Find cheap flights from Chicago to the Cayman Islands

Find cheap flights from Chicago to the Cayman Islands

Search hundreds of travel sites at once for deals on flights to the Cayman Islands. Bundle your flight + hotel and save!

Round-trip
Economy
Chicago (CHI)
Cayman Islands
Thu 9/23
Thu 9/30
Any month
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Good to know

Low season

SeptemberBest time to beat the crowds with an average 4% drop in price.

High season

DecemberMost popular time to fly with an average 9% increase in price.

Average price round-trip

$839(avg. price over the last 2 weeks)

Good deal round-trip

$388or less

Good deal one-way

$172or less

Top tips for finding cheap flights to the Cayman Islands

  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be January, November and December. The cheapest month to fly to the Cayman Islands is March.

FAQs - booking Cayman Islands flights

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Top 3 airlines serving from Chicago to the Cayman Islands

Scores according to KAYAK customer reviews

7.3
British Airways
Overall score based on 23,012 reviews
7.5
Boarding
7.2
Comfort
7.9
Crew
6.9
Entertainment
6.8
Food
Airline reviews

"The best thing was that the flight was not full. My 10y.o. was able to sleep over 3 seats. The timing was great too, the plane was leaving Chicago at 8:50 pm. That was a perfect schedule to settle down and go to sleep."

Pros: "Crew had filled overhead lockers with their bags leaving no room for ours"

Cons: "The cabin lights were left on too long for a red eye. Cramped quarters - but that is true of every airline now. We did receive a blanket and pilllow, which was nice. Did not have dinner so can’t comment. Croissant with cream cheese prior to landing was OK Nice smooth flight.Nice pleasant crew"

Cons: "Waited for over an hour for trams to retrieve us from the aircraft."

Cons: "Don’t approach"

Pros: "Service was good on the plane"
Cons: "Thought I had purchased an optima coach, but was forced to pay $60 baggage fee. At checkin, asked for aisle seat, but agent had already assigned a middle seat. Then asked to change to an aisle seat, but she demanded $30 to change. Aftwr boarding was complete, there were at least 6 aisle seats empt"

Pros: "Friendly crew,"
Cons: "Nothing"

Pros: "Punctuality!"

Pros: "The crew was friendly. The boarding process was very organized."
Cons: "The seat and entertainment were terrible. The TV worked only in the last hour and the seat was not comfortable. No leg room, and the passenger in front of me wasn't considerate -- I couldn't move in my chain when his chair was down)."

Pros: "On time"
Cons: "Better more comfortable seats"

Pros: "I loved the in flight service and entertainment. Also, the flight had seats that actually reclined and I was able to sleep."
Cons: "I did not like switching airlines between my flights. It caused a lot of confusion and made check in extremely difficult. In addition, my bag was lost between changing companies between flights. Not happy at all."

Pros: "Typical solid British Airways service."
Cons: "Delayd by 4 hours."

Cons: "Seat in row ahead was broken, causing it to recline too far and not correctly return upright"

Pros: "When we finally took off."
Cons: "Flight was delayed >3.5 hours because of an "electrical problem affecting in-flight entertainment system and 1st and Business Class seats. After powering down the aircraft c. 3 times at 11:15pm CT the electrical system miraculously worked as normal."

Pros: "Very comfortable"
Cons: "Good food"

Pros: "At least we were able to wait in the lounge."
Cons: "One of the jet bridges malfunctioned. Had to board >500 passengers via remaining bridge. An hour late departing."

Pros: "Priority boarding and bulkhead seating for family travelling with infant."
Cons: "My 'infant on lap' (23 months old) was too big for the airline-provided seat (weight limit 12.5kg, and he weighed 13kg)."

Pros: "Pilot was nice"
Cons: "The chaos boarding, unorganized crew, missing our transfer flight and not given options to book differently"

Cons: "The airline sent me on a wild goose chase through the airport only to end up back at the same counter. They then told me it was too late to check in. Do not book tickets with cheapoair-British Airlines said this releasesthem from all responsibilities and cheapoair will do nothing but send you to different people trying to sell you another flight. It was the worst experience every!"

Pros: "Food was decent and it was nice to have all drinks included (but after the first one you had to go to the galley to get a drink)."
Cons: "Definitely an older plane with very narrow seats and very little legroom compared to other long haul flights that I have been on. They only delivered drinks once and then if you wanted any more you had to climb over people and go to the galley to obtaining yourself. Plane was also very warm so it was hard to get comfortable and there was not much airflow to cool you off."

Pros: "The food, entertainment, and service was superb! Very easy to overlook how late the flight was. I appreciated the blanket and other items provided!"
Cons: "After a week, I still do not have my luggage. This is due to the flight being delayed 2 hours and I do not know why it was delayed. Because it was delayed, I missed my connecting flight."

Pros: "Good entertainment. More comfortable. The ride was smooth."
Cons: "Service. Having to ask for my food being skipped and also having food choices."

Cons: "Flight crew was just ok; nothing they did made me want to fly with British Airways again. Salad was good but the chicken nondescript."

Pros: "Excellent vegan meal selection!"
Cons: "No Wifi, average movie selection, cramped space, 2+ hour delay (half of which was spent sitting on plane)."

Pros: "smooth flight"
Cons: "no dairy free food options"

Pros: "Everything was great! Good food and service. On time flight. No complaints!"

Cons: "no air vents over seats"

Pros: "Nothing"
Cons: "Fight was delayed 30 minutes so we missed our connecting flight to Madrid. We are stuck in London for the night, the food is not edible at the hotel they gave us and now we are stuck rearranging all of our future travel plans because we can't get to Madrid until tomorrow. This is our worst travel experience ever. We will never fly British Airways again."

Pros: "So glad you do not charge for a blanket like so many airline bed (Norwegian Air for example). Staff on BA tend to be professional and low key eg quiet on long haul evening flights. It allows passengers to sleep."
Cons: "I appreciate economy is the low end but now realise I should eat before boarding or bring my own food. Apart from the salad, it was inedible."

Pros: "Timeliness"
Cons: "Food and service could be better."

Pros: "The women at BA in Chicago O'Hare airport were awesome Christine, Carole, Diane & ankther one but I forgot the last lady's name. Very polite attentive and professional. We had a difficult situation & they helped us get through our problem with the less stress as possible!"
Cons: "Airplane food was a bit below average. Also there was not a good selection in music. I did not recognize 95% of the option of music to listen to."

Pros: "Nice aircraft and nice flight overall!"
Cons: "I had reserved the 2 back seats of the aircraft--a row of only those 2 seats--so I could sleep against the window and my husband would still have the legroom he needs. Unfortunately those seats on the actual aircraft ended up being in a 3 seat row and getting a window seat and middle seat. Having booked the flight 8+ months prior, we were disappointed that we had less comfortable seats than originally reserved."

Pros: "The check-in process at the airport in Chicago was efficient and the person who helped us was friendly"
Cons: "-I was unable to check-in online and I think it's because my name got messed up in the reservation system even though I entered it correctly -Compared to other airlines, BA does not stop by frequently to offer beverages. Food and beverage service provided by BA faded in comparison to what was provided by American Airlines on the way back. - Our flight was delayed due to weather, but we also sat in the plane for a long period of time with no explanation. -We appreciated that BA automatically re-booked us on another flight (although it was not the next flight), and provided 2 meal tickets for 10 euro each. There was no other compensation for the incurred delay (about 2.5 hours)"

Pros: "Entertainment system"
Cons: "The width of the seats in economy are so narrow they don't fit my back. I am not a fat person. 6 feet 170 lbs and fit. No legroom and the tray table is not deep enough to support the food tray. Breakfast after an 8 hour flight consisted of a Kellogg's snack bar in a wrapper. I am used to Southwest Airlines which allows more than one peanut bag so I took two breakfast bars and the stewardess scolded me and said only one and made me return my extra. Not everyone in my roll even took a bar. They treat you like dirt in coach."

Pros: "Flight attendants really are nice folks"
Cons: "1. Bought ticket via kayak chicago to prague, so I got outgoing trip on British airways but they codeshare it out to Aer Lingus. Unfortunately, these dumbos haven't figured out that no matter what the gyrations they do, I still want to be able to pick my seat beforehand. Nada. Not possible online. And forget calling aer lingus 800 number. called twice and was on hold for 30 min each time, they dont bother answering. 2. At airport, I was willing to pay extra for a good seat because of the issues above, so they said they would help me out. Ha - the manager who purportedly was helping me out gave me a seat up front next to a shrieking infant and behind a bassinet (he knew exactly what he was doing but didnt care). They really lie and think we're idiots. 3. Same thing for flight from dublin to prague. This time last row next to toliets Dont fly aer lingus if you dont book directly with them, same for british airways I looked at BA's website - they do let you book a seat in advance but you must pay something for every single seat. Crazy. There are no free seats"

Pros: "Got me there"
Cons: "Basic"

Pros: "New plane, very comfortable seating. The headphones in biz class were awesome, forgot I was on the plane. Overall best American Airlines flight and I do fly them a lot. Also liked the dual screens option."
Cons: "The seat control in the touch pad - not conveniently placed"

Pros: "NOTHING!"
Cons: "I had been waiting a few hours for my next connecting flight ant at about 8:00 pm (45 minutes before departure), they announce that our flight might be delayed do to mechanical problems on our plane. It took them 4 hours to fix it. Which was not too bad. What was bad is that they lied to us. Because I missed my connecting flight, they said that they would be waiting for us with our new flights and not to worry. When we arrived in London, we were scrambling to find out where to go. there was several families in front of me that missed their flights and they were having problems trying to re-book their flights. It took about 3/4 hours for me (one person) to re-book my London to Glasgow because I was stuck behind families. I was trying to explain one of BA employees that I (1 person) needed a flight to Glasgow. It was getting late and I was worried that I might miss the last flight of the day and would be stuck in London until the next day. She didn't like that I told her that and didn't want to help me. so it took me about 4 hours in line to get my flight and had to rush to get it. I had also purchased a window sit that I was not able to get. The guy that help me re-book my flight told me that I would have to call for that. Which I did now but the first phone # I called, the guy said that I had to call this other #. I called the # he gave me and a recording comes out that they are too backed up with calls and cannot help me to go to the website. At the website, they are asking for the flight # of the re-booked flight (I only have my original flight #'s on my email). I don't know what happened to the ticket they gave me to board the re-booked flight so I don't have it. I don't know where else to call about my refund and also think I deserve some kind of compensation for missing a day at both airports with horrible treatment and service. CAN YOU HELP ME ON HOW TO TALK TO A REPRESENTATIVE ABOUT MY REFUND AND SOME SORT OF COMPENSATION?"

Pros: "nothing-"
Cons: "I flew about 1 million miles and truly felt like a sardine- absolutely NO leg room and very archaic entertainment system. NEVER AGAIN !"

Cons: "Everything was great about this flight, except that I had a row of seats that would not allow the arm rest to go down. So even though I had 2 empty seats to my left I could not utilize them, which would have made the flight so much better. When asked I was told that the "curve" of the plane would not allow it. This should have been mentioned when I booked and chose those seats."

Cons: "The flight took off and 30 minutes into the flight to Paris, we were returned to Chicago for an unexplained mechanical problem. After 5 hrs delay, the flight was cancelled. I had to run to another desk for help and was rebooked on an Air France flight but did not receive miles for either BA or AF. Completely unprofessional and chaotic. Miserable to say the least because I missed the wedding that I was flying to, the only reason I flew there!"

Pros: "Nothing"
Cons: "Worst flight ever! Crew very unprofessional. The plane was filthy and most seats did not recline. It was a night flight but they were unable to turn the lights off. We took off almost an hour later because they did not have ice nor snacks."

Pros: "Nice large plane that wasn't near capacity."
Cons: "Long delay with minimal compensation. Gave us a rebooked connection that we had near zero chance of making."

Cons: "It was extremely hot on the plane. for the first 30 minutes there was no ac available and there was little to no help from the staff. I asked for water to cool myself down and ov waited about ten minutes to get it after hitting my help button multiple times. The flight attendants may have been overwhelmed with the requests as there were many just like me who struggled so they came off very rude. The plane was also not updated at all - not personal entertainment and once again, no ac/air for people to control."

Pros: "Saved 5 hours by being changed to a non-stop for the same fee."
Cons: "Working with Iberia to get accessible seating took ten irritating phone calls."

Cons: "The flight was awful! Boarding was unorganized. Once on the plane, space was TIGHT! I have flown with Iberia before and had leg room and TVs behind the chairs. This was not like this. Seats were uncomfortable for an 8 hour flight, smelly, and flimsy. I have never been more uncomfortable. The crew were nice but one was very rude to a passenger snapping at him and all ignored a very drunk man on my flight as much as possible. This man was very disruptive for most of the flight singing, shaking seats, touching other passengers, and walking about the flight. I did not feel safe at all! The staff would tell him to sit down, walk away, and he would be instantly back up. Staff would see this and ignore. I had no idea what to do. I felt unsupported and unsafe. The flight had constant turbalence to go along with it. To the point that they canceled dinner. I wanted to kiss the ground when I got off the flight. This was absolutely miserable. I could not be more disappointed."

Pros: "A lot of people in close proximity. Very good service and food. It worked well."
Cons: "The flight was great but found out night before when I checked to confirm flights that ours were cancelled without notification. We booked through Kayak so not sure what happened. PANIC for sure but a great service provider spent an hour on the phone with me to make sure we made it."

Cons: "seats in World Traveller are the worst. I've never felt so painful sitting in an airplane seat. The curve of the seat makes it so that one must crane their neck the entire trip. The headrest sticks out a lot, further contributing to this problem. Anyone with half decent posture is going to have a bad time in these seats. I saw the club world seats while exiting the plane and wanted to cry,"

Pros: "I really liked how it was just one flight and no lay overs, the crew was very nice, and the food was good."
Cons: "It was very late and delayed."

"I need to go back to waterloo this week"

"From the moment I walked into the airport in Chicago to the moment I was walking off the plane in Florida I had an unforgettable experience! I was traveling with my 3 month old by myself and everyone just made sure I was taken care of. I couldn’t thank them enough!"

"There was no entertainment and again, the seats were very cramped and uncomfortable."

"I left my phone in seat 6C or B where I sat with my husband. The lady with the oxygen tank needed help coming back from the bathroom as we were ready to land. We stopped the movie we were watching on my phone to help her and I guess I forgot it. Please, please return my phone. Samsung note galaxy 20 ultra. It is on airplane mode. Thanks so much"

"Too busy trying to sell AA credit cards"

Pros: "The plane was really clean and they had lots of overhead storage."
Cons: "It was too crowded and cramped and UNCOMFORTABLE and there was a REALLY LOUD kid that would not shut up and nothing was done about it."

Cons: "On time take off would be nice"

Cons: "The Terminal in Chicago had no open amenities and overcrowded."

Pros: "The plane is amazing and the crew was very nice and helpful"
Cons: "Everything was all good."

Cons: "We didn’t even have a pilot, had to call and find one because our pilot that was scheduled “forgot to call in sick”. We were already delayed by 4 hrs so this made it delayed by an hour more!"

Pros: "Glad we made it back."
Cons: "Flight could have been on time. Attendants in the airline could have communicated much better to give update on delay, but they did not give any information despite several times getting up to ask questions at the main check-in. Many of the passengers were very discouraged. Plane left nearly 2 hours late due to an unclear maintenance issue, paperwork and also no fuel put in the plane until all passengers we on board."

Cons: "Change your fist class cabin. If we’re paying that much for a 4 hour flight we should be in a better cabin. The flight from Lax to O’Hare was great but the plane coming back is old and ragged"

Pros: "Fell asleep"
Cons: "Nothing"

Pros: "I like the ability to watch movies"
Cons: "The cabin was hot... air didn’t blow well... the crew was abrasive and rude. I asked simple questions and got long explanations for no reason"

Pros: "Crew was excellent especially the first class attendant very attentive and always checking on you"
Cons: "The food needs to be back to normal for first class and also baggage is very slow almost over 30 min wait"

Pros: "The aircraft was very clean, neat and well maintained. The crew was friendly. Process of checked-in luggage was seamless and straightforward."
Cons: "I found the istructions on some restricted items to be confusing and contradictory between instructions at the airport, the AA website and the TSA website. The agent at the counter was well-informed, though, and it all ended up going well."

Pros: "Great crew"
Cons: "Nothing"

Pros: "Everything was how should be"
Cons: "I like how you are now."

Pros: "The fact that no one sat next to me believe me it was not a my choice there was just not a body to put in the seat"
Cons: "The staff was not friendly or say hello or goodbye"

Cons: "None of the USB outlets were working in isle 7 A-C"

Cons: "More comfortable seats you can sleep in"

Cons: "Leave a seat empty in the middle could be good for social distancing"

Pros: "Roomy, comfy seats. Thanks for the snack and bottle water provided during covid"
Cons: "Nothing really"

Cons: "Plane had to land in a different city due to inclement weather. Very disorganized process, huge traveling setback, never got my travel voucher."

Cons: "Made it a smaller flight. It was a lot of people on the plane! We could not practice social distancing"

Pros: "The crew were wonderful and understanding and good sports."
Cons: "There were problems as soon as the plane got to the gate. After the passengers got off the plane, the man at the counter came on the P.A and said it’ll be a few minutes, they’re catering the plane now from the back to the front. The flight crew still needed to get on a preform safety checks. He apologized again. Then it was 8:40, time to take off and we’re still waiting to even board. The man at the counter said again, thank you for your patience and relayed the same message, only this time the flight attendants were walking away from the gate. Around 9 some lady higher up told the man to announce that the flight crew had timed out and stand by crew was on the way to the gate, said sorry again. A little later the man says sorry, there’s a gate change. You’re going to K6 now. When we get to the new gate it’s almost 9:30pm and while we were all gathered at the gate, the flight crew that supposedly “timed out” showed up and proceeded to get on the plane. Passengers started getting mad and saying we were lied to and to just tell us the truth. Chicago PD started showing up. We finally got on the plane but it would be another 30 minutes before we moved because of issues getting our bags off the original plane. We ended up being almost 2 hours delayed."

Pros: "The crew serving the plane didn't look like they wanted to be there. Somewhat abrasive. The entertainment was poor and not very easy to access through your mobile, Iphone and Ipad. If you want to provide a better customer experience, equip all your planes with seats video screens. Passengers on a 4 to 5 hours flight don't want to have to figure out what do to watch a movie or TV. I don't fly American that often, but wanted to give it a try to see the difference between you and the other airlines. I have to say that on the return segment (ORD to SFO), I was not that impressed."
Cons: "See above"

Pros: "The crew skipped me for breakfast and i had to ask for food."
Cons: "The food was not very good. Bread rolls stale and inedible. The rest of the flight was good."

Pros: "Nothing"
Cons: "The cliff notes of this debacle are, inbound flight arrived late to Montreal, I contacted AA social media team to make sure they could notify the gate of my connecting flight, they didn’t after they said they did. Flight arrived in Chicago a little early, I have to wait 15 min for my bags from the valet, I run to the next gate and arrive with 13 min to spare, the gate agent (not nice) goes I’m sorry we already closed the door. I’m like, huh? Then he has the gall to tell me, “well had someone called us we could of held your seat”. That’s when I lost it. Needless to say I’m now flying to Dayton and back to Dallas. That’s in lieu of a 3:50 PM flight TOMORROW!"

Pros: "Everything."
Cons: "Waiting for 30 minutes a Dublin to dock."

Pros: "Outbound, it was on time, plenty of legroom, plenty of good snacks, drinks and food. An enjoyable flight. Score 10.0"
Cons: "Return flight - The flight departed 4 hours late. The seating was so cramped my husband couldn't move his legs at all, never mind try to sleep. The staff members were not smart in appearance, some with long untidy hair, and did not interact with passengers except to hand out food. The food was reasonable. We disembarked feeling like wrecks. Score 2.0"

Cons: "Our last 6 flights have all been changed or delayed significantly. Then they loose our bags on a direct flight. Won’t fly America airlines again!"

Cons: "The flight was delayed. The food was not great. There is not a lot of space in these planes, and it was a long flight. There is no power supply."

Pros: "Eventually, the actual flight was fine."
Cons: "Initially delayed by 3hours (mechanical) which was American Eagle couldn’t get their “bucket of bolts” to Springfield, MO on time so we missed our flight out of Charlotte to Barcelona. Then we were rerouted through Chicago, but lost our first class seats and were bumped back to coach. This was after I had bought first class tickets for the entire trip only to be told 3 months before leaving that AA decided to switch planes on our domestic flight so there’s were no first class seats. THEN, in Chicago we tried to get first class seats on British Airways which would have been fine but After being sent to another terminal (after the bus to that terminal had stopped running) we were turned back because British Airways wouldn’t accept the boarding pass that AA had issued us. Now, having to go back to the first terminal to DISCUSS all this, we miss that flight and wind up stuck in Chicago for another 24 hours. Then, that flight was delayed by 3 hours, so we lost a day and a half of our vacation."

Pros: "I got here."
Cons: "Everything else. American cancelled my first flight from MSP to ORD. And when I got to Chicago, it cancelled my next flight to Nashville. The flight I managed to get on departed two hours late. There was no explanation for each of these cancellations/delays. There was virtually zero inclement weather anywhere, save for most of the country’s temperature being nearly equivalent to the surface of Neptune. And, the surly, clueless Chicago-based gate agent was the coupe de grace in my search for a reasonable explanation after which I waited impatiently for this episode to conclude. American get your act together."

Pros: "Nothing!"
Cons: "I was traveling today with my daughter, who is 6 months pregnant, my 3 1/2 & 18 month old grandsons, my husband & son-in law on an international flight from Chicago to Manchester. I was very disappointed a 757 was used for an international flight! No attempt was made by staff to accomodate our family with a extra seat for the infant, even though there were a large number of rows with empty middle seats (4 of which were directly behind them!) The 1st indication of the beginning of the NIGHTMARE was when the plane arrived in Chicago and overshot the gate, this caused almost an hour delay! (We heard our crew saying "oops" while looking out the window at the plane arriving & then again when they were discussing it would have been faster if the plane had used a different method to get to the gate again.) This was then followed by a mechanical problem with a frozen water valve, requiring us to be de-iced x2! Then we started to taxi out and again had to return because of a hydraulic problem that required repair. I think we were delayed almost 3.5 hours. The crew did bring a round of water during the onground delays, and offered free drinks later in the flight. The icing on the cake was not getting the stroller back at the gate because there were no baggage handlers. I can't tell you how much FUN that was trying to corral a toddler & 3yr old with all our carry-on bags while getting thru customs! Did I mention in our haste to get off that plane we overlooked my daughter's winter maternity coat in the overhead! May be time to switch to the Friendlier Skies of United for our UK travel!"

Cons: "American completely missed the mark. AA did not successfully change our reservation when the initial leg of our trip was delayed by an hour due to a fuel issue, which caused us to miss your connection in Chicago. Since American partners with Alaskan Airlines, American should have changed my reservations with regards to Alaska Airlines, but they failed to do that. I stood at the Alaskan Airlines counter as the plane left the gate with our empty seats because there was not a ticket. American Airlines did not change a reservation successfully and so although we had boarding passes with our names and seats and the flight number, the plane left without us. I was stranded and Seattle airport at midnight with a child and an infant with one diaper and one bottle left and it was a terrible experience with American Airlines. I do not recommend flying American they cannot get it together when problems happen with delays."

Pros: "The flight itself was fine"
Cons: "I bought the tickets together, but was informed at the ticket counter that i had only purchased tickets—not boarding passes. Boarding passes needed to be purchased by paying extra if my husband and I wanted to sit next to each other. I tried calling the customer service line through kayak and waited on hold for a long time with no indication of wait time. When the gate agent arrived, we asked and were moved to seats next to each other right away. The ticket agent at initial check in was very abrasive and non-solution oriented. if what she was saying was true— that we only paid for tickets and had to pay extra for boarding passes together— that was never made clear during the booking process. It’s unlikely I’ll use kayak again unless I know for sure what I’m buying."

Pros: "Nothing"
Cons: "I chose a package on the cheap flights that has a left hand side for choosing number of baggage which invariably inreases fare depending on the number of baggage and i choose 2 and paid for 2 baggage but the ticket came with 1 baggage and i contacted both by phone call, email and your website but did not get any fsvourable response. Had to pay again at the airport for the extra bag. This is highly unfair."

Pros: "The entertainment was good. Lots of choices. Food was about what I would expect for airline food."
Cons: "The seats were terrible. I don't know what it was about them, but I've never had a more uncomfortable flight. My husband had leg cramps for much of the flight and couldn't get comfortable. The rest of the flight was fine, but the uncomfortable seats were a huge minus. We'll probably try to avoid 787s from now on. The window-darkening system was annoying. They darkened the windows when it was dark outside and they darkened the cabin, so we couldn't look out the window. It was dark outside--why the need to darken the windows?? My husband requests window seats so he can look out the window."

Pros: "Flight was on time."

Pros: "It was on time. Crew were very good."
Cons: "Plane seemed very dated. No individual entertainment No USB chargers Not much space"

Cons: "The airline "randomly" selected me for extra security. Even though I have TSA pre-check I was jostled around, sent to multiple security lines without any reasoning and the local Chicago TSA and airport staff didn't seem to know what to do. Once it was figured out I was subjected to what was essentially a cavity search. Again I HAVE TSA-pre-check but apparently that means nothing if an airline flags you. It was an extremely upsetting experience but you were in a situation of either agree to the invasive search or get stranded over 1000 miles from home. I will NEVER fly Iberia again after a cancelled flight and being stranded in the wrong country on the way to my vacation and the horrible security experience on the way back. I seriously may never go to Chicago either after seeing the complete lack of organization and traumatizing personal invasion. I fly a lot for work and have never had such a horrible experience. I would really like to know how many terrorists are caught with these invasive searches and would love to know the justification for sticking your hands inside someone's pants and grabbing their privates after they have already gone through a metal detector AND the body scanner. Especially for someone who has already passed a federal background check to obtain pre-check status. Absolutely ridiculous."

Pros: "Seats quite comfortable. Crew ok."
Cons: "Pitiful food offering and no entertainment at all when on previous 1.5 hour AA flight choice of movies."

Pros: "I have nothing good to say about the flight to LA or the flight back to Chicago from LA."
Cons: "3 of the 4 flights were late, and the 4th was canceled. The canceled flight was due to weather, but AA's response was to connect those of us stranded with a 3rd party vendor - Travelliance - with the promise of a SUBSTANTIAL discount for a hotel (SINCE THE NEXT FLIGHT I WAS GIVEN WAS 17 HOURS LATER!) - and there was, effectively, NO DISCOUNT. I have spent thousands and thousands of dollars with you over the years, but this was a bucker of water in the face. I'm sure I'll fly with you again, but any sort of good will I held for AA is gone."

Pros: "we landed. flight was on time"
Cons: "Female flight attendants were rude. I think that if they would have smiled, their faces would have cracked. Even a complete stranger said to me, while waiting for the restroom, "I think that they hate us". One young male attendant was friendly and I believe that he was training. I fear for his training experience with this group of women. One of the lavatories was out of order {....on an international flight! Are you kidding!?!}. I think that they searched for the most antiquated plane that could limp across the ocean for this flight. Nine hours of pure discomfort. My poor 71 year old mother! Zero leg room. Tiny little screen for movies on the ceiling of the middle row. trays were not clean. We paid extra for our seats and wondered how bad the seats were for those that didn't. My mother and I determined that this was ranked as one of the worst flight experiences we have ever had. We are grateful for an amazing experience for our return flight or we would have reconsidered ever flying AA again."

Pros: "The water was clean"
Cons: "Everything else! We were first sold a British airlines flight, and then we got switched to American Airlines. I don't know if that is actually an okay thing for them to do. When we got onto to plane we were stuck on the runway for over 2 1/2 hours, where the outside temperature was 95 degrees and the AC in the plane didn't work. The delay was all due to a mechanical difficulty with the engine, this did not give us peace of mind when flying over the atlantic. while up in the air my newly wedded wife and I were hoping maybe we could watch a movie to help keep our minds off the creaking of the wings, the pool of sweat from the delay, and the grumpy flight attendants. Seeing as it was a 9 hour international flight, you would have expected some sort of entertainment. Maybe a personal TV.... nope. Maybe a community TV... nope. At least they have to have a radio....... nope. All we got were our two thumbs to twiddle. After a much needed nap. We woke up hoping maybe for a hot breakfast, but to put the cherry on top of some terrible ice cream, we got a mediocre cold breakfast. All in all I will not fly American Airlines again. I would happily and quickly pay double for any other airlines but them. It's such a poor reprisentation of our country."

Cons: "Dry / borderline rude staff and hostess. Dated plane. Tiny seats. But that is pretty much the baseline of airlines in the US. When will carriers start to take note from International carriers..leaps and bounds ahead."

Pros: "We arrived on time."
Cons: "I booked with British Airways and later noticed the plane was operated for American Airlines. The seats were cramped and the online entertainment was terrible. On an overseas flight, I expect in 2017 that there will be on-screen entertainment on the back of the seat in front of me. Instead, the movie was projected on a screen in the middle seats on an overhead that was about 10 rows away. Plus, you didn't get to pick your movie. You were stuck with the selections provided by the airline. I would have brought along my DVD player or laptop had I know this was going to happen. American flight crews are not as friendly and accommodating as European flight crews, which is why I try not to select an American carrier. Seats are less comfortable on American carriers also."

Cons: "My outbound flight to Manila had an overnight layover in Japan. I asked at the luggage check-in at O'Hare International Airport if they can check it all the way through as I had planned to go outside of the Narita airport for the layover. They told me I couldn't check the luggage all the way through and that I had to pick it up from baggage claim once I land in Narita. From there I had to check-in the luggage again on the same day. When I took my luggage out from baggage claim, I tried to check-in and the counter crew told me I was given wrong information. I had to keep my luggage with me until my flight the following day. On my return flight from Manila and another overnight layover in Narita, the check-in crew at NAIA told me I could check-in my luggage all the way through, and that they also allowed this at my outbound flight to Manila. The check-in crew at O'Hare International Airport gave me wrong information."

"Easy flight & quiet!"

"Boarding gate door was closed on connecting passengers and we missed this flight"

"Everyone was very helpfull with bording."

"Bad information from Kayak. unhelpful and confusing."

Pros: "Grew was amazing."

Pros: "Excellent experience & return flight on airbus plane was fantastic, reduced flight time by 1 hour. Great trip, thank you United Airlines"
Cons: "All great"

Pros: "Flight was quick and easy"
Cons: "Seats are small. Luckily the flight is short bit for anything longer than one hour I do not recommend this aircraft"

Pros: "Price line is better not thief like you yu take my money for nothing my husband not traveling your given me fake tickets . bring my money back on my account. am gonna take to court yu fukin beach.yubstolen my money"

Cons: "Multiple people on flight not wearing masks"

Cons: "No bad, easy"

Pros: "The boarding process was good. Departed on time and arrived on time."
Cons: "No social distancing of passengers on the plane yet there are empty rows of seats."

Pros: "One passenger was removed from the plane after 3 times he was warned about removing his mask before takeoff. Due to Covid19, United was boarding by row, from the rear to the front."
Cons: "When I made the original bookings, United was not allowing the middle site of the row to be used. Unfortunately, the plane was almost packed. 8 seats in the rear were empty."

Cons: "United Airlines in our experience runs late putting a lot of pressure on any ongoing connections . Not clean . Staff not friendly . Only sometimes helpful."

Pros: "Nothing, to be honest."
Cons: "Terrible boarding process (boarding groups one and two together for the first time, so even though we were group two priority, we did not get on until the middle of three and no overhead bin space left). There was no snack/beverage service. We did get a tiny bag of pretzels and were supposed to get either water or juice, but we never saw a beverage. Also, my seat's entertainment did not work. The worst was the HORRIBLE TINY ECON SEATS!!! Unless you are a child or a small woman/man, I would avoid this flight if at all possible. I have never been so uncomfortable on a flight, and I fly a dozen times a year for the last 25 years."

Pros: "I liked everything was excellent"
Cons: "There was a 10 minutes delay"

Pros: "Nothing!"
Cons: "Kayak sent me a message that our connecting flight out of O'Hare was boarding at gate B5. However, checking the monitors in the terminal showed the correct gate was B21, which is on the opposite end of the terminal. I don't know why Kayak had the wrong information on this. We barely made our connecting flight because our starting flight was over 30 minutes late, which was United's fault. This made rushing to the correct gate for our connecting flight all the more stressful. No time to stop at the bathrooms or pick up something to eat. Both United and Kayak let me down on getting back to Hartford. We arrived at the end of boarding with no room left for our bags in the overheads so we had to check them and pick them up at the carousel. A totally BAD flight experience."

Pros: "TV and movie choices should be according to 2018 instead of1980. Also TV should be from running Era"

Pros: "My trip started off with airplane problems from the beginning. From my flight being delayed multiple times by air china to the overly packed united to the confusion of the non updated confirmation numbers or the e-ticket number. Even on the day I left upon arriving to the airport my confirmation number they had just given me after all the prior problems still didn't work. Air china had mediocre food with okay entertainment except my headset jack on the TV was broke and I couldn't watch anything. On the last air china flight from Bejing to Bangkok. I couldn't even charge my phone, watch any entertainment and basically was just stuck with no WiFi. Justfly wouldn't compensate for the changes on their end and said I myself would have to ask the airlines for compensation which the.the airlines directed me no where for compensation or even to upgrade my seat. Now I'm finally in Thailand but I'm scared of my return."
Cons: "Everything was really not great. Air china had mediocre food that some of it wasn't bad but other was so so."

Pros: "Nothing"
Cons: "Pilot admitted error. They did not even know what was going on. 3 hours late due to last min maintenance after the plane had been on the ground since last night. No supervisor came even though we asked the captain to contact one. We were ignored. Total clusterfuck. Pilot was courteous and professional but front desk was Frazzled and incompetent. We were hugely inconvenienced and missed our obligations with no offer of compensation. Then when we finally get on the plane they kick us off!!!!!!!!!! Now they are saying a 630 departure for a 2 pm flight. This is beyond acceptable and I am about to call the local news and am sending them video of your gross incompetence. I want to be contacted at 815-527-1935 immediately. My time is valuable and no part of this delay is acceptable. I want full flight vouchers for this debacle"

Pros: "Captain and crew were brilliant, kept passengers informed throughout as to the delays, as a result all passengers were patient and understanding. Not much more could have been done to improve the experience as the snow and conditions at Dublin airport were out of their hands."

Pros: "My husband and i we want to seat next to each other"
Cons: "1) Chicago O'Hare Airport Airline staff very rude. 2) from Los Angeles to Chicago my husband and i are not sitting to each other. My husband is upset. 3) from Chicago to Los Angeles my husband and i are not sitting to each other. It happened again. Very disappointing. We think the airline doing this intentionally."

Pros: "The price was unreal so I had to jump on this, I was able to get on and off with my backpack no problem. The flights were good, captains were very communicative about times, expectations and when turbulence was present."
Cons: "The check in had to be done in person because of the need to check my bag size, I felt a little insulted that I would have to be checked on my honesty. When I got to the check in it was like watching a special forces team measuring and prodding peoples bags to get them in to the little box even when the shapes were the reason they couldn't fit, not the size of the bags. I literally watched someone fit their bag and the attendant take it out and make it misshaped for the box and show how it didn't slide in. I had no issues with my luggage, but that sucked to watch happen to others. The food and drinks came about 10 minutes before the plane landed."

Pros: "The crew The entertainment options The power options The drinks"
Cons: "10 minutes earlier and the food would have been better. Then again, 10 minutes earlier and wouldn’t have made flight."

Pros: "Crew help and service"
Cons: "Lending was bumpy. , Internet was not Working and no entertainment chenal as well"

Pros: "They got my vegetarian food order right"
Cons: "Old airplanes both there and back, we had a choice of a few movies on a TV that we couldn't access on demand so you had to start half way through, and the quality was appalling. We were supposedly promised we could stream onto our devices via wifi but this didn't happen"

Pros: "The flight crew was attentive and polite."
Cons: "Though not the fault of the crew or airlines, we were delayed almost 90 minutes because a parent took their toddler into the lavatory while at the gate and they messed it up and plugged the toilet with paper towels and/or pampers. This was after I had a 8-1/2 hour flight from Copenhagen, Denmark. Also, the seat space and amenities are so inferior to international flights. The narrowness of the seat and closeness of the rows makes it hard to be comfortable. After being treated to two meals on the international flight, one small two-inch bag of snack mix is almost pointless."

Pros: "It got us from a to b but not much more to be said!"
Cons: "The idea of the entertainment system broadcast to your hand held device is fine - it didn't work for me though."

Pros: "Helpful finding next flight worried can my son it UN traveled and is in a standby I pray he gets on this flight I am really worried. If he does he will arrive at 11:45 pm if not .... I have no clue he is so young and scARED TRACING ACROSS THE Whole country. For mistakes beyond his control saying prayers."
Cons: "I was tied to go tailgate 10 like my paper said they switched flights to gate 15 missed flight had to wait 7 extra hours flying Into Chicago and have a priority stand by pass from Chicago to Knoxville. I need to be on this flight so bad. If I dont make it i have no clue what i will Do. I need to keep my stress down and just prY i get on this flight which would have me i. Knox about 11:30 pm if not i have no clue what to do.the United Team we have talked to have been nice they just can't confirm my Chigaco flight to Knoxvile and i have 31 min. Once plane lands to get to other boarder term and Al."

Cons: "Such a downgrade from other airlines! Awful! They board backwards. Usually the back seats board on the plane after the special needs people. Makes more sense, people are out of the way. My water was poured into a cup from a big water battle. I like how Jetblue gives me a personal water bottle and a variety of snack option. I was given a "snack mix" on this flight which was not good. I hated this flight and there were NO televisions, or usb ports to charge phones. Never again. They didn't even have enough room for carry on bags for everyone. Thank god I packed light and didn't need to use that option. Good to know United Airlines has crappy everything."

Pros: "I liked that we arrived on time and that the entertainment actually worked properly."
Cons: "I didn't like the fact that my husband and i had one option only and that was Indian vegan vegetarian dish. We were told that's all there was left. We gave back our tray. I don't mind going without food for a flight but my husband had surgery die to diverticulitis and can only eat certain food. The flight attendant said that she was going to check if there is anything left in first class but it took for ever and I become impatient as the light were turned off and people were getting ready to sleep. So I switch on the light and another flight attendant came by. I explained the situation but she came back with the same Indian vegetarian dish we turned away. After more frustration and explanation the Stewart came with the. Hi Ken version. I gave my husband my share and he was able to finally take his medication and eat the chicken with the bread. I only ate the ice cream and had a glass of wine. Later on the first flight attendant who served us the meal came with a couple of oranges and a bag of chips. Saying she got this from first class. I kept the oranges and gave her back the chips. Floghing with United is very disappointing to put it mildly."

Pros: "There was a good entertainment system with a lot of new options."
Cons: "My itinerary said I fly on Brussels Airlines on a specific flight number. I went to the international terminal to discover it is not there. I then asked multiple aiport staff members if they heard of Brussels Airlines and they said they did not. One person said it may be terminal 1, so I went there based on very little information and with hopes it would be there. I got to terminal 1 to discover there is no Brussels Airlines. I walked to Lufthansa because my return flight is through them, but it was not there either. At this point I have 45 min to make it through security and board, and no one can tell me where Brussels Airlines is. The good news is the flight was delayed, and I got an email from United Airlines with the flight status. This is the first time I was contacted by United and there was a completly different flight number than the itinerary. United should be more clear on the airline and terminal information for international flights!"

Pros: "Nothing!!! It was handled in a terrible way"
Cons: "The way they didn't care"

Pros: "From what I encountered at the crack of dawn this morning... The staff handled somnolent, irratable passengers in a full capacity 757, with nothing but unwaivering efforts and kindness. (shrieking baby temper-tantrums, service dogs, and people allergic to service dogs included) Even while dealing with the most self-entitled, disappointingly inconsiderate individuals, the flight attendants kept their composure and remained understanding, professional and accomadating. As for that rude, pompous pig of a woman up in front.. try and remember we're all human here and you should attempt to treat others like so. I can't imagine the staff being particularly fond of the idea of spending an hour delay with your continuous, huffy bitching in their ear. (as if they have any control over the situation"
Cons: "Me and my boyfriend's seats were separated on both flights.. apparently it was in the fine print.. I don't know :/ kind of sleasey, kind of lame. Be transparent. Luckily, met a great guy who had no issues switching! :)"

Cons: "We reserved wheelchair assistance prior to the flight. We had to wait an extended amount of time to actually get the wheelchair assistance with 5 kids 7 and under. Due to the wait we almost missed our flight, we were literally the last to board the plane. We were hoping to grab some breakfast for the kids as we had a long flight and did not have time to do so because of this delay. This is why we called ahead to reserve the wheelchair. The people checking in did not seem to care about the delay and only told us to be patient. Sad, unfortunate experience with accessibility issues."

Pros: "Crew. Aircraft selection."

Cons: "several people assigned to the same seats, mine included. lots of last minute moving around."

Pros: "Some of the people I dealt with were nice. All of the flight attendants and pilots were nice."
Cons: "United only had one person working to check people in, and due to a lady with 8+ bags that the only agent had to take 20+ minutes with (while the line stacked up behind us), we ended up missing the first leg of our flight. Told us our bags would be checked all the way through, and they weren't. Checked bag got lost on the way back (again, due to misinformation from United on whether our bag would be checked all the way through), and when we got them back they had obviously been rooted through, with no note left by TSA. I fly often, and this was one of the worst flying experiences of my life."

Pros: "I didn't like much. The employees were great and that's about it!"
Cons: "I've only flown with United for four flights. And of those four flights they have been delayed for three of them. To be specific about this flight, straight off the bat the flight was late due to a late arriving plane.. Understandable. Then to top it off they had no pilot. So then the 1.5 hour delay has now turned into a four hour wait. But I'm still waiting for the flight so the wait could be even longer yet. The airline should consider refunding everyone's money on this flight. An hour delay is one thing, but four hours is uncalled for. Never flying with United again."

Cons: "Delay and then having to change gates - at O"Hare that means walking and walking some more !! After being insulted during check in. The RUDE woman (poor English) with assisted boarding then the RUDE man that changed my name and my luggage he chose to send to Dayton OH -never been there in my life and he "dug" thru my luggage - as if he was searching for MONEY or GOLD -he pulled out a protein drink and I asked him to hand that to me so I could drink it as I am a diabetic - he shouted at me "I THROW AWAY'. During the two hour delay I could have used it !! Poor service I will fly American from now on !!!!!!!!!!!"

Pros: "Crew staff went out of his way to find something for my aisle to snack on when the person next to me asked if there was any snacks on the plane. The plane had to be changed for another plane due to a mechanical issue on the first plane, and the new plane had not been stocked with food after it's previous flight, yet the crew member was able to scrounge up some snacks for us! Also got complimentary directtv - nice, but doesn't make up for not getting home in time yet again."
Cons: "United sucks. I have flown it maybe 10-12 times in the past 2.5 years, mostly back and forth between Chicago and Boston. I have had only 3 round trip flights go without a hitch. Every other trip was delayed. This time 4 hours on my return flight to Boston due to a plane switch, boarding of a new plane to discover a mechanical issue, deboarding, waiting for a new plane, then boarding and sitting on the ground for another 40 min before we were able to take off. I was delayed 1.5 hours on the way to Chicago due to another plane swap (no joke). Still doesn't top but my worst 5 hour delay in Chicago on the way back to Boston because the captain didn't show up. United is atrocious and is my last choice or any airline. Only fly when I'm absolutely forced to now due to no other reasonable choices. They are below delta, JetBlue, American, southwest, and embarrassingly, spirit as well. Terrible."

Cons: "We were connecting to this flight after flying in from Rome. Initially we were scheduled for an 8:30pm flight, but after landing early asked if we could change to an earlier flight. They graciously bumped us up to a 7:30pm flight, which trimmed our 4-hour layover down to 3pm. Cut to 6:15pm...we find out that the flight is not delayed AN HOUR due to a "late inbound flight." Long story short, the 7:30pm flight ended up departed later than the 8:30pm flight we were originally scheduled on so we didn't get to LA until after we were originally supposed to!!"

Cons: "While happy to have pilots concerned about my safety, it was frustrating to suffer thru 2 different mechanical delays. The first one was a missing rivet - which turned out to be so bad they had to put Us in a different plane. Then, that plane developed some mechanical/software issues as we were taxing. My 3-hour flight turned into a +5.5 HR endeavor. When you are on 2 broken planes in a row with the same airline you start to to wonder about how well they are maintaining their equipment. I feel like I deserve more than a "sorry" for the use of my extra time, but no credit or flight certificate was forthcoming."

Pros: "It left on time and arrived earlt"
Cons: "I was seated in a window seat and another woman my size about 110 pounds was seated in the aisle however there was a 400+ pound man sitting in a middle seat which made it very difficult for me especially to even sit back because it was touching me the whole time when you have somebody of that size You should make sure they are on and I'll because then the find attendance would have some difficulty getting through instead of your passengers being inconvenienced either that or force people of that size to take two seats"

Pros: "First of all, the crew was amazing. I had just been traveling for about 20 hours and I had a seat towards the back of the economy section. After traveling that long, I was getting antsy to be at my destination, and I asked the gate agent if she could bump me to a row towards the front of economy- thankfully the plane wasn't full, and she was able to! It's the little things like that, that are what make me fly United. Also, the cabin crew on the flight was great! Of course, the economy section of the plane wasn't an ideal amount of space, but come on- it was an hour flight, and they did a good job of trying to spread people out so that the rows weren't packed."
Cons: "Boarding took a little longer because the plane was being cleaned. I believe they said the overnight flight got in a little late and they still had to clean the plane. We boarded late, but still got to our destination early. Negative turned into a positive- you can't beat that!"

Pros: "Quick flight."
Cons: "Flight was delayed for 40 minutes because of "paperwork" according to the pilot. We boarded the plane on time however had to sit on it during the delay. We were not informed of what was going on until we had already been waiting for 30 minutes. When they informed us of the delay they offered everyone free direct TV in flight to make up for the delay. Once we finally took off they announced that the direct TV was not actually working. The flight attendant making the announcements was not sincere and rather unprofessional. Luckily the pilot flew fast so we ended up arriving only 10 minutes late."

Pros: "We received a free video service for the flight"
Cons: "First of all the flight was booked for a plane which was too large to land in Providence. So either way we were going to have a longer day and extra leg.....which I only paid for ONE plane change. After running to the gate because my first flight was late taking off, this flight was delayed due to engine issues. The agent had us standing in line for 1 1/2 hours while she tried to figure out what was going on. So instead of taking off at 5:40 pm, we took off at 9 pm and still had to catch a bus from Boston to Providence...HORRIBLE Flight = Long Day/Night"

Pros: "The fact that you serve a small complimentary drink and snack on such a short flight was extremely appreciated. It seems most airlines either won't serve on a short flight or charge you extra. Also, I absolutely love the new seats on the planes you guys have been using for quite a while now. They're much more sleek/minimalist so they don't take up as much room. As a disabled person, the bulky seats still employed by many planes on other airlines are incredibly hard on me getting in and out of the seat isles. The crew was very efficient and kind. I also appreciate the thank you to military personnel that they announced at the end of the flight."
Cons: "My gate was moved a few minutes prior to scheduled boarding. It was a minor inconvenience. Flight was a bit late getting out, but still arrived at designated time. Complimentary Wifi would be pretty nice, but not expected."

Cons: "Lack of communication. Kept us belted down for s very long time. Lacked food service, lacked water service till the very end of the lock down. Then we were given the option to leave the plane as the doors were to be disarmed. But if we did the plane could get clearence and leave with no warning. I missed my connecting transportation, had to scrape my weekend plans, currently searching for a place to stay tonight while they locate my bag. I am cold and left my jacket in my bag. The United counter people are blaming it on the weather. I am sure everything was delayed by the laxadaysical baggage loader. The one person ( or lack of help loading the bags on the plane completely altered my travel plans. I requested assistance for hotel only to be told they are full when in fact several are vacant on the Internet. I should of videotaped the baggage loading in Canada, it would of went viral."

Pros: "The crew on United was very helpful on my July 2 flight"
Cons: "You sold me a ticket on Lufthansa. When I got to Charles De Gaulle airport in Paris I waited 45 minutes in line to check in with Lufthansa. When I got to the counter they said they had no record of my reservation. When I showed them the Lufthansa reservation they told me it actually was for a United flight, even though it clearly said Lufthansa . I had to wait another 45 minutes in the United line to retrieve my boarding pass, then about another hour to go through passport control and security. I barely made my flight. I will never make a reservation through Kayak again. I am deleting your app."

Pros: "Punctuality"
Cons: "Food. It is a very long time and there no food enough"

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Safety measures for airlines flying from Chicago to the Cayman Islands

Airlines flying from Chicago to the Cayman Islands have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

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Daily cleaning, installation of cabin HEPA filters on flights from Chicago to the Cayman Islands

Mandatory masks

Masks required on board, masks provided on flights from Chicago to the Cayman Islands

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