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Cheap flights from Winnipeg to Grand Cayman from C$ 228

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 4/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — GCM
22 May — 29 May1
1 adult
1 adult, Economy, 0 bags

Cheap 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 22 April 2026.

Sun 10/510:30 p.m.
YWG
-
GCM
2 stops38h 15m
WestJet
Sat 16/51:45 p.m.
GCM
-
YWG
1 stop11h 10m
WestJet
Deal found 20/4C$ 526
Mon 18/59:05 p.m.
YWG
-
GCM
2 stops15h 40m
WestJet
Tue 26/51:45 p.m.
GCM
-
YWG
1 stop11h 10m
WestJet
Deal found 20/4C$ 530
Mon 11/52:55 p.m.
YWG
-
GCM
2 stops21h 50m
WestJet
Sat 16/51:45 p.m.
GCM
-
YWG
1 stop11h 10m
WestJet
Deal found 20/4C$ 543
Mon 11/56:05 p.m.
YWG
-
GCM
1 stop18h 40m
WestJet
Tue 19/51:45 p.m.
GCM
-
YWG
1 stop20h 00m
WestJet
Deal found 20/4C$ 549
Sun 17/54:15 p.m.
YWG
-
GCM
2 stops44h 30m
WestJet
Tue 26/51:45 p.m.
GCM
-
YWG
1 stop11h 10m
WestJet
Deal found 20/4C$ 569
Fri 8/59:05 p.m.
YWG
-
GCM
2 stops15h 40m
WestJet
Sat 16/51:45 p.m.
GCM
-
YWG
1 stop11h 10m
WestJet
Deal found 20/4C$ 624
Sun 10/57:20 p.m.
YWG
-
GCM
1 stop16h 05m
Multiple Airlines
Sat 16/51:45 p.m.
GCM
-
YWG
1 stop11h 10m
Multiple Airlines
Deal found 20/4C$ 629
Fri 15/56:05 p.m.
YWG
-
GCM
1 stop18h 40m
WestJet
Tue 26/51:45 p.m.
GCM
-
YWG
1 stop11h 10m
WestJet
Deal found 20/4C$ 631
Mon 18/56:05 p.m.
YWG
-
GCM
1 stop18h 40m
WestJet
Sat 23/51:45 p.m.
GCM
-
YWG
1 stop11h 10m
WestJet
Deal found 20/4C$ 638

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 22 April 2026.

Round-trip from

C$ 526

One-way from

C$ 228
WestJet
  • WestJet
  • 10/5-16/5
  • 3 total stops
  • 49h 25m total
  • Winnipeg to Grand Cayman
Search Deals
WestJet
  • WestJet
  • 4/6
  • 2 total stops
  • 38h 15m total
  • Winnipeg to Grand Cayman
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 22 April 2026.
Use the filters below to find and compare flights from Winnipeg to Grand Cayman that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 9/5

2:00 p.m.-12:30 p.m.

2 stops22h 30m

George Town Owen Roberts Intl

Sat 16/5

4:15 p.m.-11:52 a.m.

2 stops19h 37m

C$ 774

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 11/5

2:00 p.m.-12:30 p.m.

2 stops22h 30m

George Town Owen Roberts Intl

Mon 18/5

1:35 p.m.-11:52 a.m.

2 stops46h 17m

C$ 935

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 11/5

2:00 p.m.-12:30 p.m.

2 stops22h 30m

George Town Owen Roberts Intl

Thu 14/5

1:35 p.m.-11:08 a.m.

2 stops45h 33m

C$ 942

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 8/6

8:45 a.m.-12:30 p.m.

2 stops27h 45m

George Town Owen Roberts Intl

Wed 10/6

1:35 p.m.-8:57 p.m.

2 stops31h 22m

C$ 1,023

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 10/5

8:10 a.m.-12:30 p.m.

2 stops28h 20m

George Town Owen Roberts Intl

Sun 17/5

1:35 p.m.-4:18 p.m.

2 stops26h 43m

C$ 1,580

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 7/5

2:00 p.m.-12:30 p.m.

2 stops22h 30m

George Town Owen Roberts Intl

Mon 18/5

1:35 p.m.-11:52 a.m.

2 stops22h 17m

C$ 1,892
Cheapest one-way
Quickest one-way

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 4/6

10:30 p.m.-12:45 p.m.

2 stops38h 15m

C$ 228

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 4/6

4:15 p.m.-12:45 p.m.

3 stops44h 30m

C$ 369

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/4

Sorted by cheapest first

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 22 April 2026.
Get a feel of what it's like to fly with 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.
WestJet
7.2
Good
3,324 reviews
Check prices

Overall

7.2

Crew

7.9

Entertainment

6.1

Food

6.2

Boarding

7.4

Comfort

7.0

Reviews

1 / 20
10.0
Excellent

Joseph,Feb 2026

YYJ - YEG

Is just a domestic flight can't complain at all..but everything is great..
WestJet
7.2
Good
3,324 reviews
WestJet
7.2
Good
3,324 reviews
Check prices

Overall

7.2

Crew

7.9

Entertainment

6.1

Food

6.2

Boarding

7.4

Comfort

7.0

Reviews

1 / 20
10.0
Excellent

Joseph,Feb 2026

YYJ - YEG

Is just a domestic flight can't complain at all..but everything is great..

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$ 774, United Airlines can have you in Grand Cayman from Winnipeg in 22h 30m. 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

Browse thousands of different options on Cheapflights for your next trip

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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 airline flying from Winnipeg to Grand Cayman

Discover the top airline 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 22 April 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 489AverageC$ 745FlexibilityNo cancel feeOn-time60%
Search WestJet 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.

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