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Cheap flights from Winnipeg to the Cayman Islands from C$ 242

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 16/1. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — GCM
2 Jan — 9 Jan1
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 3 December 2025.

Sat 6/125:30 p.m.YWG - GCM
1 stop17h 55mAir Canada
Wed 10/125:45 p.m.GCM - YWG
2 stops31h 09mAir Canada
Deal found 30/11C$ 646
Sat 6/122:20 p.m.YWG - GCM
2 stops25h 10mUnited Airlines
Wed 10/125:45 p.m.GCM - YWG
2 stops28h 10mUnited Airlines
Deal found 2/12C$ 672

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 3 December 2025.

Round-trip from

C$ 621

One-way from

C$ 242

Popular in

July

Cheapest in

April

Average price

C$ 764
7/2-14/2
  • 7/2-14/2
  • 3 total stops
  • 39h 23m total
  • Winnipeg to Cayman Islands
Search Deals
16/1
  • 16/1
  • 1 total stop
  • 19h 05m total
  • Winnipeg to Cayman Islands
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (C$ 182 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 55 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 3 December 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

Sat 7/2

4:25 p.m.-2:00 p.m.

1 stop20h 35m

George Town Owen Roberts Intl

Sat 14/2

5:25 p.m.-11:13 a.m.

2 stops18h 48m

C$ 621

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 7/2

2:20 p.m.-1:45 p.m.

1 stop22h 25m

George Town Owen Roberts Intl

Sat 21/2

5:45 p.m.-11:57 a.m.

2 stops43h 12m

C$ 813

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Wed 11/2

5:30 p.m.-1:45 p.m.

2 stops43h 15m

George Town Owen Roberts Intl

Wed 18/2

2:25 p.m.-9:49 a.m.

2 stops20h 24m

C$ 993

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 22/1

4:25 p.m.-4:25 p.m.

2 stops47h 00m

George Town Owen Roberts Intl

Sun 1/2

3:00 p.m.-3:30 p.m.

2 stops25h 30m

C$ 1,002

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Wed 11/2

7:30 a.m.-1:43 p.m.

3 stops29h 13m

George Town Owen Roberts Intl

Wed 18/2

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

2 stops13h 24m

C$ 1,073

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Fri 16/1

8:20 p.m.-4:25 p.m.

1 stop19h 05m

C$ 242

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/12

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 3 December 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
9,064 reviews
Check prices

Food

6.6

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,064 reviews
United Airlines
7.4
Good
9,064 reviews
Check prices

Food

6.6

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
WestJet
7.2
Good
3,190 reviews
United Airlines
7.4
Good
9,064 reviews
Check prices

Food

6.6

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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.

  • 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 3 December 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 546AverageC$ 679FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 784AverageC$ 1,094FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

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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.

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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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