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$302+ Cheap flights from Madison (MSN) to Winnipeg (YWG)

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 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — YWG
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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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 June 12, 2025.

Round-trip from

$658
(Delta)

One-way from

$302
(Delta)
From Madison Truax Field to Winnipeg
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One-way flight from Madison Truax Field to Winnipeg
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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 June 12, 2025.

This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/22:44 pmMSN - YWG
1 stop8h 43mDelta
Tue 9/912:43 pmYWG - MSN
1 stop5h 14mDelta
Deal found 6/11$658
This Mytrip deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/268:46 amMSN - YWG
2 stops32h 55mMultiple Airlines
Sat 8/26:30 amYWG - MSN
2 stops11h 44mMultiple Airlines
Deal found 6/11$720
This United Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/256:40 amMSN - YWG
2 stops16h 48mUnited Airlines
Fri 8/17:00 amYWG - MSN
1 stop15h 15mUnited Airlines
Deal found 6/10$810

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 2,558,603 searches. Data last updated June 12, 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

Tue 9/2

2:44 pm-11:27 pm

1 stop8h 43m

Winnipeg

Tue 9/9

12:43 pm-5:57 pm

1 stop5h 14m

$658

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Sat 7/26

8:46 am-5:41 pm

2 stops32h 55m

Winnipeg

Sat 8/2

6:30 am-6:14 pm

2 stops11h 44m

$720

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Fri 7/25

6:40 am-11:28 pm

2 stops16h 48m

Winnipeg

Fri 8/1

7:00 am-10:15 pm

1 stop15h 15m

$810

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Tue 7/15

6:54 pm-11:25 pm

1 stop4h 31m

$302

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Mon 6/30

3:50 pm-11:07 am

2 stops19h 17m

$457

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Sat 7/26

12:20 pm-10:33 pm

1 stop10h 13m

$466

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

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.

Cheapflights Insights

Everything you need to know about your flight from Madison to Winnipeg

Rainfall in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Winnipeg ranges from 0.8 - 3.1 inches per month. June is typically the wettest month, when rainfall can reach 3.1 in. January is typically the driest time to visit Winnipeg when rainfall is around 0.8 in.

Temperature in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Winnipeg, 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 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 3.2 F).

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 June 12, 2025.
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

7.9

Crew

8.5

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
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

7.9

Crew

8.5

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
8,790 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

7.9

Crew

8.5

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!
Air Canada
7.1
Good
9,531 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

7.9

Crew

8.5

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?

    Cheapflights users have booked flights from Madison to Winnipeg round-trip from $658. Another airline that can offer you cheap pricing is United Airlines.

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

    To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $302. Air Canada flights start at $457 while deals on United Airlines start at $466 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, August is the cheapest month in which you can book a flight from Madison to Winnipeg (average of $358). Flying from Madison to Winnipeg in December is currently the most expensive (average of $497). 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

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Alternative routes for Madison to Winnipeg

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Top airline flying from Madison to Winnipeg

Discover the top airline that operate flights from Madison to Winnipeg. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$282Average$998FlexibilityNo cancel feeOn-timeN/A

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