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Cheap flights from Winnipeg to the Cayman Islands from C$ 216

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 29/5. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — GCM
15 May — 22 May1
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
Explore the most affordable flight options available from Winnipeg to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 15 April 2026.

Thu 11/61:25 p.m.
YWG
-
GCM
2 stops44h 35m
Air Canada
Mon 15/612:25 p.m.
GCM
-
YWG
1 stop22h 43m
Air Canada
Deal found 13/4C$ 525
Sat 16/51:25 p.m.
YWG
-
GCM
2 stops46h 00m
Air Canada
Sat 23/510:55 a.m.
GCM
-
YWG
2 stops23h 14m
Air Canada
Deal found 15/4C$ 792
Sat 16/51:25 p.m.
YWG
-
GCM
2 stops46h 00m
Multiple Airlines
Sat 23/51:45 p.m.
GCM
-
YWG
1 stop20h 00m
Multiple Airlines
Deal found 15/4C$ 826
Thu 14/52:00 p.m.
YWG
-
GCM
2 stops22h 30m
United Airlines
Thu 21/51:35 p.m.
GCM
-
YWG
2 stops32h 58m
United Airlines
Deal found 15/4C$ 925
Mon 8/65:10 a.m.
YWG
-
GCM
2 stops31h 20m
United Airlines
Wed 10/61:35 p.m.
GCM
-
YWG
2 stops31h 22m
United Airlines
Deal found 14/4C$ 935
Sat 18/412:20 p.m.
YWG
-
GCM
1 stop24h 24m
Multiple Airlines
Sat 25/44:25 p.m.
GCM
-
YWG
1 stop16h 15m
Multiple Airlines
Deal found 15/4C$ 954

Find flight deals from Winnipeg to Cayman Islands

Keep the following information in mind while searching for Winnipeg to Cayman Islands flight deals. Data was last updated 15 April 2026.

Round-trip from

C$ 485

One-way from

C$ 237
WestJet
  • WestJet
  • 8/6-23/6
  • 3 total stops
  • 26h 50m total
  • Winnipeg to Cayman Islands
Search Deals
Air Canada
  • Air Canada
  • 10/5
  • 1 total stop
  • 18h 15m total
  • Winnipeg to Cayman Islands
Search Deals

Cheapflights 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, Cheapflights users made 629,999 searches. Data last updated 15 April 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

Thu 11/6

1:25 p.m.-10:00 a.m.

2 stops44h 35m

George Town Owen Roberts Intl

Mon 15/6

12:25 p.m.-11:08 a.m.

1 stop22h 43m

C$ 525

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 16/5

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

2 stops46h 00m

George Town Owen Roberts Intl

Sat 23/5

10:55 a.m.-10:09 a.m.

2 stops23h 14m

C$ 792

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 16/5

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

2 stops46h 00m

George Town Owen Roberts Intl

Sat 23/5

1:45 p.m.-9:45 a.m.

1 stop20h 00m

C$ 826
Quickest round-trip

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 8/6

5:10 a.m.-12:30 p.m.

2 stops31h 20m

George Town Owen Roberts Intl

Wed 10/6

1:35 p.m.-8:57 p.m.

2 stops31h 22m

C$ 935

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 11/6

10:30 p.m.-10:00 a.m.

3 stops35h 30m

George Town Owen Roberts Intl

Mon 15/6

12:25 p.m.-8:15 p.m.

3 stops31h 50m

C$ 1,024

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 4/6

10:30 p.m.-12:45 p.m.

2 stops38h 15m

George Town Owen Roberts Intl

Thu 11/6

12:40 p.m.-9:45 a.m.

2 stops45h 05m

C$ 1,170
Cheapest one-way

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Fri 29/5

6:00 a.m.-12:45 p.m.

2 stops30h 45m

C$ 216

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 10/5

5:10 p.m.-11:25 a.m.

1 stop18h 15m

C$ 237
Quickest one-way

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Fri 29/5

8:10 p.m.-12:45 p.m.

1 stop16h 35m

C$ 290

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Tue 26/5

4:10 p.m.-11:25 a.m.

2 stops43h 15m

C$ 308

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/4

Showing 1-10 of 11 resultsSorted by cheapest first
1
2

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
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

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

Get insights into the airlines that provide service to Cayman Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Cayman Islands. Reviews last updated 15 April 2026.
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
3,320 reviews
Check prices

Entertainment

6.1

Boarding

7.4

Overall

7.2

Food

6.2

Crew

7.9

Comfort

7.0

Reviews

1 / 20
10.0
Excellent

Joseph,Feb 2026

YYJ - YEG

Is just a domestic flight can't complain at all..but everything is great..
WestJet
7.2
Good
3,320 reviews
WestJet
7.2
Good
3,320 reviews
Check prices

Entertainment

6.1

Boarding

7.4

Overall

7.2

Food

6.2

Crew

7.9

Comfort

7.0

Reviews

1 / 20
10.0
Excellent

Joseph,Feb 2026

YYJ - YEG

Is just a domestic flight can't complain at all..but everything is great..

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Cayman Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • 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$ 525, Air Canada can have you in Cayman Islands from Winnipeg in 44h 35m. 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

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Top airline flying from Winnipeg to Cayman Islands

Discover the top airline that operate flights from Winnipeg to Cayman Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 15 April 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 493AverageC$ 751FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Winnipeg to Cayman Islands?

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.

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Cayman Islands?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Winnipeg to Cayman Islands.

Can Cheapflights find flights from Winnipeg to Cayman Islands with no change fees?

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?

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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