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Cheap flights from Winnipeg to the Cayman Islands from C$ 253

YWG — GCM
2 Nov — 9 Nov1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Cayman Islands

Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to Cayman Islands

Sat 24/104:25 p.m. -
1 stop21h 10m
Mon 26/102:35 p.m. -
1 stop20h 30m
Deal found 28/9C$ 581
Sat 19/127:00 a.m. -
1 stop9h 52m
Sat 26/121:10 p.m. -
1 stop10h 14m
Deal found 2/10C$ 1,055

Find flight deals from Winnipeg to Cayman Islands

Round-trip from

C$ 581

One-way from

C$ 253
WestJet
  • WestJet
  • 24/10-26/10
  • 2 total stops
  • 41h 40m total
  • Winnipeg to Cayman Islands
Search Deals
15/11-31/12
  • 15/11-31/12
  • 1 total stop
  • 26h 35m total
  • Winnipeg to Cayman Islands
Search Deals

Cheapflights Fare Finder

 
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 Winnipeg - GCM George Town Owen Roberts Intl

YWGGCM

Winnipeg

Sun 15/11

11:00 a.m.-1:35 p.m.

1 stop26h 35m

George Town Owen Roberts Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 253

WinnipegGeorge Town

YWG Winnipeg - GCM George Town Owen Roberts Intl

YWGGCM

Winnipeg

Sun 15/11

6:00 a.m.-11:10 a.m.

2 stops53h 10m

George Town Owen Roberts Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 305
Quickest round-trip

WinnipegGeorge Town

YWG Winnipeg - GCM George Town Owen Roberts Intl

YWGGCM

Winnipeg

Sun 15/11

3:45 p.m.-1:35 p.m.

3 stops21h 50m

George Town Owen Roberts Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 554

WinnipegGeorge Town

YWG Winnipeg - GCM George Town Owen Roberts Intl

YWGGCM

Winnipeg

Fri 22/1

7:05 p.m.-4:52 p.m.

1 stop21h 47m

George Town Owen Roberts Intl

Fri 29/1

2:00 p.m.-10:57 p.m.

1 stop8h 57m

C$ 706

WinnipegGeorge Town

YWG Winnipeg - GCM George Town Owen Roberts Intl

YWGGCM

Winnipeg

Fri 22/1

2:10 p.m.-4:52 p.m.

2 stops26h 42m

George Town Owen Roberts Intl

Fri 29/1

2:00 p.m.-10:57 p.m.

1 stop8h 57m

C$ 716

WinnipegGeorge Town

YWG Winnipeg - GCM George Town Owen Roberts Intl

YWGGCM

Winnipeg

Sat 24/10

4:25 p.m.-1:35 p.m.

1 stop21h 10m

George Town Owen Roberts Intl

Mon 26/10

2:35 p.m.-11:05 a.m.

1 stop20h 30m

C$ 796

WinnipegGeorge Town

YWG Winnipeg - GCM George Town Owen Roberts Intl

YWGGCM

Winnipeg

Fri 22/1

6:00 a.m.-11:10 a.m.

2 stops29h 10m

George Town Owen Roberts Intl

Fri 29/1

1:10 p.m.-7:25 p.m.

2 stops30h 15m

C$ 885

WinnipegGeorge Town

YWG Winnipeg - GCM George Town Owen Roberts Intl

YWGGCM

Winnipeg

Sat 13/3

9:35 a.m.-12:35 p.m.

1 stop27h 00m

George Town Owen Roberts Intl

Sat 20/3

12:10 p.m.-9:17 p.m.

1 stop9h 07m

C$ 1,196

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/9

Sorted by cheapest first

Best time to book a flight from Winnipeg to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from Winnipeg with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Winnipeg to the Cayman Islands

No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Cayman Islands

Check out reviews from past customers who have flown with WestJet from Winnipeg to the Cayman Islands to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
WestJet
7.2
Good
3,450 reviews
Check prices

Boarding

7.4

Overall

7.2

Crew

7.9

Food

6.2

Entertainment

6.1

Comfort

7.1

Reviews

1 / 20
8.0
Excellent

Seth,Sep 2026

YVR - YYC

The people from check-in, to the cabin crew, to flight crew were all pleasant and efficient. The under seat space were a little cramped.
WestJet
7.2
Good
3,450 reviews
WestJet
7.2
Good
3,450 reviews
Check prices

Boarding

7.4

Overall

7.2

Crew

7.9

Food

6.2

Entertainment

6.1

Comfort

7.1

Reviews

1 / 20
8.0
Excellent

Seth,Sep 2026

YVR - YYC

The people from check-in, to the cabin crew, to flight crew were all pleasant and efficient. The under seat space were a little cramped.

Related info for your journey

  • What airport do you fly from for flights from Winnipeg to Cayman Islands?

    Located just 7.3 km from the city centre, Winnipeg (YWG) is the airport most travellers will use when flying to Cayman Islands from Winnipeg.

  • How long is the flight from Winnipeg to Cayman Islands?

    For as low as C$ 796, Porter Airlines can have you in Cayman Islands from Winnipeg in 21h 10m. Airlines will cover a distance of 3681 km. This flight may include one or multiple stops.

  • Can I find deals for flights from Winnipeg to Cayman Islands that include hotel bookings?

    Yes. In addition to deals on Winnipeg to Cayman Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to Cayman Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Cayman Islands.

  • Can I find deals for business class flights from Winnipeg to Cayman Islands?

    Yes. Cheapflights offers flight deals from Winnipeg to Cayman Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Top airline flying from Winnipeg to Cayman Islands

AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 510AverageC$ 695FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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When you search for this flight from Winnipeg to Cayman Islands, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

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Need flexible booking options for your flight to Cayman Islands from Winnipeg? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

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Yes! Start tracking prices for Winnipeg to Cayman Islands flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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