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Cheap flights from Winnipeg to the Cayman Islands from C$ 561

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 22/6. 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
7:10 p.m. - 12:45 p.m.
YWG
-
GCM
17h 35m
2 stops
WestJet Logo
1:45 p.m. - 5:25 p.m.
GCM
-
YWG
27h 40m
2 stops
C$ 561WestJet
seg, 22 jun - ter, 11 ago
WestJet Logo
10:10 a.m. - 12:45 p.m.
YWG
-
GCM
26h 35m
2 stops
WestJet Logo
1:45 p.m. - 12:00 p.m.
GCM
-
YWG
22h 15m
2 stops
C$ 562WestJet
sex, 19 jun - ter, 23 jun
WestJet Logo
12:50 p.m. - 12:45 p.m.
YWG
-
GCM
23h 55m
2 stops
WestJet Logo
1:45 p.m. - 8:20 p.m.
GCM
-
YWG
30h 35m
1 stop
C$ 565WestJet
seg, 22 jun - ter, 11 ago
WestJet Logo
6:05 p.m. - 12:45 p.m.
YWG
-
GCM
18h 40m
1 stop
WestJet Logo
1:45 p.m. - 12:00 p.m.
GCM
-
YWG
22h 15m
2 stops
C$ 566WestJet
seg, 22 jun - ter, 11 ago
WestJet Logo
6:05 p.m. - 12:45 p.m.
YWG
-
GCM
18h 40m
1 stop
WestJet Logo
1:45 p.m. - 5:15 p.m.
GCM
-
YWG
27h 30m
1 stop
C$ 570WestJet
seg, 22 jun - ter, 11 ago
Air Canada Logo
1:30 p.m. - 11:25 a.m.
YWG
-
GCM
21h 55m
2 stops
Air Canada Logo
12:25 p.m. - 10:00 a.m.
GCM
-
YWG
21h 35m
1 stop
C$ 614Air Canada
qua, 29 jul - seg, 31 ago
Air Canada Logo
1:30 p.m. - 11:25 a.m.
YWG
-
GCM
21h 55m
2 stops
Air Canada Logo
12:25 p.m. - 10:00 a.m.
GCM
-
YWG
21h 35m
1 stop
C$ 615Air Canada
qua, 29 jul - seg, 31 ago
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$ 618Air Canada
qua, 29 jul - seg, 31 ago
Air Canada Logo
1:30 p.m. - 11:25 a.m.
YWG
-
GCM
21h 55m
2 stops
Air Canada Logo
12:25 p.m. - 10:05 a.m.
GCM
-
YWG
21h 40m
2 stops
C$ 619Air Canada
qua, 29 jul - seg, 31 ago
Air Canada Logo
1:30 p.m. - 11:25 a.m.
YWG
-
GCM
21h 55m
2 stops
Air Canada Logo
12:25 p.m. - 10:05 a.m.
GCM
-
YWG
21h 40m
2 stops
C$ 621Air Canada
qua, 29 jul - seg, 31 ago

WestJet flights from Winnipeg to Cayman Islands

Our best WestJet deals on Winnipeg to Cayman Islands flight tickets
WestJet
22 Jun
YWG7:10 p.m.Winnipeg
17h 35m
2 stops
GCM12:45 p.m.George Town Owen Roberts Intl
11 Aug
GCM1:45 p.m.George Town Owen Roberts Intl
27h 40m
2 stops
YWG5:25 p.m.Winnipeg
C$ 561
WestJet
19 Jun
YWG10:10 a.m.Winnipeg
26h 35m
2 stops
GCM12:45 p.m.George Town Owen Roberts Intl
23 Jun
GCM1:45 p.m.George Town Owen Roberts Intl
22h 15m
2 stops
YWG12:00 p.m.Winnipeg
C$ 562
WestJet
22 Jun
YWG12:50 p.m.Winnipeg
23h 55m
2 stops
GCM12:45 p.m.George Town Owen Roberts Intl
11 Aug
GCM1:45 p.m.George Town Owen Roberts Intl
30h 35m
1 stop
YWG8:20 p.m.Winnipeg
C$ 565

Air Canada flights from Winnipeg to Cayman Islands

Our best Air Canada deals on Winnipeg to Cayman Islands flight tickets
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
21h 35m
1 stop
YWG10:00 a.m.Winnipeg
C$ 614
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
21h 35m
1 stop
YWG10:00 a.m.Winnipeg
C$ 615
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
22h 50m
1 stop
YWG11:15 a.m.Winnipeg
C$ 618

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 9 maio 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

seg 22/6

7:10 p.m.-12:45 p.m.

2 stops17h 35m

George Town Owen Roberts Intl

ter 11/8

1:45 p.m.-5:25 p.m.

2 stops27h 40m

C$ 561

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

sex 19/6

10:10 a.m.-12:45 p.m.

2 stops26h 35m

George Town Owen Roberts Intl

ter 23/6

1:45 p.m.-12:00 p.m.

2 stops22h 15m

C$ 562

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

seg 22/6

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

2 stops23h 55m

George Town Owen Roberts Intl

ter 11/8

1:45 p.m.-8:20 p.m.

1 stop30h 35m

C$ 565
Quickest round-trip

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

seg 22/6

6:05 p.m.-12:45 p.m.

1 stop18h 40m

George Town Owen Roberts Intl

ter 11/8

1:45 p.m.-12:00 p.m.

2 stops22h 15m

C$ 566

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

seg 22/6

6:05 p.m.-12:45 p.m.

1 stop18h 40m

George Town Owen Roberts Intl

ter 11/8

1:45 p.m.-5:15 p.m.

1 stop27h 30m

C$ 570

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

qua 29/7

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

2 stops21h 55m

George Town Owen Roberts Intl

seg 31/8

12:25 p.m.-10:00 a.m.

1 stop21h 35m

C$ 614

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

qua 29/7

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

2 stops21h 55m

George Town Owen Roberts Intl

seg 31/8

12:25 p.m.-10:00 a.m.

1 stop21h 35m

C$ 615

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

qua 29/7

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

2 stops21h 55m

George Town Owen Roberts Intl

seg 31/8

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

1 stop22h 50m

C$ 618

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

qua 29/7

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

2 stops21h 55m

George Town Owen Roberts Intl

seg 31/8

12:25 p.m.-10:05 a.m.

2 stops21h 40m

C$ 619

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

qua 29/7

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

2 stops21h 55m

George Town Owen Roberts Intl

seg 31/8

12:25 p.m.-10:05 a.m.

2 stops21h 40m

C$ 621

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

27h 45m

Direct flights

None
The fastest flight from Winnipeg to Cayman Islands takes 27h 45m
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$ 490Free CancellationRating
7.2
3,332 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.

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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$ 453