Find cheap flights from Winnipeg to Grand Cayman

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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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$ 1,008, prices are generally cheapest when you fly direct.


Good to know

Low seasonSeptember
Best time to beat the crowds (32% less expensive on average)
Most popular time to fly and prices are also 27% lower on average.

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.

Reviews of the 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 8900 reviews
7.3Comfort
8.1Crew
7.7Boarding
6.6Food
7.1Entertainment
Airline reviews

It was all good flight was on time, service was good I enjoyed a few movies and everything was smooth

10.0 ExcellentAnonymous, Jul 2025YYZ - SFO
Read more United Airlines reviews

It was all good flight was on time, service was good I enjoyed a few movies and everything was smooth

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.

7 hour layover was a drag. Free internet on the long leg was great.

Staff were courteous and helpful. The only negative was the flight delays (which are usually unavoidable) and the high baggage price.

From vancouver go calgary nd vice vetsa fligjt was delayed

Absolutely terrible, from the customer service to boarding the plane. On the phone, there was some mishaps with getting in my correct date and they did not help me retrieve a refund or any assistance. I’m gonna be reporting to all my followers and family around the region of Los Angeles to New York.

It was good! Short flight and it was on time!

Could not fly out of Canada. Called airlines on Monday, July 14th. Tried to cancel the flight 7 days away, but they said I could not cancel and there would be no refund.

A little disorganized but overall good. The Delta flights were great though

Price was good. Entertainment and food could have been better

My flight was delayed three times then eventually cancelled the next flight was the following day scheduled for 1030 it was delayed I had to cancel reservations I had to put people up in hotels on the other end as they came out of town to pick me up all at my expense because WestJet couldn’t get it together I’m very disappointed in WestJet’s performance and how they handled the situation Get your customers to where they need to be in a timely fashion, even if that means putting them on your competitors jets Customer service should be number one I will think twice now with booking with WestJet

Staff was nice, helpful, and did all they could. I understand economy seats are bottom of the barrel, but we're crammed in there with others in our row.

Everything you need to know for your flight to Grand Cayman

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