C$ 245+ Flights from Winnipeg to Kailua-Kona | Cheapflights

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Cheap flight deals from Winnipeg to Kailua-Kona

Round-trip from	C$ 358
One-way from	C$ 245

WestJet

WestJet
1/3-12/3
2 total stops
39h 08m total
Winnipeg to Kailua-Kona

WestJet

WestJet
21/2
1 total stop
30h 52m total
Winnipeg to Kailua-Kona

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 8 January 2026.

Sun 1/37:50 a.m.YWG - KOA

1 stop17h 57mWestJet

Thu 12/310:30 p.m.KOA - YWG

1 stop21h 11mWestJet

Deal found 7/1C$ 358

Tue 28/48:45 a.m.YWG - KOA

2 stops15h 57mUnited Airlines

Tue 5/51:05 p.m.KOA - YWG

2 stops17h 34mUnited Airlines

Deal found 8/1C$ 415

Mon 27/48:45 a.m.YWG - KOA

1 stop11h 45mUnited Airlines

Tue 5/58:00 p.m.KOA - YWG

1 stop19h 48mUnited Airlines

Deal found 8/1C$ 492

Fri 1/52:15 p.m.YWG - KOA

2 stops26h 35mUnited Airlines

Tue 5/51:05 p.m.KOA - YWG

2 stops17h 34mUnited Airlines

Deal found 8/1C$ 500

Tue 28/48:45 a.m.YWG - KOA

1 stop11h 45mUnited Airlines

Thu 30/410:55 p.m.KOA - YWG

2 stops31h 44mUnited Airlines

Deal found 8/1C$ 502

Tue 28/48:45 a.m.YWG - KOA

2 stops15h 57mUnited Airlines

Wed 6/510:55 p.m.KOA - YWG

2 stops31h 44mUnited Airlines

Deal found 8/1C$ 509

Sat 2/58:30 a.m.YWG - KOA

2 stops31h 17mUnited Airlines

Tue 5/51:05 p.m.KOA - YWG

2 stops17h 34mUnited Airlines

Deal found 8/1C$ 516

Fri 9/16:15 a.m.YWG - KOA

2 stops42h 13mWestJet

Fri 16/19:30 p.m.KOA - YWG

1 stop10h 23mWestJet

Deal found 8/1C$ 571

Mon 27/42:00 p.m.YWG - KOA

2 stops25h 47mUnited Airlines

Thu 30/410:55 p.m.KOA - YWG

2 stops31h 44mUnited Airlines

Deal found 8/1C$ 579

Best flights from Winnipeg to Kailua-Kona
Discover carefully curated flight deals from Winnipeg to Kailua-Kona that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 8 January 2026.

Sun 1/37:50 a.m.YWG - KOA

1 stop17h 57mWestJet

Thu 12/310:30 p.m.KOA - YWG

1 stop21h 11mWestJet

Deal found 7/1C$ 358

Sun 26/48:45 a.m.YWG - KOA

1 stop11h 45mUnited Airlines

Tue 5/51:05 p.m.KOA - YWG

2 stops17h 34mUnited Airlines

Deal found 8/1C$ 415

Tue 28/48:45 a.m.YWG - KOA

2 stops15h 57mUnited Airlines

Tue 5/51:05 p.m.KOA - YWG

2 stops17h 34mUnited Airlines

Deal found 8/1C$ 415

Wed 29/48:45 a.m.YWG - KOA

2 stops15h 57mUnited Airlines

Tue 5/51:05 p.m.KOA - YWG

2 stops17h 34mUnited Airlines

Deal found 8/1C$ 415

Mon 27/42:00 p.m.YWG - KOA

2 stops26h 50mUnited Airlines

Tue 5/51:05 p.m.KOA - YWG

2 stops17h 34mUnited Airlines

Deal found 8/1C$ 492

Tue 28/48:45 a.m.YWG - KOA

2 stops15h 57mUnited Airlines

Thu 30/410:55 p.m.KOA - YWG

2 stops31h 44mUnited Airlines

Deal found 8/1C$ 502

Wed 29/48:45 a.m.YWG - KOA

2 stops15h 57mUnited Airlines

Thu 30/410:55 p.m.KOA - YWG

2 stops31h 44mUnited Airlines

Deal found 8/1C$ 502

Sun 26/48:45 a.m.YWG - KOA

1 stop11h 45mUnited Airlines

Wed 6/510:55 p.m.KOA - YWG

2 stops31h 44mUnited Airlines

Deal found 8/1C$ 509

Tue 28/48:45 a.m.YWG - KOA

1 stop11h 45mUnited Airlines

Wed 6/510:55 p.m.KOA - YWG

2 stops31h 44mUnited Airlines

Deal found 8/1C$ 509

Last-minute flights from Winnipeg to Kailua-Kona
Discover last-minute flight deals from Winnipeg to Kailua-Kona. Data last updated 8 January 2026 and is based on user searches.

Fri 9/16:15 a.m.YWG - KOA

2 stops42h 13mWestJet

Fri 16/19:30 p.m.KOA - YWG

1 stop10h 23mWestJet

Deal found 8/1C$ 571

Tue 13/16:10 p.m.YWG - KOA

1 stop22h 34mAir Canada

Thu 15/12:20 p.m.KOA - YWG

2 stops17h 37mAir Canada

Deal found 5/1C$ 817

Tue 13/19:50 p.m.YWG - KOA

1 stop18h 54mAir Canada

Tue 20/13:59 p.m.KOA - YWG

2 stops29h 15mAir Canada

Deal found 6/1C$ 968

Tue 13/112:55 p.m.YWG - KOA

2 stops35h 34mWestJet

Thu 15/19:30 p.m.KOA - YWG

1 stop23h 09mWestJet

Deal found 6/1C$ 1,169

Mon 19/16:10 p.m.YWG - KOA

2 stops24h 34mAir Canada

Wed 28/12:00 p.m.KOA - YWG

1 stop18h 59mAir Canada

Deal found 8/1C$ 618

Sat 14/29:00 p.m.YWG - KOA

1 stop28h 47mMultiple Airlines

Sat 21/29:01 p.m.KOA - YWG

2 stops36h 51mMultiple Airlines

Deal found 7/1C$ 961

Fly from

Fly to

Route

Depart

Return

Price

WinnipegKailua-Kona

YWG - KOA

YWGKOA

Winnipeg

Sun 1/3

7:50 a.m.-9:47 p.m.

1 stop17h 57m

Kona Intl

Thu 12/3

10:30 p.m.-12:41 a.m.

1 stop21h 11m

C$ 358

WinnipegKailua-Kona

YWG - KOA

YWGKOA

Winnipeg

Sun 26/4

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

1 stop11h 45m

Kona Intl

Tue 5/5

1:05 p.m.-11:39 a.m.

2 stops17h 34m

C$ 415

WinnipegKailua-Kona

YWG - KOA

YWGKOA

Winnipeg

Tue 28/4

8:45 a.m.-7:42 p.m.

2 stops15h 57m

Kona Intl

Tue 5/5

1:05 p.m.-11:39 a.m.

2 stops17h 34m

C$ 415

WinnipegKailua-Kona

YWG - KOA

YWGKOA

Winnipeg

Wed 29/4

8:45 a.m.-7:42 p.m.

2 stops15h 57m

Kona Intl

Tue 5/5

1:05 p.m.-11:39 a.m.

2 stops17h 34m

C$ 415

WinnipegKailua-Kona

YWG - KOA

YWGKOA

Winnipeg

Mon 27/4

2:00 p.m.-11:50 a.m.

2 stops26h 50m

Kona Intl

Tue 5/5

1:05 p.m.-11:39 a.m.

2 stops17h 34m

C$ 492

WinnipegKailua-Kona

YWG - KOA

YWGKOA

Winnipeg

Tue 28/4

8:45 a.m.-7:42 p.m.

2 stops15h 57m

Kona Intl

Thu 30/4

10:55 p.m.-11:39 a.m.

2 stops31h 44m

C$ 502

WinnipegKailua-Kona

YWG - KOA

YWGKOA

Winnipeg

Wed 29/4

8:45 a.m.-7:42 p.m.

2 stops15h 57m

Kona Intl

Thu 30/4

10:55 p.m.-11:39 a.m.

2 stops31h 44m

C$ 502

WinnipegKailua-Kona

YWG - KOA

YWGKOA

Winnipeg

Sun 26/4

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

1 stop11h 45m

Kona Intl

Wed 6/5

10:55 p.m.-11:39 a.m.

2 stops31h 44m

C$ 509

WinnipegKailua-Kona

YWG - KOA

YWGKOA

Winnipeg

Tue 28/4

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

1 stop11h 45m

Kona Intl

Wed 6/5

10:55 p.m.-11:39 a.m.

2 stops31h 44m

C$ 509

WinnipegKailua-Kona

YWG - KOA

YWGKOA

Winnipeg

Sat 21/2

6:55 p.m.-9:47 p.m.

1 stop30h 52m

C$ 245

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Showing 1-10 of 11 results

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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?

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?

Vancouver (YVR) is the most affordable 1-stop option, with an average round-trip price of C$ 746.

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

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?

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

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

Reviews

1 / 20

10.0

Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.

United Airlines

7.4

Good

United Airlines

7.4

Good

Reviews

1 / 20

10.0

Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.

7.2

Good

United Airlines

7.4

Good

Reviews

1 / 20

10.0

Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.

7.1

Good

United Airlines

7.4

Good

Reviews

1 / 20

10.0

Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.

Related info for your journey

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 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$ 261, 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$ 283 and C$ 428, 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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Top 3 airlines flying from Winnipeg to Kailua-Kona

Airline	Cheapest	Average	Flexibility	On-time
Air Canada	CheapestC$ 300	AverageC$ 651	FlexibilityNo cancel fee	On-time67%	Search Air Canada flights
United Airlines	CheapestC$ 342	AverageC$ 520	FlexibilityNo cancel fee	On-time69%	Search United Airlines flights
WestJet	CheapestC$ 428	AverageC$ 697	FlexibilityNo cancel fee	On-time60%	Search WestJet flights

Fly with Cheapflights

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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