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Cheap flights from Winnipeg to Grand Cayman from C$ 588

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Winnipeg to Grand Cayman departing on 21/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

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Find the cheapest flights from Winnipeg to Grand Cayman

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
7:05 p.m. - 4:30 p.m.YWG-GCM
44h 25m2 stops
United Airlines Logo
5:45 p.m. - 9:49 a.m.GCM-YWG
41h 04m2 stops
C$ 851United Airlines
Find Deal
Sun, 23 Nov - Mon, 1 Dec
WestJet Logo
8:05 p.m. - 1:44 p.m.YWG-GCM
16h 39m1 stop
WestJet Logo
2:50 p.m. - 3:21 p.m.GCM-YWG
25h 31m2 stops
C$ 863WestJet
Find Deal
Sun, 23 Nov - Mon, 1 Dec
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$ 873WestJet
Find Deal
Sun, 23 Nov - Mon, 1 Dec
Air Canada Logo
7:05 p.m. - 12:25 p.m.YWG-GCM
16h 20m1 stop
Air Canada Logo
1:30 p.m. - 8:28 p.m.GCM-YWG
31h 58m2 stops
C$ 1,023Air Canada
Find Deal
Sat, 22 Nov - Sun, 30 Nov
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$ 1,213Porter 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$ 1,219Porter Airlines
Find Deal
Thu, 22 Jan - Sun, 1 Feb
Air Canada Logo
1:45 p.m. - 12:25 p.m.YWG-GCM
21h 40m2 stops
Air Canada Logo
1:30 p.m. - 8:28 p.m.GCM-YWG
31h 58m2 stops
C$ 1,254Air Canada
Find Deal
Sat, 22 Nov - Sun, 30 Nov
United Airlines Logo
8:40 a.m. - 1:15 p.m.YWG-GCM
27h 35m2 stops
United Airlines Logo
5:30 p.m. - 9:49 a.m.GCM-YWG
17h 19m2 stops
C$ 1,382United Airlines
Find Deal
Fri, 21 Nov - Sat, 29 Nov
American Airlines Logo
12:10 p.m. - 2:46 p.m.YWG-GCM
25h 36m3 stops
American Airlines Logo
3:36 p.m. - 11:35 p.m.GCM-YWG
56h 59m3 stops
C$ 4,245American Airlines
Find Deal
Sun, 23 Nov - Mon, 1 Dec
American Airlines Logo
12:10 p.m. - 11:57 a.m.YWG-GCM
22h 47m2 stops
American Airlines Logo
3:36 p.m. - 11:35 p.m.GCM-YWG
56h 59m3 stops
C$ 4,839American Airlines
Find Deal
Sun, 23 Nov - Mon, 1 Dec

United Airlines flights from Winnipeg to Grand Cayman

Our best United Airlines deals on Winnipeg to Grand Cayman flight tickets
United Airlines
23 Nov
YWG7:05 p.m.Winnipeg
44h 25m
2 stops
GCM4:30 p.m.George Town Owen Roberts Intl
1 Dec
GCM5:45 p.m.George Town Owen Roberts Intl
41h 04m
2 stops
YWG9:49 a.m.Winnipeg
C$ 851
Find similar
United Airlines
21 Nov
YWG8:40 a.m.Winnipeg
27h 35m
2 stops
GCM1:15 p.m.George Town Owen Roberts Intl
29 Nov
GCM5:30 p.m.George Town Owen Roberts Intl
17h 19m
2 stops
YWG9:49 a.m.Winnipeg
C$ 1,382
Find similar

WestJet flights from Winnipeg to Grand Cayman

Our best WestJet deals on Winnipeg to Grand Cayman flight tickets
WestJet
23 Nov
YWG8:05 p.m.Winnipeg
16h 39m
1 stop
GCM1:44 p.m.George Town Owen Roberts Intl
1 Dec
GCM2:50 p.m.George Town Owen Roberts Intl
25h 31m
2 stops
YWG3:21 p.m.Winnipeg
C$ 863
Find similar
WestJet
23 Nov
YWG8:05 p.m.Winnipeg
16h 39m
1 stop
GCM1:44 p.m.George Town Owen Roberts Intl
1 Dec
GCM2:50 p.m.George Town Owen Roberts Intl
21h 45m
1 stop
YWG11:35 a.m.Winnipeg
C$ 873
Find similar
WestJet
21 Nov
YWG9:00 p.m.Winnipeg
39h 44m
2 stops
GCM1:44 p.m.George Town Owen Roberts Intl
1 Dec
GCM2:50 p.m.George Town Owen Roberts Intl
10h 45m
1 stop
YWG12:35 a.m.Winnipeg
C$ 896
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Winnipeg to Grand Cayman that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 96,600 searches. Data last updated 6 November 2025.
Use the filters below to find and compare flights from Winnipeg to Grand Cayman that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 23/11

7:05 p.m.-4:30 p.m.

2 stops44h 25m

George Town Owen Roberts Intl

Mon 1/12

5:45 p.m.-9:49 a.m.

2 stops41h 04m

C$ 851

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 23/11

8:05 p.m.-1:44 p.m.

1 stop16h 39m

George Town Owen Roberts Intl

Mon 1/12

2:50 p.m.-3:21 p.m.

2 stops25h 31m

C$ 863

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 23/11

8:05 p.m.-1:44 p.m.

1 stop16h 39m

George Town Owen Roberts Intl

Mon 1/12

2:50 p.m.-11:35 a.m.

1 stop21h 45m

C$ 873

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 22/11

7:05 p.m.-12:25 p.m.

1 stop16h 20m

George Town Owen Roberts Intl

Sun 30/11

1:30 p.m.-8:28 p.m.

2 stops31h 58m

C$ 1,023

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 22/1

4:25 p.m.-2:00 p.m.

1 stop20h 35m

George Town Owen Roberts Intl

Sun 1/2

3:00 p.m.-11:13 a.m.

1 stop21h 13m

C$ 1,213

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 22/1

4:25 p.m.-4:25 p.m.

2 stops47h 00m

George Town Owen Roberts Intl

Sun 1/2

3:00 p.m.-11:13 a.m.

1 stop21h 13m

C$ 1,219

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 22/11

1:45 p.m.-12:25 p.m.

2 stops21h 40m

George Town Owen Roberts Intl

Sun 30/11

1:30 p.m.-8:28 p.m.

2 stops31h 58m

C$ 1,254

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Fri 21/11

8:40 a.m.-1:15 p.m.

2 stops27h 35m

George Town Owen Roberts Intl

Sat 29/11

5:30 p.m.-9:49 a.m.

2 stops17h 19m

C$ 1,382

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 23/11

12:10 p.m.-2:46 p.m.

3 stops25h 36m

George Town Owen Roberts Intl

Mon 1/12

3:36 p.m.-11:35 p.m.

3 stops56h 59m

C$ 4,245

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 23/11

12:10 p.m.-11:57 a.m.

2 stops22h 47m

George Town Owen Roberts Intl

Mon 1/12

3:36 p.m.-11:35 p.m.

3 stops56h 59m

C$ 4,839

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 resultsSorted by cheapest first
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See travel insights to Grand Cayman from

How to get the cheapest flight ticket from Winnipeg to Grand Cayman

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Grand Cayman?

The cheapest day to depart from Winnipeg to Grand Cayman is on a Monday when prices can be found for as low as C$ 850. Flights from Winnipeg to Grand Cayman on a Saturday will generally be more expensive and average around C$ 1,338. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Grand Cayman?

Flying to Grand Cayman from Winnipeg in the morning is the least expensive time of day to depart. momondo users have found prices as low as C$ 849 when looking at flights departing in the morning. Flights to Grand Cayman are more costly in the afternoon, with an average ticket price of C$ 1,167. Departure times in the afternoon fall within the peak daily travel times, which is why tickets can be more expensive.

Can stopping save me money on Winnipeg to Grand Cayman flights?

No. A direct flight is the cheapest option for a flight between Winnipeg to Grand Cayman.

Cheap Winnipeg to Grand Cayman flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Grand Cayman

Direct flights

None
There are no direct flights from Winnipeg to Grand Cayman. There are no popular flight routes from Winnipeg to Grand Cayman.
Search flight deals

  • When did momondo last update prices for flights from Winnipeg Airport to Grand Cayman?

    Prices for flights from Winnipeg Airport to Grand Cayman refresh daily.

  • How many operators does momondo search for flights from Winnipeg Airport to Grand Cayman?

  • How old do you have to be to fly from Winnipeg Airport to Grand Cayman?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Winnipeg Airport to Grand Cayman.

  • What documentation or ID do you need to fly to Grand Cayman?

    The travel and health documents you'll need for your trip to Grand Cayman may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Grand Cayman. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Winnipeg to Grand Cayman?

Best airlines flying from Winnipeg to Grand Cayman

Compare and see reviews for airlines that fly from Winnipeg to Grand Cayman with momondo
Airline
Rating
Free Cancellation
Price
WestJetPriceFrom C$ 549Free CancellationRating
7.2
3,154 reviews
Search WestJet flights
United AirlinesPriceFrom C$ 791Free CancellationRating
7.4
9,003 reviews
Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Winnipeg to Grand Cayman?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Grand Cayman from Winnipeg.

Can I find flights from Winnipeg to Grand Cayman with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Winnipeg to Grand Cayman flights to just show those with flexible booking policies.

How can momondo help me find flights from Winnipeg to Grand Cayman?

Once all potential Winnipeg to Grand Cayman flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Winnipeg to Grand Cayman right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Grand Cayman, momondo offers a useful price alert feature which will track prices for flights to Grand Cayman from Winnipeg and alert you when they change.

An easier way to manage your Grand Cayman trip

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