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Find cheap flights from Chicago to the Cayman Islands from $276

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 11/3. 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
0 bags
Thu 6/6
Thu 6/13

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Best Cayman Islands Flight Deals

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

George Town
George Town1 stop$418

Good to know

Low season

September

High season

March

Cheapest flight

$276
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 18% 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 to the Cayman Islands from Chicago 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 to the Cayman Islands with an airline and back to Chicago 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 to the Cayman Islands from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to the Cayman Islands

  • Morning departure is around 7% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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
DeltaOverall score based on 10818 reviews
8.0Entertainment
7.9Comfort
8.2Boarding
8.6Crew
7.4Food
Airline reviews

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

8.0 ExcellentEric, May 2024BOS - CUN
Read more about Delta reviews

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

Aircraft has better leg room than any of United's larger planes. We had requested mobility assistance for this and related flights. United's response to all was superb.

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

First time flying Air Canada and the trip was very pleasant! They did a great job getting us out of Toronto and into Rome (early!) For an international flight it was very enjoyable.

This is not a Business Class equipped airplane and even the crew apologize before take over BUT BUT Air Canada charged full business class fare

All was good, except our baggage was lost for most of a day. We are thankful that it was found quickly and delivered to our hotel. Rouge was fine outside of that problem.

You do not have a space for flight cancelled. BUT!!! Air Canada handled it great. Was booked on another airline for the next day. The original flight was booked solid. But he precheck by the maintenance found a mechanical problem and the plane was not safe to fly. It was an inconvenience to have to wait until next day but I would rather arrive safely.

Very good other than we have to wait for one crew and we’re delayed and the pilot and his co- pilot has to make a difference to be right on time arrival. Disappointed about no food service also.

I had written all my complaints on my trip from Grand Junction to Denver so I will repeat it here! I was absolutely appalled that I had to pay for a regular seat that I choose 24 hrs before boarding! Also I checked my large bag which I had to pay for as well, and by the time I boarded all the room in the bins were gone so also had to check that one. I noticed people pulling out oversized suitcases, bigger than the measurements stated for carry on, and also large pack packs stuffed full! So these people were taking up 2 or 3 spaces that the rest of us should have been able to use but couldn’t! NoTV on the flight! Thankfully I had downloaded the United Airlines app and was able to watch movies on my phone. Don’t remember the last time I flew in a plane with no movie screens!

I was appalled to have to pay for just a regular seat when I went to book 24 hrs before my flight! Because it was only an hour flight I didn’t choose a seat from Grand Junction to Denver, but I did for Toronto and had to pay just to choose a regular available seat! In my 60+ years of flying this was the first time I have heard of this. Also, allowing people to bring on “huge “ suitcases, not carry on size, but much bigger, and then a large pack pack stuffed. So they take up all the room in the overhead bins and if we are later boarding, there is no room so we have to check our small carry on. I have already paid for and checked in one bag! I certainly will not choose to fly with United again unless it is the “only” airline available!

Easy boarding, roomy seats, plenty of good food, very helpful snd friendly staff. Very smooth flight! Only thing that could have been better was to have cranberry juice. Women like this as it helps avoid UTI’s and not as sweet as other juices.

The crew was friendly, the seats are too small. Air travel is barely tolerable anymore.

Food was icecold or frozen including breakfast. Hopeless service. Rude crew.

Book cheap flights from Chicago to the Cayman Islands

Recent round-trip flight deals

5/28Tue
1 stop
18h 55mORD-GCM
5/31Fri
1 stop
26h 48mGCM-ORD
$418
6/5Wed
1 stop
24h 30mORD-GCM
6/12Wed
1 stop
21h 34mGCM-ORD
$432
6/9Sun
1 stopAir Canada
8h 35mORD-GCM
6/16Sun
1 stopAir Canada
18h 09mGCM-ORD
$468
6/9Sun
1 stopAir Canada
8h 35mORD-GCM
6/16Sun
2 stopsAir Canada
18h 16mGCM-ORD
$475
6/5Wed
1 stopDelta
5h 31mMDW-GCM
6/12Wed
1 stopDelta
8h 51mGCM-MDW
$578
8/3Sat
2 stopsAmerican Airlines
14h 33mORD-GCM
8/8Thu
2 stopsAmerican Airlines
10h 21mGCM-ORD
$581
6/11Tue
1 stopUnited Airlines
15h 04mORD-GCM
6/16Sun
nonstopUnited Airlines
4h 10mGCM-ORD
$593
8/3Sat
nonstopUnited Airlines
4h 02mORD-GCM
8/8Thu
1 stopUnited Airlines
7h 18mGCM-ORD
$599
9/6Fri
1 stopAmerican Airlines
7h 36mORD-GCM
9/13Fri
1 stopAmerican Airlines
8h 43mGCM-ORD
$600
8/16Fri
1 stopDelta
5h 30mORD-GCM
8/23Fri
1 stopDelta
11h 09mGCM-ORD
$603

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Recent one-way flight deals

11/3Sun
1 stopAmerican Airlines
5h 50mORD-GCM
$276
11/3Sun
2 stopsAmerican Airlines
14h 20mORD-GCM
$326
5/19Sun
2 stops
11h 05mORD-GCM
$358
5/19Sun
3 stops
27h 47mORD-GCM
$411
5/19Sun
1 stopAmerican Airlines
5h 55mORD-GCM
$597
5/17Fri
1 stopUnited Airlines
6h 35mORD-GCM
$602
5/19Sun
2 stopsAmerican Airlines
7h 50mORD-GCM
$626
5/19Sun
1 stopUnited Airlines
17h 40mORD-GCM
$646
5/19Sun
3 stopsBritish Airways
48h 25mORD-GCM
$6,174
5/17Fri
3 stopsBritish Airways
26h 30mORD-GCM
$11,871

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Last minute flights from Chicago to the Cayman Islands

Last minute flight, train and bus deals

5/10Fri
multi-stop
11h 23mORD-GCM
5/13Mon
multi-stop
23h 15mGCM-ORD
$685
5/10Fri
multi-stop
20h 10mORD-GCM
5/13Mon
multi-stop
7h 01mGCM-ORD
$781
5/10Fri
multi-stop
20h 10mORD-GCM
5/13Mon
multi-stop
12h 16mGCM-ORD
$784
5/10Fri
multi-stop
20h 10mORD-GCM
5/13Mon
multi-stop
25h 58mGCM-ORD
$841
5/10Fri
multi-stop
40h 50mORD-GCM
5/13Mon
multi-stop
25h 58mGCM-ORD
$901
5/8Wed
multi-stopDelta
5h 26mMDW-GCM
5/12Sun
multi-stopDelta
9h 10mGCM-MDW
$963
5/8Wed
multi-stopDelta
17h 39mMDW-GCM
5/12Sun
multi-stopDelta
9h 10mGCM-MDW
$968
5/8Wed
multi-stopDelta
17h 39mMDW-GCM
5/12Sun
multi-stopDelta
28h 15mGCM-MDW
$991
5/8Wed
multi-stopDelta
5h 26mMDW-GCM
5/12Sun
multi-stopDelta
9h 10mGCM-MDW
$1,113
5/8Wed
multi-stopDelta
22h 05mMDW-GCM
5/12Sun
multi-stopDelta
9h 10mGCM-MDW
$1,118

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Flights to the Cayman Islands

Return flight deals:

Cayman Islands - Chicago

Cabin classes:

$1,583
$1,581
$589