Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Winnipeg to the Cayman Islands from C$ 285

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 3/12. 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

Discover deals from 900+ travel sites with momondo.

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

Find the cheapest flights from Winnipeg to the Cayman Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
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
19h 12m2 stops
C$ 614United Airlines
Find Deal
Fri, 12 Dec - Tue, 16 Dec
WestJet Logo
9:00 p.m. - 1:44 p.m.YWG-GCM
39h 44m2 stops
WestJet Logo
2:50 p.m. - 10:08 a.m.GCM-YWG
20h 18m2 stops
C$ 650WestJet
Find Deal
Fri, 12 Dec - Thu, 18 Dec
WestJet Logo
9:00 p.m. - 1:44 p.m.YWG-GCM
39h 44m2 stops
WestJet Logo
2:50 p.m. - 11:35 a.m.GCM-YWG
21h 45m1 stop
C$ 657WestJet
Find Deal
Fri, 12 Dec - Thu, 18 Dec
WestJet Logo
5:00 a.m. - 1:44 p.m.YWG-GCM
7h 44m1 stop
WestJet Logo
2:50 p.m. - 12:35 a.m.GCM-YWG
10h 45m1 stop
C$ 671WestJet
Find Deal
Thu, 11 Dec - Thu, 18 Dec
WestJet Logo
9:00 p.m. - 1:44 p.m.YWG-GCM
39h 44m2 stops
WestJet Logo
2:50 p.m. - 11:35 a.m.GCM-YWG
21h 45m1 stop
C$ 687WestJet
Find Deal
Tue, 9 Dec - Mon, 15 Dec
Porter Airlines Logo
12:10 p.m. - 2:00 p.m.YWG-GCM
48h 50m2 stops
Porter Airlines Logo
5:50 p.m. - 11:35 p.m.GCM-YWG
30h 45m1 stop
C$ 699Porter Airlines
Find Deal
Mon, 15 Dec - Thu, 18 Dec
Porter Airlines Logo
4:25 p.m. - 3:05 p.m.YWG-GCM
21h 40m2 stops
Porter Airlines Logo
5:50 p.m. - 3:30 p.m.GCM-YWG
22h 40m1 stop
C$ 763Porter Airlines
Find Deal
Mon, 15 Dec - Tue, 16 Dec
United Airlines Logo
5:30 a.m. - 4:30 p.m.YWG-GCM
35h 00m2 stops
United Airlines Logo
5:30 p.m. - 7:24 p.m.GCM-YWG
26h 54m2 stops
C$ 771United Airlines
Find Deal
Sat, 1 Nov - Sat, 15 Nov
Air Canada Logo
7:05 p.m. - 12:25 p.m.YWG-GCM
17h 20m1 stop
Air Canada Logo
5:45 p.m. - 9:49 a.m.GCM-YWG
41h 04m2 stops
C$ 1,012Air Canada
Find Deal
Sat, 1 Nov - Sat, 15 Nov
Air Canada Logo
7:05 p.m. - 12:25 p.m.YWG-GCM
16h 20m1 stop
Air Canada Logo
1:30 p.m. - 9:49 a.m.GCM-YWG
21h 19m1 stop
C$ 1,016Air Canada
Find Deal
Wed, 10 Dec - Fri, 19 Dec

United Airlines flights from Winnipeg to Cayman Islands

Our best United Airlines deals on Winnipeg to Cayman Islands flight tickets
United Airlines
12 Dec
YWG2:20 p.m.Winnipeg
22h 25m
1 stop
GCM1:45 p.m.George Town Owen Roberts Intl
16 Dec
GCM5:45 p.m.George Town Owen Roberts Intl
19h 12m
2 stops
YWG11:57 a.m.Winnipeg
C$ 614
Find similar
United Airlines
1 Nov
YWG5:30 a.m.Winnipeg
35h 00m
2 stops
GCM4:30 p.m.George Town Owen Roberts Intl
15 Nov
GCM5:30 p.m.George Town Owen Roberts Intl
26h 54m
2 stops
YWG7:24 p.m.Winnipeg
C$ 771
Find similar
United Airlines
9 Dec
YWG2:20 p.m.Winnipeg
25h 10m
2 stops
GCM4:30 p.m.George Town Owen Roberts Intl
20 Dec
GCM5:45 p.m.George Town Owen Roberts Intl
19h 12m
2 stops
YWG11:57 a.m.Winnipeg
C$ 920
Find similar

WestJet flights from Winnipeg to Cayman Islands

Our best WestJet deals on Winnipeg to Cayman Islands flight tickets
WestJet
12 Dec
YWG9:00 p.m.Winnipeg
39h 44m
2 stops
GCM1:44 p.m.George Town Owen Roberts Intl
18 Dec
GCM2:50 p.m.George Town Owen Roberts Intl
20h 18m
2 stops
YWG10:08 a.m.Winnipeg
C$ 650
Find similar
WestJet
12 Dec
YWG9:00 p.m.Winnipeg
39h 44m
2 stops
GCM1:44 p.m.George Town Owen Roberts Intl
18 Dec
GCM2:50 p.m.George Town Owen Roberts Intl
21h 45m
1 stop
YWG11:35 a.m.Winnipeg
C$ 657
Find similar
WestJet
11 Dec
YWG5:00 a.m.Winnipeg
7h 44m
1 stop
GCM1:44 p.m.George Town Owen Roberts Intl
18 Dec
GCM2:50 p.m.George Town Owen Roberts Intl
10h 45m
1 stop
YWG12:35 a.m.Winnipeg
C$ 671
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 20 October 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 12/12

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

1 stop22h 25m

George Town Owen Roberts Intl

Tue 16/12

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

2 stops19h 12m

C$ 614

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Fri 12/12

9:00 p.m.-1:44 p.m.

2 stops39h 44m

George Town Owen Roberts Intl

Thu 18/12

2:50 p.m.-10:08 a.m.

2 stops20h 18m

C$ 650

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Fri 12/12

9:00 p.m.-1:44 p.m.

2 stops39h 44m

George Town Owen Roberts Intl

Thu 18/12

2:50 p.m.-11:35 a.m.

1 stop21h 45m

C$ 657

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 11/12

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

1 stop7h 44m

George Town Owen Roberts Intl

Thu 18/12

2:50 p.m.-12:35 a.m.

1 stop10h 45m

C$ 671

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Tue 9/12

9:00 p.m.-1:44 p.m.

2 stops39h 44m

George Town Owen Roberts Intl

Mon 15/12

2:50 p.m.-11:35 a.m.

1 stop21h 45m

C$ 687

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 15/12

12:10 p.m.-2:00 p.m.

2 stops48h 50m

George Town Owen Roberts Intl

Thu 18/12

5:50 p.m.-11:35 p.m.

1 stop30h 45m

C$ 699

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 15/12

4:25 p.m.-3:05 p.m.

2 stops21h 40m

George Town Owen Roberts Intl

Tue 16/12

5:50 p.m.-3:30 p.m.

1 stop22h 40m

C$ 763

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 1/11

5:30 a.m.-4:30 p.m.

2 stops35h 00m

George Town Owen Roberts Intl

Sat 15/11

5:30 p.m.-7:24 p.m.

2 stops26h 54m

C$ 771

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 1/11

7:05 p.m.-12:25 p.m.

1 stop17h 20m

George Town Owen Roberts Intl

Sat 15/11

5:45 p.m.-9:49 a.m.

2 stops41h 04m

C$ 1,012

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Wed 10/12

7:05 p.m.-12:25 p.m.

1 stop16h 20m

George Town Owen Roberts Intl

Fri 19/12

1:30 p.m.-9:49 a.m.

1 stop21h 19m

C$ 1,016

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 resultsSorted by cheapest first
1
2

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$ 844. The most expensive day to fly to Cayman Islands is Saturday, with ticket prices averaging around C$ 1,329.

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$ 844 when looking at flights departing in the morning. Flights in the afternoon are often more expensive with an average ticket price of C$ 1,160.

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.
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$ 545Free CancellationRating
7.2
3,130 reviews
Search WestJet flights
United AirlinesPriceFrom C$ 715Free CancellationRating
7.4
8,993 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

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
Wed 19/11
Wed 26/11
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$ 376