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Cheap flights from Winnipeg to the Cayman Islands from C$ 434

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 2/3. 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. - 1:44 p.m.
YWG
-
GCM
7h 44m
1 stop
WestJet Logo
1:50 p.m. - 7:09 p.m.
GCM
-
YWG
29h 19m
1 stop
C$ 434WestJet
Mon, 2 Mar - Mon, 9 Mar
WestJet Logo
5:00 a.m. - 1:44 p.m.
YWG
-
GCM
7h 44m
1 stop
WestJet Logo
1:50 p.m. - 6:05 p.m.
GCM
-
YWG
28h 15m
2 stops
C$ 445WestJet
Mon, 2 Mar - Mon, 9 Mar
Air Canada Logo
8:15 a.m. - 12:30 p.m.
YWG
-
GCM
28h 15m
2 stops
Air Canada Logo
12:30 p.m. - 8:15 p.m.
GCM
-
YWG
31h 45m
2 stops
C$ 596Air Canada
Tue, 21 Apr - Thu, 23 Apr
Air Canada Logo
6:00 a.m. - 12:25 p.m.
YWG
-
GCM
29h 25m
2 stops
Air Canada Logo
11:30 a.m. - 8:28 p.m.
GCM
-
YWG
32h 58m
2 stops
C$ 605Air Canada
Mon, 2 Mar - Mon, 9 Mar
United Airlines Logo
2:20 p.m. - 4:20 p.m.
YWG
-
GCM
25h 00m
2 stops
United Airlines Logo
2:25 p.m. - 11:57 a.m.
GCM
-
YWG
22h 32m
2 stops
C$ 611United Airlines
Fri, 27 Feb - Fri, 6 Mar
United Airlines Logo
2:20 p.m. - 1:45 p.m.
YWG
-
GCM
22h 25m
1 stop
United Airlines Logo
2:50 p.m. - 11:57 a.m.
GCM
-
YWG
22h 07m
1 stop
C$ 650United Airlines
Fri, 27 Feb - Fri, 6 Mar
United Airlines Logo
2:20 p.m. - 1:45 p.m.
YWG
-
GCM
22h 25m
1 stop
United Airlines Logo
2:25 p.m. - 9:44 a.m.
GCM
-
YWG
20h 19m
2 stops
C$ 752United Airlines
Sun, 1 Mar - Wed, 4 Mar
United Airlines Logo
2:20 p.m. - 1:45 p.m.
YWG
-
GCM
22h 25m
1 stop
United Airlines Logo
2:25 p.m. - 9:44 a.m.
GCM
-
YWG
20h 19m
2 stops
C$ 840United Airlines
Sun, 1 Mar - Wed, 4 Mar
Multiple Airlines Logo
10:55 a.m. - 1:44 p.m.
YWG
-
GCM
49h 49m
2 stops
Multiple Airlines Logo
3:00 p.m. - 7:35 p.m.
GCM
-
YWG
29h 35m
3 stops
C$ 851Multiple Airlines
Fri, 27 Feb - Fri, 6 Mar
United Airlines Logo
7:20 p.m. - 1:45 p.m.
YWG
-
GCM
17h 25m
2 stops
United Airlines Logo
2:25 p.m. - 9:44 a.m.
GCM
-
YWG
20h 19m
2 stops
C$ 853United Airlines
Sun, 1 Mar - Wed, 4 Mar

United Airlines flights from Winnipeg to Cayman Islands

Our best United Airlines deals on Winnipeg to Cayman Islands flight tickets
United Airlines
27 Feb
YWG2:20 p.m.Winnipeg
25h 00m
2 stops
GCM4:20 p.m.George Town Owen Roberts Intl
6 Mar
GCM2:25 p.m.George Town Owen Roberts Intl
22h 32m
2 stops
YWG11:57 a.m.Winnipeg
C$ 611
United Airlines
27 Feb
YWG2:20 p.m.Winnipeg
22h 25m
1 stop
GCM1:45 p.m.George Town Owen Roberts Intl
6 Mar
GCM2:50 p.m.George Town Owen Roberts Intl
22h 07m
1 stop
YWG11:57 a.m.Winnipeg
C$ 650
United Airlines
1 Mar
YWG2:20 p.m.Winnipeg
22h 25m
1 stop
GCM1:45 p.m.George Town Owen Roberts Intl
4 Mar
GCM2:25 p.m.George Town Owen Roberts Intl
20h 19m
2 stops
YWG9:44 a.m.Winnipeg
C$ 752

WestJet flights from Winnipeg to Cayman Islands

Our best WestJet deals on Winnipeg to Cayman Islands flight tickets
WestJet
2 Mar
YWG5:00 a.m.Winnipeg
7h 44m
1 stop
GCM1:44 p.m.George Town Owen Roberts Intl
9 Mar
GCM1:50 p.m.George Town Owen Roberts Intl
29h 19m
1 stop
YWG7:09 p.m.Winnipeg
C$ 434
WestJet
2 Mar
YWG5:00 a.m.Winnipeg
7h 44m
1 stop
GCM1:44 p.m.George Town Owen Roberts Intl
9 Mar
GCM1:50 p.m.George Town Owen Roberts Intl
28h 15m
2 stops
YWG6:05 p.m.Winnipeg
C$ 445

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 29 January 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

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 2/3

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

1 stop7h 44m

George Town Owen Roberts Intl

Mon 9/3

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

1 stop29h 19m

C$ 434

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 2/3

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

1 stop7h 44m

George Town Owen Roberts Intl

Mon 9/3

1:50 p.m.-6:05 p.m.

2 stops28h 15m

C$ 445

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Tue 21/4

8:15 a.m.-12:30 p.m.

2 stops28h 15m

George Town Owen Roberts Intl

Thu 23/4

12:30 p.m.-8:15 p.m.

2 stops31h 45m

C$ 596

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 2/3

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

2 stops29h 25m

George Town Owen Roberts Intl

Mon 9/3

11:30 a.m.-8:28 p.m.

2 stops32h 58m

C$ 605

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Fri 27/2

2:20 p.m.-4:20 p.m.

2 stops25h 00m

George Town Owen Roberts Intl

Fri 6/3

2:25 p.m.-11:57 a.m.

2 stops22h 32m

C$ 611

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Fri 27/2

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

1 stop22h 25m

George Town Owen Roberts Intl

Fri 6/3

2:50 p.m.-11:57 a.m.

1 stop22h 07m

C$ 650

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 1/3

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

1 stop22h 25m

George Town Owen Roberts Intl

Wed 4/3

2:25 p.m.-9:44 a.m.

2 stops20h 19m

C$ 752

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 1/3

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

1 stop22h 25m

George Town Owen Roberts Intl

Wed 4/3

2:25 p.m.-9:44 a.m.

2 stops20h 19m

C$ 840

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Fri 27/2

10:55 a.m.-1:44 p.m.

2 stops49h 49m

George Town Owen Roberts Intl

Fri 6/3

3:00 p.m.-7:35 p.m.

3 stops29h 35m

C$ 851

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 1/3

7:20 p.m.-1:45 p.m.

2 stops17h 25m

George Town Owen Roberts Intl

Wed 4/3

2:25 p.m.-9:44 a.m.

2 stops20h 19m

C$ 853

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 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 25m

Direct flights

None
The fastest flight from Winnipeg to Cayman Islands takes 22h 25m
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$ 528Free CancellationRating
7.2
3,253 reviews
Search WestJet flights
United AirlinesPriceFrom C$ 761Free CancellationRating
7.4
9,215 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$ 339