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Find cheap flights from the Cayman Islands to Winnipeg

Find cheap flights from the Cayman Islands to Winnipeg

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Boston (BOS)
Winnipeg
Fri. 22/1
Fri. 29/1
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  • Looking for cheap airfare to Winnipeg? 25% of our users found tickets to Winnipeg for the following prices or less: From George Town C$ 310 one-way - C$ 636 round-trip
  • High season is considered to be January, February and December. The cheapest month to fly to Winnipeg is January.
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Top airline flying Cayman Islands to Winnipeg

Scores according to KAYAK customer reviews

7.1
Air Canada
Overall score based on 24,775 reviews
7.3
Boarding
7.0
Comfort
7.7
Crew
6.9
Entertainment
6.5
Food
Airline reviews

Pros: "The crew on Air Transit did a good job."
Cons: "I would fly with Air Canada instead and not Air Transit."

Cons: "Took 45 minutes to get through Calgary security, long line ups"

Pros: "NA"
Cons: "The flight did not wait for me due to the 1st flight delay."

Pros: "Great Crew"
Cons: "Slight departure delay - no big deal"

Cons: "Seat didn't recline and touch screen on TV was working but it took some work -- I had to press and hold and the little arrow would fly all over the screen"

Cons: "After a delay on my first flight, I managed to get to the gate with a few minutes to spare and the door open. The desk agent refused to let me board the plane."

Pros: "While I've ranked the crew as poor, that isn't a reflection of the entire crew. The flight crew and check-in team were fine, the boarding I have as mediocre due to delay, but I don't put that on the staff."
Cons: "My issues are two part: 1 - I wasn't informed that I was required to retrieve my luggage from the carousel on this flight from George Town to Toronto. I thought perhaps I missed something, however, the three other couples that were in the same predicament I was weren't aware either. This caused a massive headache, the instructions were superbly poor on how to retrieve the luggage, and the process was completely a waste of time. We had to talk with three different people, the person that took us back to the carousel showed no urgency despite us all explaining that we were on a short layover, and might miss our next flight, and even though we had our passes to get through customs, we were made to wait in line to have our baggage inspected. A completely broken process that could've been avoided with a friendly reminder at check-in. 2 - Once I was able to retrieve my luggage I picked it up off the carousel only to find the handle on one piece of luggage had been ripped off, and the plastic lining on the other bag was destroyed. Admittedly I find this to be no surprise after seeing how mine and everyone else's luggage was handled so poorly upon being loaded into the cargo. I saw my luggage being tossed 3-5 feet into the cargo area - literally picked up, and with complete disregard flung like it was a trash bag being thrown into the dumpster. Since I didn't have time to discuss this with any staff due to my prior issue and being unable to find a representative once I landed back in Vancouver, I called the next day to discuss this over the phone, but the representative explained that I was only able to make a complaint in-person at the time of baggage retrieval. The person was absolutely useless and unwilling to help. This was by far the worst treatment I've had at any time in my life while flying any airline. The trip to George Town was with American Airlines, and even though it was longer, and a tad bit more expensive, the service I had with them was stellar by comparison to my experience with AirCanada. Going forward I will only be using AC when there are absolutely no other options."

Pros: "On board crew was friendly and capable."
Cons: "My first and last flight on the CRJ 9. It's much less comfortable than a prop plane, for a 90 minute+ flight."

Cons: "Very cramped like sardine tin. Not enough flight info boards in airport and they were hard to read m"

Pros: "The leg room in basic economy was great -- especially compared to other airlines. In seat entertainment was free."
Cons: "Entertainment movie/TV programming was limited (not live television)."

Pros: "The crew were friendly and efficient."
Cons: "Being delayed for mechanical issues seems to happen more often now, which gives pause. Obviously we want a safe aircraft and I'm glad they deal with the issues, but why are these issues popping up more frequently now? Also, the seats are very uncomfortable for a tall person - no lumbar support"

Cons: "Previous flight got delayed and Air Canada did everything possible to prevent me from taking my first available connecting flight. They always prefer that we wait!"

Cons: "Delayed without notice and broken sound system for tv screen."

Pros: "Boarding was a smooth and easy process and crew was pleasant."
Cons: "I'm only 5'2" rouge is advertised as comfort and the seats felt slightly cramped. Not sure how someone taller could be comfortable."

Cons: "I could not get a seat assignment or a boarding pass for my connecting flight"

Pros: "Aircraft was clean. Convenient connecting gates. Flight duration."
Cons: "- Meals sold in flight - Extremely poor inflight entertainment - Flight delayed no real explanation provided"

Pros: "Ease of booking"
Cons: "No complaints"

Pros: "The crew members were also friendly"
Cons: "The boardung gate was changed but no announcement was made"

Pros: "Free food and beverages"
Cons: "No snacks between meals"

Pros: "The staff was helpful and courteous. I liked the tv selection especially the Canadian content."
Cons: "The flight was delayed because of electric problems. The complimentary snacks aren't as good as other airlines."

Pros: "It was such a nice normal flight compared to the other flights on this trip."
Cons: "Still too much carry on to deal with before take off."

Pros: "Paid for the "upgraded" seat only to be told we had to be in the back of the plane. Moving back all rows had one person and one chair open, so we had to sit apart. Useless crew as an elder couple asked to sit together and were told to check with passengers. Oh and the flight was delayed 3 times."

Pros: "Our flight went by quickly, as the seats in Economy were very comfortable and the crew was very kind and accommodating. There was a great selection of movies and TV on the individual entertainment screens. We would definitely fly Air Canada again."
Cons: "Nothing- one of our best international flights!"

Pros: "The landing..."
Cons: "Left late and overall once again did not find the staff to be exceptionally helpful."

Pros: "Flight was over an hour late Boarding was chaotic from the airport staff"

Pros: "Friendly"
Cons: "French annoying"

Pros: "The flight was on time!!!"
Cons: "I find over the past 25 years that I have been flying with Air Canada the customer service has really went to the dumps !!! Every body is rude and don't understand why."

Pros: "Liked being distracted by a free movie."

Pros: "The guy who gave me the boarding pass was very nice and helpful"

Pros: "Quick easy, I hate that I have to go through sercurity again... but oh well."
Cons: "Refer to last one."

Cons: "Flight was 45 min late leaving & I only had 1 hr between the next flights. Because Winnipeg is a small airport, I just made the next connection but no time to go to the restroom."

Pros: "We checked in online and were able to very quickly and efficiently check our bags and board."
Cons: "We did not have in flight entertainment. We had to pay $10 to rent an iPad."

Pros: "Personnel were friendly aircraft was clean"
Cons: "NA"

Pros: "Everything went smoothly. The crew was fabulous and the flight smooth."
Cons: "Not a single complaint from me!"

Cons: "I attempted to check in three times the day before online- only to be told that there was an error of some sort- and to check in upon arrival. Although our arriving flight arrived over an hour before the Scheduled departure time- yet we were told that the flight had been closed. Despite the fact that she could see my name and my husbands name on the screen for the flight. We informed her that we had attempted to check in online three times but we're not allowed to. I believe it had something to do with checked baggage. After demanding to speak to someone in charge- we were told that the airport supervisor needed to be told by air canada directly to reopen the flight to allow us on. At this time my husband has been on hold ( an international call- seeing as we were on an island) for nearly 30 minutes- finially someone picked up and essentially told us that there was no way for air canada to do that and in fact it was the arriving airline that we should be communucating with. At this point- we hung up. Fearing that we would be stuck there- although the plane had still not departed- but since the supervisor of the airport never physically appeared so that we could discuss the issue in person- I went to another airline , American, to try to find and pay for, mind you, another way to get my husband and myself home. After spending another $1500 to do so- we boarded the American flight and actually made it home before our scheduled time had we been allowed to board the air canada flight. Honestly- I'm not sure if it was air canada or the airport... But I do know that my husband and I will never fly air canada or honestly- I have no desire to go back to the airport where this incident happened- which is sad because I like to contribute to the tourism economy of small island countries... But this one is no longer in my list."

Pros: "luggage intact and well kept"
Cons: "No good refreshment on flight"

Cons: "1h15 late"

Cons: "We nearly missed a chance to disembark between storms because an idiot decided to grab his bags before we could move. None of the flight crew came to yell at the dummy who was holding us up."

Pros: "Price good; seat comfort OK."
Cons: "Late to board, late to take off, late to land: no explanations other than "We're third in line.""

Cons: "Connecting from London through Toronto to Winnipeg couldn't be accomplished in a 2.25 hr layover. Long line for immigration and and enormous line to go through security again meant I missed my flight and the next one was full. It gave me 5 hours to think of all the reasons why I won't connect through Toronto again."

Cons: "Flight left almost one hour late"

Cons: "air canada overbooks their flights....consequently, i wasn't able to be on the flight that i had booked with kayak. they have flex seating which gives business people who fly alot preference to change their flights at a moment's notice. bad policy for the rest of us."

Pros: "The crew was good!"
Cons: "I wished that there were opportunities given for beverages. I also would have liked more explanations on how to connect to the entertainment."

Cons: "gate was changed without an announcement flight was twice delayed"

Pros: "Organized boarding and in flight service"
Cons: "Late departure"

Pros: "It was comfy. Individual screen."
Cons: "We took off 25 minutes late and no food was served, not even a snack. I had to pay 25$ to check in my suitcase."

Pros: "I am happy that Air Canada is unionized; the personnel are fine. I also like the tvs on the backs of the seats, with their wide range of shows. Particularly, I like Portlandia, though there was only one episode of that."
Cons: "I disliked that the airline forced me to miss my connection (inevitable, I suppose, given the excessive security and the lack of direct, affordable connections between Manitoba and the US) and I had to take a later flight to Toronto and didn't get home until 2 am."

Pros: "The seats and spacing and recline on aircraft for this leg were great"
Cons: "Flight was delayed and ended up arriving almost 2 hours later"

Pros: "Nothing."
Cons: "Everything, but specially the boarding crew was unprofessional and very rude."

Read more about Air Canada
COVID-19 information

Safety measures for airlines flying from the Cayman Islands to Winnipeg

Airlines flying from the Cayman Islands to Winnipeg 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 the Cayman Islands to Winnipeg

Mandatory masks

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

Social distancing seating

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

Pre-flight testing

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

Book cheap flights from Cayman Islands to Winnipeg

Recent round-trip flight deals

29/5
Sat.
1 stop
Air Canada
8h 08m
GCM - YWG
1/6
Tue.
2 stops
Air Canada
30h 30m
YWG - GCM
29/5
Sat.
1 stop
Air Canada
29h 08m
GCM - YWG
1/6
Tue.
2 stops
Air Canada
30h 30m
YWG - GCM
29/5
Sat.
2 stops
Air Canada
20h 23m
GCM - YWG
1/6
Tue.
2 stops
Air Canada
25h 25m
YWG - GCM
29/5
Sat.
2 stops
Air Canada
20h 23m
GCM - YWG
1/6
Tue.
2 stops
Air Canada
25h 15m
YWG - GCM

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