C$ 515 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 3/5. 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

Sun, 3 May - Sat, 16 May
WestJet Logo
10:30 p.m. - 12:45 p.m.
YWG
-
GCM
38h 15m
2 stops
WestJet Logo
1:45 p.m. - 12:55 a.m.
GCM
-
YWG
11h 10m
1 stop
C$ 515WestJet
Sun, 3 May - Sat, 16 May
WestJet Logo
10:30 p.m. - 12:45 p.m.
YWG
-
GCM
38h 15m
2 stops
WestJet Logo
1:45 p.m. - 12:00 p.m.
GCM
-
YWG
22h 15m
2 stops
C$ 520WestJet
Sun, 3 May - Sat, 16 May
Multiple Airlines Logo
7:20 p.m. - 11:30 a.m.
YWG
-
GCM
16h 10m
1 stop
Multiple Airlines Logo
1:45 p.m. - 12:55 a.m.
GCM
-
YWG
11h 10m
1 stop
C$ 567Multiple Airlines
Tue, 21 Apr - Thu, 23 Apr
Air Canada Logo
6:00 a.m. - 10:55 a.m.
YWG
-
GCM
52h 55m
2 stops
Air Canada Logo
1:35 p.m. - 11:48 p.m.
GCM
-
YWG
34h 13m
2 stops
C$ 610Air Canada
Tue, 21 Apr - Thu, 23 Apr
Air Canada Logo
6:00 a.m. - 10:55 a.m.
YWG
-
GCM
52h 55m
2 stops
Air Canada Logo
1:35 p.m. - 11:48 p.m.
GCM
-
YWG
34h 13m
2 stops
C$ 612Air Canada
Fri, 10 Apr - Sun, 19 Apr
WestJet Logo
7:50 a.m. - 12:44 p.m.
YWG
-
GCM
52h 54m
2 stops
WestJet Logo
1:50 p.m. - 10:40 p.m.
GCM
-
YWG
32h 50m
2 stops
C$ 621WestJet
Tue, 21 Apr - Thu, 23 Apr
United Airlines Logo
2:00 p.m. - 12:45 p.m.
YWG
-
GCM
22h 45m
1 stop
United Airlines Logo
1:50 p.m. - 11:52 a.m.
GCM
-
YWG
22h 02m
1 stop
C$ 630United Airlines
Sun, 5 Apr - Sun, 12 Apr
WestJet Logo
7:50 a.m. - 12:44 p.m.
YWG
-
GCM
28h 54m
2 stops
WestJet Logo
1:50 p.m. - 12:39 a.m.
GCM
-
YWG
10h 49m
1 stop
C$ 631WestJet
Tue, 21 Apr - Thu, 23 Apr
United Airlines Logo
2:00 p.m. - 12:45 p.m.
YWG
-
GCM
22h 45m
1 stop
United Airlines Logo
1:50 p.m. - 11:52 a.m.
GCM
-
YWG
22h 02m
1 stop
C$ 632United Airlines
Sun, 5 Apr - Sun, 12 Apr
WestJet Logo
8:05 p.m. - 12:44 p.m.
YWG
-
GCM
16h 39m
1 stop
WestJet Logo
1:50 p.m. - 7:09 p.m.
GCM
-
YWG
29h 19m
1 stop
C$ 641WestJet
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$ 711, prices are generally cheapest when you fly direct.

Good to know

Low seasonApril
Cheapest flightC$ 515
Best time to beat the crowds (30% less expensive on average)
Most popular time to fly and prices are also 10% 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.

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 9335 reviews
8.1Crew
6.6Food
7.3Comfort
7.1Entertainment
7.7Boarding
Airline reviews

Flight attendants had a little attitude. Food tastes no good.

6.0 Goodyun bin, Feb 2026
YYZ - SFO
Read more United Airlines reviews

Flight attendants had a little attitude. Food tastes no good.

From pre boarding to flight attendant, crew and baggage handler, excellent. Didn’t lost my luggage like West jet.

Very poor. The flight was delayed from Toronto because some forget to do there job . I got to my connecting gate in San Francisco 10 minutes before the departure.but this didn’t let me board even though the flight was still there for an other 30 minutes. The the gentleman at the unite airline desk told me that they usually wait for passengers but air Canada called and told them not to we I been rerouted to Manila instead of Hong Kong . In San Francisco they mad me check in my carryon bag . I was told the it will directly go yo ho chi minn cuyt but I was told that by the Vietnams airline desk that’s not there I’m 10 hours behind my scheduled flight and looks like I I’m going without baggage. I don’t have a chance of catching ..

It was great. There were some issues prior to takeoff. The weather was poor so we had to go through deicing, and we were delayed a bit by the pilots' concern about one of the engines, but that's aviation. The pilots handled everything with aplomb, and kept us apprised

Reliable, nice crew, I fly often on that flight and I like it all.

l really enjoy very much the flight was very pleasant

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

No kiosk to help pre boarding unlike other airlines, still lost the luggage despite its own crew/TSA or security tagging it, poor handling of lost luggage and possibly compensation is likely poor too.

Waited at airport from 10 am till 4 pm and no flight due to fog. Ugh.

As someone who never flies WestJet unless there is no other viable option I have to give this crew credit where credit is due. Extremely well done everyone.

Everything was great until we had to get our bags. The bags came out in several different batches over 90 minutes after we landed maybe more we got our bags. So much for the old West Jet where they promised bags in 20 minutes. I Next time I will pack lighter and go with a carry-on.

Flight left on time. The crew was very friendly. I had to buy a proper meal. Small cookie and a drink just doesn’t cut it for a 4.5 hours flight.

The flight was full and good as could be expected. We arrived early which is always a good thing.

Experience was good, the wifi hook up is somewhat tough

Plane was one hour late. Hardly any space for our carry-ons. Stressful to catch connections.

The delays were never ending and we were never properly informed as to why. 1st and 2nd delay were handled well, but by the time we received our 7th delay, and then subsequently asked to willingly get bumped, it turned into one of the worst flying situations of my life. I didn’t get home until 2am which is roughly 5 hours later than originally planned.

Great flight, great landing, nice staff. Our seats were a little cramped.

Everything you need to know for your flight to Grand Cayman

Information on your arrival and departure airports