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Cheap flights from Winnipeg to the Cayman Islands from C$ 235

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 8/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — GCM
27 May — 3 Jun1
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 27 April 2026.

Wed 29/75:10 a.m.
YWG
-
GCM
1 stop30h 15m
Air Canada
Mon 31/812:25 p.m.
GCM
-
YWG
1 stop30h 20m
Air Canada
Deal found 26/4C$ 585
Wed 29/75:10 a.m.
YWG
-
GCM
2 stops15h 50m
Multiple Airlines
Mon 31/812:25 p.m.
GCM
-
YWG
1 stop9h 05m
Multiple Airlines
Deal found 26/4C$ 594
Tue 9/64:05 p.m.
YWG
-
GCM
2 stops43h 20m
Air Canada
Sat 13/610:55 a.m.
GCM
-
YWG
1 stop12h 23m
Air Canada
Deal found 24/4C$ 672
Mon 8/68:45 a.m.
YWG
-
GCM
2 stops27h 45m
United Airlines
Wed 10/61:35 p.m.
GCM
-
YWG
2 stops31h 22m
United Airlines
Deal found 22/4C$ 1,183

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 27 April 2026.

Round-trip from

C$ 585

One-way from

C$ 235
Air Canada
  • Air Canada
  • 29/7-31/8
  • 2 total stops
  • 60h 35m total
  • Winnipeg to Cayman Islands
Search Deals
WestJet
  • WestJet
  • 8/6
  • 2 total stops
  • 30h 45m 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 27 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
Quickest round-trip

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Wed 29/7

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

2 stops21h 55m

George Town Owen Roberts Intl

Mon 31/8

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

2 stops21h 40m

C$ 590

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Tue 9/6

4:05 p.m.-11:25 a.m.

2 stops43h 20m

George Town Owen Roberts Intl

Sat 13/6

10:55 a.m.-11:18 p.m.

1 stop12h 23m

C$ 672

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Wed 29/7

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

2 stops21h 55m

George Town Owen Roberts Intl

Mon 31/8

7:00 a.m.-11:19 a.m.

3 stops28h 19m

C$ 1,018

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 8/6

8:45 a.m.-12:30 p.m.

2 stops27h 45m

George Town Owen Roberts Intl

Wed 10/6

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

2 stops31h 22m

C$ 1,183
Cheapest one-way

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 8/6

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

2 stops30h 45m

C$ 235
Quickest one-way

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 8/6

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

1 stop16h 00m

C$ 306

Flights are sorted by cheapest round-trip flights first.

Deals found on 24/4

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
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 27 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
3,327 reviews
Check prices

Entertainment

6.1

Crew

7.9

Boarding

7.4

Comfort

7.0

Overall

7.2

Food

6.2

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
3,327 reviews
WestJet
7.2
Good
3,327 reviews
Check prices

Entertainment

6.1

Crew

7.9

Boarding

7.4

Comfort

7.0

Overall

7.2

Food

6.2

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$ 590, Air Canada can have you in Cayman Islands from Winnipeg in 21h 55m. 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 27 April 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 489AverageC$ 746FlexibilityNo 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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