Find flights
When to book
Airlines
FAQs

Cheap flights from Winnipeg to Grand Cayman from C$ 581

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 5/3. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — GCM
13 Dec — 20 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 13 November 2025.

Wed 3/124:10 p.m.YWG - GCM
2 stops20h 34mWestJet
Mon 8/122:50 p.m.GCM - YWG
2 stops20h 18mWestJet
Deal found 11/11C$ 600
Tue 2/128:40 a.m.YWG - GCM
2 stops30h 50mUnited Airlines
Sun 7/125:45 p.m.GCM - YWG
2 stops19h 12mUnited Airlines
Deal found 11/11C$ 615
Tue 2/129:00 p.m.YWG - GCM
2 stops39h 44mWestJet
Sun 7/122:50 p.m.GCM - YWG
1 stop21h 45mWestJet
Deal found 11/11C$ 642
Wed 3/127:30 a.m.YWG - GCM
3 stops29h 15mMultiple Airlines
Mon 8/122:50 p.m.GCM - YWG
2 stops20h 18mMultiple Airlines
Deal found 11/11C$ 772
Tue 2/129:00 p.m.YWG - GCM
2 stops39h 44mMultiple Airlines
Sun 7/124:45 p.m.GCM - YWG
3 stops32h 56mMultiple Airlines
Deal found 11/11C$ 778
Tue 9/122:40 p.m.YWG - GCM
3 stops44h 45mMultiple Airlines
Sun 14/122:50 p.m.GCM - YWG
2 stops22h 19mMultiple Airlines
Deal found 11/11C$ 1,044
Wed 3/1212:10 p.m.YWG - GCM
3 stops22h 50mAmerican Airlines
Mon 8/123:45 p.m.GCM - YWG
3 stops56h 50mAmerican Airlines
Deal found 11/11C$ 3,301
Tue 9/1212:10 p.m.YWG - GCM
3 stops22h 55mAmerican Airlines
Sun 14/128:45 a.m.GCM - YWG
3 stops15h 50mAmerican Airlines
Deal found 11/11C$ 3,466

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 13 November 2025.

Round-trip from

C$ 581

Popular in

July

Cheapest in

April

Average price

C$ 577
Porter Airlines
  • Porter Airlines
  • 5/3-12/3
  • 3 total stops
  • 39h 23m total
  • Winnipeg to Grand Cayman
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (C$ 183 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
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 13 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

Thu 5/3

4:25 p.m.-2:00 p.m.

1 stop20h 35m

George Town Owen Roberts Intl

Thu 12/3

4:25 p.m.-11:13 a.m.

2 stops18h 48m

C$ 581

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 5/3

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

1 stop7h 44m

George Town Owen Roberts Intl

Thu 12/3

1:50 p.m.-12:39 a.m.

1 stop10h 49m

C$ 588

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 17/1

4:25 p.m.-2:00 p.m.

1 stop20h 35m

George Town Owen Roberts Intl

Tue 27/1

5:25 p.m.-3:30 p.m.

1 stop23h 05m

C$ 597

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Wed 3/12

4:10 p.m.-1:44 p.m.

2 stops20h 34m

George Town Owen Roberts Intl

Mon 8/12

2:50 p.m.-10:08 a.m.

2 stops20h 18m

C$ 600

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Tue 9/12

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

Tue 2/12

8:40 a.m.-4:30 p.m.

2 stops30h 50m

George Town Owen Roberts Intl

Sun 7/12

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

2 stops19h 12m

C$ 615

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Tue 2/12

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

2 stops39h 44m

George Town Owen Roberts Intl

Sun 7/12

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

1 stop21h 45m

C$ 642

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Wed 3/12

7:30 a.m.-1:45 p.m.

3 stops29h 15m

George Town Owen Roberts Intl

Mon 8/12

2:50 p.m.-10:08 a.m.

2 stops20h 18m

C$ 772

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/11

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 13 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
9,015 reviews
Check prices

Entertainment

7.1

Crew

8.1

Food

6.6

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
9,015 reviews
United Airlines
7.4
Good
9,015 reviews
Check prices

Entertainment

7.1

Crew

8.1

Food

6.6

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
3,159 reviews
United Airlines
7.4
Good
9,015 reviews
Check prices

Entertainment

7.1

Crew

8.1

Food

6.6

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$ 588, Porter Airlines 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 13 November 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 545AverageC$ 679FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 785AverageC$ 1,095FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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.

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.