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Cheap flights from Winnipeg to Grand Cayman from C$ 632

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 3/8. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — GCM
8 Jul — 15 Jul1
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 3 July 2025.

Round-trip from

C$ 632

Popular in

October

Cheapest in

September

Average price

C$ 1,011
Air Canada
  • Air Canada
  • 3/8-11/8
  • 4 total stops
  • 54h 04m total
  • Winnipeg to Grand Cayman
Search Deals
Highest demand for flights based on searches. 26% potential increase in price (C$ 383 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 13% potential price decrease (C$ 124 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

Find flight deals from Winnipeg to Grand Cayman

Cheapest flights from Winnipeg to Grand Cayman
Explore the most affordable flight options available from Winnipeg to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 3 July 2025.

Sun 3/812:00 p.m.YWG - GCM
2 stops23h 55mAir Canada
Mon 11/812:50 p.m.GCM - YWG
2 stops30h 09mAir Canada
Deal found 1/7C$ 632
Wed 6/87:00 a.m.YWG - GCM
2 stops29h 30mUnited Airlines
Wed 13/81:35 p.m.GCM - YWG
2 stops23h 34mUnited Airlines
Deal found 1/7C$ 841
Sun 3/84:35 p.m.YWG - GCM
2 stops19h 20mMultiple Airlines
Mon 11/87:00 a.m.GCM - YWG
3 stops17h 31mMultiple Airlines
Deal found 1/7C$ 1,128

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 3 July 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 3/8

12:00 p.m.-11:55 a.m.

2 stops23h 55m

George Town Owen Roberts Intl

Mon 11/8

12:50 p.m.-6:59 p.m.

2 stops30h 09m

C$ 632

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Wed 6/8

7:00 a.m.-12:30 p.m.

2 stops29h 30m

George Town Owen Roberts Intl

Wed 13/8

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

2 stops23h 34m

C$ 841

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 3/8

4:35 p.m.-11:55 a.m.

2 stops19h 20m

George Town Owen Roberts Intl

Mon 11/8

7:00 a.m.-12:31 a.m.

3 stops17h 31m

C$ 1,128

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

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 3 July 2025.
Get a feel of what it's like to fly with United Airlines and Air Canada 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
8,861 reviews
Check prices

Boarding

7.7

Food

6.6

Crew

8.1

Comfort

7.3

Entertainment

7.0

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
8,861 reviews
United Airlines
7.4
Good
8,861 reviews
Check prices

Boarding

7.7

Food

6.6

Crew

8.1

Comfort

7.3

Entertainment

7.0

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.
Air Canada
7.1
Good
9,681 reviews
United Airlines
7.4
Good
8,861 reviews
Check prices

Boarding

7.7

Food

6.6

Crew

8.1

Comfort

7.3

Entertainment

7.0

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.

  • 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 3 July 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 514AverageC$ 661FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 695AverageC$ 1,010FlexibilityNo 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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Millions of users choose and trust Cheapflights to book the best flight deals from Winnipeg to Grand Cayman for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

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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