Find flights
When to book
Airlines
FAQs

Cheap flights from Winnipeg to the Cayman Islands from C$ 263

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 1/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — GCM
18 Mar — 25 Mar1
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 16 February 2026.

Tue 21/48:15 a.m.
YWG
-
GCM
2 stops28h 15m
Air Canada
Thu 23/411:55 a.m.
GCM
-
YWG
1 stop11h 53m
Air Canada
Deal found 15/2C$ 551
Tue 21/42:00 p.m.
YWG
-
GCM
1 stop22h 45m
United Airlines
Thu 23/41:50 p.m.
GCM
-
YWG
1 stop22h 02m
United Airlines
Deal found 14/2C$ 629
Wed 25/312:40 p.m.
YWG
-
GCM
2 stops24h 04m
WestJet
Mon 30/31:50 p.m.
GCM
-
YWG
1 stop10h 49m
WestJet
Deal found 13/2C$ 630
Wed 25/39:00 a.m.
YWG
-
GCM
1 stop30h 25m
Multiple Airlines
Tue 31/34:25 p.m.
GCM
-
YWG
1 stop22h 59m
Multiple Airlines
Deal found 13/2C$ 643
Sat 12/129:00 p.m.
YWG
-
GCM
2 stops15h 44m
WestJet
Thu 24/122:50 p.m.
GCM
-
YWG
1 stop10h 55m
WestJet
Deal found 12/2C$ 799
Mon 14/125:00 a.m.
YWG
-
GCM
1 stop7h 44m
WestJet
Mon 21/122:50 p.m.
GCM
-
YWG
1 stop29h 25m
WestJet
Deal found 12/2C$ 803
Tue 15/129:00 p.m.
YWG
-
GCM
2 stops39h 44m
WestJet
Mon 21/122:50 p.m.
GCM
-
YWG
2 stops28h 15m
WestJet
Deal found 12/2C$ 813

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 16 February 2026.

Round-trip from

C$ 551

One-way from

C$ 263

Popular in

July

Cheapest in

April

Average price

C$ 780
Air Canada
  • Air Canada
  • 21/4-23/4
  • 3 total stops
  • 40h 08m total
  • Winnipeg to Cayman Islands
Search Deals
Air Canada
  • Air Canada
  • 1/4
  • 2 total stops
  • 31h 00m total
  • Winnipeg to Cayman Islands
Search Deals
Highest demand for flights based on searches. 17% potential increase in price (C$ 195 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 50 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 16 February 2026.
Use the filters below to find and compare flights from Winnipeg to the Cayman Islands that are best for you.

Fly from

Winnipeg

Fly to

Cayman Islands

Route

Depart

Return

Price

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Tue 21/4

8:15 a.m.-12:30 p.m.

2 stops28h 15m

George Town Owen Roberts Intl

Thu 23/4

11:55 a.m.-11:48 p.m.

1 stop11h 53m

C$ 551

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Tue 21/4

2:00 p.m.-12:45 p.m.

1 stop22h 45m

George Town Owen Roberts Intl

Thu 23/4

1:50 p.m.-11:52 a.m.

1 stop22h 02m

C$ 629

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Wed 25/3

12:40 p.m.-12:44 p.m.

2 stops24h 04m

George Town Owen Roberts Intl

Mon 30/3

1:50 p.m.-12:39 a.m.

1 stop10h 49m

C$ 630

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Wed 1/4

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

2 stops31h 00m

C$ 263

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Wed 1/4

5:55 a.m.-12:57 p.m.

3 stops31h 02m

C$ 392

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/2

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 16 February 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
9,299 reviews
Check prices

Entertainment

7.1

Food

6.6

Boarding

7.7

Overall

7.4

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
9,299 reviews
United Airlines
7.4
Good
9,299 reviews
Check prices

Entertainment

7.1

Food

6.6

Boarding

7.7

Overall

7.4

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
3,265 reviews
United Airlines
7.4
Good
9,299 reviews
Check prices

Entertainment

7.1

Food

6.6

Boarding

7.7

Overall

7.4

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$ 551, Air Canada can have you in Cayman Islands from Winnipeg in 28h 15m. 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 16 February 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 487AverageC$ 653FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 763AverageC$ 1,064FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.