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Find cheap flights from Chicago to Grand Cayman from $120

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 11/16. 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 6/23
Sun 6/30

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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$343

Good to know

Low season

August

High season

March

Cheapest flight

$120
Best time to beat the crowds but there is an average 5% increase 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 10554 reviews
7.9Comfort
8.0Entertainment
7.4Food
8.2Boarding
8.6Crew
Airline reviews

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

8.0 ExcellentLiam, May 2024SLC - SJC
Read more about Delta reviews

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Half the bathrooms assigned to economy were out of action

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

Standard flight experience, but there is only power at the seat to row 20 on the aircraft, on my initial check in it did not say that was the case

Energetic crew - flight full of swiftied going to Taylor's opening show in Paris! Long lines for bathroom made out kind of suck though

I’ve had a couple flights this week on United that were delayed by an hour or more

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

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.

Flight was delayed for almost 3 hours. Communication of gate change was poor. Email and screen said one gate and it was a different gate from that. Gate changed first to 64 B and then to 64 C. Originally it was 68B. 64C was not communicated properly!

This was a red eye return, so I doubt there would be anyway to make it better. Other than adding beds.

Direct nonstop flight was great. Flight was delayed and the crew announced a 2h delay on the sound system. 30 min or so later I hear my name on the sound system for immediate board. Several other passangers were late too. Reason: The crew incorrectly announced a 2h delay when in reality they meant a new boarding time at 2pm.

Plenty of room in the exit row. Sat on the plane an hour before taking off.☹️ Landed late and had to wait for gate availability.

Flight was on time early arrival better entertainment good staff.everything was excellent

Delayed leaving. On arrival we were taken to the airstrip and had to get off onto an over crowed bus, not all that passengers fit. Drove around the airport for 20 + minutes. Taken off the bus told to go upstairs 3 flights then all the passengers had to walk a mile or more , those of us old there was no one to direct us to were to go. I asked several people with no answers. Once I got to baggage claim my bags were not on the right bag claim. Once again asked for help and finally someone found my bags on a different carasel. Very frustrating.

Excellent host on board. Not so friendly check-in staff. Older plane with no food or entertainment due to short flight. Friendly captain and crew.

I don’t think there was entertainment? No mention of it. It was a good flight. Only complaint was my seat cushion was not attached and kept slipping.

They canceled the flight on us very close to the flight date .

It took 66 hours to get from Seattle to Tel Aviv. As a minor, I was left for more than 12 hours in Toronto and Frankfurt without hotel and food vouchers. It took 5 layovers. It was insane and not okay

Book cheap flights from Chicago to Grand Cayman

Recent round-trip flight deals

9/30Mon
1 stopAmerican Airlines
7h 36mORD-GCM
10/3Thu
1 stopAmerican Airlines
6h 41mGCM-ORD
$343
8/23Fri
1 stopAmerican Airlines
17h 55mORD-GCM
8/28Wed
1 stopAmerican Airlines
11h 11mGCM-ORD
$345
9/6Fri
1 stopDelta
5h 30mORD-GCM
9/13Fri
1 stopDelta
8h 14mGCM-ORD
$346
9/28Sat
1 stopDelta
5h 30mORD-GCM
10/3Thu
2 stopsDelta
18h 36mGCM-ORD
$351
6/4Tue
1 stop
18h 55mORD-GCM
6/18Tue
1 stop
20h 51mGCM-ORD
$418
6/4Tue
1 stop
18h 55mORD-GCM
6/17Mon
1 stop
15h 36mGCM-ORD
$438
6/13Thu
1 stopAir Canada
8h 35mORD-GCM
6/16Sun
1 stopAir Canada
18h 09mGCM-ORD
$451
6/6Thu
1 stopAir Canada
8h 35mORD-GCM
6/13Thu
2 stopsAir Canada
22h 56mGCM-ORD
$475
7/14Sun
nonstopUnited Airlines
4h 02mORD-GCM
7/20Sat
nonstopUnited Airlines
4h 12mGCM-ORD
$669
7/14Sun
1 stopUnited Airlines
6h 35mORD-GCM
7/20Sat
nonstopUnited Airlines
4h 12mGCM-ORD
$673

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Recent one-way flight deals

11/16Sat
1 stopAmerican Airlines
16h 30mORD-GCM
$120
11/3Sun
1 stopDelta
5h 30mORD-GCM
$121
11/16Sat
1 stopDelta
17h 15mMDW-GCM
$132
11/16Sat
2 stopsAmerican Airlines
19h 47mORD-GCM
$157
11/3Sun
2 stopsAmerican Airlines
20h 15mORD-GCM
$161
6/29Sat
1 stop
26h 44mORD-GCM
$222
6/29Sat
1 stop
28h 39mMDW-GCM
$240
6/29Sat
nonstopUnited Airlines
4h 02mORD-GCM
$298
11/16Sat
nonstopUnited Airlines
3h 57mORD-GCM
$736
11/16Sat
2 stopsWestJet
22h 30mMDW-GCM
$1,532

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Last minute flights from Chicago to Grand Cayman

Last minute flight, train and bus deals

5/29Wed
multi-stopAir Canada
22h 35mORD-GCM
6/2Sun
multi-stopAir Canada
16h 13mGCM-ORD
$621
5/29Wed
multi-stopAir Canada
20h 05mORD-GCM
6/2Sun
multi-stopAir Canada
16h 13mGCM-ORD
$622
5/29Wed
multi-stopAir Canada
22h 35mORD-GCM
6/2Sun
multi-stopAir Canada
18h 09mGCM-ORD
$644
5/29Wed
multi-stopUnited Airlines
16h 45mORD-GCM
6/2Sun
nonstopUnited Airlines
4h 10mGCM-ORD
$913
5/25Sat
multi-stopDelta
17h 29mORD-GCM
5/29Wed
multi-stopDelta
6h 44mGCM-ORD
$968
5/25Sat
multi-stopAmerican Airlines
16h 28mORD-GCM
5/29Wed
multi-stopAmerican Airlines
6h 59mGCM-ORD
$990

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Flights to Grand Cayman

Return flight deals:

Grand Cayman - Chicago

Cabin classes:

$172
$277
$277
$27