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Cheap flights from Winnipeg to Grand Cayman from C$ 615

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 6/12. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — GCM
22 Nov — 29 Nov1
1 adult
1 adult, Economy, 0 bags

Find flight deals from Winnipeg to Grand Cayman

Enter your travel dates to find the best prices.

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 23 October 2025.

Sat 6/122:20 p.m.YWG - GCM
2 stops25h 10mUnited Airlines
Sat 13/125:30 p.m.GCM - YWG
2 stops19h 27mUnited Airlines
Deal found 21/10C$ 615
Thu 20/115:00 a.m.YWG - GCM
1 stop7h 44mMultiple Airlines
Thu 27/112:50 p.m.GCM - YWG
1 stop9h 45mMultiple Airlines
Deal found 21/10C$ 654
Sat 6/1212:20 p.m.YWG - GCM
1 stop24h 24mMultiple Airlines
Sat 13/125:56 p.m.GCM - YWG
2 stops22h 11mMultiple Airlines
Deal found 21/10C$ 682
Thu 20/115:00 a.m.YWG - GCM
1 stop7h 44mWestJet
Thu 27/112:50 p.m.GCM - YWG
2 stops22h 19mWestJet
Deal found 21/10C$ 686
Sat 6/127:50 a.m.YWG - GCM
2 stops28h 54mMultiple Airlines
Sun 14/122:40 p.m.GCM - YWG
1 stop28h 23mMultiple Airlines
Deal found 21/10C$ 694
Thu 20/119:45 a.m.YWG - GCM
2 stops25h 40mAir Canada
Thu 27/111:30 p.m.GCM - YWG
2 stops31h 58mAir Canada
Deal found 21/10C$ 720
Sat 6/127:05 p.m.YWG - GCM
1 stop16h 20mAir Canada
Fri 12/125:45 p.m.GCM - YWG
2 stops24h 34mAir Canada
Deal found 21/10C$ 725
Wed 22/1011:15 a.m.YWG - GCM
2 stops24h 40mAir Canada
Tue 28/104:45 p.m.GCM - YWG
2 stops41h 31mAir Canada
Deal found 22/10C$ 1,551

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 23 October 2025.

Round-trip from

C$ 615

Popular in

July

Cheapest in

September
United Airlines
  • United Airlines
  • 6/12-13/12
  • 4 total stops
  • 44h 37m total
  • Winnipeg to Grand Cayman
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (C$ 181 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

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 23 October 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

Sat 6/12

2:20 p.m.-4:30 p.m.

2 stops25h 10m

George Town Owen Roberts Intl

Sat 13/12

5:30 p.m.-11:57 a.m.

2 stops19h 27m

C$ 615

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 6/12

2:20 p.m.-4:30 p.m.

2 stops25h 10m

George Town Owen Roberts Intl

Sun 14/12

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

2 stops19h 12m

C$ 615

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 6/12

2:20 p.m.-4:30 p.m.

2 stops25h 10m

George Town Owen Roberts Intl

Fri 12/12

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

2 stops43h 12m

C$ 615

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 20/11

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

1 stop7h 44m

George Town Owen Roberts Intl

Thu 27/11

2:50 p.m.-11:35 p.m.

1 stop9h 45m

C$ 654

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 6/12

12:20 p.m.-1:44 p.m.

1 stop24h 24m

George Town Owen Roberts Intl

Sat 13/12

5:56 p.m.-3:07 p.m.

2 stops22h 11m

C$ 682

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 20/11

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

1 stop7h 44m

George Town Owen Roberts Intl

Thu 27/11

2:50 p.m.-12:09 p.m.

2 stops22h 19m

C$ 686

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 6/12

7:50 a.m.-1:44 p.m.

2 stops28h 54m

George Town Owen Roberts Intl

Sun 14/12

2:40 p.m.-6:03 p.m.

1 stop28h 23m

C$ 694

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 20/11

9:45 a.m.-12:25 p.m.

2 stops25h 40m

George Town Owen Roberts Intl

Thu 27/11

1:30 p.m.-8:28 p.m.

2 stops31h 58m

C$ 720

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 6/12

7:05 p.m.-12:25 p.m.

1 stop16h 20m

George Town Owen Roberts Intl

Fri 12/12

5:45 p.m.-5:19 p.m.

2 stops24h 34m

C$ 725

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.-11:13 a.m.

1 stop21h 13m

C$ 1,128

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/10

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 23 October 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
8,991 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Crew

8.1

Food

6.6

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
8,991 reviews
United Airlines
7.4
Good
8,991 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Crew

8.1

Food

6.6

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
3,133 reviews
United Airlines
7.4
Good
8,991 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Crew

8.1

Food

6.6

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 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$ 615, United Airlines can have you in Grand Cayman from Winnipeg in 25h 10m. 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.

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 23 October 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 544AverageC$ 679FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 785AverageC$ 1,094FlexibilityNo 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?

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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.

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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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