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Cheap flights from Winnipeg to Maui from C$ 285

YWG — OGG
11 Oct — 18 Oct1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Maui

Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to Maui

Sat 21/117:50 p.m. -
1 stop22h 15m
Fri 27/113:05 p.m. -
1 stop29h 39m
Deal found 11/9C$ 555
Sat 24/104:15 p.m. -
2 stops26h 50m
Sat 31/1010:30 p.m. -
2 stops33h 15m
Deal found 9/9C$ 575
Sun 29/1110:55 a.m. -
1 stop14h 32m
Thu 3/1210:45 p.m. -
2 stops21h 39m
Deal found 6/9C$ 689
Sat 24/106:00 a.m. -
2 stops21h 13m
Sat 31/1011:24 a.m. -
3 stops33h 20m
Deal found 9/9C$ 694
Fri 20/113:45 p.m. -
1 stop33h 45m
Sat 28/118:55 p.m. -
2 stops21h 00m
Deal found 8/9C$ 699
Sun 29/116:00 a.m. -
1 stop19h 30m
Thu 3/1210:30 p.m. -
2 stops21h 29m
Deal found 9/9C$ 701

Find flight deals from Winnipeg to Maui

Round-trip from

C$ 555

One-way from

C$ 285

Popular in

November

Cheapest in

December

Average price

C$ 951
WestJet
  • WestJet
  • 21/11-27/11
  • 2 total stops
  • 51h 54m total
  • Winnipeg to Maui
Search Deals
WestJet
  • WestJet
  • 17/10-31/12
  • 1 total stop
  • 28h 20m total
  • Winnipeg to Maui
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 74 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease (C$ 79 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2026
Search Deals

Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Winnipeg to Maui that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegKahului

YWG Winnipeg - OGG Kahului

YWGOGG

Winnipeg

Sat 17/10

9:05 p.m.-8:25 p.m.

1 stop28h 20m

Kahului

Wed 31/12

12:00 a.m.-4:00 a.m.

Nonstop0h 00m

C$ 285

WinnipegKahului

YWG Winnipeg - OGG Kahului

YWGOGG

Winnipeg

Sun 25/10

6:35 p.m.-2:05 p.m.

2 stops24h 30m

Kahului

Wed 31/12

12:00 a.m.-4:00 a.m.

Nonstop0h 00m

C$ 286

WinnipegKahului

YWG Winnipeg - OGG Kahului

YWGOGG

Winnipeg

Sat 21/11

7:50 p.m.-2:05 p.m.

1 stop22h 15m

Kahului

Fri 27/11

3:05 p.m.-12:44 a.m.

1 stop29h 39m

C$ 555

WinnipegKahului

YWG Winnipeg - OGG Kahului

YWGOGG

Winnipeg

Tue 6/10

7:00 a.m.-10:13 p.m.

3 stops20h 13m

Kahului

Wed 31/12

12:00 a.m.-4:00 a.m.

Nonstop0h 00m

C$ 565

WinnipegKahului

YWG Winnipeg - OGG Kahului

YWGOGG

Winnipeg

Sat 24/10

6:00 a.m.-2:05 p.m.

2 stops37h 05m

Kahului

Sat 31/10

10:30 p.m.-7:45 p.m.

1 stop17h 15m

C$ 576

WinnipegKahului

YWG Winnipeg - OGG Kahului

YWGOGG

Winnipeg

Sat 27/2

12:10 p.m.-2:05 p.m.

2 stops29h 55m

Kahului

Sun 7/3

3:05 p.m.-11:59 p.m.

2 stops28h 54m

C$ 583

WinnipegKahului

YWG Winnipeg - OGG Kahului

YWGOGG

Winnipeg

Mon 18/1

6:00 a.m.-9:30 p.m.

2 stops19h 30m

Kahului

Thu 28/1

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

2 stops21h 40m

C$ 618

WinnipegKahului

YWG Winnipeg - OGG Kahului

YWGOGG

Winnipeg

Fri 15/1

6:00 a.m.-9:30 p.m.

2 stops19h 30m

Kahului

Sun 24/1

3:05 p.m.-12:50 p.m.

1 stop17h 45m

C$ 620

WinnipegKahului

YWG Winnipeg - OGG Kahului

YWGOGG

Winnipeg

Sun 29/11

10:55 a.m.-9:27 p.m.

1 stop14h 32m

Kahului

Thu 3/12

10:45 p.m.-12:24 a.m.

2 stops21h 39m

C$ 689
Quickest round-trip

WinnipegKahului

YWG Winnipeg - OGG Kahului

YWGOGG

Winnipeg

Tue 6/10

8:45 a.m.-3:05 p.m.

1 stop11h 20m

Kahului

Wed 31/12

12:00 a.m.-4:00 a.m.

Nonstop0h 00m

C$ 696

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 12 resultsSorted by cheapest first
1
2

Best time to book a flight from Winnipeg to Maui

Have a flexible travel schedule? Discover the best time to fly to Maui from Winnipeg with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Winnipeg to Maui

No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Maui

Read reviews from past customers who have flown WestJet and Air Canada from Winnipeg to Maui. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
WestJet
7.2
Good
3,445 reviews
Check prices

Boarding

7.4

Overall

7.2

Comfort

7.1

Entertainment

6.1

Food

6.2

Crew

7.9

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2026

YHZ - DTW

Better snacks I also flew Delta much better with movies and entertainment
WestJet
7.2
Good
3,445 reviews
WestJet
7.2
Good
3,445 reviews
Check prices

Boarding

7.4

Overall

7.2

Comfort

7.1

Entertainment

6.1

Food

6.2

Crew

7.9

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2026

YHZ - DTW

Better snacks I also flew Delta much better with movies and entertainment
Air Canada
7.1
Good
11,611 reviews
WestJet
7.2
Good
3,445 reviews
Check prices

Boarding

7.4

Overall

7.2

Comfort

7.1

Entertainment

6.1

Food

6.2

Crew

7.9

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2026

YHZ - DTW

Better snacks I also flew Delta much better with movies and entertainment

Related info for your journey

  • What airport do you fly from for flights from Winnipeg to Maui?

    Most people fly from Winnipeg (YWG) if they book a flight from Winnipeg to Maui. Winnipeg is conveniently located just 7.3 km from Winnipeg’s city centre.

  • How long is the flight from Winnipeg to Maui?

    Departing from Winnipeg to Maui will take you 14h 32m. Winnipeg and Maui are separated by a distance of 6054 km. Both multi-stop and direct flights can be found to your destination and back.

  • What are the most popular routes from Winnipeg to Maui?

    When deciding which route to take from Winnipeg to Maui consider Winnipeg - Kahului, Winnipeg - Hana or Winnipeg - Kapalua West Maui as they are the most popular.

  • Can I find deals for flights from Winnipeg to Maui that include hotel bookings?

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

  • How can I find direct flights from Winnipeg to Maui?

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

  • Can I find deals for business class flights from Winnipeg to Maui?

    Yes. Cheapflights offers flight deals from Winnipeg to Maui 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

Alternative routes for Winnipeg to Maui

Winnipeg to Kahului flights
Winnipeg to Honolulu flights
Winnipeg to Kailua-Kona flights
Winnipeg to Lihue flights
Winnipeg to Hana flights
Winnipeg to Kapalua flights

Top 2 airlines flying from Winnipeg to Maui

AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 341AverageC$ 507FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 443AverageC$ 760FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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When you search for this flight from Winnipeg to Maui, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

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