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Cheap flights from Winnipeg to the Cayman Islands from C$ 558

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 the Cayman Islands departing on 13/4. 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 the Cayman Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
5:00 a.m. - 12:44 p.m.
YWG
-
GCM
7h 44m
1 stop
WestJet Logo
1:50 p.m. - 11:52 a.m.
GCM
-
YWG
22h 02m
2 stops
C$ 558WestJet
Mon, 13 Apr - Thu, 16 Apr
WestJet Logo
5:00 a.m. - 12:44 p.m.
YWG
-
GCM
7h 44m
1 stop
WestJet Logo
1:50 p.m. - 10:52 a.m.
GCM
-
YWG
21h 02m
1 stop
C$ 571WestJet
Mon, 13 Apr - Thu, 16 Apr
Air Canada Logo
7:05 p.m. - 10:10 a.m.
YWG
-
GCM
15h 05m
1 stop
Air Canada Logo
11:10 a.m. - 9:53 a.m.
GCM
-
YWG
22h 43m
1 stop
C$ 605Air Canada
Thu, 9 Apr - Fri, 17 Apr
Air Canada Logo
6:00 a.m. - 10:55 a.m.
YWG
-
GCM
28h 55m
2 stops
Air Canada Logo
11:10 a.m. - 9:53 a.m.
GCM
-
YWG
22h 43m
1 stop
C$ 630Air Canada
Sat, 4 Apr - Fri, 17 Apr
Air Canada Logo
5:30 a.m. - 12:30 p.m.
YWG
-
GCM
31h 00m
2 stops
Air Canada Logo
11:10 a.m. - 9:53 a.m.
GCM
-
YWG
22h 43m
1 stop
C$ 643Air Canada
Mon, 6 Apr - Fri, 17 Apr
Air Canada Logo
7:05 p.m. - 10:10 a.m.
YWG
-
GCM
15h 05m
1 stop
Air Canada Logo
12:30 p.m. - 9:53 a.m.
GCM
-
YWG
21h 23m
1 stop
C$ 654Air Canada
Thu, 9 Apr - Tue, 14 Apr
Air Canada Logo
7:05 p.m. - 10:10 a.m.
YWG
-
GCM
15h 05m
1 stop
Air Canada Logo
11:55 a.m. - 4:29 p.m.
GCM
-
YWG
28h 34m
2 stops
C$ 660Air Canada
Thu, 9 Apr - Thu, 16 Apr
Air Canada Logo
7:10 p.m. - 12:30 p.m.
YWG
-
GCM
17h 20m
2 stops
Air Canada Logo
12:25 p.m. - 11:15 a.m.
GCM
-
YWG
22h 50m
1 stop
C$ 674Air Canada
Mon, 20 Jul - Mon, 27 Jul
Air Canada Logo
1:30 p.m. - 10:55 a.m.
YWG
-
GCM
21h 25m
1 stop
Air Canada Logo
11:55 a.m. - 11:48 p.m.
GCM
-
YWG
11h 53m
1 stop
C$ 680Air Canada
Sat, 4 Apr - Thu, 16 Apr
Air Canada Logo
6:00 a.m. - 10:55 a.m.
YWG
-
GCM
28h 55m
2 stops
Air Canada Logo
11:55 a.m. - 4:29 p.m.
GCM
-
YWG
28h 34m
2 stops
C$ 685Air Canada
Sat, 4 Apr - Thu, 16 Apr

WestJet flights from Winnipeg to Cayman Islands

Our best WestJet deals on Winnipeg to Cayman Islands flight tickets
WestJet
13 Apr
YWG5:00 a.m.Winnipeg
7h 44m
1 stop
GCM12:44 p.m.George Town Owen Roberts Intl
16 Apr
GCM1:50 p.m.George Town Owen Roberts Intl
22h 02m
2 stops
YWG11:52 a.m.Winnipeg
C$ 558
WestJet
13 Apr
YWG5:00 a.m.Winnipeg
7h 44m
1 stop
GCM12:44 p.m.George Town Owen Roberts Intl
16 Apr
GCM1:50 p.m.George Town Owen Roberts Intl
21h 02m
1 stop
YWG10:52 a.m.Winnipeg
C$ 571
WestJet
7 Apr
YWG9:00 p.m.Winnipeg
39h 44m
2 stops
GCM12:44 p.m.George Town Owen Roberts Intl
16 Apr
GCM1:50 p.m.George Town Owen Roberts Intl
20h 17m
2 stops
YWG10:07 a.m.Winnipeg
C$ 696

Air Canada flights from Winnipeg to Cayman Islands

Our best Air Canada deals on Winnipeg to Cayman Islands flight tickets
Air Canada
9 Apr
YWG7:05 p.m.Winnipeg
15h 05m
1 stop
GCM10:10 a.m.George Town Owen Roberts Intl
17 Apr
GCM11:10 a.m.George Town Owen Roberts Intl
22h 43m
1 stop
YWG9:53 a.m.Winnipeg
C$ 605
Air Canada
4 Apr
YWG6:00 a.m.Winnipeg
28h 55m
2 stops
GCM10:55 a.m.George Town Owen Roberts Intl
17 Apr
GCM11:10 a.m.George Town Owen Roberts Intl
22h 43m
1 stop
YWG9:53 a.m.Winnipeg
C$ 630
Air Canada
6 Apr
YWG5:30 a.m.Winnipeg
31h 00m
2 stops
GCM12:30 p.m.George Town Owen Roberts Intl
17 Apr
GCM11:10 a.m.George Town Owen Roberts Intl
22h 43m
1 stop
YWG9:53 a.m.Winnipeg
C$ 643

momondo Fare Finder

 
Customize your flight search to find flights from Winnipeg to Cayman Islands 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 March 2026.
Use the filters below to find and compare flights from Winnipeg to the Cayman Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 13/4

5:00 a.m.-12:44 p.m.

1 stop7h 44m

George Town Owen Roberts Intl

Thu 16/4

1:50 p.m.-11:52 a.m.

2 stops22h 02m

C$ 558
Quickest round-trip

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 13/4

5:00 a.m.-12:44 p.m.

1 stop7h 44m

George Town Owen Roberts Intl

Thu 16/4

1:50 p.m.-10:52 a.m.

1 stop21h 02m

C$ 571

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 9/4

7:05 p.m.-10:10 a.m.

1 stop15h 05m

George Town Owen Roberts Intl

Fri 17/4

11:10 a.m.-9:53 a.m.

1 stop22h 43m

C$ 605

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 4/4

6:00 a.m.-10:55 a.m.

2 stops28h 55m

George Town Owen Roberts Intl

Fri 17/4

11:10 a.m.-9:53 a.m.

1 stop22h 43m

C$ 630

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 6/4

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

2 stops31h 00m

George Town Owen Roberts Intl

Fri 17/4

11:10 a.m.-9:53 a.m.

1 stop22h 43m

C$ 643

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 9/4

7:05 p.m.-10:10 a.m.

1 stop15h 05m

George Town Owen Roberts Intl

Tue 14/4

12:30 p.m.-9:53 a.m.

1 stop21h 23m

C$ 654

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 9/4

7:05 p.m.-10:10 a.m.

1 stop15h 05m

George Town Owen Roberts Intl

Thu 16/4

11:55 a.m.-4:29 p.m.

2 stops28h 34m

C$ 660

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 20/7

7:10 p.m.-12:30 p.m.

2 stops17h 20m

George Town Owen Roberts Intl

Mon 27/7

12:25 p.m.-11:15 a.m.

1 stop22h 50m

C$ 674

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 4/4

1:30 p.m.-10:55 a.m.

1 stop21h 25m

George Town Owen Roberts Intl

Thu 16/4

11:55 a.m.-11:48 p.m.

1 stop11h 53m

C$ 680

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 4/4

6:00 a.m.-10:55 a.m.

2 stops28h 55m

George Town Owen Roberts Intl

Thu 16/4

11:55 a.m.-4:29 p.m.

2 stops28h 34m

C$ 685

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to the Cayman Islands from

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

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

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

You could potentially save up to 27% on your flight if you consider stops on a Winnipeg to Cayman Islands flight.

Cheap Winnipeg to Cayman Islands flight deals and tips

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

Fastest flight time

18h 20m

Direct flights

None
The fastest flight from Winnipeg to Cayman Islands takes 18h 20m
There are no direct flights from Winnipeg to Cayman Islands. There are no popular flight routes from Winnipeg to Cayman Islands.
Search flight deals

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

    Prices for flights from Winnipeg Airport to Cayman Islands were last updated today.

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to Cayman Islands.

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

    The necessary travel and health documents for your Cayman Islands trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Winnipeg to Cayman Islands

Compare and see reviews for airlines that fly from Winnipeg to Cayman Islands with momondo
Airline
Rating
Free Cancellation
Price
WestJetPriceFrom C$ 491Free CancellationRating
7.2
3,300 reviews
Search WestJet flights
United AirlinesPriceFrom C$ 769Free CancellationRating
7.4
9,462 reviews
Search United Airlines flights

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Winnipeg to Cayman Islands for you.

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

Yes. All flights to Cayman Islands from Winnipeg on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once you have performed a search for Winnipeg to Cayman Islands flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

If you are not ready to book a flight from Winnipeg to Cayman Islands now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Cayman Islands and let you know when they change.

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Find better results for your trip to the Cayman Islands

Popular Cities in the Cayman Islands

Popular flights according to clicks in the last 7 days on momondo
Flights to George Townfrom C$ 402