C$ 345 Find Cheap Flights from Winnipeg to Grand Cayman

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Winnipeg to Grand Cayman departing on 1/11. 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.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Grand Cayman

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Winnipeg to Grand Cayman, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Winnipeg to Grand Cayman, as well as popular online travel agencies
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Flights Deals

Best Grand Cayman Flight Deals from Winnipeg

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
George Town
George Town2 stopsC$ 345
George Town
George Town2 stopsC$ 345

Cheap Flights from Winnipeg to Grand Cayman

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Winnipeg to Grand Cayman that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent one-way flight deals from Winnipeg to Grand Cayman

Sat, 1 Nov
WestJet Logo
12:25 p.m. - 1:49 p.m.YWG-GCM
25h 24m2 stops
C$ 345WestJet
Find Deal
Sat, 1 Nov
Air Canada Logo
4:50 p.m. - 12:20 p.m.YWG-GCM
19h 30m1 stop
C$ 376Air Canada
Find Deal
Sat, 1 Nov
 Logo
8:25 p.m. - 9:20 p.m.YWG-GCM
24h 55m3 stops
C$ 399
Find Deal
Sat, 1 Nov
Air Canada Logo
4:50 p.m. - 4:25 p.m.YWG-GCM
23h 35m2 stops
C$ 444Air Canada
Find Deal
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KAYAK's insights & trends for Winnipeg to Grand Cayman flights

Get data-powered insights and trends into flights from Winnipeg to Grand Cayman to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Winnipeg to Grand Cayman?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of C$ 914, prices are generally cheapest when you fly direct.


Good to know

Low seasonSeptember
High seasonMay
Cheapest flightC$ 345
Best time to beat the crowds (31% less expensive on average)
Most popular time to fly and prices are also 26% lower on average.
Flight from Winnipeg to George Town

FAQs - booking Grand Cayman flights

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

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Winnipeg to Grand Cayman.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Winnipeg to Grand Cayman?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Winnipeg to Grand Cayman is likely to change within 7 days, so travellers know whether to wait or book now.

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

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Winnipeg to Grand Cayman with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Winnipeg to Grand Cayman?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Winnipeg to Grand Cayman up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Grand Cayman?

    The cheapest time of day to fly to Grand Cayman is generally in the morning, when round-trip flights cost C$ 602 on average. Morning departures are around 27% cheaper than evening flights, on average. The most expensive time of day to fly to Grand Cayman is generally in the evening, which is peak travel time and where the average cost of a ticket is C$ 827.

Top airlines flying from Winnipeg to Grand Cayman

 
See real verified KAYAK customer reviews for airlines flying from Winnipeg to Grand Cayman. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Winnipeg to Grand Cayman? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 8801 reviews
8.1Crew
7.0Entertainment
7.7Boarding
6.6Food
7.3Comfort
Airline reviews

Efficient, calm when things were delayed and kept us regularly informed of what was happening.

10.0 ExcellentAnonymous, Jun 2025YVR - DEN
Read more United Airlines reviews

Efficient, calm when things were delayed and kept us regularly informed of what was happening.

Airbus plane, nice and polite staff, entertainment even as it was a short flight.

Very nice and clean plane. Transit time between flights was tight though

Our flights got changed from United to Air Canada and our purchased seats did not get transferred so we had to pay for seats twice. I brought it up with Air Canada and they stated I had to go back and chase it with United. The united seats were $21 Canadian each and Air Canada were $56 each so we have paid $77 for each seat. Very unhappy

So far so good but food and entertainment are not available for this flight

Plane temperature was comfortable (not to hot) when boarding and waiting for takeoff.

Michael, our FA was very attentive, even finding me a chocolate brownie from economy class when the dessert selections were all dairy based. ( intolerant, not allergic so don’t usually need to order dairy free)

We tried to upgrade to economy premium but were told this was not possible as we had booked through United Airlines (and Air Canada was operating the flight). This seemed silly given there was ample space in economy premium. Additionally, we had to wait almost 1.5 hours upon arrival to taxi to the gate. Otherwise, the crew were very pleasant and passengers were friendly.

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

headphone jack didnt work for the first flight and not much variety

The seats are totally uncomfortable making the flight less than pleasant. The cookies & pretzels were terrible!!!

Not the greatest experience everything was pretty mediocre. My seat was by the washroom in the aisle and was not located well as everyone past each other people were right in my seat and space.

Lots of overhead storage, good crew, good service, smooth landing.

Lots of overhead storage and a good crew and service.

The small prop plane was crowded and the overhead luggage storage is a smaller than on the jets. Other than that, the crew was good, the flight was on time and the landing was smooth.

There was a medical emergency that the crew handled very well. There was no “entertainment” of any sort-no movie/music/whatever. Food was typical of airlines: mediocre.

On time. Friendly and efficient staff at check in and flight crew.

Terrible decision to take a night flight. Not enough time to sleep and premium seat has no foot rest ao couldn’t get comfortable!

Late departure, so I missed connection in Detroit. But Delta gave me a great hotel & breakfast. Just sorry I could not get anything from my checked baggage.

Crew was friendly. Lost our luggage and told us it’d be in later in the evening of the day we returned. It was not. Still after 5 days have not received it.

Everything you need to know for your flight to Grand Cayman

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