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$189+ Cheap flights from Madison (MSN) to Winnipeg (YWG)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — YWG
Jan 7 — Jan 141
Wed 1/7
Wed 1/14
1 adult, Economy
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Cheap flight deals from Madison to Winnipeg

Best flights from Madison to Winnipeg
Discover carefully curated flight deals from Madison to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 8, 2025.

This United Airlines deal was found by Cheapflights users on 12/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/176:30 amMSN - YWG
1 stop5h 27mUnited Airlines
Sat 2/212:20 pmYWG - MSN
1 stop6h 47mUnited Airlines
Deal found 12/6$432
This WestJet deal was found by Cheapflights users on 12/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/176:20 amMSN - YWG
2 stops12h 49mWestJet
Sat 2/215:00 amYWG - MSN
2 stops15h 52mWestJet
Deal found 12/6$530
This Air Canada deal was found by Cheapflights users on 12/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/175:44 pmMSN - YWG
2 stops18h 55mAir Canada
Sat 2/217:05 amYWG - MSN
2 stops7h 57mAir Canada
Deal found 12/7$554

Find flight deals from Madison to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Winnipeg (YWG). 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 December 8, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$432
(United Airlines)

One-way from

$189
(United Airlines)
Provider with most accurate pricing for Madison Truax Field-Winnipeg flight deals.
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Provider most trusted by Cheapflights users for Madison Truax Field-Winnipeg flights.
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From Madison Truax Field to Winnipeg
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One-way flight from Madison Truax Field to Winnipeg
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Winnipeg 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 2,558,603 searches. Data last updated December 8, 2025.
Use the filters below to find and compare flights from Madison to Winnipeg that are best for you.

Fly from

Madison

Fly to

Winnipeg

Route

Depart

Return

Price

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Tue 2/17

6:30 am-11:57 am

1 stop5h 27m

Winnipeg

Sat 2/21

2:20 pm-9:07 pm

1 stop6h 47m

$432

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Tue 2/17

6:20 am-7:09 pm

2 stops12h 49m

Winnipeg

Sat 2/21

5:00 am-8:52 pm

2 stops15h 52m

$530

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Tue 2/17

5:44 pm-12:39 pm

2 stops18h 55m

Winnipeg

Sat 2/21

7:05 am-3:02 pm

2 stops7h 57m

$554

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Thu 1/15

6:30 am-11:57 am

1 stop5h 27m

$189

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Thu 1/15

11:19 am-12:35 am

2 stops13h 16m

$238

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/8

  • Most accurate provider: When it comes to deals on Madison-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madison-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Madison-Winnipeg flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Madison-Winnipeg flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Madison-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Madison to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Madison 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.

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. 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 Winnipeg. Reviews last updated December 8, 2025.
Read reviews from past customers who have flown Delta from Madison to Winnipeg. 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.
Delta
7.9
Good
8,011 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.9

Food

7.3

Comfort

7.9

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,011 reviews
Delta
7.9
Good
8,011 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.9

Food

7.3

Comfort

7.9

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Madison to Winnipeg. 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 Madison to Winnipeg?

    A quick flight from Madison to Winnipeg can take about 5h 27m. United Airlines provides one of the quickest options available for as low as $432. Airlines will cover a distance of 599 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What is the cheapest airline to fly from Madison to Winnipeg round-trip?

    Cheapflights users have booked flights from Madison to Winnipeg round-trip from $282.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Madison to Winnipeg 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

Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Portage la Prairie

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Top airline flying from Madison to Winnipeg

Discover the top airline that operate flights from Madison to Winnipeg. 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 2,558,603 searches. Data last updated December 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$282Average$611FlexibilityNo cancel feeOn-timeN/A

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