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Cheap flights from Winnipeg to the Cayman Islands from C$ 254

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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — GCM
17 Oct — 24 Oct1
1 adult
1 adult, Economy

Cheap 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 17 September 2025.

Round-trip from

C$ 466

One-way from

C$ 254

Popular in

October

Cheapest in

September

Average price

C$ 543
Air Canada
  • Air Canada
  • 30/10-6/11
  • 3 total stops
  • 33h 04m total
  • Winnipeg to Cayman Islands
Search Deals
WestJet
  • WestJet
  • 1/11
  • 2 total stops
  • 30h 59m total
  • Winnipeg to Cayman Islands
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (C$ 171 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease (C$ 114 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find flight deals from Winnipeg to Cayman Islands

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 17 September 2025.

Thu 30/101:45 p.m.YWG - GCM
2 stops21h 40mAir Canada
Thu 6/111:30 p.m.GCM - YWG
1 stop11h 24mAir Canada
Deal found 16/9C$ 466
Thu 30/105:00 a.m.YWG - GCM
1 stop7h 44mWestJet
Thu 6/112:50 p.m.GCM - YWG
2 stops20h 18mWestJet
Deal found 16/9C$ 675
Wed 22/106:35 p.m.YWG - GCM
1 stop17h 20mAir Canada
Tue 28/104:45 p.m.GCM - YWG
2 stops40h 59mAir Canada
Deal found 15/9C$ 1,033

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 17 September 2025.
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

Thu 30/10

1:45 p.m.-11:25 a.m.

2 stops21h 40m

George Town Owen Roberts Intl

Thu 6/11

1:30 p.m.-11:54 p.m.

1 stop11h 24m

C$ 466

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 30/10

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

1 stop7h 44m

George Town Owen Roberts Intl

Thu 6/11

2:50 p.m.-10:08 a.m.

2 stops20h 18m

C$ 675

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Wed 22/10

3:45 p.m.-11:55 a.m.

2 stops20h 10m

George Town Owen Roberts Intl

Tue 28/10

4:45 p.m.-11:44 p.m.

2 stops30h 59m

C$ 1,033

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 1/11

6:45 a.m.-1:44 p.m.

2 stops30h 59m

C$ 254

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 1/11

8:20 p.m.-1:44 p.m.

1 stop17h 24m

C$ 274

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/9

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 17 September 2025.
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
8,926 reviews
Check prices

Overall

7.4

Boarding

7.7

Crew

8.1

Comfort

7.3

Food

6.6

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Dec 2024

YVR - SFO

It was a good experience. The flight took 45 minutes longer to fly and all passengers had to wait inside the plane till the technical issue was fixed. Overall it was a good experience.
United Airlines
7.4
Good
8,926 reviews
United Airlines
7.4
Good
8,926 reviews
Check prices

Overall

7.4

Boarding

7.7

Crew

8.1

Comfort

7.3

Food

6.6

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Dec 2024

YVR - SFO

It was a good experience. The flight took 45 minutes longer to fly and all passengers had to wait inside the plane till the technical issue was fixed. Overall it was a good experience.
WestJet
7.2
Good
3,095 reviews
United Airlines
7.4
Good
8,926 reviews
Check prices

Overall

7.4

Boarding

7.7

Crew

8.1

Comfort

7.3

Food

6.6

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Dec 2024

YVR - SFO

It was a good experience. The flight took 45 minutes longer to fly and all passengers had to wait inside the plane till the technical issue was fixed. Overall it was a good experience.

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$ 675, Air Canada can have you in Cayman Islands from Winnipeg in 7h 44m. Airlines will cover a distance of 3681 km. This flight may include one or multiple stops.

  • 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.

  • What is the cheapest month to book a flight from Winnipeg to Cayman Islands?

    Currently, June is the cheapest month in which you can book a flight from Winnipeg to Cayman Islands (average of C$ 299). Flying from Winnipeg to Cayman Islands in March is currently the most expensive (average of C$ 445). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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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 17 September 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 535AverageC$ 678FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 701AverageC$ 1,020FlexibilityNo 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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