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Cheap flights from Winnipeg to the Cayman Islands from C$ 347

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 the Cayman Islands departing on 17/10. 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 the Cayman Islands

Cheap round-trip flights

United Airlines Logo
4:25 p.m. - 12:30 p.m.YWG-GCM
44h 05m2 stops
United Airlines Logo
1:35 p.m. - 10:33 p.m.GCM-YWG
32h 58m2 stops
C$ 722United Airlines
Find Deal
Thu, 16 Oct - Sun, 19 Oct
Logo
9:00 a.m. - 9:15 p.m.YWG-GCM
12h 15m2 stops
Logo
1:45 p.m. - 7:12 p.m.GCM-YWG
29h 27m1 stop
C$ 730
Find Deal
Thu, 16 Oct - Sat, 25 Oct
Porter Airlines Logo
4:25 p.m. - 4:25 p.m.YWG-GCM
47h 00m2 stops
Porter Airlines Logo
5:25 p.m. - 11:13 a.m.GCM-YWG
18h 48m2 stops
C$ 740Porter Airlines
Find Deal
Sun, 1 Feb - Thu, 12 Feb
WestJet Logo
8:05 p.m. - 1:44 p.m.YWG-GCM
16h 39m1 stop
WestJet Logo
2:50 p.m. - 7:09 p.m.GCM-YWG
29h 19m1 stop
C$ 744WestJet
Find Deal
Sun, 1 Feb - Thu, 12 Feb
Air Canada Logo
3:45 p.m. - 11:55 a.m.YWG-GCM
20h 10m2 stops
Air Canada Logo
12:50 p.m. - 10:10 a.m.GCM-YWG
45h 20m2 stops
C$ 789Air Canada
Find Deal
Sun, 12 Oct - Thu, 23 Oct
Air Canada Logo
5:05 a.m. - 12:30 p.m.YWG-GCM
31h 25m2 stops
Air Canada Logo
12:50 p.m. - 5:45 p.m.GCM-YWG
28h 55m1 stop
C$ 818Air Canada
Find Deal
Fri, 17 Oct - Thu, 23 Oct
Porter Airlines Logo
12:10 p.m. - 4:25 p.m.YWG-GCM
27h 15m1 stop
Porter Airlines Logo
5:25 p.m. - 11:13 a.m.GCM-YWG
18h 48m2 stops
C$ 865Porter Airlines
Find Deal
Mon, 26 Jan - Tue, 10 Feb
WestJet Logo
5:00 a.m. - 1:44 p.m.YWG-GCM
7h 44m1 stop
WestJet Logo
2:50 p.m. - 7:09 p.m.GCM-YWG
29h 19m1 stop
C$ 960WestJet
Find Deal
Sun, 1 Feb - Thu, 12 Feb
Delta Logo
5:40 p.m. - 11:35 a.m.YWG-GCM
17h 55m2 stops
Delta Logo
12:55 p.m. - 11:27 p.m.GCM-YWG
10h 32m2 stops
C$ 1,235Delta
Find Deal
Wed, 15 Oct - Mon, 20 Oct
Delta Logo
5:40 p.m. - 11:35 a.m.YWG-GCM
17h 55m2 stops
Delta Logo
12:55 p.m. - 11:30 a.m.GCM-YWG
22h 35m2 stops
C$ 1,355Delta
Find Deal
Sun, 12 Oct - Fri, 24 Oct

United Airlines flights from Winnipeg to Cayman Islands

Our best United Airlines deals on Winnipeg to Cayman Islands flight tickets
United Airlines
16 Oct
YWG4:25 p.m.Winnipeg
44h 05m
2 stops
GCM12:30 p.m.George Town Owen Roberts Intl
19 Oct
GCM1:35 p.m.George Town Owen Roberts Intl
32h 58m
2 stops
YWG10:33 p.m.Winnipeg
C$ 722
Find similar
United Airlines
17 Oct
YWG4:25 p.m.Winnipeg
20h 05m
2 stops
GCM12:30 p.m.George Town Owen Roberts Intl
19 Oct
GCM1:35 p.m.George Town Owen Roberts Intl
25h 56m
2 stops
YWG3:31 p.m.Winnipeg
C$ 804
Find similar
United Airlines
16 Oct
YWG4:25 p.m.Winnipeg
44h 05m
2 stops
GCM12:30 p.m.George Town Owen Roberts Intl
25 Oct
GCM1:35 p.m.George Town Owen Roberts Intl
31h 21m
2 stops
YWG8:56 p.m.Winnipeg
C$ 906
Find similar

Porter Airlines flights from Winnipeg to Cayman Islands

Our best Porter Airlines deals on Winnipeg to Cayman Islands flight tickets
Porter Airlines
1 Feb
YWG4:25 p.m.Winnipeg
47h 00m
2 stops
GCM4:25 p.m.George Town Owen Roberts Intl
12 Feb
GCM5:25 p.m.George Town Owen Roberts Intl
18h 48m
2 stops
YWG11:13 a.m.Winnipeg
C$ 740
Find similar
Porter Airlines
26 Jan
YWG12:10 p.m.Winnipeg
27h 15m
1 stop
GCM4:25 p.m.George Town Owen Roberts Intl
10 Feb
GCM5:25 p.m.George Town Owen Roberts Intl
18h 48m
2 stops
YWG11:13 a.m.Winnipeg
C$ 865
Find similar
Porter Airlines
1 Feb
YWG4:25 p.m.Winnipeg
47h 00m
2 stops
GCM4:25 p.m.George Town Owen Roberts Intl
12 Feb
GCM5:25 p.m.George Town Owen Roberts Intl
18h 48m
2 stops
YWG11:13 a.m.Winnipeg
C$ 880
Find similar

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 2 September 2025.
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

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 16/10

4:25 p.m.-12:30 p.m.

2 stops44h 05m

George Town Owen Roberts Intl

Sun 19/10

1:35 p.m.-10:33 p.m.

2 stops32h 58m

C$ 722

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 16/10

9:00 a.m.-9:15 p.m.

2 stops12h 15m

George Town Owen Roberts Intl

Sat 25/10

1:45 p.m.-7:12 p.m.

1 stop29h 27m

C$ 730

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 1/2

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

2 stops47h 00m

George Town Owen Roberts Intl

Thu 12/2

5:25 p.m.-11:13 a.m.

2 stops18h 48m

C$ 740

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 1/2

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

1 stop16h 39m

George Town Owen Roberts Intl

Thu 12/2

2:50 p.m.-7:09 p.m.

1 stop29h 19m

C$ 744

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 12/10

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

2 stops20h 10m

George Town Owen Roberts Intl

Thu 23/10

12:50 p.m.-10:10 a.m.

2 stops45h 20m

C$ 789

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Fri 17/10

5:05 a.m.-12:30 p.m.

2 stops31h 25m

George Town Owen Roberts Intl

Thu 23/10

12:50 p.m.-5:45 p.m.

1 stop28h 55m

C$ 818

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 26/1

12:10 p.m.-4:25 p.m.

1 stop27h 15m

George Town Owen Roberts Intl

Tue 10/2

5:25 p.m.-11:13 a.m.

2 stops18h 48m

C$ 865

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 1/2

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

1 stop7h 44m

George Town Owen Roberts Intl

Thu 12/2

2:50 p.m.-7:09 p.m.

1 stop29h 19m

C$ 960

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Wed 15/10

5:40 p.m.-11:35 a.m.

2 stops17h 55m

George Town Owen Roberts Intl

Mon 20/10

12:55 p.m.-11:27 p.m.

2 stops10h 32m

C$ 1,235

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 12/10

5:40 p.m.-11:35 a.m.

2 stops17h 55m

George Town Owen Roberts Intl

Fri 24/10

12:55 p.m.-11:30 a.m.

2 stops22h 35m

C$ 1,355

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 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

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

The cheapest day to depart from Winnipeg to Cayman Islands is on a Monday. Travellers who choose to depart for Cayman Islands on a Monday will often find tickets for as low as C$ 830. The most expensive day to fly to Cayman Islands is Saturday, with ticket prices averaging around C$ 1,306.

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

Flying to Cayman Islands 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 in the afternoon are often more expensive with an average ticket price of C$ 1,139.

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

You could potentially save up to 39% 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

Direct flights

None
There are no direct flights from Winnipeg to Cayman Islands. There are no popular flight routes from Winnipeg to Cayman Islands.
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  • 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$ 536Free CancellationRating
7.2
3,082 reviews
Search WestJet flights
United AirlinesPriceFrom C$ 702Free 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 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.

An easier way to manage your Cayman Islands trip

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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$ 373