute flight deals from Chicago to the Cayman Islands
Sat, Aug 15 - Sun, Aug 23
7:30 am - 3:00 pmORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
7h 30m1 stop Charlotte Douglas
2:10 pm - 11:30 pmGCM George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
9h 20m1 stop Miami
$911American Airlines
Sat, Aug 15 - Sun, Aug 23
6:00 am - 2:17 pmORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
8h 17m1 stop Dallas/Fort Worth
12:00 pm - 11:44 pmGCM George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
11h 44m2 stops Miami Philadelphia
$916American Airlines
Sat, Aug 15 - Sun, Aug 23
5:59 pm - 11:00 amORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
17h 01m1 stop Miami
2:10 pm - 10:31 pmGCM George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
8h 21m1 stop Miami
$966American Airlines
Recent direct flight deals from Chicago to the Cayman Islands
Tue, Feb 2 - Wed, Feb 10
9:31 am - 2:35 pmORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 04mnonstop
3:25 pm - 6:49 pmGCM George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 24mnonstop
$597American Airlines
Mon, Feb 1 - Tue, Feb 9
9:31 am - 2:35 pmORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 04mnonstop
3:25 pm - 6:49 pmGCM George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 24mnonstop
$597American Airlines
Wed, Jan 13 - Wed, Jan 20
9:31 am - 2:35 pmORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 04mnonstop
3:25 pm - 6:49 pmGCM George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 24mnonstop
$602American Airlines
Sun, Feb 7 - Fri, Feb 12
8:45 am - 1:45 pmORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 00mnonstop
2:50 pm - 6:04 pmGCM George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 14mnonstop
$617United Airlines
Mon, Feb 8 - Fri, Feb 12
8:45 am - 1:45 pmORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 00mnonstop
2:50 pm - 6:04 pmGCM George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 14mnonstop
$617United Airlines
Tue, Feb 2 - Wed, Feb 10
9:31 am - 2:35 pmORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 04mnonstop
3:25 pm - 6:49 pmGCM George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 24mnonstop
$617American Airlines
Tue, Jan 12 - Wed, Jan 20
9:31 am - 2:35 pmORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 04mnonstop
3:25 pm - 6:49 pmGCM George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 24mnonstop
$617American Airlines
Wed, Jan 27 - Wed, Feb 3
8:42 am - 1:45 pmORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 03mnonstop
2:55 pm - 6:13 pmGCM George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 18mnonstop
$617United Airlines
Wed, Feb 3 - Sun, Feb 7
8:42 am - 1:45 pmORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 03mnonstop
2:50 pm - 6:04 pmGCM George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 14mnonstop
$642United Airlines
Fri, Jan 1 - Thu, Jan 7
8:42 am - 1:42 pmORD Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 00mnonstop
2:50 pm - 6:04 pmGCM George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 14mnonstop
$642United Airlines
Booking Insights
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.
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Airlines
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What is the cheapest Chicago O'Hare Intl Airport to the Cayman Islands flight route?
Data is based on round-trip flight searches on KAYAK over the past month.
The cheapest ticket to the Cayman Islands from Chicago O'Hare Intl Airport found in the last 5 days was to George Town, at $641 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 5 days was $641.
What is the cheapest time of day to fly to the Cayman Islands?
The average price for all round-trip flights from Chicago O'Hare Intl Airport 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 morning, when round-trip flights cost $632 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 $632.
Can I save money by flying with a layover from Chicago O'Hare Intl Airport 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 2 stops layover the cheapest option at $681 on average.
What is the cheapest month to fly from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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 O'Hare Intl Airport to the Cayman Islands is February, when tickets cost $530 (return) on average. On the other hand, the most expensive months are November and July, when the average cost of round-trip tickets is $972 and $806 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 O'Hare Intl Airport to the Cayman Islands clicked on KAYAK for each day over the last 12 months.
When flying from Chicago to Cayman Islands, you should consider leaving on a Thursday and avoid Sundays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Saturdays and the most expensive ones on Fridays.
How far in advance should I book a flight from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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 O'Hare Intl Airport to the Cayman Islands, you should book around 2 weeks before departure, which saves you about 16% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.
Which airlines fly non-stop between Chicago O'Hare Intl Airport and Cayman Islands?
Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from Chicago O'Hare Intl Airport to the Cayman Islands.
There are 2 airlines that fly nonstop from Chicago O'Hare Intl Airport to the Cayman Islands. They are American Airlines and United Airlines. The cheapest airline for this route is United Airlines, with the best round-trip deal found costing $341 and arriving in George Town (GCM). On average, United Airlines offers the best prices for nonstop flights between Chicago O'Hare Intl Airport and Cayman Islands.
How long does a flight from Chicago O'Hare Intl Airport to the Cayman Islands take?
The duration of a flight to the Cayman Islands depends on your arrival airport. The shortest routes to the Cayman Islands from Chicago O'Hare Intl Airport are to George Town, which takes 4h 00m, and Cayman Brac, which takes 17h 35m.
Which cabin class options are there for flights between Chicago O'Hare Intl Airport and Cayman Islands?
The average price of round-trip flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 3 cabin class options for the route. These are Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 3% 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 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 Cayman Islands.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Cayman Islands?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to 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 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 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 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 Cayman Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.
Reviews of the top airlines flying 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.
This flight has a history of leaving late, however, I was pleasantly surprised that it was not delayed this day. The flight went smooth, except I was in a window seat and the wall and my feet were freezing. I found it difficult to sleep due to being so cold, I also was using 2 provided UAL blankets and could not get my feet warm. This was annoying, but I still made it there on time and safe.
This flight has a history of leaving late, however, I was pleasantly surprised that it was not delayed this day. The flight went smooth, except I was in a window seat and the wall and my feet were freezing. I found it difficult to sleep due to being so cold, I also was using 2 provided UAL blankets and could not get my feet warm. This was annoying, but I still made it there on time and safe.
Old 757 with poor entertainment system. United no longer partners with United for free text and email. O'Hara an absolute disaster! Limited gates clauses two hour delay. Unfortunately this appears to be the norm.
It was a good experience, unfortunately my checked baggages were come late and not arrived on time.
Very stressful to locate United Airline boarding area, delayed flight, changing boarding area again to another location with all tiredness 😩. But flying was fine.
It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.
The SFO lounge closes at 12 midnight. My flight took off at 2AM
It was extremely hot in the cabin the entire flight, vent air was worn
Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.
We were forced to eat vegetarian food because non veg food ran out. The breakfast was mediocre.
My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well
Couldn't make the flight because connecting flight was canceled.
gate crew was courteous and helpful, flight attendant was nice and friendly once we got going. But we pushed off from the gate relatively on time, then sat there like 10 ft away, for an hour, with no announcement or explanation. Taxiing then took forever, and I get that there was runway congestion, but would be helpful to keep us posted on whats going on
The power outlets were not working for my row. Also felt like the seats have gotten smaller. I was in the window seat and felt like suffocated, as the two passengers next to me were tall and wide.
Terrible. The flight I booked had a convenient departure time. Quick layover. And an arrival timed that worked for the people who had to pick me up. Thanks to delays and rebooking I got none of those things
I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight
Long delays to board due to mechanical issues with plane.
Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak
The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN
I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.
The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.
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The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights from domestic origins to the Cayman Islands
Flights from all regions of Chicago 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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