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Cheap flights from Madison to Winnipeg from C$ 841

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 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — YWG
28 Aug — 4 Sep1
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 29 July 2026.

Fri 2/106:00 a.m.
MSN
-
YWG
1 stop9h 08m
WestJet
Sat 3/103:58 p.m.
YWG
-
MSN
1 stop6h 36m
WestJet
Deal found 29/7C$ 841
Tue 1/99:32 a.m.
MSN
-
YWG
2 stops15h 23m
WestJet
Wed 23/93:58 p.m.
YWG
-
MSN
1 stop7h 03m
WestJet
Deal found 28/7C$ 844
Fri 11/96:00 a.m.
MSN
-
YWG
2 stops16h 10m
WestJet
Sun 13/910:45 a.m.
YWG
-
MSN
2 stops36h 16m
WestJet
Deal found 28/7C$ 887
Thu 3/96:05 a.m.
MSN
-
YWG
1 stop5h 49m
WestJet
Thu 10/96:40 a.m.
YWG
-
MSN
1 stop4h 40m
WestJet
Deal found 25/7C$ 971
Sun 6/96:05 a.m.
MSN
-
YWG
2 stops16h 05m
WestJet
Thu 10/96:40 a.m.
YWG
-
MSN
1 stop4h 40m
WestJet
Deal found 25/7C$ 978
Tue 17/119:26 a.m.
MSN
-
YWG
2 stops9h 49m
WestJet
Sat 21/116:35 a.m.
YWG
-
MSN
1 stop3h 40m
WestJet
Deal found 25/7C$ 989

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 29 July 2026.

Round-trip from

C$ 841
WestJet
  • WestJet
  • 2/10-3/10
  • 2 total stops
  • 15h 44m 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 29 July 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

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Tue 1/9

1:35 p.m.-12:55 a.m.

2 stops11h 20m

Winnipeg

Wed 23/9

7:00 a.m.-11:01 p.m.

2 stops16h 01m

C$ 842

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Fri 2/10

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

2 stops16h 10m

Winnipeg

Sat 3/10

3:58 p.m.-10:34 p.m.

1 stop6h 36m

C$ 844

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Fri 23/10

7:00 a.m.-12:55 a.m.

2 stops17h 55m

Winnipeg

Tue 27/10

5:40 p.m.-8:55 p.m.

1 stop3h 15m

C$ 845

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Fri 11/9

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

2 stops16h 10m

Winnipeg

Sun 13/9

10:45 a.m.-11:01 p.m.

2 stops36h 16m

C$ 887
Quickest round-trip

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Sun 6/9

6:05 a.m.-10:10 p.m.

2 stops16h 05m

Winnipeg

Thu 10/9

6:40 a.m.-11:20 a.m.

1 stop4h 40m

C$ 978

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/7

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 WestJet fly from Madison to Winnipeg in about 11h 20m. The time it takes to get you to your destination can typically vary by up to . Madison and Winnipeg are separated by a distance of 964 km.

  • 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

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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?

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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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