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Cheap flights from Winnipeg to Grand Cayman from C$ 875

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 1/2. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — GCM
29 Aug — 5 Sep1
1 adult

Cheap flight deals from Winnipeg to Grand Cayman

Keep the following information in mind while searching for Winnipeg to Grand Cayman flight deals. Data was last updated 24 August 2025.

Round-trip from

C$ 875

Popular in

October

Cheapest in

September
Porter Airlines
  • Porter Airlines
  • 1/2-12/2
  • 4 total stops
  • 65h 48m total
  • Winnipeg to Grand Cayman
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (C$ 180 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease (C$ 115 potential savings vs. average RT price).
Search Deals

Find flight deals from Winnipeg to Grand Cayman

Best flights from Winnipeg to Grand Cayman
Discover carefully curated flight deals from Winnipeg to Grand Cayman that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 24 August 2025.

Sun 1/24:25 p.m.YWG - GCM
2 stops47h 00mPorter Airlines
Thu 12/25:25 p.m.GCM - YWG
2 stops18h 48mPorter Airlines
Deal found 22/8C$ 875
Sun 1/25:00 a.m.YWG - GCM
1 stop7h 44mWestJet
Thu 12/22:50 p.m.GCM - YWG
1 stop29h 19mWestJet
Deal found 23/8C$ 955

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Grand Cayman 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 24 August 2025.
Use the filters below to find and compare flights from Winnipeg to Grand Cayman that are best for you.

Fly from

Winnipeg

Fly to

Grand Cayman

Route

Depart

Return

Price

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 1/2

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

2 stops47h 00m

George Town Owen Roberts Intl

Thu 12/2

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

2 stops18h 48m

C$ 875

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 1/2

5:00 a.m.-1:44 p.m.

1 stop7h 44m

George Town Owen Roberts Intl

Thu 12/2

2:50 p.m.-7:09 p.m.

1 stop29h 19m

C$ 955

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/8

Best time to book a flight from Winnipeg to Grand Cayman

Have a flexible travel schedule? Discover the best time to fly to Grand Cayman 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 Grand Cayman
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Grand Cayman

Get insights into the airlines that provide service to Grand Cayman. 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 Grand Cayman. Reviews last updated 24 August 2025.
Get a feel of what it's like to fly with United Airlines and WestJet from Winnipeg to Grand Cayman by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,937 reviews
Check prices

Crew

8.1

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

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
8,937 reviews
United Airlines
7.4
Good
8,937 reviews
Check prices

Crew

8.1

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

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
3,048 reviews
United Airlines
7.4
Good
8,937 reviews
Check prices

Crew

8.1

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

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 Grand Cayman. 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 Grand Cayman?

    Located just 7.3 km from the city centre, Winnipeg (YWG) is the airport most travellers will use when flying to Grand Cayman from Winnipeg.

  • How long is the flight from Winnipeg to Grand Cayman?

    For as low as C$ 875, Porter Airlines can have you in Grand Cayman from Winnipeg in 47h. The distance between Winnipeg and Grand Cayman is about 3681 km.

  • Can I find deals for flights from Winnipeg to Grand Cayman that include hotel bookings?

    Yes. In addition to deals on Winnipeg to Grand Cayman flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to Grand Cayman?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Grand Cayman.

  • Can I find deals for business class flights from Winnipeg to Grand Cayman?

    Yes. Cheapflights offers flight deals from Winnipeg to Grand Cayman 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 Grand Cayman?

    Currently, June is the cheapest month in which you can book a flight from Winnipeg to Grand Cayman (average of C$ 299). Flying from Winnipeg to Grand Cayman 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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Alternative routes for Winnipeg to Grand Cayman

See prices for flight routes from nearby airports that may be better suited for you.
Winnipeg to George Town flights

Top 2 airlines flying from Winnipeg to Grand Cayman

Discover the top 2 airlines that operate flights from Winnipeg to Grand Cayman. 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 24 August 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 538AverageC$ 681FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 705AverageC$ 1,025FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Winnipeg to Grand Cayman?

Cheapflights makes it easy to find Winnipeg to Grand Cayman flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

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Can Cheapflights find flights from Winnipeg to Grand Cayman with no change fees?

Certainly. Search results for flights to Grand Cayman from Winnipeg shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Winnipeg to Grand Cayman become cheaper?

Not ready to book yet? You can track prices for flights from Winnipeg to Grand Cayman on Cheapflights with our Price Alert feature and get notified when better prices are available.

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