How long is the flight from Winnipeg to Madison?

For as low as C$ 864, United Airlines can have you in Madison from Winnipeg in 5h 13m. There are 964 km between Winnipeg and Madison. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

In terms of precipitation, rainfall in Madison ranges from 31.0 - 114.0 mm per month. June is typically the wettest month, when rainfall can reach 114.0 mm. January is typically the driest time to visit Madison when rainfall is around 31.0 mm.

If weather is an important factor for your trip to Madison, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 22.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -7.0 C).

What is the cheapest time of day to fly from YWG to MSN?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Madison as you normally would.

Can I find deals for flights from Winnipeg to Madison that include hotel bookings?

Yes. In addition to deals on Winnipeg to Madison flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Winnipeg to Madison?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Madison.

Can I find deals for business class flights from Winnipeg to Madison?

Yes. Cheapflights offers flight deals from Winnipeg to Madison by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

C$ 799+ Cheap Flights from Winnipeg to Madison

Cheap flight deals from Winnipeg to Madison

Enter your travel dates to find the best prices.

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Cheapest flights from Winnipeg to Madison
Explore the most affordable flight options available from Winnipeg to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 11 September 2026.

Fri 11/128:30 a.m. -

1 stop12h 04m

Sun 13/1210:42 a.m. -

2 stops10h 42m

Deal found 9/9C$ 799

Fri 11/122:15 p.m. -

1 stop5h 13m

Sun 13/125:00 a.m. -

1 stop7h 23m

Deal found 9/9C$ 864

Mon 21/128:40 a.m. -

1 stop11h 58m

Sun 27/126:00 a.m. -

1 stop6h 52m

Deal found 7/9C$ 865

Mon 21/125:22 p.m. -

1 stop16h 57m

Sun 27/127:51 p.m. -

1 stop15h 34m

Deal found 11/9C$ 960

Find flight deals from Winnipeg to Madison

Round-trip from	C$ 799

Air Canada
11/12-13/12
3 total stops
22h 46m total
Winnipeg to Madison

Search Deals

Fly from

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Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

WinnipegMadison

YWG Winnipeg - MSN Madison Truax Field

YWGMSN

Winnipeg

Fri 11/12

2:15 p.m.-7:28 p.m.

1 stop5h 13m

Madison Truax Field

Sun 13/12

5:00 a.m.-12:23 p.m.

1 stop7h 23m

C$ 864

WinnipegMadison

YWG Winnipeg - MSN Madison Truax Field

YWGMSN

Winnipeg

Mon 21/12

8:40 a.m.-8:38 p.m.

1 stop11h 58m

Madison Truax Field

Sun 27/12

6:00 a.m.-12:52 p.m.

1 stop6h 52m

C$ 865

WinnipegMadison

YWG Winnipeg - MSN Madison Truax Field

YWGMSN

Winnipeg

Mon 21/12

5:22 p.m.-10:19 a.m.

1 stop16h 57m

Madison Truax Field

Sun 27/12

7:51 p.m.-11:25 a.m.

1 stop15h 34m

C$ 960

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Sorted by cheapest first

Best time to book a flight from Winnipeg to Madison

Have a flexible travel schedule? Discover the best time to fly to Madison from Winnipeg with our price prediction graph.

YWG-MSN

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

How long is the flight from Winnipeg to Madison?
For as low as C$ 864, United Airlines can have you in Madison from Winnipeg in 5h 13m. There are 964 km between Winnipeg and Madison. 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 Winnipeg to Madison that include hotel bookings?
Yes. In addition to deals on Winnipeg to Madison flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Winnipeg to Madison?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Madison.
Can I find deals for business class flights from Winnipeg to Madison?
Yes. Cheapflights offers flight deals from Winnipeg to Madison by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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Cheap flights from Winnipeg to Madison from C$ 799

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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.

Cheap flight deals from Winnipeg to Madison

Cheapest flights from Winnipeg to MadisonExplore the most affordable flight options available from Winnipeg to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 11 September 2026.

Explore the most affordable flight options available from Winnipeg to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 11 September 2026.

Best flights from Winnipeg to MadisonDiscover carefully curated flight deals from Winnipeg to Madison that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 11 September 2026.

Discover carefully curated flight deals from Winnipeg to Madison that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 11 September 2026.

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Best time to book a flight from Winnipeg to Madison

Have a flexible travel schedule? Discover the best time to fly to Madison from Winnipeg with our price prediction graph.

Related info for your journey

How long is the flight from Winnipeg to Madison?

Can I find deals for flights from Winnipeg to Madison that include hotel bookings?

How can I find direct flights from Winnipeg to Madison?

Can I find deals for business class flights from Winnipeg to Madison?

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Winnipeg to Madison

See prices for flight routes from nearby airports that may be better suited for you.

Complete your trip

Complete your trip to Madison by adding a car rental and/or hotel reservation to your travel itinerary.

Direct flights to United States

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Search flights from Winnipeg to Madison by cabin class

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Winnipeg and Madison flights

Browse other Winnipeg and Madison flight options. Last updated on 11 September 2026.

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

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

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

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

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Cheapest flights from Winnipeg to Madison
Explore the most affordable flight options available from Winnipeg to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 11 September 2026.

Best flights from Winnipeg to Madison
Discover carefully curated flight deals from Winnipeg to Madison that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 11 September 2026.