Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Winnipeg to the Cayman Islands from C$ 809

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 29/7. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Winnipeg to the Cayman Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
5:00 a.m. - 9:00 p.m.
YWG
-
GCM
16h 00m
2 stops
Multiple Airlines Logo
12:25 p.m. - 8:01 p.m.
GCM
-
YWG
31h 36m
2 stops
C$ 809Multiple Airlines
Wed, 29 Jul - Mon, 31 Aug
Air Canada Logo
7:10 p.m. - 11:25 a.m.
YWG
-
GCM
16h 15m
1 stop
Air Canada Logo
12:25 p.m. - 8:01 p.m.
GCM
-
YWG
31h 36m
2 stops
C$ 901Air Canada
Wed, 29 Jul - Mon, 31 Aug
Air Canada Logo
5:00 a.m. - 11:25 a.m.
YWG
-
GCM
30h 25m
1 stop
Air Canada Logo
12:25 p.m. - 11:15 a.m.
GCM
-
YWG
22h 50m
1 stop
C$ 905Air Canada
Wed, 29 Jul - Mon, 31 Aug
Air Canada Logo
1:30 p.m. - 11:25 a.m.
YWG
-
GCM
21h 55m
2 stops
Air Canada Logo
12:25 p.m. - 8:01 p.m.
GCM
-
YWG
31h 36m
2 stops
C$ 907Air Canada
Wed, 29 Jul - Mon, 31 Aug
Air Canada Logo
1:30 p.m. - 11:25 a.m.
YWG
-
GCM
21h 55m
2 stops
Air Canada Logo
12:25 p.m. - 8:01 p.m.
GCM
-
YWG
31h 36m
2 stops
C$ 949Air Canada
Wed, 29 Jul - Mon, 31 Aug
Air Canada Logo
1:30 p.m. - 11:25 a.m.
YWG
-
GCM
21h 55m
2 stops
Air Canada Logo
12:25 p.m. - 11:15 a.m.
GCM
-
YWG
22h 50m
1 stop
C$ 951Air Canada
Wed, 29 Jul - Mon, 31 Aug
Air Canada Logo
1:30 p.m. - 11:25 a.m.
YWG
-
GCM
21h 55m
2 stops
Air Canada Logo
12:25 p.m. - 8:01 p.m.
GCM
-
YWG
31h 36m
2 stops
C$ 955Air Canada
Wed, 29 Jul - Mon, 31 Aug
WestJet Logo
5:00 a.m. - 1:44 p.m.
YWG
-
GCM
7h 44m
1 stop
WestJet Logo
2:50 p.m. - 10:50 p.m.
GCM
-
YWG
33h 00m
2 stops
C$ 1,003WestJet
Thu, 17 Dec - Mon, 28 Dec
Air Canada Logo
3:20 p.m. - 11:25 a.m.
YWG
-
GCM
20h 05m
1 stop
Air Canada Logo
12:25 p.m. - 11:15 a.m.
GCM
-
YWG
22h 50m
1 stop
C$ 1,022Air Canada
Wed, 29 Jul - Mon, 31 Aug
Air Canada Logo
12:20 p.m. - 11:25 a.m.
YWG
-
GCM
23h 05m
1 stop
Air Canada Logo
12:25 p.m. - 11:15 a.m.
GCM
-
YWG
22h 50m
1 stop
C$ 1,050Air Canada
Wed, 29 Jul - Mon, 31 Aug

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Air Canada flights from Winnipeg to Cayman Islands

Our best Air Canada deals on Winnipeg to Cayman Islands flight tickets
Air Canada
29 Jul
YWG7:10 p.m.Winnipeg
16h 15m
1 stop
GCM11:25 a.m.George Town Owen Roberts Intl
31 Aug
GCM12:25 p.m.George Town Owen Roberts Intl
31h 36m
2 stops
YWG8:01 p.m.Winnipeg
C$ 901
Air Canada
29 Jul
YWG5:00 a.m.Winnipeg
30h 25m
1 stop
GCM11:25 a.m.George Town Owen Roberts Intl
31 Aug
GCM12:25 p.m.George Town Owen Roberts Intl
22h 50m
1 stop
YWG11:15 a.m.Winnipeg
C$ 905
Air Canada
29 Jul
YWG1:30 p.m.Winnipeg
21h 55m
2 stops
GCM11:25 a.m.George Town Owen Roberts Intl
31 Aug
GCM12:25 p.m.George Town Owen Roberts Intl
31h 36m
2 stops
YWG8:01 p.m.Winnipeg
C$ 907

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 28 June 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

Wed 29/7

5:00 a.m.-9:00 p.m.

2 stops16h 00m

George Town Owen Roberts Intl

Mon 31/8

12:25 p.m.-8:01 p.m.

2 stops31h 36m

C$ 809

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Wed 29/7

7:10 p.m.-11:25 a.m.

1 stop16h 15m

George Town Owen Roberts Intl

Mon 31/8

12:25 p.m.-8:01 p.m.

2 stops31h 36m

C$ 901

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Wed 29/7

5:00 a.m.-11:25 a.m.

1 stop30h 25m

George Town Owen Roberts Intl

Mon 31/8

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

1 stop22h 50m

C$ 905

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Wed 29/7

1:30 p.m.-11:25 a.m.

2 stops21h 55m

George Town Owen Roberts Intl

Mon 31/8

12:25 p.m.-8:01 p.m.

2 stops31h 36m

C$ 907

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Wed 29/7

1:30 p.m.-11:25 a.m.

2 stops21h 55m

George Town Owen Roberts Intl

Mon 31/8

12:25 p.m.-8:01 p.m.

2 stops31h 36m

C$ 949

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Wed 29/7

1:30 p.m.-11:25 a.m.

2 stops21h 55m

George Town Owen Roberts Intl

Mon 31/8

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

1 stop22h 50m

C$ 951

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Wed 29/7

1:30 p.m.-11:25 a.m.

2 stops21h 55m

George Town Owen Roberts Intl

Mon 31/8

12:25 p.m.-8:01 p.m.

2 stops31h 36m

C$ 955
Quickest round-trip

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 17/12

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

1 stop7h 44m

George Town Owen Roberts Intl

Mon 28/12

2:50 p.m.-10:50 p.m.

2 stops33h 00m

C$ 1,003

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Wed 29/7

3:20 p.m.-11:25 a.m.

1 stop20h 05m

George Town Owen Roberts Intl

Mon 31/8

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

1 stop22h 50m

C$ 1,022

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Wed 29/7

12:20 p.m.-11:25 a.m.

1 stop23h 05m

George Town Owen Roberts Intl

Mon 31/8

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

1 stop22h 50m

C$ 1,050

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

7h 44m

Direct flights

None
The fastest flight from Winnipeg to Cayman Islands takes 7h 44m
There are no direct flights from Winnipeg to Cayman Islands. There are no popular flight routes from Winnipeg to Cayman Islands.
Search flight deals

Frequently asked questions about flying from Winnipeg to the Cayman Islands

  • 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$ 508Free CancellationRating
7.2
3,385 reviews
Search WestJet 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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Tue 28/7
Tue 4/8
By creating a price alert you accept our terms of use and privacy policy.

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$ 468