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$432+ Cheap flights from Madison (MSN) to Winnipeg (YWG)

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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — YWG
Dec 24 — Dec 311
Wed 12/24
Wed 12/31
1 adult, Economy
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Find flight deals from Madison to Winnipeg

Cheapest flights from Madison to Winnipeg
Explore the most affordable flight options available from Madison to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 24, 2025.

This United Airlines deal was found by Cheapflights users on 11/22. 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.
Mon 12/86:30 amMSN - YWG
1 stop5h 27mUnited Airlines
Wed 12/102:20 pmYWG - MSN
1 stop4h 56mUnited Airlines
Deal found 11/22$719
This Delta deal was found by Cheapflights users on 11/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/86:00 amMSN - YWG
2 stops16h 41mDelta
Wed 12/106:40 amYWG - MSN
2 stops6h 10mDelta
Deal found 11/22$836
This FlightHub deal was found by Cheapflights users on 11/23. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/301:24 pmMSN - YWG
1 stop3h 35mWestJet
Fri 12/56:40 amYWG - MSN
1 stop3h 35mWestJet
Deal found 11/23$935
This American Airlines deal was found by Cheapflights users on 11/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/305:00 amMSN - YWG
3 stops18h 35mAmerican Airlines
Fri 12/512:10 pmYWG - MSN
2 stops21h 16mAmerican Airlines
Deal found 11/23$1,394

Cheap 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 November 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$432
(United Airlines)
Provider with most accurate pricing for Madison Truax Field-Winnipeg flight deals.
Search Deals
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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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 November 24, 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 1/6

6:30 am-11:57 am

1 stop5h 27m

Winnipeg

Tue 1/13

2:20 pm-9:05 pm

1 stop6h 45m

$432

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Sat 2/21

6:20 am-11:32 am

2 stops29h 12m

Winnipeg

Wed 2/25

5:21 pm-10:19 am

1 stop16h 58m

$542

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Sat 2/21

6:30 am-11:57 am

1 stop5h 27m

Winnipeg

Wed 2/25

2:20 pm-9:07 pm

1 stop6h 47m

$575

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Mon 12/8

6:30 am-11:57 am

1 stop5h 27m

Winnipeg

Wed 12/10

2:20 pm-7:16 pm

1 stop4h 56m

$719

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Mon 12/8

6:00 am-10:41 pm

2 stops16h 41m

Winnipeg

Wed 12/10

6:40 am-12:50 pm

2 stops6h 10m

$836

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

  • 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 November 24, 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
7,997 reviews

Food

7.3

Entertainment

7.9

Overall

7.9

Comfort

7.9

Crew

8.5

Boarding

8.1

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
7,997 reviews
Delta
7.9
Good
7,997 reviews

Food

7.3

Entertainment

7.9

Overall

7.9

Comfort

7.9

Crew

8.5

Boarding

8.1

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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Alternative routes for Madison to Winnipeg

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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 November 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$282Average$611FlexibilityNo cancel feeOn-timeN/A

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