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$408+ Cheap flights from Madison (MSN) to Winnipeg (YWG)

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 6/6. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — YWG
May 29 — Jun 51
Fri 5/29
Fri 6/5
1 adult, Economy
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Cheap 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 April 29, 2026.

This lastminute.com deal was found by Cheapflights users on 4/28. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/66:29 pm
MSN
-
YWG
1 stop17h 27m
WestJet
Sat 6/136:00 am
YWG
-
MSN
2 stops11h 09m
WestJet
Deal found 4/28$408
This Justfly.com deal was found by Cheapflights users on 4/27. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:30 am
MSN
-
YWG
1 stop4h 24m
WestJet
Sun 6/75:41 pm
YWG
-
MSN
1 stop5h 21m
WestJet
Deal found 4/27$433
This FlightHub deal was found by Cheapflights users on 4/24. 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.
Tue 5/261:29 pm
MSN
-
YWG
2 stops11h 26m
WestJet
Thu 5/286:40 am
YWG
-
MSN
1 stop7h 13m
WestJet
Deal found 4/24$434
This FlightHub deal was found by Cheapflights users on 4/27. 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.
Sun 9/66:15 am
MSN
-
YWG
2 stops15h 55m
WestJet
Fri 9/187:00 am
YWG
-
MSN
2 stops14h 57m
WestJet
Deal found 4/27$440
This Priceline deal was found by Cheapflights users on 4/24. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/81:31 pm
MSN
-
YWG
2 stops11h 24m
WestJet
Mon 6/155:42 pm
YWG
-
MSN
1 stop5h 20m
WestJet
Deal found 4/24$451
This Justfly.com deal was found by Cheapflights users on 4/26. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/66:30 am
MSN
-
YWG
1 stop4h 24m
WestJet
Mon 6/159:05 pm
YWG
-
MSN
2 stops25h 57m
WestJet
Deal found 4/26$469
This Justfly.com deal was found by Cheapflights users on 4/27. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/139:00 am
MSN
-
YWG
1 stop14h 27m
WestJet
Thu 9/246:40 am
YWG
-
MSN
1 stop15h 17m
WestJet
Deal found 4/27$470
This Justfly.com deal was found by Cheapflights users on 4/27. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/116:19 pm
MSN
-
YWG
1 stop20h 48m
WestJet
Mon 7/204:25 pm
YWG
-
MSN
2 stops16h 27m
WestJet
Deal found 4/27$477

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 April 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$408
(lastminute.com)
Provider with most accurate pricing for Madison Truax Field-Winnipeg flight deals.
Search Deals
Provider most trusted by Cheapflights users for Madison Truax Field-Winnipeg flights.
Search Deals
From Madison Truax Field to Winnipeg
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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 April 29, 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

Sat 6/6

6:29 pm-11:56 am

1 stop17h 27m

Winnipeg

Sat 6/13

6:00 am-5:09 pm

2 stops11h 09m

$408
Quickest round-trip

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Tue 5/26

6:30 am-10:54 am

1 stop4h 24m

Winnipeg

Thu 5/28

6:40 am-1:53 pm

1 stop7h 13m

$446

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Mon 6/8

1:31 pm-12:55 am

2 stops11h 24m

Winnipeg

Mon 6/15

5:42 pm-11:02 pm

1 stop5h 20m

$451

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Sat 6/6

6:30 am-10:54 am

1 stop4h 24m

Winnipeg

Mon 6/15

9:05 pm-11:02 pm

2 stops25h 57m

$469

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Wed 6/10

9:30 am-12:55 am

2 stops15h 25m

Winnipeg

Wed 6/17

7:10 pm-11:02 pm

2 stops27h 52m

$532

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Wed 6/10

9:02 am-4:51 pm

1 stop7h 49m

Winnipeg

Wed 6/17

5:41 pm-11:02 pm

1 stop5h 21m

$640

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Sat 7/11

2:45 pm-11:29 pm

1 stop8h 44m

Winnipeg

Mon 7/20

3:59 pm-11:00 pm

1 stop7h 01m

$740

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Mon 5/11

6:30 am-2:55 pm

1 stop8h 25m

Winnipeg

Wed 5/13

3:50 pm-9:27 pm

1 stop5h 37m

$956

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Sorted by cheapest first
  • Most accurate provider: When it comes to deals on Madison-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madison-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Madison-Winnipeg flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Madison-Winnipeg flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Madison-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 April 29, 2026.
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
7.9
Good
8,467 reviews

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Crew

8.5

Food

7.2

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,467 reviews
Delta
7.9
Good
8,467 reviews

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Crew

8.5

Food

7.2

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 17h 27m. WestJet provides one of the quickest options available for as low as $408. Airlines will cover a distance of 599 mi.

  • 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

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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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 April 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$188Average$591FlexibilityNo cancel feeOn-timeN/A

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