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Cheap flights from Winnipeg to Grand Cayman from C$ 229

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 25/10. 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

Air Canada Logo
6:35 p.m. - 11:55 a.m.YWG-GCM
17h 20m1 stop
Air Canada Logo
4:45 p.m. - 12:39 p.m.GCM-YWG
43h 54m2 stops
C$ 924Air Canada
Find Deal
Wed, 22 Oct - Tue, 28 Oct
WestJet Logo
12:20 p.m. - 1:44 p.m.YWG-GCM
24h 24m1 stop
WestJet Logo
1:50 p.m. - 11:32 a.m.GCM-YWG
21h 42m1 stop
C$ 967WestJet
Find Deal
Sun, 1 Feb - Sun, 15 Mar
WestJet Logo
4:10 p.m. - 1:44 p.m.YWG-GCM
20h 34m2 stops
WestJet Logo
1:50 p.m. - 11:32 a.m.GCM-YWG
21h 42m1 stop
C$ 995WestJet
Find Deal
Sun, 1 Feb - Sun, 15 Mar
WestJet Logo
6:55 p.m. - 1:44 p.m.YWG-GCM
17h 49m2 stops
WestJet Logo
1:50 p.m. - 12:07 p.m.GCM-YWG
46h 17m2 stops
C$ 1,002WestJet
Find Deal
Sun, 1 Feb - Sun, 15 Mar
Air Canada Logo
3:45 p.m. - 11:55 a.m.YWG-GCM
20h 10m2 stops
Air Canada Logo
4:45 p.m. - 5:19 p.m.GCM-YWG
24h 34m2 stops
C$ 1,038Air Canada
Find Deal
Wed, 22 Oct - Tue, 28 Oct
Air Canada Logo
6:35 p.m. - 11:55 a.m.YWG-GCM
17h 20m1 stop
Air Canada Logo
4:45 p.m. - 5:19 p.m.GCM-YWG
24h 34m2 stops
C$ 1,194Air Canada
Find Deal
Wed, 22 Oct - Tue, 28 Oct

Air Canada flights from Winnipeg to Grand Cayman

Our best Air Canada deals on Winnipeg to Grand Cayman flight tickets
Air Canada
22 Oct
YWG6:35 p.m.Winnipeg
17h 20m
1 stop
GCM11:55 a.m.George Town Owen Roberts Intl
28 Oct
GCM4:45 p.m.George Town Owen Roberts Intl
43h 54m
2 stops
YWG12:39 p.m.Winnipeg
C$ 924
Find similar
Air Canada
22 Oct
YWG3:45 p.m.Winnipeg
20h 10m
2 stops
GCM11:55 a.m.George Town Owen Roberts Intl
28 Oct
GCM4:45 p.m.George Town Owen Roberts Intl
24h 34m
2 stops
YWG5:19 p.m.Winnipeg
C$ 1,038
Find similar
Air Canada
22 Oct
YWG6:35 p.m.Winnipeg
17h 20m
1 stop
GCM11:55 a.m.George Town Owen Roberts Intl
28 Oct
GCM4:45 p.m.George Town Owen Roberts Intl
24h 34m
2 stops
YWG5:19 p.m.Winnipeg
C$ 1,194
Find similar

WestJet flights from Winnipeg to Grand Cayman

Our best WestJet deals on Winnipeg to Grand Cayman flight tickets
WestJet
1 Feb
YWG12:20 p.m.Winnipeg
24h 24m
1 stop
GCM1:44 p.m.George Town Owen Roberts Intl
15 Mar
GCM1:50 p.m.George Town Owen Roberts Intl
21h 42m
1 stop
YWG11:32 a.m.Winnipeg
C$ 967
Find similar
WestJet
1 Feb
YWG4:10 p.m.Winnipeg
20h 34m
2 stops
GCM1:44 p.m.George Town Owen Roberts Intl
15 Mar
GCM1:50 p.m.George Town Owen Roberts Intl
21h 42m
1 stop
YWG11:32 a.m.Winnipeg
C$ 995
Find similar
WestJet
1 Feb
YWG6:55 p.m.Winnipeg
17h 49m
2 stops
GCM1:44 p.m.George Town Owen Roberts Intl
15 Mar
GCM1:50 p.m.George Town Owen Roberts Intl
46h 17m
2 stops
YWG12:07 p.m.Winnipeg
C$ 1,002
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 11 September 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

Wed 22/10

6:35 p.m.-11:55 a.m.

1 stop17h 20m

George Town Owen Roberts Intl

Tue 28/10

4:45 p.m.-12:39 p.m.

2 stops43h 54m

C$ 924

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 1/2

12:20 p.m.-1:44 p.m.

1 stop24h 24m

George Town Owen Roberts Intl

Sun 15/3

1:50 p.m.-11:32 a.m.

1 stop21h 42m

C$ 967

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 1/2

4:10 p.m.-1:44 p.m.

2 stops20h 34m

George Town Owen Roberts Intl

Sun 15/3

1:50 p.m.-11:32 a.m.

1 stop21h 42m

C$ 995

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 1/2

6:55 p.m.-1:44 p.m.

2 stops17h 49m

George Town Owen Roberts Intl

Sun 15/3

1:50 p.m.-12:07 p.m.

2 stops46h 17m

C$ 1,002

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Wed 22/10

3:45 p.m.-11:55 a.m.

2 stops20h 10m

George Town Owen Roberts Intl

Tue 28/10

4:45 p.m.-5:19 p.m.

2 stops24h 34m

C$ 1,038

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Wed 22/10

6:35 p.m.-11:55 a.m.

1 stop17h 20m

George Town Owen Roberts Intl

Tue 28/10

4:45 p.m.-5:19 p.m.

2 stops24h 34m

C$ 1,194

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 25/10

5:30 p.m.-12:44 p.m.

2 stops43h 14m

C$ 229

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 25/10

5:30 p.m.-12:44 p.m.

3 stops43h 14m

C$ 330

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 25/10

6:30 p.m.-11:25 a.m.

1 stop16h 55m

C$ 485

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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$ 834. Flights from Winnipeg to Grand Cayman on a Saturday will generally be more expensive and average around C$ 1,314. 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$ 834 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$ 1,146. 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$ 539Free CancellationRating
7.2
3,091 reviews
Search WestJet flights
United AirlinesPriceFrom C$ 706Free CancellationRating
7.4
8,937 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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Popular flights according to clicks in the last 7 days on momondo
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