C$ 542 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 18/12. 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, 17 Jan - Sat, 24 Jan
Multiple Airlines Logo
4:25 p.m. - 2:00 p.m.
YWG
-
GCM
20h 35m1 stop
Multiple Airlines Logo
5:25 p.m. - 3:30 p.m.
GCM
-
YWG
23h 05m1 stop
C$ 542Multiple Airlines
Sun, 11 Jan - Sun, 18 Jan
WestJet Logo
6:55 p.m. - 1:44 p.m.
YWG
-
GCM
17h 49m2 stops
WestJet Logo
2:50 p.m. - 3:21 p.m.
GCM
-
YWG
25h 31m2 stops
C$ 576WestJet
Sun, 11 Jan - Sun, 18 Jan
WestJet Logo
8:05 p.m. - 1:44 p.m.
YWG
-
GCM
16h 39m1 stop
WestJet Logo
2:50 p.m. - 11:35 a.m.
GCM
-
YWG
21h 45m1 stop
C$ 592WestJet
Sun, 11 Jan - Sun, 18 Jan
WestJet Logo
12:40 p.m. - 1:44 p.m.
YWG
-
GCM
24h 04m2 stops
WestJet Logo
2:50 p.m. - 7:12 p.m.
GCM
-
YWG
29h 22m1 stop
C$ 598WestJet
Sat, 17 Jan - Sat, 24 Jan
Multiple Airlines Logo
4:25 p.m. - 2:00 p.m.
YWG
-
GCM
20h 35m1 stop
Multiple Airlines Logo
5:25 p.m. - 11:13 a.m.
GCM
-
YWG
18h 48m2 stops
C$ 609Multiple Airlines
Sat, 17 Jan - Sat, 24 Jan
Air Canada Logo
6:00 a.m. - 12:25 p.m.
YWG
-
GCM
53h 25m2 stops
Air Canada Logo
5:45 p.m. - 10:16 a.m.
GCM
-
YWG
41h 31m2 stops
C$ 620Air Canada
Sun, 11 Jan - Thu, 15 Jan
WestJet Logo
8:05 p.m. - 1:44 p.m.
YWG
-
GCM
16h 39m1 stop
WestJet Logo
2:50 p.m. - 11:50 p.m.
GCM
-
YWG
34h 00m2 stops
C$ 630WestJet
Sun, 11 Jan - Thu, 15 Jan
WestJet Logo
8:05 p.m. - 1:44 p.m.
YWG
-
GCM
16h 39m1 stop
WestJet Logo
2:50 p.m. - 12:35 a.m.
GCM
-
YWG
10h 45m1 stop
C$ 632WestJet
Sun, 1 Mar - Tue, 24 Mar
Multiple Airlines Logo
8:05 p.m. - 1:44 p.m.
YWG
-
GCM
16h 39m1 stop
Multiple Airlines Logo
2:25 p.m. - 3:09 p.m.
GCM
-
YWG
24h 44m2 stops
C$ 639Multiple Airlines
Sun, 1 Mar - Tue, 24 Mar
Multiple Airlines Logo
5:00 a.m. - 1:44 p.m.
YWG
-
GCM
7h 44m1 stop
Multiple Airlines Logo
2:25 p.m. - 6:05 p.m.
GCM
-
YWG
27h 40m3 stops
C$ 645Multiple Airlines
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$ 667, prices are generally cheapest when you fly direct.

Good to know

Low seasonApril
Cheapest flightC$ 450
Best time to beat the crowds (27% less expensive on average)
Most popular time to fly and prices are also 21% 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$ 833 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$ 1,145.

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 9095 reviews
7.1Entertainment
6.6Food
7.7Boarding
7.3Comfort
8.1Crew
Airline reviews

The Sears in the 800s are not too good perfect Airbus why cant the new 737 fix that

8.0 ExcellentAnonymous, Dec 2025
YEG - IAH
Read more United Airlines reviews

The Sears in the 800s are not too good perfect Airbus why cant the new 737 fix that

Quick and seamless boarding. No entertainment but fast Starlink wifi for this short trip and the staff was really friendly.

I dread trans-Pacific flights. They are very long. This was my first time on Universal, and it was my best crossing ever. The staff were professional, the hospitality was great, and the food was delicious. The entertainment system filled the long flight hours. I will seek out Universal flights from now onwards. 🙂

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

8 hrs. Of waiting instead of couple of hours..the only good thing I'm still able to go to my destination...

Flight delayed missed connecting flight crew not very helpful very frustrating customer service

Our biggest complaint was a major schedule change that was not communicated to us in any way. Luckily the time change went later not earlier so we did not miss the flight. Our email addresses and phone numbers were on file but we received no email no text message no nothing. Short flight so not much to say.

Airplane is too small. Crew, especially the flight attendant who looked after our area, was not at all friendly and a touch authoratative. She may have been the most gruff flight attendant i've come across in 40 years of business travel

I when to Jamaica for my dad funeral and I did not get my luggage from westjet . I add to buy clothes putting me financial debt i did no want to be in Westjet did not call me to apologize are to inquire about my luggage I am still angry about it

Ground staff was not helpful, but staff at the business counter were excellent.

I selected "carry-on" for a round trip on Kayak, but my return flight on WestJet did not include a carry-on and they would not allow me to add one. My only option was to add a "checked bag" which I had to wait for on the luggage carousel after landing. Not a good experience.

The plug in to charge our phones are all loose my block would not stay in!!

My flight was cancelled due to weather but Westjet got me on a new flight in a timely and efficient manor.

It was disappointing to see the huge number of people who were allowed to board who were claiming to either be disabled or needed extra time to board who practically ran to the gate as soon as boarding opened. One of the female flight attendants in the premium economy section refused to let a lady with an infant use the toilet next to row 9 to change her baby even though the path back to the rear toilets was blocked by staff and trolleys and said she would have to carry the baby to the toilet during the descent phase when turbulence was present. The passenger refused and the baby had to wait until landing. It would have been no problem to allow this infringement of weathers petty rules. The flight was also very cold due to a cold draft throughout the flight from the bulkhead ceiling which was not controllable.

Everything you need to know for your flight to Grand Cayman

Information on your arrival and departure airports