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Cheap flights from Madison to Winnipeg from C$ 505

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 27/7. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — YWG
15 Jul — 22 Jul1
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 June 2026.

Tue 18/88:10 a.m.
MSN
-
YWG
1 stop14h 23m
United Airlines
Wed 19/82:00 p.m.
YWG
-
MSN
1 stop5h 03m
United Airlines
Deal found 11/6C$ 910
Wed 8/76:41 a.m.
MSN
-
YWG
1 stop5h 11m
United Airlines
Wed 15/77:00 a.m.
YWG
-
MSN
1 stop4h 49m
United Airlines
Deal found 10/6C$ 947
Wed 7/1011:00 a.m.
MSN
-
YWG
1 stop9h 16m
WestJet
Tue 13/106:00 a.m.
YWG
-
MSN
2 stops14h 45m
WestJet
Deal found 11/6C$ 977
Wed 7/102:40 p.m.
MSN
-
YWG
1 stop6h 17m
United Airlines
Tue 13/107:00 a.m.
YWG
-
MSN
1 stop8h 04m
United Airlines
Deal found 11/6C$ 996
Wed 8/78:52 a.m.
MSN
-
YWG
2 stops32h 23m
WestJet
Wed 15/77:45 a.m.
YWG
-
MSN
2 stops25h 07m
WestJet
Deal found 10/6C$ 1,014
Tue 18/82:47 p.m.
MSN
-
YWG
1 stop7h 46m
Air Canada
Wed 19/87:55 a.m.
YWG
-
MSN
2 stops9h 18m
Air Canada
Deal found 12/6C$ 1,043
Thu 9/76:00 a.m.
MSN
-
YWG
2 stops11h 15m
WestJet
Wed 15/710:45 a.m.
YWG
-
MSN
2 stops22h 07m
WestJet
Deal found 11/6C$ 1,070

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 June 2026.

Round-trip from

C$ 910

One-way from

C$ 505
United Airlines
  • United Airlines
  • 18/8-19/8
  • 2 total stops
  • 19h 26m total
  • Madison to Winnipeg
Search Deals
WestJet
  • WestJet
  • 27/7
  • 1 total stop
  • 22h 38m 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 June 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 18/8

8:10 a.m.-10:33 p.m.

1 stop14h 23m

Winnipeg

Wed 19/8

2:00 p.m.-7:03 p.m.

1 stop5h 03m

C$ 910

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Thu 9/7

8:10 a.m.-10:38 p.m.

1 stop14h 28m

Winnipeg

Wed 15/7

7:00 a.m.-11:49 a.m.

1 stop4h 49m

C$ 910
Quickest round-trip

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Wed 8/7

6:41 a.m.-11:52 a.m.

1 stop5h 11m

Winnipeg

Wed 15/7

7:00 a.m.-11:49 a.m.

1 stop4h 49m

C$ 947

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Wed 7/10

11:00 a.m.-8:16 p.m.

1 stop9h 16m

Winnipeg

Tue 13/10

6:00 a.m.-8:45 p.m.

2 stops14h 45m

C$ 977

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Wed 7/10

2:40 p.m.-8:57 p.m.

1 stop6h 17m

Winnipeg

Tue 13/10

7:00 a.m.-3:04 p.m.

1 stop8h 04m

C$ 996

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Wed 8/7

8:52 a.m.-5:15 p.m.

2 stops32h 23m

Winnipeg

Wed 15/7

7:45 a.m.-8:52 a.m.

2 stops25h 07m

C$ 1,014
Cheapest one-way

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Mon 27/7

6:13 p.m.-4:51 p.m.

1 stop22h 38m

C$ 505
Quickest one-way

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Mon 27/7

3:18 p.m.-11:52 a.m.

3 stops20h 34m

C$ 1,040

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/6

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 fly from Madison to Winnipeg in about 14h 23m. 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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Fly with Cheapflights

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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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