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Cheap flights from Winnipeg to Kailua-Kona from C$ 500

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 7/3. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — KOA
5 Feb — 12 Feb1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Kailua-Kona

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to Kailua-Kona (KOA). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 6 January 2026.

Round-trip from

C$ 500
WestJet
  • WestJet
  • 7/3-19/3
  • 2 total stops
  • 41h 43m total
  • Winnipeg to Kailua-Kona
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Find flight deals from Winnipeg to Kailua-Kona

Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to Kailua-Kona
Explore the most affordable flight options available from Winnipeg to Kailua-Kona. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 6 January 2026.

Sat 7/312:55 p.m.YWG - KOA
2 stops13h 32mWestJet
Thu 19/310:30 p.m.KOA - YWG
2 stops20h 17mWestJet
Deal found 3/1C$ 500
Wed 4/26:55 p.m.YWG - KOA
2 stops31h 32mWestJet
Wed 11/210:55 p.m.KOA - YWG
1 stop21h 45mWestJet
Deal found 5/1C$ 531
Tue 3/29:50 p.m.YWG - KOA
1 stop18h 54mAir Canada
Tue 10/23:59 p.m.KOA - YWG
2 stops25h 05mAir Canada
Deal found 4/1C$ 541
Sun 1/29:50 p.m.YWG - KOA
2 stops20h 54mAir Canada
Sun 8/23:59 p.m.KOA - YWG
2 stops25h 05mAir Canada
Deal found 5/1C$ 585
Sun 1/27:50 a.m.YWG - KOA
1 stop17h 57mMultiple Airlines
Sun 8/29:54 a.m.KOA - YWG
2 stops23h 58mMultiple Airlines
Deal found 5/1C$ 611
Wed 29/48:45 a.m.YWG - KOA
1 stop11h 45mUnited Airlines
Wed 6/512:02 p.m.KOA - YWG
2 stops18h 37mUnited Airlines
Deal found 5/1C$ 642
Mon 23/29:00 p.m.YWG - KOA
2 stops29h 27mMultiple Airlines
Mon 2/34:53 p.m.KOA - YWG
2 stops21h 12mMultiple Airlines
Deal found 4/1C$ 653
Thu 12/34:10 p.m.YWG - KOA
2 stops19h 16mMultiple Airlines
Fri 20/39:55 p.m.KOA - YWG
1 stop15h 10mMultiple Airlines
Deal found 5/1C$ 658
Tue 13/19:50 p.m.YWG - KOA
1 stop18h 54mAir Canada
Thu 15/12:20 p.m.KOA - YWG
2 stops17h 37mAir Canada
Deal found 4/1C$ 681

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Kailua-Kona 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 January 2026.
Use the filters below to find and compare flights from Winnipeg to Kailua-Kona that are best for you.

Fly from

Winnipeg

Fly to

Kailua-Kona

Route

Depart

Return

Price

WinnipegKailua-Kona

YWG - KOA

YWGKOA

Winnipeg

Wed 4/2

6:55 p.m.-10:27 p.m.

2 stops31h 32m

Kona Intl

Wed 11/2

10:55 p.m.-12:40 a.m.

1 stop21h 45m

C$ 531

WinnipegKailua-Kona

YWG - KOA

YWGKOA

Winnipeg

Tue 3/2

9:50 p.m.-12:44 p.m.

1 stop18h 54m

Kona Intl

Tue 10/2

3:59 p.m.-9:04 p.m.

2 stops25h 05m

C$ 541

WinnipegKailua-Kona

YWG - KOA

YWGKOA

Winnipeg

Wed 29/4

8:45 a.m.-3:30 p.m.

1 stop11h 45m

Kona Intl

Wed 6/5

12:02 p.m.-11:39 a.m.

2 stops18h 37m

C$ 642

WinnipegKailua-Kona

YWG - KOA

YWGKOA

Winnipeg

Mon 23/2

9:00 p.m.-10:27 p.m.

2 stops29h 27m

Kona Intl

Mon 2/3

4:53 p.m.-6:05 p.m.

2 stops21h 12m

C$ 653

WinnipegKailua-Kona

YWG - KOA

YWGKOA

Winnipeg

Sun 1/2

6:15 a.m.-9:47 p.m.

1 stop19h 32m

Kona Intl

Sun 8/2

10:55 p.m.-12:07 p.m.

2 stops33h 12m

C$ 793

WinnipegKailua-Kona

YWG - KOA

YWGKOA

Winnipeg

Mon 25/5

7:00 a.m.-8:02 p.m.

2 stops18h 02m

Kona Intl

Tue 2/6

1:10 p.m.-11:39 a.m.

2 stops17h 29m

C$ 840

WinnipegKailua-Kona

YWG - KOA

YWGKOA

Winnipeg

Sun 1/2

2:20 p.m.-2:44 p.m.

2 stops28h 24m

Kona Intl

Sun 8/2

3:59 p.m.-11:57 a.m.

2 stops15h 58m

C$ 999

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Best time to book a flight from Winnipeg to Kailua-Kona

Have a flexible travel schedule? Discover the best time to fly to Kailua-Kona 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 Kailua-Kona

What’s the top layover airport for flights from Winnipeg to Kailua-Kona?

Share of one-stop round-trip flights from Winnipeg to Kailua-Kona chosen by Cheapflights users in the past 12 months, using the same layover each way.

Vancouver (YVR) – chosen by Cheapflights users on 83% of one-stop itineraries from Winnipeg to Kailua-Kona on Cheapflights.

What’s the cheapest layover airport for flights from Winnipeg to Kailua-Kona?

Average round-trip fare for 1-stop flights from Winnipeg to Kailua-Kona, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Vancouver (YVR) is the most affordable 1-stop option, with an average round-trip price of C$ 743.

What’s the fastest layover option from Winnipeg to Kailua-Kona?

Shortest average travel time for 1-stop one-way flights from Winnipeg to Kailua-Kona, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Vancouver (YVR) have the shortest average one-way travel time for 1-stop routes: 13h 02m.

Which airport typically offers the quickest layover for flights from Winnipeg to Kailua-Kona?

Average layover duration for 1-stop one-way flights from Winnipeg to Kailua-Kona, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Vancouver (YVR) offer the fastest connection on this route, with an average layover time of 4h 50m.

Reviews of airlines servicing Kailua-Kona

Get insights into the airlines that provide service to Kailua-Kona. 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 Kailua-Kona. Reviews last updated 6 January 2026.
Read reviews from past customers who have flown United Airlines,WestJet, andAir Canada from Winnipeg to Kailua-Kona. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,132 reviews
Check prices

Entertainment

7.1

Overall

7.4

Food

6.6

Crew

8.1

Comfort

7.3

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
United Airlines
7.4
Good
9,132 reviews
United Airlines
7.4
Good
9,132 reviews
Check prices

Entertainment

7.1

Overall

7.4

Food

6.6

Crew

8.1

Comfort

7.3

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
WestJet
7.2
Good
3,235 reviews
United Airlines
7.4
Good
9,132 reviews
Check prices

Entertainment

7.1

Overall

7.4

Food

6.6

Crew

8.1

Comfort

7.3

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
Air Canada
7.1
Good
10,597 reviews
United Airlines
7.4
Good
9,132 reviews
Check prices

Entertainment

7.1

Overall

7.4

Food

6.6

Crew

8.1

Comfort

7.3

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Kailua-Kona. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Winnipeg to Kailua-Kona?

    There are many flights that can get you from Winnipeg to Kailua-Kona in 11h 45m. Fly via WestJet, Air Canada, or United Airlines to get the fastest option. The distance between Winnipeg and Kailua-Kona is about 6122 km. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Winnipeg to Kailua-Kona round-trip?

    Currently priced at C$ 260, United Airlines will fly you from Winnipeg to Kailua-Kona and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Air Canada and WestJet - these airlines can fly you to your destination from C$ 282 and C$ 426, respectively.

  • Can I find deals for flights from Winnipeg to Kailua-Kona that include hotel bookings?

    Yes. In addition to deals on Winnipeg to Kailua-Kona flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to Kailua-Kona?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Kailua-Kona.

  • Can I find deals for business class flights from Winnipeg to Kailua-Kona?

    Yes. Cheapflights offers flight deals from Winnipeg to Kailua-Kona 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 Kailua-Kona

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Winnipeg to Kailua-Kona

Discover the top 3 airlines that operate flights from Winnipeg to Kailua-Kona. 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 January 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 299AverageC$ 648FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 340AverageC$ 517FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 426AverageC$ 694FlexibilityNo 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 Kailua-Kona?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Winnipeg to Kailua-Kona. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Kailua-Kona?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Kailua-Kona from Winnipeg.

Can Cheapflights find flights from Winnipeg to Kailua-Kona with no change fees?

Certainly. Search results for flights to Kailua-Kona 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 Kailua-Kona become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Kailua-Kona from Winnipeg today and book when prices fit your budget.

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