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Cheap flights from Winnipeg to Grand Cayman from C$ 588

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 21/12. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — GCM
6 Dec — 13 Dec1
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 6 November 2025.

Sun 23/117:05 p.m.YWG - GCM
2 stops44h 25mUnited Airlines
Mon 1/125:45 p.m.GCM - YWG
2 stops41h 04mUnited Airlines
Deal found 5/11C$ 851
Sun 23/118:05 p.m.YWG - GCM
1 stop16h 39mWestJet
Mon 1/122:50 p.m.GCM - YWG
2 stops25h 31mWestJet
Deal found 5/11C$ 863
Fri 21/119:00 p.m.YWG - GCM
2 stops39h 44mWestJet
Mon 1/122:50 p.m.GCM - YWG
1 stop10h 45mWestJet
Deal found 5/11C$ 896
Sat 22/1112:20 p.m.YWG - GCM
1 stop24h 24mWestJet
Mon 1/122:50 p.m.GCM - YWG
2 stops20h 18mWestJet
Deal found 5/11C$ 908
Sat 22/117:05 p.m.YWG - GCM
1 stop16h 20mAir Canada
Sun 30/111:30 p.m.GCM - YWG
2 stops31h 58mAir Canada
Deal found 5/11C$ 1,023
Sat 22/118:20 p.m.YWG - GCM
1 stop16h 24mMultiple Airlines
Sat 29/117:00 a.m.GCM - YWG
2 stops18h 42mMultiple Airlines
Deal found 5/11C$ 1,248
Sun 23/118:05 p.m.YWG - GCM
1 stop16h 39mMultiple Airlines
Sat 29/117:00 a.m.GCM - YWG
2 stops18h 42mMultiple Airlines
Deal found 5/11C$ 1,271

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 6 November 2025.

Round-trip from

C$ 851

One-way from

C$ 588

Popular in

July

Cheapest in

September

Average price

C$ 581
United Airlines
  • United Airlines
  • 23/11-1/12
  • 4 total stops
  • 85h 29m total
  • Winnipeg to Grand Cayman
Search Deals
United Airlines
  • United Airlines
  • 21/12
  • 2 total stops
  • 41h 40m total
  • Winnipeg to Grand Cayman
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (C$ 184 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 56 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 6 November 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 23/11

7:05 p.m.-4:30 p.m.

2 stops44h 25m

George Town Owen Roberts Intl

Mon 1/12

5:45 p.m.-9:49 a.m.

2 stops41h 04m

C$ 851

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Fri 21/11

9:00 p.m.-1:44 p.m.

2 stops39h 44m

George Town Owen Roberts Intl

Mon 1/12

2:50 p.m.-6:06 p.m.

2 stops28h 16m

C$ 918

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 22/11

6:45 a.m.-1:44 p.m.

2 stops29h 59m

George Town Owen Roberts Intl

Mon 1/12

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

2 stops34h 00m

C$ 918

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 22/11

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

1 stop16h 20m

George Town Owen Roberts Intl

Sun 30/11

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

2 stops31h 58m

C$ 1,023

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$ 1,226

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 22/11

8:20 p.m.-1:44 p.m.

1 stop16h 24m

George Town Owen Roberts Intl

Sat 29/11

7:00 a.m.-12:42 a.m.

2 stops18h 42m

C$ 1,248

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 23/11

8:05 p.m.-1:44 p.m.

1 stop16h 39m

George Town Owen Roberts Intl

Sat 29/11

7:00 a.m.-12:42 a.m.

2 stops18h 42m

C$ 1,271

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 23/11

7:30 a.m.-11:35 a.m.

2 stops27h 05m

George Town Owen Roberts Intl

Sun 30/11

2:50 p.m.-7:12 p.m.

1 stop29h 22m

C$ 1,301

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 21/12

7:05 p.m.-1:45 p.m.

2 stops41h 40m

C$ 588

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 21/12

5:40 p.m.-9:15 p.m.

3 stops26h 35m

C$ 719

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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 6 November 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
9,003 reviews
Check prices

Crew

8.1

Food

6.6

Entertainment

7.1

Boarding

7.7

Comfort

7.3

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
9,003 reviews
United Airlines
7.4
Good
9,003 reviews
Check prices

Crew

8.1

Food

6.6

Entertainment

7.1

Boarding

7.7

Comfort

7.3

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
3,154 reviews
United Airlines
7.4
Good
9,003 reviews
Check prices

Crew

8.1

Food

6.6

Entertainment

7.1

Boarding

7.7

Comfort

7.3

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$ 1,023, United Airlines can have you in Grand Cayman from Winnipeg in 16h 20m. 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.

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 6 November 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 549AverageC$ 684FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 791AverageC$ 1,103FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

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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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