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Cheap flights from Madison to Winnipeg from C$ 596

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 8/1. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — YWG
11 Jan — 18 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Madison to Winnipeg

Enter your travel dates to find the best prices.

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 12 December 2025.

Thu 11/123:09 p.m.MSN - YWG
1 stop5h 46mUnited Airlines
Fri 19/127:05 a.m.YWG - MSN
2 stops15h 25mUnited Airlines
Deal found 9/12C$ 1,586

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 12 December 2025.

Round-trip from

C$ 596
United Airlines
  • United Airlines
  • 17/2-21/2
  • 2 total stops
  • 12h 14m total
  • Madison to Winnipeg
Search Deals

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 629,999 searches. Data last updated 12 December 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

Sun 25/1

6:30 a.m.-11:57 a.m.

1 stop5h 27m

Winnipeg

Sun 1/2

2:20 p.m.-7:07 p.m.

1 stop4h 47m

C$ 596

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Thu 8/1

6:30 a.m.-11:03 a.m.

1 stop4h 33m

Winnipeg

Mon 12/1

5:21 p.m.-10:50 p.m.

1 stop5h 29m

C$ 596

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Tue 17/2

6:30 a.m.-11:57 a.m.

1 stop5h 27m

Winnipeg

Sat 21/2

2:20 p.m.-9:07 p.m.

1 stop6h 47m

C$ 596

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Thu 8/1

6:30 a.m.-11:03 a.m.

1 stop4h 33m

Winnipeg

Mon 12/1

9:00 p.m.-10:50 p.m.

2 stops25h 50m

C$ 662

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Sun 25/1

6:00 a.m.-11:35 p.m.

2 stops17h 35m

Winnipeg

Sun 1/2

12:10 p.m.-10:55 a.m.

2 stops22h 45m

C$ 732

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

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.

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?

    Airlines like United Airlines and Delta fly from Madison to Winnipeg in about 4h 33m. The time it takes to get you to your destination can typically vary by up to 54m. Madison and Winnipeg are separated by a distance of 964 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • 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

Travelling to a place near Winnipeg?

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

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Alternative routes for Madison to Winnipeg

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How does Cheapflights help users find flights from Madison to Winnipeg?

Cheapflights helps you search for flights from Madison to Winnipeg via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets from Madison to Winnipeg?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Madison to Winnipeg.

Can Cheapflights find flights from Madison to Winnipeg with no change fees?

Yes, we can. To see specific flights from Madison to Winnipeg with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Madison to Winnipeg become cheaper?

Not ready to book yet? You can track prices for flights from Madison to Winnipeg on Cheapflights with our Price Alert feature and get notified when better prices are available.

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