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Find cheap flights from Chicago to Grand Cayman from $162

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 6/2. 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
Sun 6/2
Sun 6/9

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Best Grand Cayman Flight Deals

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

George Town
George Town1 stop$414

Good to know

Low season

September

High season

March

Cheapest flight

$162
Best time to beat the crowds with an average 20% 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 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 to Grand Cayman 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 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 to Grand Cayman 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 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 to Grand Cayman 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 4 airlines serving from Chicago to Grand Cayman

 
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
DeltaOverall score based on 10848 reviews
8.2Boarding
8.0Entertainment
7.9Comfort
8.6Crew
7.4Food
Airline reviews

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

10.0 ExcellentAllan, May 2024SUN - SLC
Read more about Delta reviews

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 !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

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.

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.

The flight was very uncomfortable and there was no snacks served for the 13 hours international flight. In addition, the flight was delayed 3 hours

Due to a strike taking place with the airline, it negatively impacted my flight in multiple ways. My flight was delayed over 2 hours and the food served was mediocre at best.

Book cheap flights from Chicago to Grand Cayman

Recent round-trip flight deals

6/5Wed
1 stop
24h 30mORD-GCM
6/10Mon
1 stop
22h 51mGCM-ORD
$414
5/27Mon
1 stop
22h 45mORD-GCM
5/31Fri
1 stop
27h 47mGCM-ORD
$458
5/29Wed
1 stopAir Canada
22h 35mORD-GCM
6/6Thu
1 stopAir Canada
18h 09mGCM-ORD
$505
5/29Wed
2 stopsAir Canada
24h 40mORD-GCM
6/6Thu
2 stopsAir Canada
16h 15mGCM-ORD
$507
6/8Sat
1 stopAmerican Airlines
15h 01mORD-GCM
6/15Sat
1 stopAmerican Airlines
15h 08mGCM-ORD
$602
9/6Fri
1 stopDelta
5h 30mMDW-GCM
9/13Fri
1 stopDelta
8h 54mGCM-MDW
$603
6/8Sat
2 stopsAmerican Airlines
14h 17mORD-GCM
6/15Sat
1 stopAmerican Airlines
16h 20mGCM-ORD
$606
6/5Wed
1 stopDelta
5h 31mMDW-GCM
6/10Mon
2 stopsDelta
19h 53mGCM-MDW
$608
7/13Sat
nonstopUnited Airlines
4h 02mORD-GCM
7/21Sun
nonstopUnited Airlines
4h 10mGCM-ORD
$704
7/13Sat
1 stopUnited Airlines
17h 00mORD-GCM
7/21Sun
nonstopUnited Airlines
4h 10mGCM-ORD
$708

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Recent one-way flight deals

6/2Sun
1 stop
9h 37mORD-GCM
$162
6/6Thu
1 stop
10h 53mORD-GCM
$185
6/1Sat
1 stopAir Canada
22h 35mORD-GCM
$204
6/4Tue
2 stopsAir Canada
44h 05mORD-GCM
$205
6/3Mon
2 stopsAmerican Airlines
7h 50mORD-GCM
$276
6/2Sun
2 stopsDelta
17h 44mMDW-GCM
$277
6/5Wed
2 stopsDelta
25h 59mMDW-GCM
$301
6/2Sun
nonstopUnited Airlines
4h 02mORD-GCM
$323
6/1Sat
2 stopsAmerican Airlines
19h 35mORD-GCM
$336
6/1Sat
nonstopUnited Airlines
4h 02mORD-GCM
$348

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Last minute flights from Chicago to Grand Cayman

Last minute flight, train and bus deals

5/8Wed
multi-stop
24h 05mORD-GCM
5/13Mon
multi-stop
23h 15mGCM-ORD
$506
5/8Wed
multi-stop
23h 55mORD-GCM
5/13Mon
multi-stop
23h 15mGCM-ORD
$564
5/8Wed
multi-stop
26h 03mMDW-GCM
5/13Mon
multi-stop
8h 57mGCM-MDW
$616
5/8Wed
multi-stop
21h 15mORD-GCM
5/13Mon
multi-stop
19h 55mGCM-ORD
$685
5/8Wed
multi-stopDelta
5h 26mMDW-GCM
5/12Sun
multi-stopDelta
9h 10mGCM-MDW
$883
5/8Wed
multi-stopDelta
25h 54mMDW-GCM
5/12Sun
multi-stopDelta
9h 10mGCM-MDW
$888
5/8Wed
multi-stopDelta
25h 54mMDW-GCM
5/12Sun
multi-stopDelta
44h 15mGCM-MDW
$910
5/8Wed
multi-stopDelta
5h 26mMDW-GCM
5/12Sun
multi-stopDelta
9h 10mGCM-MDW
$963
5/8Wed
multi-stopBritish Airways
43h 15mORD-GCM
5/13Mon
multi-stopBritish Airways
24h 55mGCM-ORD
$9,227
5/8Wed
multi-stopBritish Airways
43h 15mORD-GCM
5/13Mon
multi-stopBritish Airways
24h 05mGCM-ORD
$9,240

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Flights to Grand Cayman

Return flight deals:

Grand Cayman - Chicago

Cabin classes:

$234
$328
$256
$27