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Cheap flights from Winnipeg to the Cayman Islands from C$ 229

YWG — GCM
2 Oct — 9 Oct1
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. -
2 stops34h 25m
Deal found 1/9C$ 534
Sat 7/116:55 p.m. -
1 stop16h 15m
Fri 13/111:10 p.m. -
2 stops30h 15m
Deal found 28/8C$ 589
Sat 19/1212:10 p.m. -
2 stops25h 25m
Sat 26/121:10 p.m. -
2 stops45h 50m
Deal found 1/9C$ 843
Sat 7/1111:10 a.m. -
2 stops24h 00m
Fri 13/117:00 a.m. -
3 stops30h 50m
Deal found 28/8C$ 1,049
Sat 26/126:00 a.m. -
3 stops35h 38m
Sat 9/16:50 p.m. -
2 stops22h 35m
Deal found 31/8C$ 1,316

Find flight deals from Winnipeg to Cayman Islands

Round-trip from

C$ 534

One-way from

C$ 229
WestJet
  • WestJet
  • 24/10-26/10
  • 2 total stops
  • 41h 40m total
  • Winnipeg to Cayman Islands
Search Deals
Air Canada
  • Air Canada
  • 3/10
  • 2 total stops
  • 45h 55m 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

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.-1:00 a.m.

2 stops34h 25m

C$ 534

WinnipegGeorge Town

YWG Winnipeg - GCM George Town Owen Roberts Intl

YWGGCM

Winnipeg

Sat 7/11

6:55 p.m.-12:10 p.m.

1 stop16h 15m

George Town Owen Roberts Intl

Fri 13/11

1:10 p.m.-6:25 p.m.

2 stops30h 15m

C$ 589
Quickest round-trip

WinnipegGeorge Town

YWG Winnipeg - GCM George Town Owen Roberts Intl

YWGGCM

Winnipeg

Sat 19/12

12:10 p.m.-2:35 p.m.

2 stops25h 25m

George Town Owen Roberts Intl

Sat 26/12

1:10 p.m.-9:24 p.m.

1 stop9h 14m

C$ 844

WinnipegGeorge Town

YWG Winnipeg - GCM George Town Owen Roberts Intl

YWGGCM

Winnipeg

Sat 16/1

12:10 p.m.-2:35 p.m.

2 stops49h 25m

George Town Owen Roberts Intl

Sat 23/1

6:50 p.m.-9:15 a.m.

1 stop15h 25m

C$ 872
Cheapest one-way

WinnipegGeorge Town

YWG Winnipeg - GCM George Town Owen Roberts Intl

YWGGCM

Winnipeg

Sat 3/10

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

2 stops45h 55m

C$ 229
Quickest one-way

WinnipegGeorge Town

YWG Winnipeg - GCM George Town Owen Roberts Intl

YWGGCM

Winnipeg

Sat 7/11

6:55 p.m.-12:10 p.m.

1 stop16h 15m

C$ 293

WinnipegGeorge Town

YWG Winnipeg - GCM George Town Owen Roberts Intl

YWGGCM

Winnipeg

Sat 7/11

6:10 a.m.-2:35 p.m.

3 stops31h 25m

C$ 464

WinnipegGeorge Town

YWG Winnipeg - GCM George Town Owen Roberts Intl

YWGGCM

Winnipeg

Sat 3/10

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

3 stops40h 15m

C$ 536

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/8

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
3,446 reviews
Check prices

Entertainment

6.1

Crew

7.9

Boarding

7.4

Food

6.2

Comfort

7.1

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2026

YHZ - DTW

Better snacks I also flew Delta much better with movies and entertainment
WestJet
7.2
Good
3,446 reviews
WestJet
7.2
Good
3,446 reviews
Check prices

Entertainment

6.1

Crew

7.9

Boarding

7.4

Food

6.2

Comfort

7.1

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2026

YHZ - DTW

Better snacks I also flew Delta much better with movies and entertainment

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$ 534, WestJet can have you in Cayman Islands from Winnipeg in 21h 10m. Airlines will cover a distance of 3681 km.

  • 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$ 497AverageC$ 678FlexibilityNo 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.

Can Cheapflights notify me if prices for flights from Winnipeg to Cayman Islands become cheaper?

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