C$ 252 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 25/5. 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

Mon, 8 Jun - Sat, 20 Jun
WestJet Logo
9:05 p.m. - 12:45 p.m.
YWG
-
GCM
15h 40m
2 stops
WestJet Logo
1:45 p.m. - 12:55 a.m.
GCM
-
YWG
11h 10m
1 stop
C$ 487WestJet
Mon, 8 Jun - Tue, 23 Jun
WestJet Logo
6:05 p.m. - 12:45 p.m.
YWG
-
GCM
18h 40m
1 stop
WestJet Logo
1:45 p.m. - 12:55 a.m.
GCM
-
YWG
11h 10m
1 stop
C$ 494WestJet
Mon, 8 Jun - Tue, 23 Jun
WestJet Logo
7:00 a.m. - 12:45 p.m.
YWG
-
GCM
29h 45m
2 stops
WestJet Logo
1:45 p.m. - 2:15 p.m.
GCM
-
YWG
48h 30m
2 stops
C$ 498WestJet
Sun, 7 Jun - Tue, 23 Jun
WestJet Logo
6:00 a.m. - 12:45 p.m.
YWG
-
GCM
54h 45m
2 stops
WestJet Logo
1:45 p.m. - 2:15 p.m.
GCM
-
YWG
48h 30m
2 stops
C$ 529WestJet
Wed, 10 Jun - Mon, 22 Jun
Air Canada Logo
2:00 p.m. - 11:25 a.m.
YWG
-
GCM
21h 25m
1 stop
Air Canada Logo
12:25 p.m. - 11:15 a.m.
GCM
-
YWG
22h 50m
1 stop
C$ 578Air Canada
Thu, 11 Jun - Mon, 15 Jun
Air Canada Logo
1:25 p.m. - 10:00 a.m.
YWG
-
GCM
44h 35m
2 stops
Air Canada Logo
12:25 p.m. - 11:08 a.m.
GCM
-
YWG
22h 43m
1 stop
C$ 581Air Canada
Sun, 7 Jun - Mon, 22 Jun
Air Canada Logo
8:10 a.m. - 11:25 a.m.
YWG
-
GCM
27h 15m
1 stop
Air Canada Logo
12:25 p.m. - 10:05 a.m.
GCM
-
YWG
45h 40m
2 stops
C$ 584Air Canada
Tue, 9 Jun - Mon, 22 Jun
Air Canada Logo
4:05 p.m. - 11:25 a.m.
YWG
-
GCM
43h 20m
2 stops
Air Canada Logo
12:25 p.m. - 10:05 a.m.
GCM
-
YWG
45h 40m
2 stops
C$ 588Air Canada
Sat, 6 Jun - Mon, 22 Jun
Air Canada Logo
1:25 p.m. - 11:25 a.m.
YWG
-
GCM
46h 00m
2 stops
Air Canada Logo
12:25 p.m. - 11:15 a.m.
GCM
-
YWG
22h 50m
1 stop
C$ 613Air Canada
Sat, 6 Jun - Mon, 22 Jun
Air Canada Logo
1:25 p.m. - 11:25 a.m.
YWG
-
GCM
46h 00m
2 stops
Air Canada Logo
12:25 p.m. - 10:05 a.m.
GCM
-
YWG
45h 40m
2 stops
C$ 617Air 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$ 692, prices are generally cheapest when you fly direct.

Find deals

Good to know

Cheapest flightC$ 252
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 3320 reviews
7.0Comfort
6.1Entertainment
6.2Food
7.9Crew
7.4Boarding
Airline reviews

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

10.0 ExcellentKimberley, Apr 2026
YYC - YOW
Read more WestJet reviews

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.

Access to movies was rather confusing. Apart from that, I have no complaints.

I wasn’t able to book or pay for a seat and they forgot to check me in for my third flight so I spent 24 hours in Toronto waiting for another one.

I wasn’t checked in for the third leg of my flight, my bag was checked through to Dublin but when I went to the gate in Toronto they said I wasn’t on the flight and had given my seat away. I had to wait 24 hours for another flight and instead on the one I had booked it was now 2 flights.

Flight was delayed for 5hours. Food vouchers just aren’t good enough

The agents at the Kelowna YLW airport were really grumpy. Same with oversized baggage person. Staff on the plane were great.

Flight was early. That’s the only positive I can share. I paid for wifi on the flight and it didn’t allow me to use any streaming services so it was a waste of $20. West Jet also lost my ski equipment on my way to a ski vacation. They told me it would be delivered to the hotel as soon as it arrived at the airport. It was never delivered. I had to pick it up at the airport on my way home. I am completely disgusted with my experience on west jet

Everything you need to know for your flight to Grand Cayman

Information on your arrival and departure airports

Winnipeg (YWG)