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Cheap flights from Winnipeg to Grand Cayman from C$ 558

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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — GCM
7 Jan — 14 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Grand Cayman

Enter your travel dates to find the best prices.

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 8 December 2025.

Fri 27/312:40 p.m.YWG - GCM
2 stops48h 04mWestJet
Sun 5/41:50 p.m.GCM - YWG
1 stop29h 19mWestJet
Deal found 7/12C$ 616
Sun 11/12:20 p.m.YWG - GCM
2 stops45h 55mUnited Airlines
Sun 18/12:50 p.m.GCM - YWG
1 stop22h 07mUnited Airlines
Deal found 7/12C$ 727
Fri 27/38:20 p.m.YWG - GCM
1 stop19h 05mMultiple Airlines
Sun 5/41:50 p.m.GCM - YWG
1 stop29h 19mMultiple Airlines
Deal found 7/12C$ 793
Thu 22/16:00 a.m.YWG - GCM
1 stop9h 25mPorter Airlines
Sun 1/23:00 p.m.GCM - YWG
1 stop21h 13mPorter Airlines
Deal found 7/12C$ 996
Sun 11/112:40 p.m.YWG - GCM
2 stops24h 04mWestJet
Thu 15/12:50 p.m.GCM - YWG
2 stops28h 16mWestJet
Deal found 6/12C$ 631

Find 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 8 December 2025.

Round-trip from

C$ 558

Popular in

December

Cheapest in

April

Average price

C$ 1,335
WestJet
  • WestJet
  • 11/1-18/1
  • 4 total stops
  • 52h 40m total
  • Winnipeg to Grand Cayman
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (C$ 193 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 10% potential price decrease (C$ 93 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 8 December 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

Fri 27/3

12:40 p.m.-12:44 p.m.

2 stops48h 04m

George Town Owen Roberts Intl

Sun 5/4

1:50 p.m.-7:09 p.m.

1 stop29h 19m

C$ 616

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 11/1

12:40 p.m.-1:44 p.m.

2 stops24h 04m

George Town Owen Roberts Intl

Thu 15/1

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

2 stops28h 16m

C$ 631

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 11/1

2:20 p.m.-1:15 p.m.

2 stops45h 55m

George Town Owen Roberts Intl

Sun 18/1

2:50 p.m.-11:57 a.m.

1 stop22h 07m

C$ 727

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Fri 27/3

8:20 p.m.-3:25 p.m.

1 stop19h 05m

George Town Owen Roberts Intl

Sun 5/4

1:50 p.m.-7:09 p.m.

1 stop29h 19m

C$ 793

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 22/1

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

1 stop9h 25m

George Town Owen Roberts Intl

Sun 1/2

3:00 p.m.-11:13 a.m.

1 stop21h 13m

C$ 996

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/12

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 8 December 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
9,078 reviews
Check prices

Boarding

7.7

Crew

8.1

Overall

7.4

Entertainment

7.1

Food

6.6

Comfort

7.3

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
9,078 reviews
United Airlines
7.4
Good
9,078 reviews
Check prices

Boarding

7.7

Crew

8.1

Overall

7.4

Entertainment

7.1

Food

6.6

Comfort

7.3

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
3,193 reviews
United Airlines
7.4
Good
9,078 reviews
Check prices

Boarding

7.7

Crew

8.1

Overall

7.4

Entertainment

7.1

Food

6.6

Comfort

7.3

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$ 616, WestJet can have you in Grand Cayman from Winnipeg in 48h 04m. 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 8 December 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 539AverageC$ 670FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 774AverageC$ 1,080FlexibilityNo 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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