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Find cheap flights from Chicago to the Cayman Islands from $159

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 6/25. 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
Mon 6/10
Mon 6/17

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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$464

Good to know

Low season

September

High season

March

Cheapest flight

$159
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 27% 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 10751 reviews
7.9Comfort
7.4Food
8.6Crew
8.0Entertainment
8.2Boarding
Airline reviews

Boarding was chaotic. I didn’t finish dinner because I went to bed early. Breakfast omelet was overcooked and tasteless but croissant was better than usual. Plane was dirty—crumbs in every seam and lavatory was poorly maintained (paint peeling, etc.) and toilet paper had not been refreshed before takeoff. No cubby for storage in first and seat was narrow.

4.0 OkayPatricia, May 2024DTW - CDG
Read more about Delta reviews

Boarding was chaotic. I didn’t finish dinner because I went to bed early. Breakfast omelet was overcooked and tasteless but croissant was better than usual. Plane was dirty—crumbs in every seam and lavatory was poorly maintained (paint peeling, etc.) and toilet paper had not been refreshed before takeoff. No cubby for storage in first and seat was narrow.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

West Jet has a horrible boarding process and the seats have no cushion.

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.

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

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.

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.

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

It was delayed but got us to YYZ. I had great copassengers.

Flew SEA-CA, then CA-NRT. First flight was short but very uncomfortable, dirty, and had very small overhead storage space. The seats and fans were not cleaned and had visible dirt on them. Second flight was perfect.

My second flight ended up being through United and it was fine. Again, just frustrating that it was so late.

My experience was pretty frustrating because the first leg of my flight on United (though booked through Air Canada) was delayed causing me to miss my connecting flight on Air Canada. This could have been an easy solve as there was a direct flight later that morning via Air Canada that they easily could have put me on which would have only gotten me to my destination 2 1/2 hours later but because United and Air Canada don’t seem to have good communication they gave me the run around both telling me to talk with the other which I did three times to no avail. I ended up taking the delayed flight and getting on a new connecting flight which ended up getting me to my destination 6 hours later and I missed the event I was planning to go to this evening.

Everything went smoothly and as expected. We were on time and one flight arrived early.

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.

Book cheap flights from Chicago to the Cayman Islands

Recent round-trip flight deals

9/26Thu
1 stop
12h 03mORD-GCM
10/1Tue
1 stop
10h 26mGCM-ORD
$464
5/26Sun
1 stopAir Canada
8h 35mORD-GCM
6/2Sun
1 stopAir Canada
17h 06mGCM-ORD
$468
5/29Wed
1 stopAir Canada
22h 35mORD-GCM
6/6Thu
1 stopAir Canada
18h 09mGCM-ORD
$475
8/4Sun
1 stopDelta
15h 31mORD-GCM
8/16Fri
1 stopDelta
8h 21mGCM-ORD
$578
8/7Wed
1 stopAmerican Airlines
6h 18mORD-GCM
8/13Tue
2 stopsAmerican Airlines
10h 49mGCM-ORD
$580
8/4Sun
1 stopDelta
15h 31mORD-GCM
8/16Fri
2 stopsDelta
20h 37mGCM-ORD
$583
7/4Thu
1 stopUnited Airlines
15h 20mORD-GCM
7/7Sun
nonstopUnited Airlines
4h 10mGCM-ORD
$593
9/6Fri
1 stopAmerican Airlines
7h 36mORD-GCM
9/13Fri
1 stopAmerican Airlines
8h 43mGCM-ORD
$600
6/19Wed
1 stopUnited Airlines
6h 13mORD-GCM
6/23Sun
nonstopUnited Airlines
4h 10mGCM-ORD
$683
6/29Sat
2 stopsWestJet
24h 32mMDW-GCM
7/6Sat
2 stopsWestJet
25h 10mGCM-MDW
$2,968

Search by stops

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Recent one-way flight deals

6/25Tue
1 stop
8h 34mORD-GCM
$159
6/27Thu
1 stopAir Canada
8h 35mORD-GCM
$215
6/26Wed
2 stopsAir Canada
20h 05mORD-GCM
$216
6/26Wed
1 stopDelta
15h 40mORD-GCM
$274
11/3Sun
1 stopAmerican Airlines
14h 30mORD-GCM
$276
6/25Tue
2 stopsDelta
16h 05mORD-GCM
$280
11/3Sun
2 stopsAmerican Airlines
14h 20mORD-GCM
$281
5/18Sat
nonstopUnited Airlines
4h 02mORD-GCM
$598
5/18Sat
1 stopUnited Airlines
14h 58mORD-GCM
$602
5/18Sat
3 stopsBritish Airways
45h 25mORD-GCM
$5,669

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Last minute flights from Chicago to the Cayman Islands

Last minute flight, train and bus deals

5/11Sat
multi-stop
27h 35mORD-GCM
5/16Thu
multi-stop
16h 10mGCM-ORD
$639
5/11Sat
multi-stop
20h 13mORD-GCM
5/16Thu
multi-stop
15h 04mGCM-ORD
$794
5/11Sat
multi-stop
20h 13mORD-GCM
5/16Thu
multi-stop
31h 44mGCM-ORD
$906
5/11Sat
nonstopUnited Airlines
4h 02mORD-GCM
5/16Thu
multi-stopUnited Airlines
9h 23mGCM-ORD
$1,109

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Flights to the Cayman Islands

Return flight deals:

Cayman Islands - Chicago

Cabin classes:

$1,583
$1,581
$589