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Cheap flights from Madison to Winnipeg from C$ 292

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 26/4. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — YWG
14 Apr — 21 Apr1
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 15 March 2026.

Tue 28/46:30 a.m.
MSN
-
YWG
1 stop5h 22m
United Airlines
Sat 2/52:00 p.m.
YWG
-
MSN
1 stop5h 07m
United Airlines
Deal found 10/3C$ 617
Thu 10/99:00 a.m.
MSN
-
YWG
1 stop11h 09m
WestJet
Mon 14/96:40 a.m.
YWG
-
MSN
1 stop15h 17m
WestJet
Deal found 12/3C$ 645
Mon 20/46:30 p.m.
MSN
-
YWG
1 stop16h 26m
WestJet
Thu 23/49:00 p.m.
YWG
-
MSN
2 stops25h 51m
WestJet
Deal found 13/3C$ 653
Tue 28/46:00 a.m.
MSN
-
YWG
1 stop4h 56m
WestJet
Sat 2/55:20 p.m.
YWG
-
MSN
1 stop16h 49m
WestJet
Deal found 14/3C$ 674
Sat 25/42:41 p.m.
MSN
-
YWG
2 stops26h 34m
WestJet
Sat 2/55:20 p.m.
YWG
-
MSN
1 stop16h 49m
WestJet
Deal found 11/3C$ 693
Mon 20/48:35 p.m.
MSN
-
YWG
1 stop15h 17m
United Airlines
Thu 23/42:00 p.m.
YWG
-
MSN
1 stop9h 49m
United Airlines
Deal found 13/3C$ 742
Thu 10/95:00 a.m.
MSN
-
YWG
2 stops11h 17m
United Airlines
Mon 14/92:05 p.m.
YWG
-
MSN
2 stops8h 37m
United Airlines
Deal found 12/3C$ 882
Tue 28/43:53 p.m.
MSN
-
YWG
2 stops7h 55m
Air Canada
Sat 2/58:10 a.m.
YWG
-
MSN
2 stops10h 57m
Air Canada
Deal found 14/3C$ 892

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 15 March 2026.

Round-trip from

C$ 617

One-way from

C$ 292
United Airlines
  • United Airlines
  • 28/4-2/5
  • 2 total stops
  • 10h 29m total
  • Madison to Winnipeg
Search Deals
WestJet
  • WestJet
  • 26/4
  • 1 total stop
  • 4h 56m 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 15 March 2026.
Use the filters below to find and compare flights from Madison to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Tue 28/4

6:30 a.m.-11:52 a.m.

1 stop5h 22m

Winnipeg

Sat 2/5

2:00 p.m.-7:07 p.m.

1 stop5h 07m

C$ 617

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Thu 10/9

9:00 a.m.-8:09 p.m.

1 stop11h 09m

Winnipeg

Mon 14/9

6:40 a.m.-9:57 p.m.

1 stop15h 17m

C$ 645

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Sat 25/4

2:41 p.m.-10:56 a.m.

1 stop20h 15m

Winnipeg

Sat 2/5

5:20 p.m.-10:51 p.m.

1 stop5h 31m

C$ 674

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Tue 28/4

6:30 p.m.-10:56 a.m.

1 stop16h 26m

Winnipeg

Sat 2/5

5:20 p.m.-10:09 a.m.

1 stop16h 49m

C$ 674
Cheapest one-way

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Sun 26/4

6:00 a.m.-10:10 p.m.

2 stops16h 10m

C$ 292

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Sat 15/8

6:15 a.m.-12:15 p.m.

2 stops30h 00m

C$ 329

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Sat 15/8

11:53 a.m.-8:09 p.m.

1 stop8h 16m

C$ 348
Quickest one-way

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Sat 15/8

2:45 p.m.-10:33 p.m.

1 stop7h 48m

C$ 381

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/3

Sorted by cheapest first

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 WestJet fly from Madison to Winnipeg in about 5h 22m. The time it takes to get you to your destination can typically vary by up to 5h 47m. 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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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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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