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Cheap flights from Madison to Winnipeg from C$ 400

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 13/9. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — YWG
5 Aug — 12 Aug1
1 adult

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 31 July 2025.

Round-trip from

C$ 1,029

One-way from

C$ 400
United Airlines
  • United Airlines
  • 27/8-3/9
  • 2 total stops
  • 17h 04m total
  • Madison to Winnipeg
Search Deals
13/9
  • 13/9
  • 3 total stops
  • 33h 35m 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 31 July 2025.

Wed 27/86:30 a.m.MSN - YWG
1 stop9h 01mUnited Airlines
Wed 3/92:20 p.m.YWG - MSN
1 stop8h 03mUnited Airlines
Deal found 29/7C$ 1,029
Wed 27/86:05 a.m.MSN - YWG
2 stops15h 26mWestJet
Wed 3/96:30 a.m.YWG - MSN
2 stops11h 27mWestJet
Deal found 29/7C$ 1,124
Sat 9/85:40 a.m.MSN - YWG
2 stops17h 45mDelta
Fri 29/812:43 p.m.YWG - MSN
1 stop5h 14mDelta
Deal found 30/7C$ 1,196
Wed 27/88:46 a.m.MSN - YWG
3 stops32h 40mMultiple Airlines
Wed 3/99:05 p.m.YWG - MSN
2 stops19h 12mMultiple Airlines
Deal found 29/7C$ 1,757

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 31 July 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

Wed 27/8

6:30 a.m.-3:31 p.m.

1 stop9h 01m

Winnipeg

Wed 3/9

2:20 p.m.-10:23 p.m.

1 stop8h 03m

C$ 1,029

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Wed 27/8

6:05 a.m.-9:31 p.m.

2 stops15h 26m

Winnipeg

Wed 3/9

6:30 a.m.-5:57 p.m.

2 stops11h 27m

C$ 1,124

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Sun 10/8

6:45 a.m.-4:50 p.m.

1 stop10h 05m

Winnipeg

Fri 29/8

12:43 p.m.-5:57 p.m.

1 stop5h 14m

C$ 1,313

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Wed 27/8

8:46 a.m.-5:26 p.m.

3 stops32h 40m

Winnipeg

Wed 3/9

9:05 p.m.-4:17 p.m.

2 stops19h 12m

C$ 1,757

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Sat 13/9

9:48 a.m.-7:23 p.m.

3 stops33h 35m

C$ 400

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Sat 13/9

3:58 p.m.-10:33 p.m.

1 stop6h 35m

C$ 459

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Sun 14/9

7:00 a.m.-11:10 p.m.

2 stops16h 10m

C$ 506

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Fri 8/8

11:53 a.m.-4:50 p.m.

1 stop4h 57m

C$ 755

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/7

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.

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Winnipeg. Reviews last updated 31 July 2025.
Read through reviews of airlines operating flights from Madison to Winnipeg, such as Delta,United Airlines, andWestJet. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,980 reviews
Check prices

Food

7.3

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews
Check prices

Food

7.3

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,902 reviews
Delta
8.0
Very good
7,980 reviews
Check prices

Food

7.3

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
WestJet
7.2
Good
2,977 reviews
Delta
8.0
Very good
7,980 reviews
Check prices

Food

7.3

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • What are the cheapest airlines flying from Madison to Winnipeg round-trip?

    According to our current data, United Airlines (C$ 1,029), WestJet (C$ 1,124), and Delta (C$ 1,313) offers the cheapest pricing from Madison to Winnipeg.

  • What are the cheapest airlines to fly from Madison to Winnipeg one-way?

    To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at C$ 459. WestJet flights start at C$ 506 while deals on Delta start at C$ 755 one-way.

  • 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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