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Cheap flights from Madison to Winnipeg from C$ 909

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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — YWG
11 Oct — 18 Oct1
1 adult
1 adult, Economy

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 11 September 2025.

Round-trip from

C$ 909
WestJet
  • WestJet
  • 9/10-15/10
  • 3 total stops
  • 49h 06m total
  • Madison to Winnipeg
Search Deals

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 11 September 2025.

Thu 9/107:59 p.m.MSN - YWG
2 stops45h 41mMultiple Airlines
Wed 15/108:00 a.m.YWG - MSN
1 stop3h 25mMultiple Airlines
Deal found 11/9C$ 909
Sat 11/1010:58 a.m.MSN - YWG
1 stop24h 32mDelta
Thu 16/106:40 a.m.YWG - MSN
1 stop4h 45mDelta
Deal found 11/9C$ 930
Thu 9/102:46 p.m.MSN - YWG
1 stop24h 45mUnited Airlines
Wed 15/107:00 a.m.YWG - MSN
1 stop11h 55mUnited Airlines
Deal found 11/9C$ 1,003
Tue 7/106:00 a.m.MSN - YWG
1 stop17h 27mDelta
Thu 16/106:40 a.m.YWG - MSN
1 stop4h 45mDelta
Deal found 11/9C$ 1,007
Thu 4/129:38 a.m.MSN - YWG
2 stops9h 34mWestJet
Sat 6/125:45 p.m.YWG - MSN
1 stop16h 30mWestJet
Deal found 9/9C$ 1,038
Sun 12/106:00 a.m.MSN - YWG
1 stop5h 30mDelta
Thu 16/106:40 a.m.YWG - MSN
1 stop4h 45mDelta
Deal found 11/9C$ 1,039
Thu 4/129:38 a.m.MSN - YWG
2 stops9h 34mWestJet
Fri 5/1210:55 a.m.YWG - MSN
2 stops12h 01mWestJet
Deal found 9/9C$ 1,045
Wed 8/106:00 a.m.MSN - YWG
2 stops15h 25mWestJet
Thu 16/106:15 p.m.YWG - MSN
2 stops28h 14mWestJet
Deal found 11/9C$ 1,052
Mon 6/102:46 p.m.MSN - YWG
1 stop7h 47mUnited Airlines
Thu 16/107:00 a.m.YWG - MSN
1 stop6h 50mUnited Airlines
Deal found 11/9C$ 1,074
Tue 7/106:30 a.m.MSN - YWG
2 stops16h 55mUnited Airlines
Thu 16/107:00 a.m.YWG - MSN
1 stop4h 45mUnited Airlines
Deal found 11/9C$ 1,089
Thu 9/106:30 a.m.MSN - YWG
1 stop9h 01mUnited Airlines
Thu 16/105:15 p.m.YWG - MSN
2 stops16h 40mUnited Airlines
Deal found 11/9C$ 1,122

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 11 September 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

Thu 9/10

7:59 p.m.-5:40 p.m.

2 stops45h 41m

Winnipeg

Wed 15/10

8:00 a.m.-11:25 a.m.

1 stop3h 25m

C$ 909

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Sat 11/10

10:58 a.m.-11:30 a.m.

1 stop24h 32m

Winnipeg

Thu 16/10

6:40 a.m.-11:25 a.m.

1 stop4h 45m

C$ 930

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Thu 4/12

5:32 p.m.-11:45 p.m.

1 stop6h 13m

Winnipeg

Sat 6/12

12:46 p.m.-8:52 p.m.

1 stop8h 06m

C$ 930

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Wed 8/10

6:00 a.m.-8:10 p.m.

1 stop14h 10m

Winnipeg

Thu 16/10

6:40 a.m.-11:25 a.m.

1 stop4h 45m

C$ 1,007

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Fri 10/10

6:00 a.m.-11:27 p.m.

1 stop17h 27m

Winnipeg

Thu 16/10

6:40 a.m.-11:25 a.m.

1 stop4h 45m

C$ 1,007

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Thu 9/10

6:00 a.m.-11:27 p.m.

1 stop17h 27m

Winnipeg

Thu 16/10

8:00 a.m.-11:25 a.m.

1 stop3h 25m

C$ 1,007

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Tue 7/10

6:00 a.m.-11:27 p.m.

1 stop17h 27m

Winnipeg

Thu 16/10

6:40 a.m.-11:25 a.m.

1 stop4h 45m

C$ 1,007

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Thu 4/12

9:38 a.m.-7:12 p.m.

2 stops9h 34m

Winnipeg

Sat 6/12

5:45 p.m.-10:15 a.m.

1 stop16h 30m

C$ 1,038

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Thu 4/12

9:38 a.m.-7:12 p.m.

2 stops9h 34m

Winnipeg

Fri 5/12

5:45 p.m.-10:56 p.m.

1 stop5h 11m

C$ 1,038

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Thu 4/12

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

1 stop5h 27m

Winnipeg

Fri 5/12

2:20 p.m.-7:16 p.m.

1 stop4h 56m

C$ 1,039

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/9

Showing 1-10 of 11 results
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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 Delta fly from Madison to Winnipeg in about 24h 32m. 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.

  • What is the cheapest month to book a flight from Madison to Winnipeg?

    Currently, January is the cheapest month in which you can book a flight from Madison to Winnipeg (average of C$ 123). Flying from Madison to Winnipeg in July is currently the most expensive (average of C$ 232). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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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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?

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