C$ 280 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 24/7. 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

Wed, 29 Jul - Mon, 31 Aug
Air Canada Logo
1:30 p.m. - 11:25 a.m.
YWG
-
GCM
21h 55m
2 stops
Air Canada Logo
12:25 p.m. - 10:05 a.m.
GCM
-
YWG
21h 40m
2 stops
C$ 692Air Canada
Wed, 29 Jul - Mon, 31 Aug
Air Canada Logo
1:30 p.m. - 11:25 a.m.
YWG
-
GCM
21h 55m
2 stops
Air Canada Logo
12:25 p.m. - 10:05 a.m.
GCM
-
YWG
21h 40m
2 stops
C$ 693Air Canada
Tue, 18 Aug - Sat, 22 Aug
Multiple Airlines Logo
7:40 p.m. - 9:00 p.m.
YWG
-
GCM
25h 20m
2 stops
Multiple Airlines Logo
10:40 a.m. - 10:05 a.m.
GCM
-
YWG
23h 25m
2 stops
C$ 695Multiple Airlines
Mon, 26 Oct - Wed, 28 Oct
Air Canada Logo
5:15 a.m. - 3:30 p.m.
YWG
-
GCM
34h 15m
2 stops
Air Canada Logo
12:10 p.m. - 6:29 p.m.
GCM
-
YWG
30h 19m
1 stop
C$ 698Air Canada
Mon, 26 Oct - Wed, 28 Oct
Air Canada Logo
5:15 a.m. - 3:30 p.m.
YWG
-
GCM
34h 15m
2 stops
Air Canada Logo
12:10 p.m. - 9:44 a.m.
GCM
-
YWG
21h 34m
1 stop
C$ 700Air Canada
Mon, 26 Oct - Wed, 28 Oct
Air Canada Logo
7:20 p.m. - 3:30 p.m.
YWG
-
GCM
20h 10m
2 stops
Air Canada Logo
12:10 p.m. - 10:16 a.m.
GCM
-
YWG
46h 06m
2 stops
C$ 703Air Canada
Mon, 26 Oct - Wed, 28 Oct
Air Canada Logo
5:15 a.m. - 3:30 p.m.
YWG
-
GCM
34h 15m
2 stops
Air Canada Logo
12:10 p.m. - 10:16 a.m.
GCM
-
YWG
22h 06m
2 stops
C$ 704Air Canada
Wed, 29 Jul - Mon, 31 Aug
Air Canada Logo
1:30 p.m. - 11:25 a.m.
YWG
-
GCM
21h 55m
2 stops
Air Canada Logo
12:25 p.m. - 11:20 p.m.
GCM
-
YWG
10h 55m
1 stop
C$ 760Air Canada
Tue, 18 Aug - Sat, 22 Aug
Multiple Airlines Logo
3:20 p.m. - 9:00 p.m.
YWG
-
GCM
29h 40m
2 stops
Multiple Airlines Logo
1:45 p.m. - 12:55 a.m.
GCM
-
YWG
11h 10m
1 stop
C$ 761Multiple Airlines
Wed, 29 Jul - Mon, 31 Aug
Air Canada Logo
1:30 p.m. - 11:25 a.m.
YWG
-
GCM
21h 55m
2 stops
Air Canada Logo
12:25 p.m. - 11:15 a.m.
GCM
-
YWG
22h 50m
1 stop
C$ 783Air Canada
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$ 702, prices are generally cheapest when you fly direct.

Good to know

Cheapest flightC$ 280
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.

Reviews of the top airline 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.
7.2
WestJetOverall score based on 3350 reviews
6.2Food
7.0Comfort
6.1Entertainment
7.4Boarding
7.9Crew
Airline reviews

I like that we landed safely and that my dog was safe underneath as well. Outside of that, we were 45 mins late for a direct flight that is 1.5 hours long. And 2 of my 3 bags did not make the flight. Only my dog was onboard.

4.0 OkayMatthew, May 2026
YYJ - YYC
Read more WestJet reviews

I like that we landed safely and that my dog was safe underneath as well. Outside of that, we were 45 mins late for a direct flight that is 1.5 hours long. And 2 of my 3 bags did not make the flight. Only my dog was onboard.

Service was okay except attendant over served alcohol to passenger and passenger got tipsy and made me uncomfortable

Food was not inspired but was satisfying. Same for infotainment selection. You’d think business class would come with complimentary WiFi. Crew was uniformly attentive and excellent.

Could not make the flight. No one would help us at all

Decent entertainment although my wife was not offered any ear buds so couldn’t enjoy. Real issue was the appalling food. Presentation was unacceptable with cheap hard to open packaged bread, plastic cheese again in hard to open shrink wrap, main course in small cardboard box again hard to open, wooden utensils which lack substance making the whole experience poor. Surprised I didn’t cover myself or neighbour as the food moved all over the place. Breakfast calzone was dry and unappealing with the staff basically throwing them around. Very disappointed

Better movie options. More diligence on the size and amount of bags people bring on board. Lady across aisle from me had a bucket style bag that would only go so far under the seat in front of her. She was not told once that the whole bag is supposed to be under the seat. Crew is very hardworking however.

I didn’t have any food but my Prosecco hit the spot. We left on time and the crew was friendly.

The pricing was split into an ultra basic fare with a comfort seat upgrade. This is misleading. Never were we shown an ultra basic fare. What this did because the fare category was ultra basic we could not bid on an upgrade first class seat. All e mails from WestJet were for ultra basic category with my wife and I upset as we could not confirm this with anyone from your firm.The check in counter were not going to allow our carry on but after some checking saw we had ultra basic and a comfort seat upgrade. They could not figure out how this was done. Now we have to go through this again at the gate in Mexico. Unless I missed it - please let customers know the billing in future. Respectfully. Gary & Nancy Moughtin

Flight didn’t happen because both my connections were lost and Toronto wouldn’t let me board. I was checked in to all 3 flights at the check-in fest in Dublin.

The flight didn’t happen because they apparently lost my check in and wouldn’t let me board.

Everything you need to know for your flight to Grand Cayman

Information on your arrival and departure airports