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Cheap flights from Winnipeg to Grand Cayman from C$ 468

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 30/10. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — GCM
16 Oct — 23 Oct1
1 adult
1 adult, Economy

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 16 September 2025.

Round-trip from

C$ 468

Popular in

October

Cheapest in

September

Average price

C$ 546
Air Canada
  • Air Canada
  • 30/10-6/11
  • 3 total stops
  • 33h 04m total
  • Winnipeg to Grand Cayman
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (C$ 172 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
Average for round-trip flights in September 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 16 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$ 468
Thu 13/111:45 p.m.YWG - GCM
2 stops21h 40mAir Canada
Wed 19/115:45 p.m.GCM - YWG
2 stops30h 59mAir Canada
Deal found 13/9C$ 663
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$ 678
Mon 22/1212:10 p.m.YWG - GCM
1 stop27h 15mPorter Airlines
Tue 30/125:25 p.m.GCM - YWG
2 stops18h 48mPorter Airlines
Deal found 14/9C$ 841
Sat 20/126:00 a.m.YWG - GCM
1 stop9h 25mPorter Airlines
Tue 30/125:25 p.m.GCM - YWG
2 stops18h 48mPorter Airlines
Deal found 14/9C$ 850
Sun 21/124:25 p.m.YWG - GCM
2 stops47h 00mPorter Airlines
Tue 30/125:25 p.m.GCM - YWG
2 stops18h 48mPorter Airlines
Deal found 14/9C$ 919
Mon 22/124:25 p.m.YWG - GCM
2 stops23h 00mMultiple Airlines
Thu 1/15:25 p.m.GCM - YWG
2 stops18h 48mMultiple Airlines
Deal found 14/9C$ 928
Sat 20/126:00 a.m.YWG - GCM
1 stop9h 25mMultiple Airlines
Thu 1/15:25 p.m.GCM - YWG
2 stops18h 48mMultiple Airlines
Deal found 14/9C$ 939

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 16 September 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

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$ 468

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 13/11

1:45 p.m.-12:25 p.m.

2 stops21h 40m

George Town Owen Roberts Intl

Wed 19/11

5:45 p.m.-11:44 p.m.

2 stops30h 59m

C$ 663

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$ 678

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 22/12

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

2 stops23h 00m

George Town Owen Roberts Intl

Tue 30/12

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

2 stops18h 48m

C$ 841

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 20/12

6:00 a.m.-4:25 p.m.

1 stop9h 25m

George Town Owen Roberts Intl

Tue 30/12

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

2 stops18h 48m

C$ 850

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 21/12

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

2 stops47h 00m

George Town Owen Roberts Intl

Tue 30/12

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

2 stops18h 48m

C$ 919

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 22/12

12:10 p.m.-4:25 p.m.

1 stop27h 15m

George Town Owen Roberts Intl

Thu 1/1

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

2 stops18h 48m

C$ 932

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 20/12

6:00 a.m.-4:25 p.m.

1 stop9h 25m

George Town Owen Roberts Intl

Thu 1/1

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

2 stops18h 48m

C$ 939

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 21/12

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

2 stops47h 00m

George Town Owen Roberts Intl

Thu 1/1

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

2 stops18h 48m

C$ 1,007

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/9

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 16 September 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
8,924 reviews
Check prices

Comfort

7.3

Overall

7.4

Boarding

7.7

Entertainment

7.1

Food

6.6

Crew

8.1

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
8,924 reviews
United Airlines
7.4
Good
8,924 reviews
Check prices

Comfort

7.3

Overall

7.4

Boarding

7.7

Entertainment

7.1

Food

6.6

Crew

8.1

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
3,093 reviews
United Airlines
7.4
Good
8,924 reviews
Check prices

Comfort

7.3

Overall

7.4

Boarding

7.7

Entertainment

7.1

Food

6.6

Crew

8.1

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 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$ 678, Air Canada can have you in Grand Cayman from Winnipeg in 7h 44m. The distance between Winnipeg and Grand Cayman is about 3681 km. This flight may include one or multiple stops.

  • 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 16 September 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 537AverageC$ 681FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 704AverageC$ 1,024FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

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

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Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Grand Cayman?

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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