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Find cheap flights from Winnipeg to the Cayman Islands

Find cheap flights from Winnipeg to the Cayman Islands

Round-trip
Economy
Winnipeg (YWG)
Cayman Islands
Thu. 28/1
Thu. 4/2
Any month
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Top tips for finding cheap flights to the Cayman Islands

  • Book at least 1 week 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 the Cayman Islands is September.

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Top airline flying Winnipeg to Cayman Islands

Scores according to KAYAK customer reviews

7.0
United Airlines
Overall score based on 67,875 reviews
7.4
Boarding
6.9
Comfort
7.7
Crew
6.5
Entertainment
6.4
Food
Airline reviews

Cons: "Only bathroom on the plane was closed due to issues. Plane was cold and cramped."

Cons: "Flight was on an older CRJ 200, which was a little cramped and grungy-appearing."

Cons: "Gate area very crowded."

Cons: "The United App for entertainment would not work. It kept closing. The cabin was cold."

Cons: "Communication about the delay was poor. The captain acted like he had no idea how maintenance clearances work."

Cons: "Charge for baggage. Pretzels - ugh!"

Cons: "Naplaćene su mi torbe u San Diego po 58$ iako je to bilo uračunato u cenu pri kupovini karata !!! Za torbu od22kg(48),i torbu od15kg 116$! Nije korektno!!!! Brukaaa!!!Sramota!!Nikad više sa tom compani!! Never again!!!! Never!!!!"

Pros: "Steward and Stewardess very nice and helpful"
Cons: "Walk between flights was extreme - tracked at about a mile! The video movie was incredibly choppy making entertainment frustrating."

Cons: "No entertainment on this flight"

Pros: "On time"
Cons: "The flight attendants were rude, impatient and generally seemed unhappy to be working on this particular flight."

Pros: "Crew still came through cabin even though it was an overnight flight to see if anyone needed anything."
Cons: "The way the plane was boarded which I have found is the way United boards."

Pros: "Really disatisfied"
Cons: "the poor attempt to help me when they canceled my flight 3 times"

Pros: "Crew was great, very accomodating. Seats were fantastic."
Cons: "Plane leaked water from overhead compartment onto to my seat. Crew member used napkins & band aids (seriously) to patch up the drips. Food was horrible (jumbalaya) and hardly a portion. No idea how to operate the entertainment system ? We sat on the taxi runway for over 30 minutes waiting for a parking space at the terminal. Nearly missed connection."

Cons: "Need to pay for everything... internet, tv, and snack. Long flight when you cant fork out more money for what was free with canadian airline"

Pros: "Nothing"
Cons: "Change of seat w/o any notification."

Cons: "NA"

Cons: "I would have liked to arrive home before 12 noon but due to United delaying my fligh twice and not being able to make the connection in washington . I had to plead with them to put me on a direct flight to Newark which made me fly another carrier "American airlines". I'm not sure what the issue was for the delays but it was frustrated."

Pros: "Everyone was friendly"
Cons: "A fight attendant accidentally spilled a drink down my back. To compensate, she offered me an alcoholic drink. I can't drink alcohol. I asked if I could move to another seat that was dry and she said I'd have to pay $130."

Pros: "Quick easy trip"
Cons: "I couldn't put my Cary on luggage in cabin.."

Cons: "4 hours delay. Missed appointment."

Pros: "Flight was delayed but the pilots got us there in time to make our connecting flight. Thank you!"
Cons: "On an international flight didn't expect to pay for movies and our seats didn't recline. Made for a long and uncomfortable flight."

Cons: "San Francisco to Ontario Delay for 10 min Then another dealy for 30 min After we board we had to waite inside the air craft for Cataring company to delever food for first classe"

Pros: "It was great all the way. No complaints"

Cons: "Delayed 4 hours."

Pros: "All went well on on time and service was good."

Cons: "Our flight was an hour and a half late. The seats are very new on this configuration is perfect. The entertainment system is old and you pay for everything."

Pros: "Nothing. Smelled and looked like death. Got better service from zombies."
Cons: "Worst service from an airline and 3rd party vendor. I couldn't believe the level of disorganization from their "core" team. I will NOT ever use this service and especially not the American airlines staff, crew or phone staff. This did not only affect my day poorly, but also impacted my family and disrupted my finances. This will not be the last time you hear from me I was very unimpressed."

Pros: "clean; good movies"
Cons: "no kosher food option"

Cons: "the wifi connection did not work."

Pros: "Nothing"
Cons: "The united staff kept skipping the lines to drop off the bags. They didn't care when multiple people in line said they were skipping people. After paying once for my checked bag they tried to make me pay again. Asked to see in writing what they were trying to explain and the manager couldn't do it. They never gave me my ticket stub for my checked bag. So if it hadn't arrived I wouldn't have had anyway to find it. Very disappointing staff in SFO. Seemed aa if no one at SFO was happy to be working there or even worse didnt know what to do most of the time. VERY different than the DEN united experience."

Pros: "WIFI allowed access to imessage"
Cons: ""Free" movies and TV didn't work"

Pros: "I liked the Dutch sweet breakfast waffle very much."

Cons: "Very poor entertainment"

Pros: "I liked that the attendant suggested that anyone who wished, could move to unsold seats! Nice!"

Pros: "Food in the airplane and the quickness of the arrival."
Cons: "They left us at the gate waiting for a long time without an assigned seat. They didn't announce boarding time, we were waiting for so long and the crew saw us sitting down and didn't call us. The flight almost left us. The lady at the airport was extremely rude, I asked her her name and she refused to give it to us. The delay was absurd."

Pros: "Easy to board and everyone very friendly"
Cons: "Nothing negative to say"

Pros: "Good crew"
Cons: "The usual. - crowded, smelly"

Cons: "Not even beverage service. Water only"

Cons: "Wifi should be free"

Pros: "We landed earlier than expected and the pilot kept communication open to us. Onboarding from Austin was smooth and the agents were friendly at the gate."
Cons: "Boarding was a challenge as there was not enough overhead room, delaying getting on/off the plane because my bags ended up in the back of the plane far from my seat. No TVs, tight space / small plane."

Cons: "It was a new plane and they added another row of seats in economy. My knee hurt for two days."

Pros: "The flight was good, no delays and we made good time. I was glad that the fasten seat belt sign wasn't on the entire flight."
Cons: "I spent 9 hours without in-seat entertainment because the system was broken. I had to follow up with the crew several times and no one ever checked with me to see if I was satisfied."

Pros: "Great service"
Cons: "Assent into Lincoln faster than usual pilot did not get to see pilot."

Pros: "They worked hard to try and get people to their connecting flights since there was a delay"
Cons: "They were overbooked They delayed my flight by about 20-30 minutes"

Pros: "The staff was friendly and accommodating. The flight was smooth."
Cons: "Nothing"

Cons: "There was only one person rescheduling and we got a faster reroute get plan on the phone. It was all pretty awful and we did not get to our destination until many hours after scheduled. Not at all a good trip."

Pros: "From Chicago to San Francisco was great"

Pros: "First time in a plane and it was the smoothest ride"

Pros: "Easy mobile boarding pass was great on the way to Mexico City. I was kept up to date on the delay coming back to Houston."

Read more about United Airlines
COVID-19 information

Safety measures for airlines flying from Winnipeg to the Cayman Islands

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

Heightened sanitation

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

Mandatory masks

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

Social distancing seating

Middle seats unavailable to book on flights from Winnipeg to the Cayman Islands

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Winnipeg to the Cayman Islands

Book cheap flights from Winnipeg to Cayman Islands

Recent round-trip flight deals

28/4
Wed.
2 stops
Multiple Airlines
32h 25m
YWG - GCM
2/5
Sun.
2 stops
Multiple Airlines
12h 18m
GCM - YWG
28/4
Wed.
2 stops
Multiple Airlines
24h 25m
YWG - GCM
2/5
Sun.
2 stops
Multiple Airlines
12h 18m
GCM - YWG
28/4
Wed.
2 stops
United Airlines
21h 27m
YWG - GCM
2/5
Sun.
1 stop
United Airlines
22h 03m
GCM - YWG
28/4
Wed.
2 stops
United Airlines
27h 13m
YWG - GCM
2/5
Sun.
1 stop
United Airlines
22h 03m
GCM - YWG
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