C$ 820 Find Cheap Flights from Winnipeg to Grand Cayman

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Winnipeg to Grand Cayman departing on 28/3. 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, 0 bags

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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Flight Deals

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 round-trip flight deals from Winnipeg to Grand Cayman

Sat, 28 Mar - Sat, 4 Apr
Multiple Airlines Logo
9:00 p.m. - 12:44 p.m.YWG-GCM
15h 44m2 stops
Multiple Airlines Logo
4:25 p.m. - 11:13 a.m.GCM-YWG
18h 48m2 stops
C$ 796Multiple Airlines
Find Deal
Sat, 28 Mar - Sat, 4 Apr
Multiple Airlines Logo
9:00 p.m. - 12:44 p.m.YWG-GCM
15h 44m2 stops
Multiple Airlines Logo
4:25 p.m. - 11:13 a.m.GCM-YWG
18h 48m2 stops
C$ 820Multiple Airlines
Find Deal
Sat, 28 Mar - Sat, 4 Apr
Multiple Airlines Logo
5:30 p.m. - 11:10 a.m.YWG-GCM
17h 40m1 stop
Multiple Airlines Logo
4:25 p.m. - 11:13 a.m.GCM-YWG
18h 48m2 stops
C$ 868Multiple Airlines
Find Deal
Sat, 28 Mar - Sat, 4 Apr
Multiple Airlines Logo
7:05 p.m. - 11:10 a.m.YWG-GCM
16h 05m1 stop
Multiple Airlines Logo
4:25 p.m. - 11:13 a.m.GCM-YWG
18h 48m2 stops
C$ 891Multiple Airlines
Find Deal
Thu, 22 Jan - Sun, 1 Feb
Porter Airlines Logo
4:25 p.m. - 4:25 p.m.YWG-GCM
47h 00m2 stops
Porter Airlines Logo
3:00 p.m. - 11:13 a.m.GCM-YWG
21h 13m1 stop
C$ 995Porter Airlines
Find Deal
Thu, 22 Jan - Sun, 1 Feb
Porter Airlines Logo
4:25 p.m. - 4:25 p.m.YWG-GCM
47h 00m2 stops
Porter Airlines Logo
3:00 p.m. - 3:30 p.m.GCM-YWG
49h 30m2 stops
C$ 1,001Porter Airlines
Find Deal
Sat, 28 Mar - Sat, 4 Apr
Multiple Airlines Logo
9:00 p.m. - 12:44 p.m.YWG-GCM
15h 44m2 stops
Multiple Airlines Logo
8:50 a.m. - 11:13 a.m.GCM-YWG
26h 23m3 stops
C$ 1,174Multiple Airlines
Find Deal
Thu, 22 Jan - Sun, 1 Feb
Porter Airlines Logo
4:25 p.m. - 2:00 p.m.YWG-GCM
20h 35m1 stop
Porter Airlines Logo
3:00 p.m. - 11:13 a.m.GCM-YWG
21h 13m1 stop
C$ 1,220Porter Airlines
Find Deal
Sat, 28 Mar - Sat, 4 Apr
American Airlines Logo
12:10 p.m. - 1:20 p.m.YWG-GCM
25h 10m3 stops
American Airlines Logo
2:55 p.m. - 11:35 p.m.GCM-YWG
32h 40m3 stops
C$ 4,064American Airlines
Find Deal
Sat, 28 Mar - Sat, 4 Apr
American Airlines Logo
12:10 p.m. - 1:20 p.m.YWG-GCM
25h 10m3 stops
American Airlines Logo
3:15 p.m. - 11:35 p.m.GCM-YWG
32h 20m3 stops
C$ 4,065American Airlines
Find Deal
Booking Insights

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$ 700, prices are generally cheapest when you fly direct.

Good to know

Low seasonSeptember
Cheapest flightC$ 796
Best time to beat the crowds (21% less expensive on average)
Most popular time to fly and prices are also 15% 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$ 845 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$ 1,161.

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 8998 reviews
6.6Food
7.7Boarding
7.3Comfort
8.1Crew
7.1Entertainment
Airline reviews

The food quality sucks. One must starve if they do not eat flesh Or wheat based products Some variety would be expected. The trivial amount of snacks and or food is inhumane

4.0 OkayAnonymous, Oct 2025YVR - SFO
Read more United Airlines reviews

The food quality sucks. One must starve if they do not eat flesh Or wheat based products Some variety would be expected. The trivial amount of snacks and or food is inhumane

We Left Calgary 1/2 hour late and that made for a tight connection in Denver. After arriving everything was done to help us make our connection. That was a great effort. Thank You United

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

Overall, it was good. I was seating next to a wonderful lady and did not notice how time flew. Thanks

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

The experience was great, the crew was very polite and hospitable. I will definitely make if my go to airlines.

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

When flying premium on a two our flight a light lunch would have been nice considering the price you pay. A Kit Kat bar and bag of chips is rather cheap service.

I was seated near a "stinky" person. That's not the fault of Westjet🙁😶‍🌫️

The only thing I can't give good or really good is the fact that we didn't have food ,just a packet of pretzels or cookies which is normal,and ofcourse there isn't any entertainment. I've always flowen WestJet ..I really like the airlines..this plane was smaller one ,pretty tight seating.

Again, flight was late. It’s expected of this airline now i guess.

The ceiling leaked water on me. The toilets smelled very bad in the rear cabin

Counter representative refused to check my luggage despite paying for it in advance

We landed 26 min early. It was awesome! Smooth ride too.

When I purchased the flights I included the luggage, the luggage was not added and got charged the full price anyway. Had to pay for the luggage at check in. Initial flight was delayed, we missed our 9am connection (flew with my wife), then the airline rebooks us to the next flights, putting my wife in at 1.40pm and me at 4pm, what a crazy wait time. We managed to fix it with customer service and they put me in the 1:40pm flight too, but they left my baggage behind in the 4pm flight. When arrived to my destination, of course no luggage. It was delivered to the address thankfully late at night. The experience sucked.

Very good experience. Great cabin crew. Much better than expected

There is no snack and nit much that would be considered gluten free in yiur food selections. One of your snacks should be a gluten free cookie or small bar etc. maybe it was me but I didn’t see any free movies just internet connection and YouTube .

Everything you need to know for your flight to Grand Cayman

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