Find cheap flights from Chicago O'Hare Airport to Grand Cayman

Find cheap flights from Chicago O'Hare Airport to Grand Cayman

Round-trip
Economy
Chicago (ORD)
Grand Cayman
Sun 11/29
Sun 12/6
Any month
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Good to know

Low season

September Best time to beat the crowds with an average 1% drop in price.

High season

December Most popular time to fly with an average 2% increase in price.

Average price round-trip

$436 (avg. price over the last 2 weeks)

Good deal round-trip

$346 or less

Good deal one-way

$163 or less

Top tips for finding cheap flights to Grand Cayman

  • Book at least 4 weeks before departure in order to get a below-average price.
  • High season is considered to be September, October and November. The cheapest month to fly to Grand Cayman is January.
  • Morning departure is around 60% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs - booking Grand Cayman flights

How long is the flight to Grand Cayman from Chicago O'Hare Intl?

Are there Grand Cayman travel restrictions currently due to Coronavirus?

How does KAYAK find such low prices on flights to Grand Cayman?

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago O'Hare Airport to Grand Cayman?

What is the Hacker Fare option on flights to Grand Cayman?

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Top airlines flying Chicago O'Hare Intl to Grand Cayman

Scores according to KAYAK customer reviews

8.1
JetBlue
Overall score based on 19,290 reviews
8.3
Boarding
8.2
Comfort
8.6
Crew
7.9
Entertainment
7.8
Food
Airline reviews

Pros: "Seat space for each passenger"

Pros: "crew was supportive. wifi in the flight"
Cons: "the wait time and the boarding, off boarding of the flight. No electricity in the aircraft."

Pros: "Nothing!"
Cons: "IT WAS TWO BOURS LATE!"

Pros: "More leg room Affordable prices Snacks dunkin donut coffee Pleasant flight attendant Punctuality"
Cons: "Nothing"

Pros: "This flight is 3 + hours delayed, and I think it’s because Jet Blue didn’t have a full flight for the 8:30 am departure, this is unacceptable and I need to be compensated for my time Winston White"
Cons: "This flight is 3 + hours delayed, and I think it’s because Jet Blue didn’t have a full flight for the 8:30 am departure, this is unacceptable and I need to be compensated for my time Winston White"

Pros: "The crew talked a big game. They were ready for anything, including loss of cabin pressure, paid snacks, and even a water landing."
Cons: "No water landing! I was excited to float around on a hot day, go down an awesome slide, and catch some sick waves, but come on people, we never even got a chance!"

Cons: "could not make it in time. Then we got on plane and pilot said it was an electrical problem on the flight but the generators were now up and at em again. Very hair raising ride for me - got in at 2:30 am with another hour to drive home - and I lost a LOT of confidence which I have always had in Jet Blue. I hope this is not the future we can expect with you"

Pros: "How easy it was to board"
Cons: "When I asked if there was any chance I could sit with my family they were nice enough to change are setting. Just a thought if the setting is random when you check in for your flight somewhere the computer should at least work with putting the last names together just a thought."

Pros: "The crews were very friendly A lot of options from direct tv and other entertainment programs The seats were wide enough Free Wifi"
Cons: "The plane got 2 hours delayed The screen was too small There was no charger on the plane Food option was limited"

Pros: "Entertainment, food, crew, and cleanliness were 100000% on point. Loved it."
Cons: "Turbulence and the flight was longer than necessary because we had to go around bad weather. Not the fault of JetBlue!"

Pros: "Cheerful, efficient service. No hidden costs. Free gate to gate WiFi. Comfortable seats. Never flown them before and they are now at the top of my list."
Cons: "Nothing yet."

Pros: "The seats were comfortable."
Cons: "Flight was very late leaving Chicago. We sat on the plane for quite a while (over 30 min) shut up tight with little air circulation AND no information about why we were not leaving the gate. Flight crew were not very friendly - almost "marched" up and down the aisle and barked at people."

Pros: "Adequate leg room and ability to take a carry on we if your extra charge"

Pros: "Easy boarding, friendly staff, nice choice of snacks and beverages. The JetBlue app is very useful."
Cons: "My in flight entertainment never worked. All I had available to look at was the JetBlue commercial channel showing me all of the entertainment I wasn’t able to watch. Not even the live view map worked. One of the attendants said something about resetting the system but I didn’t notice a change. I said something to one of the attendants a little later and she tried doing a reset again, but still no success. I could see other screens working fine and people were watching various programs while I just stared at a static map of the continental United States. Oh well, at least I was able to stream Netflix because of the free inflight WiFi."

Pros: "comfortable seats TV great beverages--actually get can or bottle"
Cons: "when we checked it, did not put us together"

Cons: "The flight was delayed and we would have missed our connection in NYC. So we had to cancel the trip."

Pros: "Good snacks, entertainment and excellent WiFi. Boarding was efficient and seats were comfortable."

Cons: "We arrived later for almost 2 hours"

Pros: "Per usual crew and plan itself were nice"
Cons: "Flight was delayed about 3 hours from scheduled take off"

Cons: "my flight was delayed for 2 hours and there was no compensation for it"

Pros: "Our flight attendant Jeramy was FABULOUS!!"

Pros: "The comfort of the seats are amazing. I was able to sleep through almost all of the flight."

Pros: "Bring her own earphones as then u can listen to their varied entertainment channels. Gave free snacks & there was quite an assortment so I wasn’t stuck w pretzels again. Free soft drinks; nice flight attendants & smooth ride from Chicago to NY"

Pros: "No gate, waited 2 hours in plane"

Cons: "Late boarding with little communication. Equipment failure delayed the flight after pushing from the gate. Additional delay of 10 mins one we got to the destination gate."

Pros: "Everything is ok"
Cons: "Not a thing"

Cons: "When I scanned my boarding pass the Jetblue staff member told me my carry on was too big and had to be checked. This was puzzling to me because I travel often and do not have a problem with that bag. As I was sitting on the plane I saw everyone's bag's were bigger especially the man next to me. His was significantly larger and he had a large duffle bag between his legs causing him to manspread into my area. and yet i was told "make sure your purse is under the seat" seriously?! What about his giant duffle bag and huge carry on roller?!"

Cons: "Flight was delayed by over an hour and we never got an explanation as to why. Just an apology from the pilot once we finally took off."

Pros: "Captain and crew"
Cons: "Luggage handling"

Pros: "You took great care of my wife who needed a wheelchair. the flight itself was delayed due to weather. I totally understand. I love the extra legroom"

Cons: "Movies didn't work and we were one hour delayed on the runway."

Pros: "The only good things about this flight were: - The crew at the gate were very friendly and attentive - We arrived safely without incident"
Cons: "We were delayed 2 times before boarding. We were delayed 1 more time while on the plane. The pilot told us there was equipment trouble that had been fixed, but there was paperwork to fill out and it would only be a few minutes...and then radio silence for 30 minutes before pulling back. The flight attendants rushed through the pre-flight announcents and I could only understand about 60% of it due to speed, volume and accent. Despite asking me for my drink order, it never came...and I only heard a few soda cans pop open at all. Did they just decide not to serve us? She even gave me a napkin for it. Luckily when they put the snack basket in front of me, there was a tiny bottle of water, which I grabbed...little did I know, that was all I would get. The flight attendants were just tapping in the back of the plane the rest of the flight. They didn’t even bother collecting garbage until we were on final approach. They also never did the normal checks before landing."

Cons: "flight was delayed 2 hours :("

Pros: "Crew was happy and friendly"
Cons: "Can’t think of anything"

Pros: "They refund me the money"
Cons: "I almost lost my international connection, had to pay double to get my destination on time"

Pros: "Ez check in with kiosk"
Cons: "I would like to see an organic food option, even with a fee if necessary. Recommendation, fruit like banana or apple. Certified organic."

Pros: "Boarding system efficient. Lots of leg room. Choice of snacks. Good service."

Pros: "Entertainment on board"
Cons: "My flights was delayed"

Pros: "Gave me my refund!"
Cons: "Flight was delayed 5 times without sufficient reason. Weather was clear. Had to ask for a refund after the 6th delay. Missed an important event."

Pros: "Extra leg room"
Cons: "On both legs of our vacation, going and coming we experienced long delays , 2 hours Boston.to Vhicago and 3 hours Chicago to Boston"

Pros: "This was my first time with JetBlue and I was pleasantly surprised with the size of the plane. It was pretty comfortable"

Pros: "Friendly staff and the on board entertainment and snacks"
Cons: "The last time I took JetBlue the flight was delayed by almost 3 hours"

Cons: "Both ways my flight was significantly delayed. Although Jet Blue sent me notices, none of those came before I was on my way to the airport."

Pros: "L.L Bean crew was amazing!! The tv channels and movies!!"

Pros: "the plane was good!"
Cons: "the plane boarded late"

Pros: "Crew was great. Captain provided lots of updates and provided useful site information prior to landing"
Cons: "TV kept on blacking out"

Pros: "The staff is great, the seats are comfortable, and the food is good"

Pros: "Very helpful customer service, really appreciate their help."
Cons: "I took two JetBlue flights within 4 days, both with delays > 2 hr for mechanical issues. I can count on one hand the number of times I've been significantly delayed in the past 5 years, especially when not in the winter. JetBlue, please fix whatever is wrong with your planes. I've otherwise had nothing but positive experiences with them."

Pros: "Nothing to like. Got to destination 3 hours late each way."
Cons: "No apparent reason for delays except poor planning and inefficiency."

Pros: "Everything was great. Easy boarding great comfortable seating and friendly efficient stewardship"

Cons: "Boarding was a little chaotic. Could have been more organized."

Pros: "staff was amazing, entertainment great, dasani sparkling lime water tasty, very clean and reasonably comfortable"
Cons: "the breakfast was made of 90% sugar - this was very disappointing."

Pros: "Everything was on time!"

Pros: "I got the vegetarian meal I asked for."
Cons: "Flight was delayed, because of the boarding process with immigration"

Pros: "This flight left about 90 minutes late again due to weather issues. The crew was excellent which made this long flight enjoyable."

Pros: "Staff extremely friendly and helpful"
Cons: "Old plane with no individual tv screens!!! Didn't know these planes still existed!"

Pros: "Extra blanket and pillow. Empty seat to sleep in. Fairly clean interior for the most part."

Pros: "Flight attendants were nice"
Cons: "The seats were incredibly uncomfortable. There was no leg room and 122 of the space below the seat in front of me was taken up by a metal box attached to the seat. I couldn't put both feet under the seat in front of me. The food was bad tasting and overly processed. We were fed a lean cuisine. The entertainment was from mounted tv's in the aisle. At this point, all planes crossing the ocean should have individual tvs for a customer to watch. They had this 15 years ago, how do they not have it now."

Pros: "All good! Nice staff. Easy travel."

Pros: "The crew was very efficient and friendly while handling everyone. Flight was smooth, food was good. I went to the wrong terminal and did not know that the advertised finair flight was actually American Airlines, the AA ticket counter attendant went all out to make sure I made it to the gate. All this with less than an hour before departure."
Cons: "I went to the wrong terminal, the email ticket had finair in large print and in smaller print indicated American. Luckily I was able to literally run and make my flight. Would be better to more clearly indicate actual airline."

Cons: "Small seats, no wifi, no chargers, terrible entertainment."

Pros: "Once we got on the plane, everything was pretty standard"
Cons: "Flight was delayed 5 hours."

Pros: "The staff were fine and boarding went relatively smoothly."
Cons: "The plane was dated and small. There were no individual screens for entertainment. I've flown internationally with American before and felt this specific experience was worse."

Cons: "This made the check in process extremely frustrating and confusing. Traveling with my elderly dad who had to squeeze between two large men for 7 hours because people who actually booked the airline got priority seating. We had to pay an extra $500 to upgrade to comfortable seats. Not pleased w Kayak."

Pros: "I did not have a seat! Waiting for people to give up their seats!"

Cons: "Poor entertainment, wifi option. Overhead lighting was on entire flight. AA flight attendants were over it. A bad experience"

Cons: "Old plane with no plug-ins and outdated media."

Pros: "it was a reasonably priced flight, so I guess having to put up with the delay and a cramped plane is what you should expect"
Cons: "the fact that we were delayed for over 3 hours (mechanical? then switched plane). The plane itself was really cramped - I realize you have to put up with that on domestic flights, but international, really??? American should figure out other ways to cut costs."

Pros: "finally made it to our destination"
Cons: "our flight was delayed 3 hours, they finally changed planes, and the one we took for a trans-Atlantic flight was cramped, poor service on the plane, all-in-all an uncomfortable flight - I've had much better on other carriers, and won't be likely to use American Airlines again :("

Pros: "Not much to like, plus we were late"
Cons: "Seats were uncomfortable, no in-seat or personalized entertainment."

Pros: "Staff on the plane were nice."
Cons: "5 hour delay, fear of cancellation ruining a trip planned for years, not feeling we were told what was happening, series of delays extending decision time, unappetizing sandwiches during delay."

Pros: "An agent found me a window seat for the Chicago-Barcelona leg of the trip with extra leg room. That was amazing. Also, the lost luggage assistant for American Airlines was super helpful and nice. Also, the 787 (I think that was the Chicago-Barcelona craft) was a very enjoyable airplane. It was super smooth. It had high tech windows that adjusted the amount or type of light that could filter through the windows depending on the settings."
Cons: "When I arrived in Barcelona my Bag went missing. It showed up an two hours after my flight landed."

Pros: "Nice head rest (although it did not stay bent at angle, so could actually rest against it)."
Cons: "Think it is ridiculous that I had to pay so much to select a seat ahead of time, and it was just a regular seat. I can understand for extra legroom or exit row, but for a regular seat, that is ridiculous. Then there was a fee to change priority boarding, so I could ensure I was able to have my carry-on with me, instead of risk having it go underneath."

Pros: "Free alcohol and good passenger friends and friendly service."
Cons: "No outlets for phones"

Pros: "Food on time. Good Food. Good Entertainment like watching movies. Top priority for Diabetes or any other patients."
Cons: "Little guidelines for new comers especially while changing the flights."

Pros: "Flight was on time. Smooth flight."
Cons: "In flight entertainment was below expectations"

Pros: "The American Air crew was great very attentive and they pass out free drinks"
Cons: "The 787 is tight and when the fight is 7 plus hours it tends to ware on you"

Pros: "All the movies"
Cons: "Legroom"

Pros: "Very nice plane with a good entertainment system."
Cons: "The flight attendants seemed almost angry. Banging trays,. bumping carts into nearly every row and even skipping some rows on drink service."

Cons: "The flight left almost 6 hours late, and the delay was not directly due to weather. Another flight from and to the same airports left as scheduled 3 hours before this one finally left."

Pros: "The crew were exceptionally friendly and helpful. They made the negatives about the flight much more bearably be their excellence service whether during boarding, in flight, or after landing."
Cons: "I booked the flight originally through british airways and expected your standard, modern plane for cross atlantic travel. Boarding to find myself on a 767 designed (and likely built) in the 80s was rather disappointing."

Cons: "Could not read paper when passenger in front reclined seat. No space between rows."

Pros: "Crew was excellent but it was literally the most uncomfortable plane ride I have ever been. There was even an empty seat in the middle and I couldn't sleep at all. The seats were super shOrr and the headrests sucked"

Cons: "My flight was actually processed under American Airlines. Oddly, the confirmation email stated it was Finnair."

Pros: "On time"
Cons: "Cramped seats. Entertainment system outdated"

Pros: "Efficient boarding. Plane clean. Seats lean back far but that being said the individual in front of you ends up in your lap."
Cons: "As night went on a couple of the flight attendants in the premium cabin seats with standard legroom appeared grumpy and short with patrons. No gluten free options. In flight entertainment and reading lights not working for my dad or I. A long flight for that to be out."

Cons: "Plane was too old, flight attendants were rude"

Pros: "The departure time. This left enough time to get to the airport and go through security without rushing!"
Cons: "Sitting in the middle Paying for luggage ( I wish Southwest flew out of ORD)"

Cons: "No complaints."

Cons: "Boarding seemed extremely unorganized. Crew skipped group 2 when calling groups to board, resulting in a mad rush."

Cons: "Due to two flight delays, I traveled an additional 24 hours, on top of my 20 hour original flight. Albuquerque Airline staff were rude, dismissive, incompetent, and each individual I spoke with gave me wildly differing information. The two delays (leading to approximately 48 hours of travel) would have been stressful enough, but the callous, ignorant and unprofessional attitudes of American Airlines staff (and staff in general at Chicago O'Hare Airport) really disappointed me. This was even more striking compared with the professional service I received from British Airways (from whom I purchased the tickets). I was ashamed that my country could lag so far behind in terms of basic customer service and problem solving."

Cons: "Requested for wheelchair assistance but none provided?!!"

Pros: "Seats had enough room. Inhad been worred they'd be too close since iwas the middle of a 5 person row."
Cons: "The boarding was terirble. We were over and hr late take off and it was very hot boarding and it took a long time. Also the air was so dry i got a nose bleed."

Pros: "I was served breakfast and lunch/dinner"
Cons: "Trying to sleep in an airport is near impossible"

Pros: "Timing and transit time was excellent"

Pros: "Everything."
Cons: "Nothing."

Cons: "Food was horribe and no dedicated tv per seat"

Cons: "They cancelled the flight and put me to fly the next day"

Cons: "overcharges"

Read more about JetBlue

Book cheap flights from Chicago O'Hare Airport to Grand Cayman

Recent round-trip flight deals

2/23
Tue
1 stop
JetBlue
7h 02m
ORD - GCM
2/27
Sat
1 stop
JetBlue
10h 14m
GCM - ORD
4/2
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JetBlue
7h 02m
ORD - GCM
4/7
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JetBlue
10h 14m
GCM - ORD
4/5
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JetBlue
7h 02m
ORD - GCM
4/7
Wed
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JetBlue
10h 14m
GCM - ORD
2/11
Thu
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JetBlue
7h 06m
ORD - GCM
2/15
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JetBlue
9h 21m
GCM - ORD
2/20
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JetBlue
7h 06m
ORD - GCM
3/1
Mon
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JetBlue
10h 14m
GCM - ORD
4/2
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JetBlue
7h 02m
ORD - GCM
4/12
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JetBlue
10h 14m
GCM - ORD
4/5
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JetBlue
7h 02m
ORD - GCM
4/12
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JetBlue
10h 14m
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2/11
Thu
3 stops
Multiple Airlines
40h 56m
ORD - GCM
2/15
Mon
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Multiple Airlines
13h 02m
GCM - ORD
2/11
Thu
2 stops
Multiple Airlines
30h 24m
ORD - GCM
2/15
Mon
1 stop
Multiple Airlines
13h 02m
GCM - ORD
2/27
Sat
1 stop
Multiple Airlines
7h 02m
ORD - GCM
3/6
Sat
nonstop
Multiple Airlines
4h 22m
GCM - ORD
3/21
Sun
1 stop
Multiple Airlines
7h 02m
ORD - GCM
3/28
Sun
nonstop
Multiple Airlines
4h 05m
GCM - ORD
4/2
Fri
1 stop
JetBlue
7h 02m
ORD - GCM
4/8
Thu
1 stop
JetBlue
10h 14m
GCM - ORD
2/27
Sat
1 stop
Multiple Airlines
7h 02m
ORD - GCM
3/6
Sat
1 stop
Multiple Airlines
8h 06m
GCM - ORD
3/21
Sun
1 stop
Multiple Airlines
7h 02m
ORD - GCM
3/28
Sun
1 stop
Multiple Airlines
8h 03m
GCM - ORD
3/13
Sat
1 stop
Multiple Airlines
7h 02m
ORD - GCM
3/20
Sat
nonstop
Multiple Airlines
4h 22m
GCM - ORD
2/3
Wed
3 stops
Multiple Airlines
32h 40m
ORD - GCM
2/7
Sun
1 stop
Multiple Airlines
26h 19m
GCM - ORD
4/2
Fri
1 stop
Multiple Airlines
7h 02m
ORD - GCM
4/11
Sun
nonstop
Multiple Airlines
4h 05m
GCM - ORD
4/5
Mon
1 stop
JetBlue
7h 02m
ORD - GCM
4/10
Sat
1 stop
JetBlue
10h 14m
GCM - ORD
3/13
Sat
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Multiple Airlines
7h 02m
ORD - GCM
3/20
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Multiple Airlines
6h 07m
GCM - ORD
4/3
Sat
1 stop
JetBlue
7h 02m
ORD - GCM
4/12
Mon
1 stop
JetBlue
10h 14m
GCM - ORD
Show more results

Recent one-way flight deals

12/19
Sat
1 stop
Multiple Airlines
8h 48m
ORD - GCM
12/19
Sat
2 stops
American Airlines
18h 46m
ORD - GCM

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