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$164+ 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 10/8. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — YWG
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$613
(Kiwi.com)

One-way from

$164
(Kiwi.com)
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 September 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/89:48 amMSN - YWG
2 stops30h 34mMultiple Airlines
Sun 10/128:00 amYWG - MSN
1 stop3h 25mMultiple Airlines
Deal found 9/17$613
This Delta deal was found by Cheapflights users on 9/16. 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.
Thu 10/1612:05 pmMSN - YWG
1 stop11h 22mDelta
Mon 10/205:40 pmYWG - MSN
1 stop14h 57mDelta
Deal found 9/16$672
This deal was found by Cheapflights users on 9/16. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/176:00 amMSN - YWG
1 stop5h 30mDelta
Tue 10/216:40 amYWG - MSN
1 stop7h 22mDelta
Deal found 9/16$681
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/49:48 amMSN - YWG
2 stops34h 42mMultiple Airlines
Sun 10/128:00 amYWG - MSN
1 stop3h 25mMultiple Airlines
Deal found 9/17$709
This Delta deal was found by Cheapflights users on 9/16. 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.
Wed 10/1512:05 pmMSN - YWG
1 stop11h 22mDelta
Mon 10/205:40 pmYWG - MSN
1 stop14h 57mDelta
Deal found 9/16$728
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/97:59 pmMSN - YWG
2 stops39h 42mMultiple Airlines
Sun 10/128:00 amYWG - MSN
1 stop3h 25mMultiple Airlines
Deal found 9/17$730
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Wed 10/88:15 amMSN - YWG
1 stop14h 18mUnited Airlines
Sun 10/122:20 pmYWG - MSN
1 stop19h 35mUnited Airlines
Deal found 9/17$735
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Tue 10/712:26 pmMSN - YWG
1 stop27h 05mUnited Airlines
Sun 10/122:20 pmYWG - MSN
1 stop24h 46mUnited Airlines
Deal found 9/17$740
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Thu 10/1612:26 pmMSN - YWG
1 stop27h 05mUnited Airlines
Mon 10/204:25 pmYWG - MSN
2 stops21h 25mUnited Airlines
Deal found 9/16$744
This FlightHub deal was found by Cheapflights users on 9/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/166:00 amMSN - YWG
2 stops15h 25mWestJet
Mon 10/204:30 pmYWG - MSN
2 stops29h 59mWestJet
Deal found 9/16$745
This deal was found by Cheapflights users on 9/16. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/186:00 amMSN - YWG
1 stop5h 30mDelta
Tue 10/218:00 amYWG - MSN
1 stop6h 02mDelta
Deal found 9/16$750

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 September 17, 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 10/8

9:48 am-4:22 pm

2 stops30h 34m

Winnipeg

Sun 10/12

8:00 am-11:25 am

1 stop3h 25m

$613

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Thu 10/16

9:34 am-4:50 pm

1 stop7h 16m

Winnipeg

Tue 10/21

6:40 am-2:02 pm

1 stop7h 22m

$672

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Fri 10/17

9:34 am-8:10 pm

1 stop10h 36m

Winnipeg

Mon 10/20

5:40 pm-8:37 am

1 stop14h 57m

$672

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Thu 10/16

12:05 pm-11:27 pm

1 stop11h 22m

Winnipeg

Mon 10/20

5:40 pm-8:37 am

1 stop14h 57m

$672

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Fri 10/17

6:00 am-11:30 am

1 stop5h 30m

Winnipeg

Tue 10/21

6:40 am-2:02 pm

1 stop7h 22m

$681

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Wed 10/15

12:05 pm-11:27 pm

1 stop11h 22m

Winnipeg

Mon 10/20

5:40 pm-8:37 am

1 stop14h 57m

$728

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Thu 10/9

7:59 pm-11:41 am

2 stops39h 42m

Winnipeg

Sun 10/12

8:00 am-11:25 am

1 stop3h 25m

$730

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Wed 10/8

8:15 am-10:33 pm

1 stop14h 18m

Winnipeg

Sun 10/12

2:20 pm-9:55 am

1 stop19h 35m

$735

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Thu 10/9

8:15 am-10:33 pm

1 stop14h 18m

Winnipeg

Sun 10/12

2:20 pm-9:55 am

1 stop19h 35m

$735

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Fri 10/10

10:51 am-10:33 pm

1 stop11h 42m

Winnipeg

Sun 10/12

2:20 pm-9:55 am

1 stop19h 35m

$735

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 20 results
1
2

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 September 17, 2025.
Read reviews from past customers who have flown Delta from Madison to Winnipeg. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,961 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

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
7,961 reviews
Delta
8.0
Very good
7,961 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

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.

  • How long is the flight from Madison to Winnipeg?

    A quick flight from Madison to Winnipeg can take about 7h 16m. Delta provides one of the quickest options available for as low as $672. Airlines will cover a distance of 599 mi.

  • What is the cheapest airline to fly from Madison to Winnipeg round-trip?

    Cheapflights users have booked flights from Madison to Winnipeg round-trip from $282.

  • 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 $501). 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

Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Portage la Prairie

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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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$282Average$659FlexibilityNo cancel feeOn-timeN/A

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