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Cheap flights from Winnipeg to the Cayman Islands from C$ 536

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 13/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — GCM
10 Apr — 17 Apr1
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 11 March 2026.

Mon 13/45:00 a.m.
YWG
-
GCM
1 stop7h 44m
WestJet
Thu 16/41:50 p.m.
GCM
-
YWG
2 stops20h 17m
WestJet
Deal found 10/3C$ 536
Thu 23/47:05 p.m.
YWG
-
GCM
1 stop15h 05m
Air Canada
Fri 1/51:35 p.m.
GCM
-
YWG
2 stops44h 34m
Air Canada
Deal found 8/3C$ 616
Mon 13/47:05 p.m.
YWG
-
GCM
2 stops41h 25m
Air Canada
Thu 16/411:55 a.m.
GCM
-
YWG
2 stops28h 34m
Air Canada
Deal found 6/3C$ 625
Mon 19/102:55 p.m.
YWG
-
GCM
2 stops21h 50m
WestJet
Sat 24/101:45 p.m.
GCM
-
YWG
1 stop21h 50m
WestJet
Deal found 6/3C$ 633

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 11 March 2026.

Round-trip from

C$ 536
WestJet
  • WestJet
  • 13/4-16/4
  • 3 total stops
  • 28h 01m 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 11 March 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

Mon 13/4

5:00 a.m.-12:44 p.m.

1 stop7h 44m

George Town Owen Roberts Intl

Thu 16/4

1:50 p.m.-11:32 a.m.

1 stop21h 42m

C$ 543

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 13/4

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

2 stops55h 00m

George Town Owen Roberts Intl

Thu 16/4

11:55 a.m.-10:09 a.m.

2 stops46h 14m

C$ 626

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 23/4

7:05 p.m.-12:30 p.m.

2 stops41h 25m

George Town Owen Roberts Intl

Fri 1/5

1:35 p.m.-10:09 a.m.

2 stops44h 34m

C$ 649

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 23/4

5:00 a.m.-12:44 p.m.

1 stop7h 44m

George Town Owen Roberts Intl

Sat 2/5

1:45 p.m.-5:25 p.m.

2 stops27h 40m

C$ 653

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/3

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 11 March 2026.
Check out reviews from past customers who have flown with United Airlines and 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.
United Airlines
7.4
Good
9,413 reviews
Check prices

Boarding

7.7

Overall

7.4

Food

6.6

Entertainment

7.1

Comfort

7.3

Crew

8.1

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
United Airlines
7.4
Good
9,413 reviews
United Airlines
7.4
Good
9,413 reviews
Check prices

Boarding

7.7

Overall

7.4

Food

6.6

Entertainment

7.1

Comfort

7.3

Crew

8.1

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
WestJet
7.2
Good
3,288 reviews
United Airlines
7.4
Good
9,413 reviews
Check prices

Boarding

7.7

Overall

7.4

Food

6.6

Entertainment

7.1

Comfort

7.3

Crew

8.1

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats

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$ 543, WestJet can have you in Cayman Islands from Winnipeg in 7h 44m. 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 2 airlines flying from Winnipeg to Cayman Islands

Discover the top 2 airlines 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 11 March 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 486AverageC$ 741FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 761AverageC$ 1,061FlexibilityNo cancel feeOn-time69%
Search United Airlines 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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