App
Customer Support
DKK
Find Bookings
Trip.com
>
Cheap Flights
>
Cayman Islands
>
Bodden Town
>
Grand Cayman
>
Flights from Winnipeg to Grand Cayman
Worldwide Coverage
Worldwide Coverage
Flights to over 5,000 cities
One-stop Service Guarantee
One-stop Service Guarantee
Price guaranteed upon confirmed payment, booking guaranteed once tickets issued
Secure Payment
Secure Payment
Convenient & reliable booking and payment system

Flights from Winnipeg to Grand Cayman Starting at DKK 1,034

We've found these cheap flights for you. You can book one-way or return flight tickets.

  • One way
  • Round-trip
      • YWG05:00
        7h 43m
        1 stop
        GCM12:43
        Mon, Mar 31|Winnipeg - Grand Cayman|WestJet
        DKK 1,034DKK 4,278
        76% OFF
        76% OFF
        DKK 4,278DKK 1,034

        Choose WestJet flights from Winnipeg to Grand Cayman. The one-way connecting flight with WestJet departs from Winnipeg James Armstrong Richardson International Airport on Mon, Mar 31, arriving at Owen Roberts International Airport. One-way Prices start from DKK 1,034 including taxes and charges.

      • YWG12:20
        24h 23m
        1 stop
        GCM13:43
        Sat, Feb 22|Winnipeg - Grand Cayman|WestJet
        DKK 1,473DKK 4,278
        66% OFF
        66% OFF
        DKK 4,278DKK 1,473

        Choose WestJet flights from Winnipeg to Grand Cayman. The one-way connecting flight with WestJet departs from Winnipeg James Armstrong Richardson International Airport on Sat, Feb 22, arriving at Owen Roberts International Airport. One-way Prices start from DKK 1,473 including taxes and charges.

      • YWG20:00
        16h 43m
        1 stop
        GCM13:43
        Sun, Feb 23|Winnipeg - Grand Cayman|WestJet
        DKK 1,474DKK 4,278
        66% OFF
        66% OFF
        DKK 4,278DKK 1,474

        Choose WestJet flights from Winnipeg to Grand Cayman. The one-way connecting flight with WestJet departs from Winnipeg James Armstrong Richardson International Airport on Sun, Feb 23, arriving at Owen Roberts International Airport. One-way Prices start from DKK 1,474 including taxes and charges.

      • YWG05:00
        7h 43m
        1 stop
        GCM13:43
        Thu, Feb 27|Winnipeg - Grand Cayman|WestJet
        DKK 1,522
        DKK 1,522

        Choose WestJet flights from Winnipeg to Grand Cayman. The one-way connecting flight with WestJet departs from Winnipeg James Armstrong Richardson International Airport on Thu, Feb 27, arriving at Owen Roberts International Airport. One-way Prices start from DKK 1,522 including taxes and charges.

      • YWG20:15
        16h 28m
        1 stop
        GCM13:43
        Wed, Feb 19|Winnipeg - Grand Cayman|Flair Airlines
        DKK 1,544
        DKK 1,544

        Choose Flair Airlines flights from Winnipeg to Grand Cayman. The one-way connecting flight with Flair Airlines departs from Winnipeg James Armstrong Richardson International Airport on Wed, Feb 19, arriving at Owen Roberts International Airport. One-way Prices start from DKK 1,544 including taxes and charges.

      • YWG18:50
        17h 53m
        1 stop
        GCM13:43
        Sun, Feb 23|Winnipeg - Grand Cayman|Porter Airlines
        DKK 1,598
        DKK 1,598

        Choose Porter Airlines flights from Winnipeg to Grand Cayman. The one-way connecting flight with Porter Airlines departs from Winnipeg James Armstrong Richardson International Airport on Sun, Feb 23, arriving at Owen Roberts International Airport. One-way Prices start from DKK 1,598 including taxes and charges.

      • YWG20:15
        16h 28m
        1 stop
        GCM13:43
        Sun, Feb 23|Winnipeg - Grand Cayman|Flair Airlines
        DKK 1,620
        DKK 1,620

        Choose Flair Airlines flights from Winnipeg to Grand Cayman. The one-way connecting flight with Flair Airlines departs from Winnipeg James Armstrong Richardson International Airport on Sun, Feb 23, arriving at Owen Roberts International Airport. One-way Prices start from DKK 1,620 including taxes and charges.

      • YWG18:50
        17h 53m
        1 stop
        GCM13:43
        Wed, Feb 19|Winnipeg - Grand Cayman|Porter Airlines
        DKK 1,822
        DKK 1,822

        Choose Porter Airlines flights from Winnipeg to Grand Cayman. The one-way connecting flight with Porter Airlines departs from Winnipeg James Armstrong Richardson International Airport on Wed, Feb 19, arriving at Owen Roberts International Airport. One-way Prices start from DKK 1,822 including taxes and charges.

      • YWG14:15
        22h 30m
        1 stop
        GCM13:45
        Wed, Mar 5|Winnipeg - Grand Cayman|United Airlines
        DKK 1,953
        DKK 1,953

        Choose United Airlines flights from Winnipeg to Grand Cayman. The one-way connecting flight with United Airlines departs from Winnipeg James Armstrong Richardson International Airport on Wed, Mar 5, arriving at Owen Roberts International Airport. One-way Prices start from DKK 1,953 including taxes and charges.

      • YWG18:50
        17h 53m
        1 stop
        GCM13:43
        Sun, Mar 2|Winnipeg - Grand Cayman|Porter Airlines
        DKK 2,040
        DKK 2,040

        Choose Porter Airlines flights from Winnipeg to Grand Cayman. The one-way connecting flight with Porter Airlines departs from Winnipeg James Armstrong Richardson International Airport on Sun, Mar 2, arriving at Owen Roberts International Airport. One-way Prices start from DKK 2,040 including taxes and charges.

      • YWG01:00 pm
        3h 5m
        Nonstop
        GCM02:00 pm
        Sun, Feb 23|Winnipeg - Grand Cayman|WestJet
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Winnipeg to Grand Cayman flight time & flight schedules

Flight info.
Departure
Arrival
Weekly Schedule

  1. WS520

    WestJet

    06:30

    YWG

    2.5h

    09:57

    YYZ

    SMTWTFS
    Search

  2. WS2032

    WestJet

    09:25

    YYZ

    4.3h

    13:43

    GCM

    S--W--S

  3. PD292

    Porter Airlines

    11:45

    YWG

    2.6h

    15:21

    YOW

    SMTWTFS
    Search

  4. UA3691

    United Airlines

    17:50

    YOW

    1.7h

    19:32

    EWR

    SMTWTFS

  5. UA2119

    United Airlines

    09:06

    EWR

    4.2h

    13:15

    GCM

    SMTWTFS

  6. UA5639

    United Airlines

    14:15

    YWG

    2.4h

    16:36

    ORD

    SMTWTFS
    Search

  7. UA322

    United Airlines

    08:39

    ORD

    3.9h

    13:35

    GCM

    -----F-

  8. WS306

    WestJet

    14:35

    YWG

    2.5h

    18:04

    YYZ

    SMTWTFS
    Search

  9. WS2032

    WestJet

    09:25

    YYZ

    4.3h

    13:43

    GCM

    S--W--S

  10. UA5623

    United Airlines

    16:25

    YWG

    2.6h

    17:59

    DEN

    SMTWTFS
    Search

  11. UA1291

    United Airlines

    23:59

    DEN

    3.7h

    05:41

    EWR

    SMTWTFS

  12. UA2119

    United Airlines

    09:06

    EWR

    4.2h

    13:15

    GCM

    SMTWTFS

  13. F8640

    Flair Airlines

    17:10

    YWG

    2.5h

    20:40

    YYZ

    SMTWTFS
    Search

  14. WS2032

    WestJet

    09:25

    YYZ

    4.3h

    13:43

    GCM

    S--W--S

  15. F8640

    Flair Airlines

    17:10

    YWG

    2.5h

    20:40

    YYZ

    SMTWTFS
    Search

  16. AA5046

    American Airlines

    06:00

    YYZ

    2.4h

    08:25

    CLT

    SMTWTFS

  17. AA301

    American Airlines

    09:20

    CLT

    3.0h

    11:20

    GCM

    SMTWTFS

  18. PD438

    Porter Airlines

    18:30

    YWG

    2.6h

    22:05

    YYZ

    SMTWTFS
    Search

  19. WS2032

    WestJet

    09:25

    YYZ

    4.3h

    13:43

    GCM

    S--W--S

  20. WS536

    WestJet

    21:24

    YWG

    2.5h

    00:54

    YYZ

    SMTWT-S
    Search

  21. WS2032

    WestJet

    09:25

    YYZ

    4.3h

    13:43

    GCM

    S--W--S

  22. WS536

    WestJet

    21:24

    YWG

    2.5h

    00:54

    YYZ

    SMTWT-S
    Search

  23. AA5046

    American Airlines

    06:00

    YYZ

    2.4h

    08:25

    CLT

    SMTWTFS

  24. AA301

    American Airlines

    09:20

    CLT

    3.0h

    11:20

    GCM

    SMTWTFS
Find more flights and airlines

Find the best time to fly from Winnipeg to Grand Cayman

We monitor flight fares to help you find the best deals effortlessly

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

FAQ

  • When are flight tickets from Winnipeg (YWG) to Grand Cayman (GCM) the cheapest?

    Airlines adjust prices for flights from Winnipeg to Grand Cayman based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Winnipeg (YWG) to Grand Cayman (GCM) cost?

    According to Trip.com's data, the lowest price is around DKK 3,526.

  • What is the transportation method from the main airport to downtown in Grand Cayman?

    • The distance from Owen Roberts International Airport to downtown is about 11 km. It takes about 30 minutes by taxi.

How to find a cheap flight from Winnipeg to Grand Cayman

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Winnipeg to Grand Cayman. Book your flights at the right time and save more.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Information from Winnipeg to Grand Cayman

Cheapest nonstop flight priceDKK 1,033
Off-season for travelFebruary
Peak season for travelDecember
Flight distance3,679.95 km
Popular airlineDelta Air Lines

Contact Us

About

Other Services

Payment Methods
Our Partners
Copyright © 2025 Trip.com Travel Singapore Pte. Ltd. All rights reserved
Site Operator: Trip.com Travel Singapore Pte. Ltd.