$168 Find Cheap Flights from Chicago to the Cayman Islands
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 12/4. 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.
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Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
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Low season | October |
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High season | March |
Cheapest flight | $168 |
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Top 3 airlines serving from Chicago to the Cayman Islands
All fine save for the abominable catering. Really gone downhill. We found it all inedible.
All fine save for the abominable catering. Really gone downhill. We found it all inedible.
I upgraded to first class only to find out that I still had no access to the sky lounge without a sky miles card or AmEx (something that should be emphasized outside of the fine print!) Also, no food or drink service provided during the flight, so I basically paid 4x more just for “free” checked baggage and a bigger seat. Not worth it.
I appreciated friendly service from check-in, to boarding, to in-flight amenities! Attendants were accommodating and helpful. Thank you! Elaine
Delta was really good about being transparent with why we were delayed it’s just that’s the plane was really old and outdated and a lot of the comfort and amenities we know Delta to have did not shine through
Bottom seat cushion is almost non existent. Very uncomfortable seat.
Delta was great the entertainment was outdated. Screen was very small and didn’t work.
Flight did not have seat back entertainment and the wifi was iffy.
Pretty standard flight. Delta has a good selection of movies.
The WiFi has been awful on my last few Delta Air Lines flights.
The seats are uncomfortable, feels like a small seat pad on plywood.
They need to improve their boarding process. Group 1 and/or paying first class passengers shouldn't be in the middle of boarding process
late departure due to some unspecified issue with ventilating the cabin. They got it running but it was FREEZING for the whole flight. I asked for a blanket but they didn't provide one. They could not turn up the heat. it was quite miserable.
We were delayed because of ground crew, not because the plane wasn’t ready to go. The food was better than usual!
I still prefer Delta, but Delta doesn’t fly to State College PA.
Everything was fantastic. Modern plane. All the amenities! Although the paid snacks and meals are pure robbery. Like i understand airlines need to make money, but 11$ USD for an overnight oats with some nuts in it and barely any pieces of apple.... Highway robbery
United needs to figure out its Economy PLUS standards; its better than economy but that's not saying much. It seems like United stripped away all the basics for an international flight (such as In Seat entertainment) and repackaged some of them as plus. Would not fly United internationally again.
The flight was bumpy. No Breakfast or coffee was served, not even a bottle of water. The food was okay but odd. Rice with peas instead of couscous with some unknown green thing. United Airlines did not tell me that there was VERY LIMITED HANDICAP SERVICE IN NAPLES. De-plane via 20 aluminum steps. Taken to Van. You must walk into the terminal, find luggage, and then walk out to the rental car pickup spot that is 1 block from the terminal.
Crew did their best but the plane configuration is too tight if you're bigger than an average sardine. Controls for the entertainment system didn't all work. The aircraft hadn't been cleaned in awhile.
Flight was delayed due to weather and clogged toilet. Had to deplane. Flight was 3 hours delayed. Crew was awesome and offered water and snacks.
Didn't make it dir to delays - no support from United staff
I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.
Baby cried a lot. Nothing anyone could do about it. Just part of flying.
The flight crew was fantastic! Which the seats had a small TV.
The flight was delayed till next day ! They kept delaying every 30 minutes then after 3 hours they delayed it till next day. We kept waiting in line standing more than an hour to get the hotel and meal vouchers. There was no communication at all. Everything was bad
Smoothe flight. Pilot and crew did a great job. Uncomfortable seat in this jet, felt worn out
seats were way too small. Too short of a flight to offer amenities.
The main problem was delay. The plane was at the gate early and bags were loaded. However, there was no crew for the flight. They were inbound from LGA and had to land and make their way to our gate. It took more than 40 minutes. Then, once the crew arrived and boarded, one of the crew members had to deplane and then a replacement crew member had to be found. It took another 40 minutes or so to get the final crew member. In all, we took off about 2 hours later than our scheduled departure time. Once in the air, the flight was great. Smooth most of the way. The crew was professional and efficient.
Perfect flight. Efficient boarding, on time take off and early arrival. Generally smooth flight.
American is a steady for me. I always get what I expect from them. Sincere effort to get me from one place to another.
BAD. As a family could not sit together. The gate agent told us there was only one seat in the middle left, when we got on the plane the situation was very different with whole rows of seats empty