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Cheap flights from Winnipeg to the Cayman Islands from C$ 241

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 16/1. 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 the Cayman Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
6:55 p.m. - 12:44 p.m.
YWG
-
GCM
41h 49m2 stops
WestJet Logo
1:50 p.m. - 7:09 p.m.
GCM
-
YWG
29h 19m1 stop
C$ 620WestJet
Fri, 27 Mar - Mon, 6 Apr
WestJet Logo
6:45 a.m. - 12:44 p.m.
YWG
-
GCM
29h 59m2 stops
WestJet Logo
1:50 p.m. - 10:07 a.m.
GCM
-
YWG
20h 17m2 stops
C$ 631WestJet
Sat, 28 Mar - Mon, 6 Apr
WestJet Logo
5:00 a.m. - 12:44 p.m.
YWG
-
GCM
7h 44m1 stop
WestJet Logo
1:50 p.m. - 7:09 p.m.
GCM
-
YWG
29h 19m1 stop
C$ 730WestJet
Thu, 26 Mar - Sun, 5 Apr
United Airlines Logo
2:20 p.m. - 1:45 p.m.
YWG
-
GCM
22h 25m1 stop
United Airlines Logo
5:45 p.m. - 11:57 a.m.
GCM
-
YWG
43h 12m2 stops
C$ 811United Airlines
Sat, 7 Feb - Sat, 21 Feb
Multiple Airlines Logo
8:05 p.m. - 3:25 p.m.
YWG
-
GCM
19h 20m1 stop
Multiple Airlines Logo
1:50 p.m. - 11:13 a.m.
GCM
-
YWG
21h 23m2 stops
C$ 819Multiple Airlines
Fri, 27 Mar - Mon, 6 Apr
United Airlines Logo
7:05 p.m. - 1:45 p.m.
YWG
-
GCM
41h 40m2 stops
United Airlines Logo
5:45 p.m. - 11:57 a.m.
GCM
-
YWG
43h 12m2 stops
C$ 822United Airlines
Sat, 7 Feb - Sat, 21 Feb
Air Canada Logo
6:00 a.m. - 11:25 a.m.
YWG
-
GCM
29h 25m2 stops
Air Canada Logo
12:30 p.m. - 10:07 a.m.
GCM
-
YWG
45h 37m2 stops
C$ 890Air Canada
Thu, 26 Mar - Sun, 5 Apr
Multiple Airlines Logo
8:05 p.m. - 3:25 p.m.
YWG
-
GCM
19h 20m1 stop
Multiple Airlines Logo
1:50 p.m. - 11:32 a.m.
GCM
-
YWG
21h 42m1 stop
C$ 904Multiple Airlines
Fri, 27 Mar - Mon, 6 Apr
Multiple Airlines Logo
12:20 p.m. - 12:44 p.m.
YWG
-
GCM
24h 24m1 stop
Multiple Airlines Logo
1:50 p.m. - 7:35 p.m.
GCM
-
YWG
29h 45m1 stop
C$ 964Multiple Airlines
Sat, 28 Mar - Mon, 6 Apr
Multiple Airlines Logo
9:05 a.m. - 3:25 p.m.
YWG
-
GCM
30h 20m3 stops
Multiple Airlines Logo
1:50 p.m. - 3:20 p.m.
GCM
-
YWG
25h 30m2 stops
C$ 970Multiple Airlines
Fri, 27 Mar - Mon, 6 Apr

United Airlines flights from Winnipeg to Cayman Islands

Our best United Airlines deals on Winnipeg to Cayman Islands flight tickets
United Airlines
6 Dec
YWG2:20 p.m.Winnipeg
25h 10m
2 stops
GCM4:30 p.m.George Town Owen Roberts Intl
10 Dec
GCM5:45 p.m.George Town Owen Roberts Intl
28h 10m
2 stops
YWG8:55 p.m.Winnipeg
C$ 670
Find similar
United Airlines
6 Dec
YWG2:20 p.m.Winnipeg
25h 10m
2 stops
GCM4:30 p.m.George Town Owen Roberts Intl
10 Dec
GCM5:45 p.m.George Town Owen Roberts Intl
43h 12m
2 stops
YWG11:57 a.m.Winnipeg
C$ 671
Find similar
United Airlines
6 Dec
YWG8:40 a.m.Winnipeg
30h 50m
2 stops
GCM4:30 p.m.George Town Owen Roberts Intl
10 Dec
GCM5:45 p.m.George Town Owen Roberts Intl
28h 10m
2 stops
YWG8:55 p.m.Winnipeg
C$ 673
Find similar

Porter Airlines flights from Winnipeg to Cayman Islands

Our best Porter Airlines deals on Winnipeg to Cayman Islands flight tickets
Porter Airlines
22 Jan
YWG4:25 p.m.Winnipeg
47h 00m
2 stops
GCM4:25 p.m.George Town Owen Roberts Intl
1 Feb
GCM3:00 p.m.George Town Owen Roberts Intl
21h 13m
1 stop
YWG11:13 a.m.Winnipeg
C$ 1,006
Find similar
Porter Airlines
22 Jan
YWG4:25 p.m.Winnipeg
47h 00m
2 stops
GCM4:25 p.m.George Town Owen Roberts Intl
1 Feb
GCM3:00 p.m.George Town Owen Roberts Intl
25h 30m
2 stops
YWG3:30 p.m.Winnipeg
C$ 1,015
Find similar
Porter Airlines
22 Jan
YWG4:25 p.m.Winnipeg
47h 00m
2 stops
GCM4:25 p.m.George Town Owen Roberts Intl
1 Feb
GCM3:00 p.m.George Town Owen Roberts Intl
25h 30m
2 stops
YWG3:30 p.m.Winnipeg
C$ 1,016
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 4 December 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

Fri 27/3

6:55 p.m.-12:44 p.m.

2 stops41h 49m

George Town Owen Roberts Intl

Mon 6/4

1:50 p.m.-7:09 p.m.

1 stop29h 19m

C$ 620

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 28/3

6:45 a.m.-12:44 p.m.

2 stops29h 59m

George Town Owen Roberts Intl

Mon 6/4

1:50 p.m.-10:07 a.m.

2 stops20h 17m

C$ 631

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 26/3

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

1 stop7h 44m

George Town Owen Roberts Intl

Sun 5/4

1:50 p.m.-7:09 p.m.

1 stop29h 19m

C$ 730

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 7/2

2:20 p.m.-1:45 p.m.

1 stop22h 25m

George Town Owen Roberts Intl

Sat 21/2

5:45 p.m.-11:57 a.m.

2 stops43h 12m

C$ 811

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Fri 27/3

8:05 p.m.-3:25 p.m.

1 stop19h 20m

George Town Owen Roberts Intl

Mon 6/4

1:50 p.m.-11:13 a.m.

2 stops21h 23m

C$ 819

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 7/2

7:05 p.m.-1:45 p.m.

2 stops41h 40m

George Town Owen Roberts Intl

Sat 21/2

5:45 p.m.-11:57 a.m.

2 stops43h 12m

C$ 822

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 26/3

6:00 a.m.-11:25 a.m.

2 stops29h 25m

George Town Owen Roberts Intl

Sun 5/4

12:30 p.m.-10:07 a.m.

2 stops45h 37m

C$ 890

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Fri 27/3

8:05 p.m.-3:25 p.m.

1 stop19h 20m

George Town Owen Roberts Intl

Mon 6/4

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

1 stop21h 42m

C$ 904

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 28/3

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

1 stop24h 24m

George Town Owen Roberts Intl

Mon 6/4

1:50 p.m.-7:35 p.m.

1 stop29h 45m

C$ 964

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Fri 27/3

9:05 a.m.-3:25 p.m.

3 stops30h 20m

George Town Owen Roberts Intl

Mon 6/4

1:50 p.m.-3:20 p.m.

2 stops25h 30m

C$ 970

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$ 840. The most expensive day to fly to Cayman Islands is Saturday, with ticket prices averaging around C$ 1,323.

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$ 840 when looking at flights departing in the morning. Flights in the afternoon are often more expensive with an average ticket price of C$ 1,154.

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

Fastest flight time

22h 10m

Direct flights

None
The fastest flight from Winnipeg to Cayman Islands takes 22h 10m
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$ 544Free CancellationRating
7.2
3,191 reviews
Search WestJet flights
United AirlinesPriceFrom C$ 782Free CancellationRating
7.4
9,063 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$ 359