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Cheap flights from Winnipeg to Grand Cayman from C$ 515

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Winnipeg to Grand Cayman departing on 11/1. 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.
WestJet Logo
8:05 p.m. - 1:44 p.m.
YWG
-
GCM
16h 39m1 stop
WestJet Logo
2:50 p.m. - 12:42 a.m.
GCM
-
YWG
10h 52m1 stop
C$ 515WestJet
Sun, 11 Jan - Sun, 18 Jan
WestJet Logo
5:00 a.m. - 1:44 p.m.
YWG
-
GCM
7h 44m1 stop
WestJet Logo
2:50 p.m. - 12:09 p.m.
GCM
-
YWG
46h 19m2 stops
C$ 523WestJet
Sun, 11 Jan - Sun, 18 Jan
Air Canada Logo
7:05 p.m. - 12:25 p.m.
YWG
-
GCM
16h 20m1 stop
Air Canada Logo
1:30 p.m. - 11:54 p.m.
GCM
-
YWG
11h 24m1 stop
C$ 548Air Canada
Mon, 12 Jan - Mon, 19 Jan
WestJet Logo
9:00 p.m. - 1:44 p.m.
YWG
-
GCM
39h 44m2 stops
WestJet Logo
2:50 p.m. - 11:35 a.m.
GCM
-
YWG
21h 45m1 stop
C$ 549WestJet
Fri, 9 Jan - Thu, 15 Jan
Air Canada Logo
7:05 p.m. - 12:25 p.m.
YWG
-
GCM
16h 20m1 stop
Air Canada Logo
1:30 p.m. - 10:16 a.m.
GCM
-
YWG
21h 46m2 stops
C$ 553Air Canada
Mon, 12 Jan - Thu, 15 Jan
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$ 581Air Canada
Thu, 8 Jan - Mon, 19 Jan
Air Canada Logo
6:00 a.m. - 12:25 p.m.
YWG
-
GCM
53h 25m2 stops
Air Canada Logo
1:30 p.m. - 4:35 p.m.
GCM
-
YWG
28h 05m2 stops
C$ 587Air Canada
Fri, 9 Jan - Fri, 16 Jan
Multiple Airlines Logo
8:20 p.m. - 4:25 p.m.
YWG
-
GCM
19h 05m1 stop
Multiple Airlines Logo
2:50 p.m. - 7:35 p.m.
GCM
-
YWG
29h 45m1 stop
C$ 593Multiple Airlines
Mon, 12 Jan - Sun, 18 Jan
Multiple Airlines Logo
8:05 p.m. - 1:44 p.m.
YWG
-
GCM
16h 39m1 stop
Multiple Airlines Logo
5:25 p.m. - 7:35 p.m.
GCM
-
YWG
27h 10m1 stop
C$ 595Multiple Airlines
Sun, 11 Jan - Sat, 17 Jan
Multiple Airlines Logo
8:20 p.m. - 1:44 p.m.
YWG
-
GCM
16h 24m1 stop
Multiple Airlines Logo
2:34 p.m. - 11:35 a.m.
GCM
-
YWG
22h 01m2 stops
C$ 602Multiple Airlines
Sun, 11 Jan - Sat, 17 Jan

WestJet flights from Winnipeg to Grand Cayman

Our best WestJet deals on Winnipeg to Grand Cayman flight tickets
WestJet
11 Jan
YWG8:05 p.m.Winnipeg
16h 39m
1 stop
GCM1:44 p.m.George Town Owen Roberts Intl
18 Jan
GCM2:50 p.m.George Town Owen Roberts Intl
10h 52m
1 stop
YWG12:42 a.m.Winnipeg
C$ 515
Find similar
WestJet
11 Jan
YWG5:00 a.m.Winnipeg
7h 44m
1 stop
GCM1:44 p.m.George Town Owen Roberts Intl
18 Jan
GCM2:50 p.m.George Town Owen Roberts Intl
46h 19m
2 stops
YWG12:09 p.m.Winnipeg
C$ 523
Find similar
WestJet
9 Jan
YWG9:00 p.m.Winnipeg
39h 44m
2 stops
GCM1:44 p.m.George Town Owen Roberts Intl
15 Jan
GCM2:50 p.m.George Town Owen Roberts Intl
21h 45m
1 stop
YWG11:35 a.m.Winnipeg
C$ 549
Find similar

Air Canada flights from Winnipeg to Grand Cayman

Our best Air Canada deals on Winnipeg to Grand Cayman flight tickets
Air Canada
12 Jan
YWG7:05 p.m.Winnipeg
16h 20m
1 stop
GCM12:25 p.m.George Town Owen Roberts Intl
19 Jan
GCM1:30 p.m.George Town Owen Roberts Intl
11h 24m
1 stop
YWG11:54 p.m.Winnipeg
C$ 548
Find similar
Air Canada
12 Jan
YWG7:05 p.m.Winnipeg
16h 20m
1 stop
GCM12:25 p.m.George Town Owen Roberts Intl
15 Jan
GCM1:30 p.m.George Town Owen Roberts Intl
21h 46m
2 stops
YWG10:16 a.m.Winnipeg
C$ 553
Find similar
Air Canada
8 Jan
YWG7:05 p.m.Winnipeg
16h 20m
1 stop
GCM12:25 p.m.George Town Owen Roberts Intl
19 Jan
GCM1:30 p.m.George Town Owen Roberts Intl
31h 58m
2 stops
YWG8:28 p.m.Winnipeg
C$ 581
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 23 December 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 11/1

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

1 stop16h 39m

George Town Owen Roberts Intl

Sun 18/1

2:50 p.m.-12:42 a.m.

1 stop10h 52m

C$ 515

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 11/1

5:00 a.m.-1:44 p.m.

1 stop7h 44m

George Town Owen Roberts Intl

Sun 18/1

2:50 p.m.-12:09 p.m.

2 stops46h 19m

C$ 523

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 12/1

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

1 stop16h 20m

George Town Owen Roberts Intl

Mon 19/1

1:30 p.m.-11:54 p.m.

1 stop11h 24m

C$ 548

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Fri 9/1

9:00 p.m.-1:44 p.m.

2 stops39h 44m

George Town Owen Roberts Intl

Thu 15/1

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

1 stop21h 45m

C$ 549

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 12/1

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

1 stop16h 20m

George Town Owen Roberts Intl

Thu 15/1

1:30 p.m.-10:16 a.m.

2 stops21h 46m

C$ 553

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 8/1

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

1 stop16h 20m

George Town Owen Roberts Intl

Mon 19/1

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

2 stops31h 58m

C$ 581

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Fri 9/1

6:00 a.m.-12:25 p.m.

2 stops53h 25m

George Town Owen Roberts Intl

Fri 16/1

1:30 p.m.-4:35 p.m.

2 stops28h 05m

C$ 586

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 12/1

8:20 p.m.-4:25 p.m.

1 stop19h 05m

George Town Owen Roberts Intl

Sun 18/1

2:50 p.m.-7:35 p.m.

1 stop29h 45m

C$ 593

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 11/1

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

1 stop16h 39m

George Town Owen Roberts Intl

Sat 17/1

5:25 p.m.-7:35 p.m.

1 stop27h 10m

C$ 595

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 11/1

8:20 p.m.-1:44 p.m.

1 stop16h 24m

George Town Owen Roberts Intl

Sat 17/1

2:34 p.m.-11:35 a.m.

2 stops22h 01m

C$ 602

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$ 829. Flights from Winnipeg to Grand Cayman on a Saturday will generally be more expensive and average around C$ 1,306. 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$ 829 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$ 1,139. 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

Fastest flight time

7h 44m

Direct flights

None
The fastest flight from Winnipeg to Grand Cayman takes 7h 44m
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$ 537Free CancellationRating
7.2
3,209 reviews
Search WestJet flights
United AirlinesPriceFrom C$ 772Free CancellationRating
7.4
9,102 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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