C$ 290 Find Cheap Flights from Winnipeg to Maui

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Winnipeg to Maui departing on 28/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Maui

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Winnipeg to Maui, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Winnipeg to Maui, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Winnipeg to Maui

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Winnipeg to Maui that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Winnipeg to Maui

Mon, 27 Apr - Tue, 12 May
Air Canada Logo
9:15 p.m. - 8:53 p.m.
YWG
-
OGG
28h 38m
2 stops
Air Canada Logo
12:03 p.m. - 11:52 a.m.
OGG
-
YWG
18h 49m
2 stops
C$ 645Air Canada
Mon, 1 Jun - Mon, 8 Jun
Delta Logo
6:40 a.m. - 7:35 p.m.
YWG
-
OGG
17h 55m
2 stops
Delta Logo
12:50 p.m. - 11:56 a.m.
OGG
-
YWG
18h 06m
2 stops
C$ 652Delta
Wed, 27 May - Tue, 2 Jun
Delta Logo
6:40 a.m. - 7:35 p.m.
YWG
-
OGG
17h 55m
2 stops
Delta Logo
10:00 p.m. - 11:26 p.m.
OGG
-
YWG
20h 26m
2 stops
C$ 682Delta
Thu, 28 May - Thu, 4 Jun
WestJet Logo
12:50 p.m. - 9:50 p.m.
YWG
-
OGG
38h 00m
2 stops
WestJet Logo
10:50 p.m. - 2:40 p.m.
OGG
-
YWG
10h 50m
1 stop
C$ 700WestJet
Mon, 27 Apr - Tue, 12 May
United Airlines Logo
8:45 a.m. - 3:15 p.m.
YWG
-
OGG
11h 30m
1 stop
United Airlines Logo
1:10 p.m. - 11:52 a.m.
OGG
-
YWG
17h 42m
2 stops
C$ 703United Airlines
Thu, 28 May - Thu, 4 Jun
WestJet Logo
4:15 p.m. - 9:50 p.m.
YWG
-
OGG
34h 35m
2 stops
WestJet Logo
10:50 p.m. - 2:40 p.m.
OGG
-
YWG
10h 50m
1 stop
C$ 707WestJet
Thu, 28 May - Thu, 4 Jun
WestJet Logo
4:15 p.m. - 9:50 p.m.
YWG
-
OGG
34h 35m
2 stops
WestJet Logo
10:50 p.m. - 2:40 p.m.
OGG
-
YWG
10h 50m
1 stop
C$ 710WestJet
Thu, 28 May - Thu, 4 Jun
WestJet Logo
4:15 p.m. - 9:50 p.m.
YWG
-
OGG
34h 35m
2 stops
WestJet Logo
10:50 p.m. - 2:40 p.m.
OGG
-
YWG
10h 50m
1 stop
C$ 713WestJet
Thu, 28 May - Thu, 4 Jun
WestJet Logo
4:15 p.m. - 9:50 p.m.
YWG
-
OGG
34h 35m
2 stops
WestJet Logo
10:50 p.m. - 2:40 p.m.
OGG
-
YWG
10h 50m
1 stop
C$ 715WestJet
Thu, 28 May - Thu, 4 Jun
WestJet Logo
6:05 a.m. - 9:50 p.m.
YWG
-
OGG
20h 45m
1 stop
WestJet Logo
10:50 p.m. - 2:40 p.m.
OGG
-
YWG
10h 50m
1 stop
C$ 721WestJet
Booking Insights

KAYAK's insights & trends for Winnipeg to Maui flights

Get data-powered insights and trends into flights from Winnipeg to Maui to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Winnipeg to Maui?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of C$ 688, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Winnipeg to Maui?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Winnipeg to Maui, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Winnipeg to Maui is January, when tickets cost C$ 473 (return) on average. On the other hand, the most expensive months are November and March, when the average cost of round-trip tickets is C$ 1,026 and C$ 809 respectively.

How far in advance should I book a flight from Winnipeg to Maui?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Winnipeg to Maui, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below-average price on a flight from Winnipeg to Maui, you should book around 4 weeks before departure, which saves you about 74% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low seasonAugust
Cheapest flightC$ 290
Best time to beat the crowds (18% less expensive on average)
Most popular time to fly and prices are also 21% lower on average.
Flight from Winnipeg to Kahului

FAQs - booking Maui flights

  • How does KAYAK find such low prices on flights from Winnipeg to Maui?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Winnipeg to Maui.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Winnipeg to Maui?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Winnipeg to Maui is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Winnipeg to Maui?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Winnipeg to Maui with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Winnipeg to Maui?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Winnipeg to Maui up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines flying from Winnipeg to Maui

 
See real verified KAYAK customer reviews for airlines flying from Winnipeg to Maui. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Winnipeg to Maui? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9595 reviews
6.6Food
7.7Boarding
7.1Entertainment
7.3Comfort
8.1Crew
Airline reviews

It was a more comfortable seat don't get stuck in middle, makes for uncomfortable situation

6.0 GoodAnonymous, Apr 2026
GUM - HNL
Read more United Airlines reviews

It was a more comfortable seat don't get stuck in middle, makes for uncomfortable situation

They were fast and I like how they used to entertainment system to play video about the safety.

Hopped on time for the flight only to get deplaned and delayed another 2.5 hours.

Given I (and I’m assuming most people) have both carry in and a personal item included in their fare, I find it very unfair that on neither of my flights I was able to use the overhead for my small backpack because they were completely rammed with luggage, people personal items, jackets, hats and other items. So the only item I brought in had to be stuffed under my seat while they had their leg room and sat comfortable with all of their items in the overhead. This has to stop because I was uncomfortable on both flights when I only had one smaller item that could not be checked due to its contents (medication etc). Plenty of people could have checked theirs but chose not to and then took up the space allotment for 2 people.

Flight attendants had a little attitude. Food tastes no good.

So bad, flight was been cancelled due to aircraft problem, so ended up buying anothet ticket.

From pre boarding to flight attendant, crew and baggage handler, excellent. Didn’t lost my luggage like West jet.

Very poor. The flight was delayed from Toronto because some forget to do there job . I got to my connecting gate in San Francisco 10 minutes before the departure.but this didn’t let me board even though the flight was still there for an other 30 minutes. The the gentleman at the unite airline desk told me that they usually wait for passengers but air Canada called and told them not to we I been rerouted to Manila instead of Hong Kong . In San Francisco they mad me check in my carryon bag . I was told the it will directly go yo ho chi minn cuyt but I was told that by the Vietnams airline desk that’s not there I’m 10 hours behind my scheduled flight and looks like I I’m going without baggage. I don’t have a chance of catching ..

It was great. There were some issues prior to takeoff. The weather was poor so we had to go through deicing, and we were delayed a bit by the pilots' concern about one of the engines, but that's aviation. The pilots handled everything with aplomb, and kept us apprised

Reliable, nice crew, I fly often on that flight and I like it all.

The agents at the Kelowna YLW airport were really grumpy. Same with oversized baggage person. Staff on the plane were great.

Flight was early. That’s the only positive I can share. I paid for wifi on the flight and it didn’t allow me to use any streaming services so it was a waste of $20. West Jet also lost my ski equipment on my way to a ski vacation. They told me it would be delivered to the hotel as soon as it arrived at the airport. It was never delivered. I had to pick it up at the airport on my way home. I am completely disgusted with my experience on west jet

The window seat on the emergency row was too small. I had a different seat booked and they moved me. My seat remained open. It was very uncomfortable.

Experience was good, the wifi hook up is somewhat tough

Great flight, great landing, nice staff. Our seats were a little cramped.

I will not be flying with westjet again. I was uncomfortable in my seat. The position made my back hurt so bad. My wife was able to fit the seatbelt around her with out an extension but was unable to put the tray table down or fit in the seat for that matter. Our bag was smashed and I spent two hours trying to fill out the application for a damaged bag before I gave up. The 80 photos I took would not work and nothing telling me the format to upload them as.. I made the mistake of unpacking the bag before taking photos so no claim for me. Next trip to Canada I will have to use air Canada.

Overall good experience. The wait for baggage at our destination was quite long, but other than that everything was good as expected

Airplane is too small. Crew, especially the flight attendant who looked after our area, was not at all friendly and a touch authoratative. She may have been the most gruff flight attendant i've come across in 40 years of business travel

I selected "carry-on" for a round trip on Kayak, but my return flight on WestJet did not include a carry-on and they would not allow me to add one. My only option was to add a "checked bag" which I had to wait for on the luggage carousel after landing. Not a good experience.

My flight was cancelled due to weather but Westjet got me on a new flight in a timely and efficient manor.

After 3 hours of delays, they ended up cancelling my flight. And although I could purchase one-way tickets to get to my destination, they would not offer me these flights as compensation for the cancelled flight, and I didn't end up making it home until 13 hours after I was originally supposed to arrive. It made for an extremely strenuous end to an otherwise good trip.

Be careful about the bad policy and when purchasing seats

Very disappointed with premier lounge. Food selection very poor, both coffee machines out of order. For the price you charge for an upgrade, the seats don’t fully recline, movie selection is old. Not very good value. Asian airlines are light years ahead at a more affordable price.

The seat design in the premium economy section leaves virtually no room under the seat to store a bag or purse. Other than that, it was a great flight. Arrived early.

The flight was delayed, but not for weather. We landed over 3hrs later than planned.

The stag were helpful, kind and liked the passengers. The plane was pristinely clean! Great flight!

My flight was delayed more than once, but Air Canada updated us regularly. Friends on other airlines had much worse experiences.

My ticket did not exist when I got to the airport. I had to book another flight and was still charged by Kayak

Got denied my flight was told on Google that Air Canada was supposed to book me a flight back home because I never was able to go to my destination. They did not help me whatsoever. I had to book a whole new flight for that reason I would write this is zero

The plane was delayed an hour. Heard from other passengers that the Vancouver connection to SFO was never on-time.

Everything you need to know for your flight to Maui

Information on your arrival and departure airports